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EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village’s acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

5 Beds ⋅ 3 Baths ⋅ 5113873 MLS

EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village’s acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

18 Pleasant St, Woodstock

$1,749,000

Located right in the Village of Woodstock, 81 Central Street has both excellent visibility, road and sign frontage on Central Street (Rt 4) and an easy walk to everything. It is currently divided up as three connected units and is zoned "Office/Residential". The charming brick cape house in the front (c. 1821) is currently configured as an office but was formerly a residence, and rented for $5,000 per month. The downstairs office area has an open floorplan plus a full bath, but could easily be reconfigured differently with the addition of interior walls. Upstairs are two rooms (formerly bedrooms) and a shell-bathroom which is plumbed and ready for appliances and finishing. The middle building is now a 3 bedroom 2 bath apartment with full kitchen, laundry, living room, office and central A/C and is currently rented for $5,000/month. The rear studio is a 1 bedroom 1 1/2 bath apartment with open living room / kitchen area, currently rented for $2,200 per month. The property also features a two-car detached, heated garage plus parking for 5-6 other cars, plus a lovely shaded lawn.

5 Beds ⋅ 5 Baths ⋅ 5113766 MLS

Located right in the Village of Woodstock, 81 Central Street has both excellent visibility, road and sign frontage on Central Street (Rt 4) and an easy walk to everything. It is currently divided up as three connected units and is zoned "Office/Residential". The charming brick cape house in the front (c. 1821) is currently configured as an office but was formerly a residence, and rented for $5,000 per month. The downstairs office area has an open floorplan plus a full bath, but could easily be reconfigured differently with the addition of interior walls. Upstairs are two rooms (formerly bedrooms) and a shell-bathroom which is plumbed and ready for appliances and finishing. The middle building is now a 3 bedroom 2 bath apartment with full kitchen, laundry, living room, office and central A/C and is currently rented for $5,000/month. The rear studio is a 1 bedroom 1 1/2 bath apartment with open living room / kitchen area, currently rented for $2,200 per month. The property also features a two-car detached, heated garage plus parking for 5-6 other cars, plus a lovely shaded lawn.

81 Central St, Woodstock

$549,000

Welcome to this newly updated sun-filled craftsman home, ideally located just 4 miles from the heart of Woodstock Village and 11 miles from Killington Ski Resort. Set on 5 acres with a lovely pond, this property offers the perfect blend of privacy, convenience, and Vermont charm. The home features a bright and inviting interior with one bedroom on the main level and two additional bedrooms and a full bath on the lower level. A spacious wraparound porch extends the living space outdoors, providing the perfect spot to relax, entertain, and enjoy the peaceful surroundings. Whether you’re looking for a primary residence, Vermont getaway, or a home base for year-round recreation, this beautifully updated chalet offers easy access to skiing, dining, shopping, hiking, and everything the Woodstock and Killington areas have to offer.

3 Beds ⋅ 2 Baths ⋅ 5113572 MLS

Welcome to this newly updated sun-filled craftsman home, ideally located just 4 miles from the heart of Woodstock Village and 11 miles from Killington Ski Resort. Set on 5 acres with a lovely pond, this property offers the perfect blend of privacy, convenience, and Vermont charm. The home features a bright and inviting interior with one bedroom on the main level and two additional bedrooms and a full bath on the lower level. A spacious wraparound porch extends the living space outdoors, providing the perfect spot to relax, entertain, and enjoy the peaceful surroundings. Whether you’re looking for a primary residence, Vermont getaway, or a home base for year-round recreation, this beautifully updated chalet offers easy access to skiing, dining, shopping, hiking, and everything the Woodstock and Killington areas have to offer.

139 Doe Hill Way, Woodstock

$549,000

Nestled in the heart of historic Woodstock. This 1875 colonial abuts Mt. Peg with direct access to the trail system. A large shed in the backyard could be used as a workshop and/or storage, ample space for gardening and very private backyard for entertaining. The house had some upgrades to the kitchen and bathrooms and still boasts some of the original features including hardwood floors in the bedrooms upstairs. First floor has a mudroom, large oversized kitchen with cherry cabinets, stainless steel appliances and stone countertops anchored with an island and opens to the dining area. There is a handsome set of French doors that walk out onto a stone patio. The living room is spacious with a wood burning fireplace and a small room that could be used as an office. The second floor has 3 bedrooms and a full bath. The primary bedroom has ample space to add a separate bathroom. This home has a newer heating system. It's a great project for a buyer wanting to put in some sweat equity and refurbish this lovely old home. Walk to town with easy access to all amenities including restaurants and stores. Easy access to mountain biking, hiking and cross country skiing. There is an inspection report available. Come take a look- this house is located in a wonderful neighborhood and waiting for the perfect buyer to embrace a fun project.

3 Beds ⋅ 2 Baths ⋅ 5113119 MLS

Nestled in the heart of historic Woodstock. This 1875 colonial abuts Mt. Peg with direct access to the trail system. A large shed in the backyard could be used as a workshop and/or storage, ample space for gardening and very private backyard for entertaining. The house had some upgrades to the kitchen and bathrooms and still boasts some of the original features including hardwood floors in the bedrooms upstairs. First floor has a mudroom, large oversized kitchen with cherry cabinets, stainless steel appliances and stone countertops anchored with an island and opens to the dining area. There is a handsome set of French doors that walk out onto a stone patio. The living room is spacious with a wood burning fireplace and a small room that could be used as an office. The second floor has 3 bedrooms and a full bath. The primary bedroom has ample space to add a separate bathroom. This home has a newer heating system. It's a great project for a buyer wanting to put in some sweat equity and refurbish this lovely old home. Walk to town with easy access to all amenities including restaurants and stores. Easy access to mountain biking, hiking and cross country skiing. There is an inspection report available. Come take a look- this house is located in a wonderful neighborhood and waiting for the perfect buyer to embrace a fun project.

8 Golf Ave, Woodstock

$2,600,000

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dramatic vaulted great room–showcasing exposed hand-hewn beams and a wood-burning fireplace–as well as a sizable screened porch overlooking the grounds, all of which provide an ideal setting for entertaining family and friends. Adjacent to the kitchen on the other side of the house is a more intimate living room with a second fireplace, an office, and a bedroom with full bath, offering the possibility of one-level living. Upstairs, there is an en suite bedroom and two additional bedrooms that share a full bath. The lower level adds versatile finished space with a 5th bedroom guest suite with recreation space. An attached three-bay garage and barn provide ample room for vehicles, outdoor equipment, and all the gear that comes with four-season Vermont living. The attached barn has two horse stalls. There are two beautiful ponds on the property, the larger is well positioned in the backyard towards the view. Beyond the property, Woodstock’s extensive network of hiking and biking trails, nearby rivers, golf, skiing, and other year-round recreation along with shops, restaurants, and galleries are all within easy reach. Some photos are digitally enhanced.

5 Beds ⋅ 5 Baths ⋅ 5112419 MLS

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dramatic vaulted great room–showcasing exposed hand-hewn beams and a wood-burning fireplace–as well as a sizable screened porch overlooking the grounds, all of which provide an ideal setting for entertaining family and friends. Adjacent to the kitchen on the other side of the house is a more intimate living room with a second fireplace, an office, and a bedroom with full bath, offering the possibility of one-level living. Upstairs, there is an en suite bedroom and two additional bedrooms that share a full bath. The lower level adds versatile finished space with a 5th bedroom guest suite with recreation space. An attached three-bay garage and barn provide ample room for vehicles, outdoor equipment, and all the gear that comes with four-season Vermont living. The attached barn has two horse stalls. There are two beautiful ponds on the property, the larger is well positioned in the backyard towards the view. Beyond the property, Woodstock’s extensive network of hiking and biking trails, nearby rivers, golf, skiing, and other year-round recreation along with shops, restaurants, and galleries are all within easy reach. Some photos are digitally enhanced.

2687 Garvin Hill Rd, Woodstock

$2,175,000

Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built in 1811, and listed on the National Historic Register, this stately home has been thoughtfully restored, and lovingly stewarded over the years honoring the period detail while creating the perfect unification of antiquity and modern functionality. The bright, spacious rooms flow seamlessly for daily living or entertaining. The impressive Kitchen-Great Room is anchored by a generous brick fireplace, and sweeping 17’ cathedral ceiling, and steps out to a private deck overlooking the brook, fields and trail systems beyond. There is a lovely Primary ensuite bedroom, two additional guest rooms and a cozy loft space on the second level. The Kingsley Barn has been transformed into an impeccably appointed two-bedroom lofted guest house with a heated studio space below, and a strong rental history. Cross the brook to the fields and find another barn for storage or animals. Direct access to the GMHA and VAST trail systems for riding, hiking, cross country skiing, and recreation. A short stroll to South Woodstock Store, Kedron Valley Inn and Ransom Tavern. 5 minutes drive to Woodstock Village Green. Furnishings available.

5 Beds ⋅ 4 Baths ⋅ 5111700 MLS

Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built in 1811, and listed on the National Historic Register, this stately home has been thoughtfully restored, and lovingly stewarded over the years honoring the period detail while creating the perfect unification of antiquity and modern functionality. The bright, spacious rooms flow seamlessly for daily living or entertaining. The impressive Kitchen-Great Room is anchored by a generous brick fireplace, and sweeping 17’ cathedral ceiling, and steps out to a private deck overlooking the brook, fields and trail systems beyond. There is a lovely Primary ensuite bedroom, two additional guest rooms and a cozy loft space on the second level. The Kingsley Barn has been transformed into an impeccably appointed two-bedroom lofted guest house with a heated studio space below, and a strong rental history. Cross the brook to the fields and find another barn for storage or animals. Direct access to the GMHA and VAST trail systems for riding, hiking, cross country skiing, and recreation. A short stroll to South Woodstock Store, Kedron Valley Inn and Ransom Tavern. 5 minutes drive to Woodstock Village Green. Furnishings available.

4945 South Rd, Woodstock

$1,795,000

HILLSIDE FARM - SOUTH WOODSTOCK, VERMONT. Hillside Farm estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the heart of the home, the spacious country kitchen features cherry cabinetry, gas cooktop, and an antique Stewart woodstove. The 20’ x 18’ great room offers wide pine floors, exposed framing and a soaring cathedral ceiling, overlooking a lovely 14 foot deep pond and scenic vista. The primary suite includes double closets and an ensuite bath with radiant heat, Jacuzzi tub and shower. Additional bedrooms, dining room, and a home office provide flexible living space. The lower level offers a game room with woodstove and pool table, a small kitchenette, and 3/4 bath. The property is remarkably well equipped with a greenhouse, two-stall horse stable, multiple barns and outbuildings, garage workshop, mechanic’s shop, and a substantial 23’ x 35’ woodworking shop. Tucked into the woods is a delightful rustic cabin complete with kitchenette, woodstove, porch and nearby outhouse; an inviting retreat surrounded by nature and set just above one of two babbling brooks. Located in the heart of South Woodstock’s celebrated horse country, Hillside Farm enjoys proximity to the renowned GMHA and the area’s extensive network of scenic riding trails. This is a rare opportunity to own a gentleman's farm that is move-in ready for a VT homestead or second home. Photos electronically decluttered.

3 Beds ⋅ 4 Baths ⋅ 5111623 MLS

HILLSIDE FARM - SOUTH WOODSTOCK, VERMONT. Hillside Farm estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the heart of the home, the spacious country kitchen features cherry cabinetry, gas cooktop, and an antique Stewart woodstove. The 20’ x 18’ great room offers wide pine floors, exposed framing and a soaring cathedral ceiling, overlooking a lovely 14 foot deep pond and scenic vista. The primary suite includes double closets and an ensuite bath with radiant heat, Jacuzzi tub and shower. Additional bedrooms, dining room, and a home office provide flexible living space. The lower level offers a game room with woodstove and pool table, a small kitchenette, and 3/4 bath. The property is remarkably well equipped with a greenhouse, two-stall horse stable, multiple barns and outbuildings, garage workshop, mechanic’s shop, and a substantial 23’ x 35’ woodworking shop. Tucked into the woods is a delightful rustic cabin complete with kitchenette, woodstove, porch and nearby outhouse; an inviting retreat surrounded by nature and set just above one of two babbling brooks. Located in the heart of South Woodstock’s celebrated horse country, Hillside Farm enjoys proximity to the renowned GMHA and the area’s extensive network of scenic riding trails. This is a rare opportunity to own a gentleman's farm that is move-in ready for a VT homestead or second home. Photos electronically decluttered.

6405 Folding Hills Rd, Woodstock

$359,900

Welcome to this beautifully maintained 4-bedroom, 2-bath home offering over 2,000 square feet of comfortable living space in a prime location. Ideally situated just minutes from Loon Mountain and walking distance to the Pemi River, this property offers the perfect combination of convenience, space, and outdoor enjoyment. Inside, you’ll find a bright, open-concept kitchen and dining area, along with two separate living room spaces providing plenty of room for entertaining, relaxing, or accommodating guests. The spacious primary suite features two generous walk-in closets, a jetted Jacuzzi tub, and a double vanity, creating a comfortable private retreat. Step outside to a large deck overlooking the nicely manicured backyard, where you’ll find an above-ground pool-perfect for summer gatherings. Picture warm afternoons by the pool, evening barbecues on the deck, and cool mountain nights spent relaxing with family and friends. Set on a slab, this double-wide offers generous living space and an exceptional location for year-round living, a vacation getaway, or investment potential. With easy access to the White Mountains, Loon Mountain, I-93, and downtown Lincoln/Woodstock, this property puts everything you need and love about the area close at hand.

4 Beds ⋅ 2 Baths ⋅ 5111583 MLS

Welcome to this beautifully maintained 4-bedroom, 2-bath home offering over 2,000 square feet of comfortable living space in a prime location. Ideally situated just minutes from Loon Mountain and walking distance to the Pemi River, this property offers the perfect combination of convenience, space, and outdoor enjoyment. Inside, you’ll find a bright, open-concept kitchen and dining area, along with two separate living room spaces providing plenty of room for entertaining, relaxing, or accommodating guests. The spacious primary suite features two generous walk-in closets, a jetted Jacuzzi tub, and a double vanity, creating a comfortable private retreat. Step outside to a large deck overlooking the nicely manicured backyard, where you’ll find an above-ground pool-perfect for summer gatherings. Picture warm afternoons by the pool, evening barbecues on the deck, and cool mountain nights spent relaxing with family and friends. Set on a slab, this double-wide offers generous living space and an exceptional location for year-round living, a vacation getaway, or investment potential. With easy access to the White Mountains, Loon Mountain, I-93, and downtown Lincoln/Woodstock, this property puts everything you need and love about the area close at hand.

811 Eastside Rd, Woodstock

$2,095,000

Privately set on 6.7 acres just three minutes from the Woodstock Village Green, this Greek Revival-inspired farmhouse offers views of Mount Tom and the Pomfret Hills. Built by noted local designer and builder Chris Ambrose, it combines the character of the 115-year-old farmhouse that once stood here with energy-efficient modern living. Salvaged floors, beams, doors and hardware bring history to light-filled rooms with oversized Andersen windows and French doors. Custom cabinetry, honed granite and quartz countertops, and carefully chosen fixtures complement the reclaimed details. The kitchen features a five-burner range, pot filler, farmhouse sink, beverage center and generous pantry. The vaulted primary suite offers reclaimed beams, mountain views, a walk-in closet and a bath with a cast-iron clawfoot tub. A second spacious suite has built-ins and a marble bath. Gather by the fireplace, currently fitted with a gas insert, relax on the screened porch, or entertain on the 18-by-32-foot terrace overlooking the hills. A finished lower level with a family room, bunkroom and full bath helps the home sleep up to 13. Radiant heat, mini-split heating and cooling, a Viessmann tankless water heater, whole-house water filtration and high-speed internet support year-round comfort. A standing-seam metal roof, copper details, stone walls, birch trees and an outdoor shower complete this distinctive Woodstock retreat. SEE 306MEOKIWAY PROPERTY WEBSITE FOR VIDEO, VIRTUAL WALK-THROUGH, FLOORPLANS AND MORE.

4 Beds ⋅ 5 Baths ⋅ 5111035 MLS

Privately set on 6.7 acres just three minutes from the Woodstock Village Green, this Greek Revival-inspired farmhouse offers views of Mount Tom and the Pomfret Hills. Built by noted local designer and builder Chris Ambrose, it combines the character of the 115-year-old farmhouse that once stood here with energy-efficient modern living. Salvaged floors, beams, doors and hardware bring history to light-filled rooms with oversized Andersen windows and French doors. Custom cabinetry, honed granite and quartz countertops, and carefully chosen fixtures complement the reclaimed details. The kitchen features a five-burner range, pot filler, farmhouse sink, beverage center and generous pantry. The vaulted primary suite offers reclaimed beams, mountain views, a walk-in closet and a bath with a cast-iron clawfoot tub. A second spacious suite has built-ins and a marble bath. Gather by the fireplace, currently fitted with a gas insert, relax on the screened porch, or entertain on the 18-by-32-foot terrace overlooking the hills. A finished lower level with a family room, bunkroom and full bath helps the home sleep up to 13. Radiant heat, mini-split heating and cooling, a Viessmann tankless water heater, whole-house water filtration and high-speed internet support year-round comfort. A standing-seam metal roof, copper details, stone walls, birch trees and an outdoor shower complete this distinctive Woodstock retreat. SEE 306MEOKIWAY PROPERTY WEBSITE FOR VIDEO, VIRTUAL WALK-THROUGH, FLOORPLANS AND MORE.

306 Meoki Way, Woodstock

$449,000

This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, or even an easy-to-care for vacation home. There is plenty of storage for skis or other recreation equipment in the oversized two-plus car garage and two bay shed with a concrete floor. Sellers have spent 12 years gradually improving the property with new vertical wood siding, windows, doors, deck, stone steps, kitchen cabinets,appliances, wood flooring, interior doors and trim,radon mitigation system, a great mudroom entry and more. There are apple trees, a pear tree, gardens and a large fenced in area in back. Bourdon Maple Farm is just up the hill and the Ottauquechee River is across the road below the property. Recreation opportunities are abundant with mountain biking, hiking, skiing, racquet sports and swimming in town and beyond. Dining and Shops in Woodstock Village, Schools, Killington and Pico are all nearby. ArtisTree, Barnarts, Feast and Field and Pentangle Arts offer many opportunities for music, theater, movies, art classes and galleries all just minutes away. Everything that the the Upper Valley has to offer is less than an hour's drive away-including DHMC, Dartmouth College, shopping and dining galore. Don't miss this rare opportunity to own a home in a wonderful country setting convenient to everything at a reasonable price!

3 Beds ⋅ 1 Baths ⋅ 5110580 MLS

This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, or even an easy-to-care for vacation home. There is plenty of storage for skis or other recreation equipment in the oversized two-plus car garage and two bay shed with a concrete floor. Sellers have spent 12 years gradually improving the property with new vertical wood siding, windows, doors, deck, stone steps, kitchen cabinets,appliances, wood flooring, interior doors and trim,radon mitigation system, a great mudroom entry and more. There are apple trees, a pear tree, gardens and a large fenced in area in back. Bourdon Maple Farm is just up the hill and the Ottauquechee River is across the road below the property. Recreation opportunities are abundant with mountain biking, hiking, skiing, racquet sports and swimming in town and beyond. Dining and Shops in Woodstock Village, Schools, Killington and Pico are all nearby. ArtisTree, Barnarts, Feast and Field and Pentangle Arts offer many opportunities for music, theater, movies, art classes and galleries all just minutes away. Everything that the the Upper Valley has to offer is less than an hour's drive away-including DHMC, Dartmouth College, shopping and dining galore. Don't miss this rare opportunity to own a home in a wonderful country setting convenient to everything at a reasonable price!

23 Biscuit Hollow Rd, Woodstock

$1,395,000

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

4 Beds ⋅ 3 Baths ⋅ 5110412 MLS

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

2033 South Rd, Woodstock

$1,040,000

Woodstock Village Home~ A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town's blacksmith shop. Just steps from the heart of the village, you can leave the car at home and walk to shops, restaurants, galleries, cafés, and everything that makes Woodstock one of Vermont's most beloved destinations. Inside, an open-concept floor plan, beautiful wood floors, and abundant natural light create a warm and inviting atmosphere. Recent improvements include a new heat pump providing efficient heating and air conditioning, electrical upgrades, interior painting, and extensive basement work, enhancing both comfort and functionality. Outside is where this village property becomes truly special. The spacious fenced yard borders the Kedron Brook, creating a surprisingly peaceful setting in the heart of town. Relax on the deck and listen to the water, enjoy the newly planted fruit trees, or step through the yard to the nearby village footbridge spanning the brook--a picturesque connection to the surrounding neighborhood. Historic character, thoughtful improvements, a wonderful yard, and an exceptional walkable location come together in a home that captures the charm and ease of life in Woodstock Village.

3 Beds ⋅ 2 Baths ⋅ 5105489 MLS

Woodstock Village Home~ A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town's blacksmith shop. Just steps from the heart of the village, you can leave the car at home and walk to shops, restaurants, galleries, cafés, and everything that makes Woodstock one of Vermont's most beloved destinations. Inside, an open-concept floor plan, beautiful wood floors, and abundant natural light create a warm and inviting atmosphere. Recent improvements include a new heat pump providing efficient heating and air conditioning, electrical upgrades, interior painting, and extensive basement work, enhancing both comfort and functionality. Outside is where this village property becomes truly special. The spacious fenced yard borders the Kedron Brook, creating a surprisingly peaceful setting in the heart of town. Relax on the deck and listen to the water, enjoy the newly planted fruit trees, or step through the yard to the nearby village footbridge spanning the brook--a picturesque connection to the surrounding neighborhood. Historic character, thoughtful improvements, a wonderful yard, and an exceptional walkable location come together in a home that captures the charm and ease of life in Woodstock Village.

13 High St, Woodstock

$195,000

property being sold by trustee, seller has no knowledge of age, or systems within the home. There is no Zoning in the town Woodstock. This property will need work to make it livable.

2 Beds ⋅ 2 Baths ⋅ 5104613 MLS

property being sold by trustee, seller has no knowledge of age, or systems within the home. There is no Zoning in the town Woodstock. This property will need work to make it livable.

88 Lost River Rd, Woodstock

$899,900

Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bedrooms that can be combined with or leased separately with a studio apartment that has its own kitchen, bath, porch and private entry. The home offers great White Mountain Views, is directly across the Street from Lost River (swimming and waterfalls) and providing easy access to all the Lincoln / Woodstock attractions and Loon Mountain skiing. This was a primary home for decades, and the apartment was added for a caretaker to live on site. It has been meticulously updated and maintained through the years and a whole house generator provided comfort on those harsh winter nights. The Cottage or shed structure offers a place for projects or additional storage.

5 Beds ⋅ 4 Baths ⋅ 5104119 MLS

Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bedrooms that can be combined with or leased separately with a studio apartment that has its own kitchen, bath, porch and private entry. The home offers great White Mountain Views, is directly across the Street from Lost River (swimming and waterfalls) and providing easy access to all the Lincoln / Woodstock attractions and Loon Mountain skiing. This was a primary home for decades, and the apartment was added for a caretaker to live on site. It has been meticulously updated and maintained through the years and a whole house generator provided comfort on those harsh winter nights. The Cottage or shed structure offers a place for projects or additional storage.

5 & 7 Mountainside Rd, Woodstock

$1,695,000

"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a bright, open gathering space where spectacular mountain views are always on display. The newer gourmet kitchen features a large center island, Thermador appliances, quartz countertops, and abundant custom cabinetry. The spacious living room is centered around a handsome stone fireplace and offers multiple seating areas. French doors open to a newer southwest-facing deck with a large hot tub, creating the perfect setting to enjoy sunsets and panoramic views throughout the year. The main level also includes a generous primary suite with a walk-in closet and an ensuite bath featuring a soaking tub with mountain views and a separate shower. A mudroom with laundry connects directly to the oversized attached two-car garage. A circular staircase leads from the kitchen to a charming renovated tavern and wine room with French doors opening to a private brick patio, ideal for entertaining. Upstairs are a comfortable office, study, or media room, three additional bedrooms (two with long-range views), an updated full bath, and a separate half bath. The full concrete basement provides abundant storage and houses the mechanical systems. Additional amenities include a full-house automatic generator, ample parking for four or more vehicles in addition to the attached garage, and well-maintained grounds. BLISS HOUSE combines privacy, stunning views, quality renovations, and an exceptional location just minutes from Woodstock Village. Walk-through tour, video, drone aerials, and floor plans available online.

4 Beds ⋅ 3 Baths ⋅ 5102668 MLS

"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a bright, open gathering space where spectacular mountain views are always on display. The newer gourmet kitchen features a large center island, Thermador appliances, quartz countertops, and abundant custom cabinetry. The spacious living room is centered around a handsome stone fireplace and offers multiple seating areas. French doors open to a newer southwest-facing deck with a large hot tub, creating the perfect setting to enjoy sunsets and panoramic views throughout the year. The main level also includes a generous primary suite with a walk-in closet and an ensuite bath featuring a soaking tub with mountain views and a separate shower. A mudroom with laundry connects directly to the oversized attached two-car garage. A circular staircase leads from the kitchen to a charming renovated tavern and wine room with French doors opening to a private brick patio, ideal for entertaining. Upstairs are a comfortable office, study, or media room, three additional bedrooms (two with long-range views), an updated full bath, and a separate half bath. The full concrete basement provides abundant storage and houses the mechanical systems. Additional amenities include a full-house automatic generator, ample parking for four or more vehicles in addition to the attached garage, and well-maintained grounds. BLISS HOUSE combines privacy, stunning views, quality renovations, and an exceptional location just minutes from Woodstock Village. Walk-through tour, video, drone aerials, and floor plans available online.

353 Cabot Rd, Woodstock

$1,195,000

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools, basketball courts, and the Town’s recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

4 Beds ⋅ 3 Baths ⋅ 5100512 MLS

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools, basketball courts, and the Town’s recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

16 Church St, Woodstock

$5,350,000

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

3 Beds ⋅ 4 Baths ⋅ 5099532 MLS

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

115 Eastman Rd, Woodstock

$400,000

Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with stairs to the basement, a full bath with laundry, and a mudroom. The 2nd floor attic, with a large dormer, offers many possibilities for additional space but requires installing stairs and building out the open area. The basement houses utilities and allows for significant storage. The house needs a few updates but has lots of potential and is a wonderful investment opportunity or a great way to get into a starter home in the Woodstock area. It is conveniently located just minutes from Woodstock Village and only a few miles from the Kedron Valley Inn, the South Woodstock Store, and the Green Mountain Horse Association.

2 Beds ⋅ 1 Baths ⋅ 5099229 MLS

Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with stairs to the basement, a full bath with laundry, and a mudroom. The 2nd floor attic, with a large dormer, offers many possibilities for additional space but requires installing stairs and building out the open area. The basement houses utilities and allows for significant storage. The house needs a few updates but has lots of potential and is a wonderful investment opportunity or a great way to get into a starter home in the Woodstock area. It is conveniently located just minutes from Woodstock Village and only a few miles from the Kedron Valley Inn, the South Woodstock Store, and the Green Mountain Horse Association.

2556 Church Hill Rd, Woodstock

$2,300,000

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

5 Beds ⋅ 6 Baths ⋅ 5098424 MLS

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

915 Peterkin Hill Rd, Woodstock

$399,000

Welcome to 5 Downing Drive, where a peaceful setting and convenient location come together in the heart of the White Mountains. Expansive windows fill the home with abundant natural light, creating warm, inviting living spaces that bring the outdoors in. Step outside onto the spacious new wraparound deck, the perfect place to enjoy your morning coffee, entertain family and friends, or simply unwind while taking in the tranquil surroundings. Just minutes from Interstate 93, this property offers exceptional access to year-round recreation and local amenities. Loon Mountain, Cannon Mountain, hiking and biking trails, golf courses, rivers, restaurants, shopping, and the attractions of Lincoln and North Woodstock are all nearby. Whether you're looking for a full-time residence, a weekend getaway, or an investment property, this home offers the ideal combination of comfort, privacy, and accessibility in one of New Hampshire's premier four-season destinations.

3 Beds ⋅ 2 Baths ⋅ 5098036 MLS

Welcome to 5 Downing Drive, where a peaceful setting and convenient location come together in the heart of the White Mountains. Expansive windows fill the home with abundant natural light, creating warm, inviting living spaces that bring the outdoors in. Step outside onto the spacious new wraparound deck, the perfect place to enjoy your morning coffee, entertain family and friends, or simply unwind while taking in the tranquil surroundings. Just minutes from Interstate 93, this property offers exceptional access to year-round recreation and local amenities. Loon Mountain, Cannon Mountain, hiking and biking trails, golf courses, rivers, restaurants, shopping, and the attractions of Lincoln and North Woodstock are all nearby. Whether you're looking for a full-time residence, a weekend getaway, or an investment property, this home offers the ideal combination of comfort, privacy, and accessibility in one of New Hampshire's premier four-season destinations.

5 Downing Dr, Woodstock

$1,050,000

OPEN HOUSE - SUNDAY 10/11 - 10:00AM TO 12:00PM. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain view settings in the White Mountains. With over 90 degrees of unobstructed views stretching across Franconia Notch and the surrounding peaks, this extraordinary property combines exceptional privacy with easy access to Lincoln, Woodstock, Loon Mountain Resort, hiking, golf, and year-round recreation. Blending historic New England character with thoughtful modern updates, the home has been carefully maintained and improved while preserving its timeless appeal. Warm, inviting living spaces, handcrafted details, and expansive windows create the perfect backdrop for gathering with family and friends after a day spent exploring the mountains. A truly rare offering, the property is configured in a unique tri-plex-style layout connected by enclosed breezeways, providing outstanding flexibility for today's buyers. With three full kitchens and accommodations for 18+ guests, it's ideally suited as a luxury vacation home, multi-generational retreat, corporate getaway, or income-producing investment with outstanding short-term rental potential. The thoughtful design allows large groups to enjoy time together while still providing privacy and separate living spaces. Major updates include standing seam metal roofing, updated electrical, plumbing, and heating systems, along with the added security of a whole-home standby propane generator, providing comfort and peace of mind in every season. Whether you're searching for an unforgettable second home, a one-of-a-kind family compound, or a versatile investment property in one of New Hampshire's premier four-season destinations, 81 Meadow Lane is a rare opportunity to own an exceptional mountaintop retreat where breathtaking sunsets, unmatched privacy, and endless mountain adventures await.

5 Beds ⋅ 4 Baths ⋅ 5097556 MLS

OPEN HOUSE - SUNDAY 10/11 - 10:00AM TO 12:00PM. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain view settings in the White Mountains. With over 90 degrees of unobstructed views stretching across Franconia Notch and the surrounding peaks, this extraordinary property combines exceptional privacy with easy access to Lincoln, Woodstock, Loon Mountain Resort, hiking, golf, and year-round recreation. Blending historic New England character with thoughtful modern updates, the home has been carefully maintained and improved while preserving its timeless appeal. Warm, inviting living spaces, handcrafted details, and expansive windows create the perfect backdrop for gathering with family and friends after a day spent exploring the mountains. A truly rare offering, the property is configured in a unique tri-plex-style layout connected by enclosed breezeways, providing outstanding flexibility for today's buyers. With three full kitchens and accommodations for 18+ guests, it's ideally suited as a luxury vacation home, multi-generational retreat, corporate getaway, or income-producing investment with outstanding short-term rental potential. The thoughtful design allows large groups to enjoy time together while still providing privacy and separate living spaces. Major updates include standing seam metal roofing, updated electrical, plumbing, and heating systems, along with the added security of a whole-home standby propane generator, providing comfort and peace of mind in every season. Whether you're searching for an unforgettable second home, a one-of-a-kind family compound, or a versatile investment property in one of New Hampshire's premier four-season destinations, 81 Meadow Lane is a rare opportunity to own an exceptional mountaintop retreat where breathtaking sunsets, unmatched privacy, and endless mountain adventures await.

81 Meadow Ln, Woodstock

$299,900

Nestled in a peaceful, natural setting overlooking scenic Mirror Lake, this small and charming cabin offers a true retreat for those seeking simplicity and a connection to nature. With its rustic appeal, the property could be a cozy year-round residence, vacation rental or getaway escape, with three private rooms as well as a shared kitchen and common space. Located on 2.30 conserved acres with its own driveway, adjacent to the Hubbard Brook Research Foundation's Likens Conservation Campus, the home offers tranquil lake views and the soothing sounds of bird song and breezes through the trees. The cozy interior provides a comfortable space to unwind, while the compact footprint ensures easy maintenance and a low-impact lifestyle. Please note: although there is a friendly relationship with the neighbors, there is no legal right to access the nearby lakeshore, and access is subject to revocable permission. This property is priced to reflect the need for a new septic system installation (a septic system has already been designed) which may limit some loan types. This unique offering is perfect for buyers who value privacy, conservation, and a quiet lakeside ambiance.

3 Beds ⋅ 2 Baths ⋅ 5097289 MLS

Nestled in a peaceful, natural setting overlooking scenic Mirror Lake, this small and charming cabin offers a true retreat for those seeking simplicity and a connection to nature. With its rustic appeal, the property could be a cozy year-round residence, vacation rental or getaway escape, with three private rooms as well as a shared kitchen and common space. Located on 2.30 conserved acres with its own driveway, adjacent to the Hubbard Brook Research Foundation's Likens Conservation Campus, the home offers tranquil lake views and the soothing sounds of bird song and breezes through the trees. The cozy interior provides a comfortable space to unwind, while the compact footprint ensures easy maintenance and a low-impact lifestyle. Please note: although there is a friendly relationship with the neighbors, there is no legal right to access the nearby lakeshore, and access is subject to revocable permission. This property is priced to reflect the need for a new septic system installation (a septic system has already been designed) which may limit some loan types. This unique offering is perfect for buyers who value privacy, conservation, and a quiet lakeside ambiance.

19 Hamlet Dr, Woodstock

$750,000

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.

3 Beds ⋅ 3 Baths ⋅ 5097258 MLS

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.

1326 Curtis Hollow Rd, Woodstock

$1,645,000

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! *Main Level Photos Have Been Electronically Decluttered*

4 Beds ⋅ 4 Baths ⋅ 5096963 MLS

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! *Main Level Photos Have Been Electronically Decluttered*

2706 E Woodstock Rd, Woodstock

$2,950,000

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

8 Beds ⋅ 8 Baths ⋅ 5094600 MLS

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

5798 South Rd, Woodstock

$895,000

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock just seven minutes to the Woodstock Green, this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies, ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you’re seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!

3 Beds ⋅ 3 Baths ⋅ 5094379 MLS

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock just seven minutes to the Woodstock Green, this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies, ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you’re seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!

358 Cowdrey Path, Woodstock

$2,650,000

CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef’s kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead—with its native timbers and stone fireplace—creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House—a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

5 Beds ⋅ 4 Baths ⋅ 5091062 MLS

CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef’s kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead—with its native timbers and stone fireplace—creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House—a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

66 Hollow Farm Rd, Woodstock

$695,000

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

3 Beds ⋅ 2 Baths ⋅ 5089949 MLS

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

47 Pleasant St, Woodstock

$1,395,000

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

5 Beds ⋅ 4 Baths ⋅ 5089552 MLS

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

1522 Barnard Rd, Woodstock

$595,000

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

4 Beds ⋅ 2 Baths ⋅ 5088170 MLS

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

11 Maple St, Woodstock