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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

$99,000

This much sought after location in Woodstock features a inground pool for summer fun, close to both Loon and Cannon Mountains for your year round activities to enjoy . Just a few minute walk to downtown Woodstock and most nightlife in the area . Small association with limited restrictions and a very low annual fee of $350.00. Come see your new homesite in the White Mountains and enjoy all this location has to offer .

5102599 MLS

This much sought after location in Woodstock features a inground pool for summer fun, close to both Loon and Cannon Mountains for your year round activities to enjoy . Just a few minute walk to downtown Woodstock and most nightlife in the area . Small association with limited restrictions and a very low annual fee of $350.00. Come see your new homesite in the White Mountains and enjoy all this location has to offer .

40 Sundance 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

$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

$500,000

Rare opportunity to own a multi-acre lot within walking distance of downtown North Woodstock. Level parcel with road frontage on Lost River Road and also frontage on Gordon Pond Brook. This would be a perfect location for a home with lots of privacy and still be within walking distance of downtown restaurants, shops and natural attractions. Close to Loon and Cannon Mountains too!

5098035 MLS

Rare opportunity to own a multi-acre lot within walking distance of downtown North Woodstock. Level parcel with road frontage on Lost River Road and also frontage on Gordon Pond Brook. This would be a perfect location for a home with lots of privacy and still be within walking distance of downtown restaurants, shops and natural attractions. Close to Loon and Cannon Mountains too!

Map 105 Lot 20 Map 105, 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

$169,000

Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a seasonal retreat surrounded by classic Vermont scenery, this blank canvas is entirely ready for whatever you wish. Enjoy total autonomy and peaceful seclusion, all while remaining just minutes from the historic charm of Woodstock Village, local dining, and premier outdoor recreation. A rare, high-value investment opportunity where financial strategy meets local beauty. Bring your architect, your builder, and your dreams!

5095630 MLS

Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a seasonal retreat surrounded by classic Vermont scenery, this blank canvas is entirely ready for whatever you wish. Enjoy total autonomy and peaceful seclusion, all while remaining just minutes from the historic charm of Woodstock Village, local dining, and premier outdoor recreation. A rare, high-value investment opportunity where financial strategy meets local beauty. Bring your architect, your builder, and your dreams!

Iver Johnson Way, 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!

5095205 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

$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

$10,500

This Quarter Share ownership, one 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 1 bedroom, 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.

1 Beds ⋅ 2 Baths ⋅ 5092964 MLS

This Quarter Share ownership, one 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 1 bedroom, 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 168D, Woodstock

$395,000

Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a wonderful , open site ideal for building your dream home offering privacy , trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn , dining at the Ransom Tavern and a swim in the Kedron pond ! 5 miles into Woodstock Village , skiing available at multiple resorts including Okemo and Killington as well as local Saskadena Six. Green Mt. Horse Association is around the corner . The year round access to outdoor activities is endless. Call today for more information and a viewing . Subject to completion of the subdivision of the parcel.

5092107 MLS

Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a wonderful , open site ideal for building your dream home offering privacy , trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn , dining at the Ransom Tavern and a swim in the Kedron pond ! 5 miles into Woodstock Village , skiing available at multiple resorts including Okemo and Killington as well as local Saskadena Six. Green Mt. Horse Association is around the corner . The year round access to outdoor activities is endless. Call today for more information and a viewing . Subject to completion of the subdivision of the parcel.

Rte 106, 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

$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

$220,000

This beautifully updated 1-bed, 1-bath condo offers the perfect combination of modern comfort and an unbeatable mountain-town location. Outdoor enthusiasts will appreciate the prime location between Loon & Cannon Mountains, with hiking, skiing, and recreational trails accessible right from your doorstep. Summertime activities include mountain biking cycling, camping, and opportunities to explore local swimming holes along the Pemigewassett River and beyond!. Ideally situated on Main Street in downtown North Woodstock, you’ll enjoy being just steps from local restaurants, breweries, coffee shops, & charming boutiques, while also being minutes from amenities in vibrant downtown Lincoln. Fully renovated at the end of 2024, this unit showcases an open concept layout with lots of natural light, brand-new flooring, a completely redesigned kitchen & full bathroom, updated plumbing, a newly installed water heater, and is being offered almost fully furnished, delivering a truly turnkey, move-in-ready experience. The bedroom is spacious and large enough for a king-sized bed and dressers, and has a walk-in closet. As a desirable 1st-floor unit, the condo features dual entry points for added convenience and easy accessibility. Additional highlights include low HOA fees, a private porch with outdoor storage closet, and convenient on-site laundry within the building. There is also a separate closet in the building for bike storage if desired. The association is pet friendly & allows rentals with a 30-day minimum, offering excellent flexibility for extended stays or investment potential while maintaining a welcoming residential atmosphere. Whether you’re searching for a full-time residence, weekend retreat, or investment opportunity in one of New Hampshire’s most sought-after destinations, this turnkey condo offers the very best of mountain living with downtown convenience.

1 Beds ⋅ 1 Baths ⋅ 5089181 MLS

This beautifully updated 1-bed, 1-bath condo offers the perfect combination of modern comfort and an unbeatable mountain-town location. Outdoor enthusiasts will appreciate the prime location between Loon & Cannon Mountains, with hiking, skiing, and recreational trails accessible right from your doorstep. Summertime activities include mountain biking cycling, camping, and opportunities to explore local swimming holes along the Pemigewassett River and beyond!. Ideally situated on Main Street in downtown North Woodstock, you’ll enjoy being just steps from local restaurants, breweries, coffee shops, & charming boutiques, while also being minutes from amenities in vibrant downtown Lincoln. Fully renovated at the end of 2024, this unit showcases an open concept layout with lots of natural light, brand-new flooring, a completely redesigned kitchen & full bathroom, updated plumbing, a newly installed water heater, and is being offered almost fully furnished, delivering a truly turnkey, move-in-ready experience. The bedroom is spacious and large enough for a king-sized bed and dressers, and has a walk-in closet. As a desirable 1st-floor unit, the condo features dual entry points for added convenience and easy accessibility. Additional highlights include low HOA fees, a private porch with outdoor storage closet, and convenient on-site laundry within the building. There is also a separate closet in the building for bike storage if desired. The association is pet friendly & allows rentals with a 30-day minimum, offering excellent flexibility for extended stays or investment potential while maintaining a welcoming residential atmosphere. Whether you’re searching for a full-time residence, weekend retreat, or investment opportunity in one of New Hampshire’s most sought-after destinations, this turnkey condo offers the very best of mountain living with downtown convenience.

193 Main St Unit 115, Woodstock

$429,000

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower corner. Parcel is mostly wooded with a large Maple Grove currently tapped by a local syrup producer. Green Mountain Horse Assoc. is just around the bend and the South Woodstock Country Store and Kedron Valley Inn are just a few minutes away. Woodstock Village is 6 miles down the road. Amazing spot to build your primary residence or second home getaway.

5088279 MLS

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower corner. Parcel is mostly wooded with a large Maple Grove currently tapped by a local syrup producer. Green Mountain Horse Assoc. is just around the bend and the South Woodstock Country Store and Kedron Valley Inn are just a few minutes away. Woodstock Village is 6 miles down the road. Amazing spot to build your primary residence or second home getaway.

Noah Wood Road, 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

$2,500,000

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities. Some photos are digitally enhanced.

4 Beds ⋅ 4 Baths ⋅ 5087228 MLS

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities. Some photos are digitally enhanced.

114 Oak Ridge Way, Woodstock

$345,000

Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires architects and homeowners alike. Picture your morning coffee on a wraparound porch, overlooking the existing neighboring pond and seasonal splendor that make this corner of New England absolutely legendary. The generous lot size provides ample outdoor space for landscaping, gardens, recreational areas, or whatever your imagination conjures. A septic permit is already in place and a house site has been cleared removing two of the biggest hurdles in the building process and letting you move forward with confidence and momentum. The surrounding community adds tremendous value to daily life here. Outdoor enthusiasts will appreciate nearby Aqueduct Trails for recreation and exploration, while the breathtaking Quechee Gorge is just a short drive away. The beloved Woodstock Farmers'Market keeps your kitchen stocked with fresh, local goodness all season long or spend the day downtown shopping in the unique shops and restaurants plus it's just a short drive to I89. Opportunities like this in Woodstock don't sit around waiting. Contact us today to learn more about this remarkable lot and start turning your vision into reality.

5085318 MLS

Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires architects and homeowners alike. Picture your morning coffee on a wraparound porch, overlooking the existing neighboring pond and seasonal splendor that make this corner of New England absolutely legendary. The generous lot size provides ample outdoor space for landscaping, gardens, recreational areas, or whatever your imagination conjures. A septic permit is already in place and a house site has been cleared removing two of the biggest hurdles in the building process and letting you move forward with confidence and momentum. The surrounding community adds tremendous value to daily life here. Outdoor enthusiasts will appreciate nearby Aqueduct Trails for recreation and exploration, while the breathtaking Quechee Gorge is just a short drive away. The beloved Woodstock Farmers'Market keeps your kitchen stocked with fresh, local goodness all season long or spend the day downtown shopping in the unique shops and restaurants plus it's just a short drive to I89. Opportunities like this in Woodstock don't sit around waiting. Contact us today to learn more about this remarkable lot and start turning your vision into reality.

Oak Ridge Way, Woodstock

$1,695,000

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

2 Beds ⋅ 3 Baths ⋅ 5084536 MLS

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

2394 Fletcher Hill Rd, Woodstock