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Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to harvesting honey and gathering fresh eggs for breakfast. Miles of trails traverse varied terrain, including the summit of Old Baldy Mountain (2,409 feet). The retreat includes a lodge-style residence, a modern barn, and several ancillary farm buildings. The wood and stone lodge-style home carries a relaxed mountain vibe. Thoughtfully renovated in 2026, the interiors balance scale and warmth: exposed beams, a cathedral ceiling in the great room, and a substantial wood-burning stone fireplace anchor the space, while floor-to-ceiling windows draw in sweeping views of the mountains. The wrap-around deck takes in an infinity pool, hot tub, and stocked pond. In spring, wild lupine carpet the meadow; in autumn, the apple orchard comes into its own. Landscape design by Shep Butler includes 10’ hydrangea bushes, perennials gardens, stone walls and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with 7 box stalls, a farm manager’s office/tack room, and a versatile upper level for entertaining, recreation, and movie night as well as accommodating an overflow of guests. Nine fenced pastures, run-in sheds, chicken coop, apiary, and direct access to GMHA’s trail network support an exceptional equestrian and recreational lifestyle. 157 acres conserved by VLT. 3.1 miles from GMHA, 3.8 miles from South Woodstock Country Store and Post Office, Less than a half hour from Killington, 2.5 hours from Boston.

5 Beds ⋅ 4 Baths ⋅ 5089158 MLS

Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to harvesting honey and gathering fresh eggs for breakfast. Miles of trails traverse varied terrain, including the summit of Old Baldy Mountain (2,409 feet). The retreat includes a lodge-style residence, a modern barn, and several ancillary farm buildings. The wood and stone lodge-style home carries a relaxed mountain vibe. Thoughtfully renovated in 2026, the interiors balance scale and warmth: exposed beams, a cathedral ceiling in the great room, and a substantial wood-burning stone fireplace anchor the space, while floor-to-ceiling windows draw in sweeping views of the mountains. The wrap-around deck takes in an infinity pool, hot tub, and stocked pond. In spring, wild lupine carpet the meadow; in autumn, the apple orchard comes into its own. Landscape design by Shep Butler includes 10’ hydrangea bushes, perennials gardens, stone walls and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with 7 box stalls, a farm manager’s office/tack room, and a versatile upper level for entertaining, recreation, and movie night as well as accommodating an overflow of guests. Nine fenced pastures, run-in sheds, chicken coop, apiary, and direct access to GMHA’s trail network support an exceptional equestrian and recreational lifestyle. 157 acres conserved by VLT. 3.1 miles from GMHA, 3.8 miles from South Woodstock Country Store and Post Office, Less than a half hour from Killington, 2.5 hours from Boston.

2358 Long Hill Rd, Woodstock

$5,950,000

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef’s kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby. Additional land available.

4 Beds ⋅ 5 Baths ⋅ 5044620 MLS

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef’s kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby. Additional land available.

412 Skyland Ln, Woodstock

$2,999,000

Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980’s, providing a great room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef’s kitchen, all located on the main level. There is an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens.

6 Beds ⋅ 8 Baths ⋅ 5096089 MLS

Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980’s, providing a great room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef’s kitchen, all located on the main level. There is an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens.

18 The Grn, 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

$2,500,000

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.

6 Beds ⋅ 6 Baths ⋅ 5002873 MLS

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.

61 Academy Cir, Woodstock

$2,485,000

Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern and lodging for members of Vermont’s early legislature, giving the property an uncommon connection to both the town’s and the state’s history. Over a century later, it became the Daughters of the American Revolution House Museum. Listed on the historic register, the home underwent a comprehensive restoration in 1995 by noted preservationist Doug Guest, along with a thoughtfully designed addition. Distinctive original details remain, including five teardrop ornaments above the first-floor windows and the beautiful Palladian window over the front entrance. Together with the patina of more than two centuries, they give the house an authenticity that has been carefully preserved while incorporating the comforts of contemporary living. Inside, wide-board floors, finely proportioned rooms, five working fireplaces, period millwork, and abundant natural light create a sense of warmth and character. The capacious renovated kitchen opens to a sun-filled dining area overlooking the rear stone terrace, while gracious gathering rooms retain the scale and character of the original house. All bedrooms are en suite, an unusual convenience in a home of this age. Set back from Main Street along a quieter parallel road, the property enjoys one of Woodstock Village’s most appealing locations, with dining, the theater, galleries, cultural events, and the trails of Mount Tom all within an easy walk. A detached two-bay garage and off-street parking add another uncommon convenience for a village property. Beautifully restored and turnkey, 26 The Green offers the opportunity to live in an important early Vermont home without sacrificing the ease of contemporary village life.

4 Beds ⋅ 5 Baths ⋅ 5107880 MLS

Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern and lodging for members of Vermont’s early legislature, giving the property an uncommon connection to both the town’s and the state’s history. Over a century later, it became the Daughters of the American Revolution House Museum. Listed on the historic register, the home underwent a comprehensive restoration in 1995 by noted preservationist Doug Guest, along with a thoughtfully designed addition. Distinctive original details remain, including five teardrop ornaments above the first-floor windows and the beautiful Palladian window over the front entrance. Together with the patina of more than two centuries, they give the house an authenticity that has been carefully preserved while incorporating the comforts of contemporary living. Inside, wide-board floors, finely proportioned rooms, five working fireplaces, period millwork, and abundant natural light create a sense of warmth and character. The capacious renovated kitchen opens to a sun-filled dining area overlooking the rear stone terrace, while gracious gathering rooms retain the scale and character of the original house. All bedrooms are en suite, an unusual convenience in a home of this age. Set back from Main Street along a quieter parallel road, the property enjoys one of Woodstock Village’s most appealing locations, with dining, the theater, galleries, cultural events, and the trails of Mount Tom all within an easy walk. A detached two-bay garage and off-street parking add another uncommon convenience for a village property. Beautifully restored and turnkey, 26 The Green offers the opportunity to live in an important early Vermont home without sacrificing the ease of contemporary village life.

26 The Grn, 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

$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

$1,100,000

Lovely cottage nestled on the Ottauquechee River in the heart of historic Woodstock. Incredible river frontage with sprawling lawn for entertaining or just sitting enjoying the river tranquility in adirondack chairs. This charming cottage boasts 4 bedrooms with an open plan. An abundance of light, antique characteristics with wide pine floors, large fireplace in the living room and surrounded by lots of windows and French doors leading out to a large deck overlooking the river. The first floor consists of a large living room, dining room, eat-in kitchen and small bedroom/office. Second floor consists of primary suite with private bathroom and 2 more guest bedrooms with bath. The basement has a family room that has direct access to the back lawn adjacent to a good size storage room with ample space for bikes, kayaks and toys. A short walk into the village to all amenities, theatre, shops and restaurants. Just 3 miles to skiing and golf. Mt Tom trail access is across the street with miles of trails for hiking or cross country skiing. Incredible location!

4 Beds ⋅ 3 Baths ⋅ 5106838 MLS

Lovely cottage nestled on the Ottauquechee River in the heart of historic Woodstock. Incredible river frontage with sprawling lawn for entertaining or just sitting enjoying the river tranquility in adirondack chairs. This charming cottage boasts 4 bedrooms with an open plan. An abundance of light, antique characteristics with wide pine floors, large fireplace in the living room and surrounded by lots of windows and French doors leading out to a large deck overlooking the river. The first floor consists of a large living room, dining room, eat-in kitchen and small bedroom/office. Second floor consists of primary suite with private bathroom and 2 more guest bedrooms with bath. The basement has a family room that has direct access to the back lawn adjacent to a good size storage room with ample space for bikes, kayaks and toys. A short walk into the village to all amenities, theatre, shops and restaurants. Just 3 miles to skiing and golf. Mt Tom trail access is across the street with miles of trails for hiking or cross country skiing. Incredible location!

2 River St, Woodstock

$865,000

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples.

4 Beds ⋅ 3 Baths ⋅ 5052613 MLS

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples.

1782 Randall Rd, Woodstock

$515,000

$10,000 PRICE REDUCTION on this 3 bedroom unit at The Glen at Deer Park. Furnished 3rd floor unit with vaulted ceilings, skylight, and balcony overlooking the river. Wake up listening to the calming sounds of the river bubbling outside your window. Enjoy all 4 seasons, from skiing at Loon Mountain in winter, to hiking in Franconia Notch in Summer. Or stay right on property and enjoy all the amenities Deer Park has to offer, including 2 beaches, tennis court, and rec center.

3 Beds ⋅ 2 Baths ⋅ 5092031 MLS

$10,000 PRICE REDUCTION on this 3 bedroom unit at The Glen at Deer Park. Furnished 3rd floor unit with vaulted ceilings, skylight, and balcony overlooking the river. Wake up listening to the calming sounds of the river bubbling outside your window. Enjoy all 4 seasons, from skiing at Loon Mountain in winter, to hiking in Franconia Notch in Summer. Or stay right on property and enjoy all the amenities Deer Park has to offer, including 2 beaches, tennis court, and rec center.

45 Riverfront Dr Unit 243, Woodstock

$465,900

Where Mountain Living Meets Riverfront Charm! Welcome to your dream White Mountains retreat! This well maintained, completely renovated 2-bedroom, 2-bath condo sits in the most prime location within Deer Park with one of the best views of the Pemi River you could ask for. Step inside to discover an inviting open-concept layout where the kitchen, dining, and living areas flow seamlessly from room to room. Natural wood accents and a wood-burning fireplace create the quintessential New Hampshire ambiance you've been searching for. The master bedroom features a private en-suite bathroom, while a second bedroom and another full bath ensure comfort for the entire family or guests. Thoughtful updates including new kitchen cabinets, light fixtures, stainless appliances, updated baths w/granite featuring a custom walk-in tile shower in the master bath and Viessman heating system making this a true turnkey property. You’ll even marvel at the one of a kind river stone inlay in the kitchen breakfast bar illuminated with multi color Led lighting The Deer Park community is a four-season playground. The impressive clubhouse boasts an indoor pool, hot tub, cardio and weight rooms, racquetball & pickleball courts, and an inviting great room anchored by a double-sided stone fireplace. Summer days call you to the gorgeous 5-acre lake and sandy beach just steps from your door. Adventure seekers will love the proximity to Loon Mountain Resort, complete with seasonal shuttle service, along with easy access to Cannon Mountain, the scenic Kancamagus Highway, and the stunning Pemigewasset River. This is more than a home, it's a lifestyle waiting for you.

2 Beds ⋅ 2 Baths ⋅ 5112728 MLS

Where Mountain Living Meets Riverfront Charm! Welcome to your dream White Mountains retreat! This well maintained, completely renovated 2-bedroom, 2-bath condo sits in the most prime location within Deer Park with one of the best views of the Pemi River you could ask for. Step inside to discover an inviting open-concept layout where the kitchen, dining, and living areas flow seamlessly from room to room. Natural wood accents and a wood-burning fireplace create the quintessential New Hampshire ambiance you've been searching for. The master bedroom features a private en-suite bathroom, while a second bedroom and another full bath ensure comfort for the entire family or guests. Thoughtful updates including new kitchen cabinets, light fixtures, stainless appliances, updated baths w/granite featuring a custom walk-in tile shower in the master bath and Viessman heating system making this a true turnkey property. You’ll even marvel at the one of a kind river stone inlay in the kitchen breakfast bar illuminated with multi color Led lighting The Deer Park community is a four-season playground. The impressive clubhouse boasts an indoor pool, hot tub, cardio and weight rooms, racquetball & pickleball courts, and an inviting great room anchored by a double-sided stone fireplace. Summer days call you to the gorgeous 5-acre lake and sandy beach just steps from your door. Adventure seekers will love the proximity to Loon Mountain Resort, complete with seasonal shuttle service, along with easy access to Cannon Mountain, the scenic Kancamagus Highway, and the stunning Pemigewasset River. This is more than a home, it's a lifestyle waiting for you.

75 Riverfront Dr Unit 205, 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

$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

15 Jack O Lantern Dr Unit Unit 34, Woodstock

$390,000

Welcome to Jack O’Lantern Resort! This well-maintained 3-bedroom, 2-bathroom condo offers a versatile layout with a spacious loft and lock-off suite, giving you plenty of options for family, guests, or rental use. The living room opens to a screened-in 3-season porch, creating a great spot to unwind and enjoy the peaceful surroundings. The condo has been exceptionally well cared for and is tucked into a quiet area of the resort while still being close to everything. If rental income is part of your plans, the property is ready to go and offers the potential to start generating income right away. Ask about the local rental management options and the popular Stay & Play packages offered in partnership with the Jack Golf Course. Owners enjoy access to a great selection of resort amenities, including an indoor heated pool, hot tub, outdoor pool, recreation room, basketball hoop, new playground, and tennis/pickleball courts. Outdoor enthusiasts will love the direct access to Corridor 11 for snowmobiling, with trailer storage available in the resort’s overflow lot. Located right next to the newly renovated Jack Golf Course, restaurant, and bar, this property is set up to be enjoyed in every season whether you're looking for a mountain getaway, a place to gather with family and friends, or a rental investment.

3 Beds ⋅ 2 Baths ⋅ 5110824 MLS

Welcome to Jack O’Lantern Resort! This well-maintained 3-bedroom, 2-bathroom condo offers a versatile layout with a spacious loft and lock-off suite, giving you plenty of options for family, guests, or rental use. The living room opens to a screened-in 3-season porch, creating a great spot to unwind and enjoy the peaceful surroundings. The condo has been exceptionally well cared for and is tucked into a quiet area of the resort while still being close to everything. If rental income is part of your plans, the property is ready to go and offers the potential to start generating income right away. Ask about the local rental management options and the popular Stay & Play packages offered in partnership with the Jack Golf Course. Owners enjoy access to a great selection of resort amenities, including an indoor heated pool, hot tub, outdoor pool, recreation room, basketball hoop, new playground, and tennis/pickleball courts. Outdoor enthusiasts will love the direct access to Corridor 11 for snowmobiling, with trailer storage available in the resort’s overflow lot. Located right next to the newly renovated Jack Golf Course, restaurant, and bar, this property is set up to be enjoyed in every season whether you're looking for a mountain getaway, a place to gather with family and friends, or a rental investment.

15 Jack O Lantern Dr Unit Unit 34, 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

42-18 Heritage Condo Way Unit Unit 18D, Woodstock

$244,000

Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offers a private living space. The deck looks out to well maintained grounds and woodlands. The updated kitchen and bathroom are well appointed. The main level has an open floor plan that includes the kitchen, dining area and living room . Upstairs , in addition to the bedroom, bath and laundry there is a wonderful bonus area that can be used in multiple ways and the sliding barn door provides privacy to the area. Located across from Woodstock Middle and Senior High School as well as the Woodstock Senior Center and just minutes from the center of the historic town of Woodstock voted one of the prettiest small towns in America ! Close to skiing at Killington and Woodstock's own Saskadena Six there is access to sports and activities for every season. Call for a private viewing .

1 Beds ⋅ 1 Baths ⋅ 5101220 MLS

Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offers a private living space. The deck looks out to well maintained grounds and woodlands. The updated kitchen and bathroom are well appointed. The main level has an open floor plan that includes the kitchen, dining area and living room . Upstairs , in addition to the bedroom, bath and laundry there is a wonderful bonus area that can be used in multiple ways and the sliding barn door provides privacy to the area. Located across from Woodstock Middle and Senior High School as well as the Woodstock Senior Center and just minutes from the center of the historic town of Woodstock voted one of the prettiest small towns in America ! Close to skiing at Killington and Woodstock's own Saskadena Six there is access to sports and activities for every season. Call for a private viewing .

42-18 Heritage Condo Way Unit Unit 18D, Woodstock

42 Heritage Condo Way Unit 24, Woodstock

$238,000

Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. Quiet setting in a low density area. This end unit condo has had many updates and is ready for new owners to add their personal touch. A private deck looking out to woodlands and lawn. The bright kitchen is a pleasure to work in . Upstairs the den with skylight offers an opportunity for many uses. There is private storage space in the historic red barn. Woodstock Middle and High Schools are across the road. It is a short distance to all of the amenities historic Woodstock Village offers including dining , shopping and entertainment. Ski at Woodstock's own Saskadena Six or head over to Killington Ski Resort.

1 Beds ⋅ 1 Baths ⋅ 5103476 MLS

Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. Quiet setting in a low density area. This end unit condo has had many updates and is ready for new owners to add their personal touch. A private deck looking out to woodlands and lawn. The bright kitchen is a pleasure to work in . Upstairs the den with skylight offers an opportunity for many uses. There is private storage space in the historic red barn. Woodstock Middle and High Schools are across the road. It is a short distance to all of the amenities historic Woodstock Village offers including dining , shopping and entertainment. Ski at Woodstock's own Saskadena Six or head over to Killington Ski Resort.

42 Heritage Condo Way Unit 24, Woodstock

$130,000

Low Maintenance Mountain Living, Minutes from Loon Tucked into a quiet corner of the park with more privacy than you'd expect, this clean, well-kept home has a warm, rustic feel. It can come fully furnished, so it's ready to enjoy from day one. Loon Mountain Resort and downtown Lincoln are less than 15 minutes away, putting ski days, the Kancamagus, and the town's restaurants and shops all within easy reach. You enter through a mudroom addition, the perfect drop zone for boots, skis, and gear after a day outside. The oversized kitchen and living area gives you plenty of room to cook, gather, and spread out, and two bedrooms complete the layout. A second exit opens directly to the private backyard and its outdoor fireplace, made for cool White Mountain evenings. The property directly borders White Mountain Motorsports Park, so racing fans can have Saturday nights at the track right next door. If you're looking for a convenient, low-maintenance place in the mountains without the constraints of condominium living, this one deserves a look. With the option to purchase fully furnished, you could be settled in for ski season without hauling a single piece of furniture up north. Reach out for more details or to schedule a showing.

2 Beds ⋅ 1 Baths ⋅ 5113028 MLS

Low Maintenance Mountain Living, Minutes from Loon Tucked into a quiet corner of the park with more privacy than you'd expect, this clean, well-kept home has a warm, rustic feel. It can come fully furnished, so it's ready to enjoy from day one. Loon Mountain Resort and downtown Lincoln are less than 15 minutes away, putting ski days, the Kancamagus, and the town's restaurants and shops all within easy reach. You enter through a mudroom addition, the perfect drop zone for boots, skis, and gear after a day outside. The oversized kitchen and living area gives you plenty of room to cook, gather, and spread out, and two bedrooms complete the layout. A second exit opens directly to the private backyard and its outdoor fireplace, made for cool White Mountain evenings. The property directly borders White Mountain Motorsports Park, so racing fans can have Saturday nights at the track right next door. If you're looking for a convenient, low-maintenance place in the mountains without the constraints of condominium living, this one deserves a look. With the option to purchase fully furnished, you could be settled in for ski season without hauling a single piece of furniture up north. Reach out for more details or to schedule a showing.

21 Scenic Dr, Woodstock

$26,000

This Quarter Share ownership, two bedroom condo (you have use 1 week per month) is a nicely updated unit located in the Notchbrook building. Step out your door to The Pemi River and just a short stroll to the club house. Inside you'll find 2 bedrooms, 2 full baths plus a Jaccuzi tub. Also features a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Owning a quarter share is an affordable alternative to whole ownership. This is NOT a time share, you own the actual real estate. Condo fees include all utilities, maintenance and full use of all facilities. Deer Park has a fantastic amenities package which includes a beautiful spring fed pond with beach for swimming, indoor pool, hot tub, racquetball, weight & cardio rooms, tennis courts, ice skating, shuttle bus to Loon Mountain during the ski season and more. There is also an on-site rental program with worldwide RCI Exchange. Sorry, no pets allowed in the quarter share buildings

2 Beds ⋅ 2 Baths ⋅ 5111647 MLS

This Quarter Share ownership, two bedroom condo (you have use 1 week per month) is a nicely updated unit located in the Notchbrook building. Step out your door to The Pemi River and just a short stroll to the club house. Inside you'll find 2 bedrooms, 2 full baths plus a Jaccuzi tub. Also features a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Owning a quarter share is an affordable alternative to whole ownership. This is NOT a time share, you own the actual real estate. Condo fees include all utilities, maintenance and full use of all facilities. Deer Park has a fantastic amenities package which includes a beautiful spring fed pond with beach for swimming, indoor pool, hot tub, racquetball, weight & cardio rooms, tennis courts, ice skating, shuttle bus to Loon Mountain during the ski season and more. There is also an on-site rental program with worldwide RCI Exchange. Sorry, no pets allowed in the quarter share buildings

164 Deer Park Dr Unit 175B, Woodstock

$24,000

This main floor Quarter Share (you have use 1 week per month) is a corner unit located in the Notchbrook building. Enjoy great views of the Loon Slopes and Franconia Notch and just a short stroll to the club house. Inside you'll find 2 large bedrooms, 2 full baths, a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Relax on one of the two decks overlooking the water or walk out your back door and throw a fishing line in. Owning a quarter share is an affordable alternative to whole ownership. It is NOT a time share; you own the actual real estate. Deer Park has a fantastic amenities package which includes an indoor pool, Jacuzzi, racquetball, weight room, cardio room, outdoor tennis courts, ice skating and shuttle bus to Loon Mountain during the ski season. During the summer go for a swim or sit on the beach of the 5-acre, crystal clear water of the Deer Park lake literally steps form your front door.

2 Beds ⋅ 2 Baths ⋅ 5107344 MLS

This main floor Quarter Share (you have use 1 week per month) is a corner unit located in the Notchbrook building. Enjoy great views of the Loon Slopes and Franconia Notch and just a short stroll to the club house. Inside you'll find 2 large bedrooms, 2 full baths, a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Relax on one of the two decks overlooking the water or walk out your back door and throw a fishing line in. Owning a quarter share is an affordable alternative to whole ownership. It is NOT a time share; you own the actual real estate. Deer Park has a fantastic amenities package which includes an indoor pool, Jacuzzi, racquetball, weight room, cardio room, outdoor tennis courts, ice skating and shuttle bus to Loon Mountain during the ski season. During the summer go for a swim or sit on the beach of the 5-acre, crystal clear water of the Deer Park lake literally steps form your front door.

164 Deer Park Dr Unit 166C, Woodstock

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