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304 Peterkin Hill Rd, Woodstock
$879,000
3 Beds ⋅ 3 Baths ⋅ 5116353 MLS
Tucked into the hills of South Woodstock, this charming Cape-style home offers privacy, mountain views, and a wonderful setting on 4.6 acres of lawn and woodland. Built in 1988 and thoughtfully remodeled in 2014, the home combines classic Vermont character with inviting, updated living spaces across three levels. The heart of the house is an open kitchen, dining, and gathering area with wide-plank wood floors, exposed timber accents, natural wood cabinetry, granite countertops, a professional-style gas range, and a breakfast bar. A woodstove set against a striking stone surround adds warmth to the gathering room, while generous windows bring the outdoors in. A separate living room provides a comfortable place to unwind. Upstairs, two bedrooms feature charming rooflines and wood floors, while a beautifully appointed bath offers a clawfoot soaking tub, separate tiled shower, and beadboard detailing. The walkout lower level features a spacious third bedroom, a three-quarter bath, and attractive cork flooring, providing comfortable accommodations for guests and additional living flexibility. Outside, an expansive deck overlooks the lawn, woodland, and surrounding hills, ideal for relaxing or entertaining. A covered entry, standing-seam metal roof, and attached two-car garage add practical appeal. Conveniently located near South Woodstock, Woodstock Village, and Route 4 toward Killington, the property offers year-round access to skiing at Killington and Saskadena Six, hiking, recreation, restaurants, and shopping throughout the Ottauquechee Valley. An inviting primary residence or Vermont getaway.

304 Peterkin Hill Rd, Woodstock

156 Deer Park Dr Unit 137D, Woodstock
$12,000
1 Beds ⋅ 1 Baths ⋅ 5115503 MLS
Charming 1-Bedroom Condo at Deer Park Resort – Quarter Share Ownership Discover your own getaway in the heart of the White Mountains! This charming upper level garden-style condo at Deer Park Resort features 1 bedroom, 1 full bath, propane fireplace and 886 square feet of comfortable living space, making it an ideal retreat for a small family or a relaxing mountain escape. This quarter-share property offers 13 weeks of ownership per year, with use of the property one week out of every four, providing a wonderful opportunity to enjoy all four seasons in the White Mountains. Conveniently located just off I-93, the condo is a short distance from local shops, restaurants, and area attractions. Loon Mountain is approximately 3 miles away, offering easy access to a fun-filled day on the slopes during the winter months. In the summer, enjoy Deer Park’s beautiful spring-fed pond and beach area. The on-site health club features an indoor swimming pool, racquetball courts, and a spacious great room overlooking the pond, complete with a pool table, foosball, and air hockey.

156 Deer Park Dr Unit 137D, Woodstock

19 Jack O Lantern Dr Unit Unit 16, Woodstock
$405,000
3 Beds ⋅ 3 Baths ⋅ 5115334 MLS
Welcome to Jack O’Lantern Resort! Situated along the first hole of the The Jack golf course, this 3-bedroom, 2.5-bathroom condo offers some of the best golf views in the resort. Enjoy the beautiful surroundings and four-season recreation that make this community such a desirable place to own. Whether you’re looking for a mountain getaway, a place to gather with family and friends, or a property with rental potential, this condo offers plenty of possibilities. 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 Jack Golf Course, restaurant, and bar, this property is set up to be enjoyed in every season, whether you’re golfing in the summer, enjoying the fall foliage, or hitting the slopes in winter.

19 Jack O Lantern Dr Unit Unit 16, Woodstock

45 Pleasant St, Woodstock
$1,595,000
5 Beds ⋅ 6 Baths ⋅ 5115063 MLS
Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

45 Pleasant St, Woodstock

18 Pleasant St, Woodstock
$1,750,000
5 Beds ⋅ 3 Baths ⋅ 5113873 MLS
EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village’s acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

18 Pleasant St, Woodstock

Lot 206-044 Lost River, Woodstock
$575,000
5113870 MLS
64 Acres in the Heart of the White Mountains! Discover an incredible opportunity to own 63.64 acres of wooded land in desirable Woodstock, NH, just minutes from Lincoln, Loon Mountain Resort, and the area’s most popular attractions! With approximately 1,830 feet of road frontage along scenic Lost River Road (Route 112), this expansive parcel offers privacy, rolling terrain, seasonal streams, beautiful mountain surroundings, and endless possibilities. Located in a town without traditional zoning, the property offers exciting potential for a private mountain retreat, family compound, or future development, subject to applicable town and state approvals. Enjoy year-round adventures with skiing at Loon Mountain, hiking throughout Franconia Notch and the White Mountain National Forest, exploring Lost River Gorge, visiting the magical Ice Castles, and taking scenic drives along the Kancamagus Highway. Experience breathtaking fall foliage, nearby rivers and lakes, snowmobiling, and endless outdoor recreation. Just minutes from downtown Lincoln and North Woodstock’s restaurants, shops, and family attractions. A rare opportunity to own a substantial piece of the White Mountains in one of New Hampshire’s most sought-after four-season destinations!

Lot 206-044 Lost River, Woodstock

121 Townhouse Way Unit 20, Woodstock
$495,000
2 Beds ⋅ 3 Baths ⋅ 5113819 MLS
**Classic Woodstock character, generous living spaces, and the ease of low-maintenance living.** Just minutes from Woodstock Village, this beautifully maintained Federal-style brick townhouse offers privacy, comfort, and convenience in an established residential community. With approximately 2,268 square feet of finished living space across three levels, the home offers the comfort and flexibility of a single-family residence without the demands of extensive property maintenance. Freshly painted and updated with new hardwood floors, the inviting interior features a fireplace, comfortable gathering spaces, and a versatile first-floor bonus room with pocket doors, ideal for an office, den, or studio. The eat-in kitchen opens to an oversized deck overlooking lawns, perennial gardens, mature trees, and surrounding woodland. A finished walkout lower level adds valuable living space, with natural light, a full bathroom, laundry, and direct backyard access. Association services include lawn care, snow removal, trash collection, and common grounds maintenance, leaving more time to enjoy Woodstock. The location is exceptional. Woodstock Farmers' Market is just down the street, while nearby trailheads connect to Marsh-Billings-Rockefeller National Historical Park. Woodstock Village, the Woodstock Inn & Resort, Billings Farm & Museum, and outstanding dining and shopping are minutes away.

121 Townhouse Way Unit 20, Woodstock

75 Riverfront Dr Unit 208, Woodstock
$449,900
2 Beds ⋅ 2 Baths ⋅ 5113760 MLS
Deer Park Resort is just over an hour from Manchester and two hours north of Boston in the heart of the White Mountains. Set on 65 manicured acres, including a private five-acre lake, Deer Park offers year-round enjoyment. Deer Park is located in Grafton County 30 miles N of Plymouth along Highway 112 off exit 32 on I93 near Loon Mountain Ski Area. Lincoln/ Woodstock area is the gateway to one of the state's most popular scenic drives, the Kancamagus Highway. North Woodstock is a quaint little walking town just five minute walk from Deer Park local restaurants and shopping just around the corner. Whatever your pleasure, Franconia Notch State Park in the White Mountains of NH consists of 6,693 acres for swimming, camping, scenic driving, picnicking, biking, and hiking. Use our distinctive resort community as home base to enjoy fabulous scenic drives, some of the county's finest hiking, marvelous fishing, challenging golf, glider rides, horsebackriding in franconia are just a short drive up 93 thrilling moose-watching adventures and much more.... This property has a fantastic location just a short stroll to the Rec center or the beach area for summer fun and winter shuttle service to Loon ski area for winter enjoyment . Vaulted ceilings in main living area opens up to a beautiful porch overlooking the river and multiple options for mtn biking or skiing at Cannon, Bretton Woods , or Loon . Consider this your basecamp in the White mountains . .

75 Riverfront Dr Unit 208, Woodstock

156 Deer Park Dr Unit 128TD, Woodstock
$12,000
1 Beds ⋅ 1 Baths ⋅ 5113684 MLS
Charming 1-Bedroom Condo at Deer Park Resort – Quarter Share Ownership Discover your own getaway in the heart of the White Mountains! This charming lower level garden-style condo at Deer Park Resort features 1 bedroom, 1 full bath, propane fireplace and 886 square feet of comfortable living space, making it an ideal retreat for a small family or a relaxing mountain escape. This quarter-share property offers 13 weeks of ownership per year, with use of the property one week out of every four, providing a wonderful opportunity to enjoy all four seasons in the White Mountains. Conveniently located just off I-93, the condo is a short distance from local shops, restaurants, and area attractions. Loon Mountain is approximately 3 miles away, offering easy access to a fun-filled day on the slopes during the winter months. In the summer, enjoy Deer Park’s beautiful spring-fed pond and beach area. The on-site health club features an indoor swimming pool, racquetball courts, and a spacious great room overlooking the pond, complete with a pool table, foosball, and air hockey.

156 Deer Park Dr Unit 128TD, Woodstock

1190 Long Hill Rd, Woodstock
$350,000
1 Beds ⋅ 1 Baths ⋅ 5113625 MLS
A rare opportunity to own 11.58 private acres in S. Woodstock, ideally situated in one of Vermont’s most sought-after rural settings. With an existing driveway, well, electric service, septic system, and a modest mobile home already in place, this property offers the infrastructure and flexibility to enjoy the land now while considering its future potential. The land is the true centerpiece. Wooded acreage, natural clearings, gentle slopes, and a peaceful country setting create an ideal backdrop for a Vermont getaway, recreational property, hunting retreat, equestrian use, or future building site. The existing 536-square-foot, 1-bed, 1-bath mobile home provides a simple place to stay while enjoying everything the property and surrounding area have to offer. For equestrian enthusiasts, the location is especially compelling. The property is within approximately two miles of the Green Mountain Horse Association (GMHA) and sits directly along the GMHA Paul Kendall Trail, providing an exceptional connection to one of Vermont’s premier equestrian communities and trail networks. The surrounding area is renowned for its horse farms, riding trails, open countryside, and beautiful back roads. The property is also well positioned for the quintessential Vermont second-home lifestyle, with Killington Resort, Saskadena Six, Billings Farm & Museum, Woodstock, and South Woodstock all within easy reach. Enjoy skiing, hiking, horseback riding, cycling, farm visits, fine dining, and the timeless character of the Woodstock area, then return to your own private acreage. From 1985 through 2020, a family of four occupied a three-bedroom home and used the existing septic system without reported issues. The seller has also completed a soil evaluation and septic inspection, with both reports available in the attached documents. Lastly, the seller would be willing to discuss removal of the mobile home if it is not needed by the new buyer. Schedule a private tour today!

1190 Long Hill Rd, Woodstock

1190 Long Hill Rd, Woodstock
$350,000
5113624 MLS
A rare opportunity to own 11.58 private acres in S. Woodstock, ideally situated in one of Vermont’s most sought-after rural settings. With an existing driveway, well, electric service, septic system, and a modest mobile home already in place, this property offers the infrastructure and flexibility to enjoy the land now while considering its future potential. The land is the true centerpiece. Wooded acreage, natural clearings, gentle slopes, and a peaceful country setting create an ideal backdrop for a Vermont getaway, recreational property, hunting retreat, equestrian use, or future building site. The existing 536-square-foot, 1-bed, 1-bath mobile home provides a simple place to stay while enjoying everything the property and surrounding area have to offer. For equestrian enthusiasts, the location is especially compelling. The property is within approximately two miles of the Green Mountain Horse Association (GMHA) and sits directly along the GMHA Paul Kendall Trail, providing an exceptional connection to one of Vermont’s premier equestrian communities and trail networks. The surrounding area is renowned for its horse farms, riding trails, open countryside, and beautiful back roads. The property is also well positioned for the quintessential Vermont second-home lifestyle, with Killington Resort, Saskadena Six, Billings Farm & Museum, Woodstock, and South Woodstock all within easy reach. Enjoy skiing, hiking, horseback riding, cycling, farm visits, fine dining, and the timeless character of the Woodstock area all while returning to your own private acreage. From 1985 through 2020, a three-bedroom home occupied by a family of four utilized the existing septic system without reported issues. The seller has also completed a soil evaluation and septic inspection, with both reports available in the attached documents. Lastly, the seller would be willing to discuss removal of the mobile home if it is not needed by the new buyer. Schedule a private tour today!

1190 Long Hill Rd, Woodstock

139 Doe Hill Way, Woodstock
$549,000
3 Beds ⋅ 2 Baths ⋅ 5113572 MLS
Welcome to this newly updated sun-filled craftsman home, ideally located just 4 miles from the heart of Woodstock Village and 11 miles from Killington Ski Resort. Set on 5 acres with a lovely pond, this property offers the perfect blend of privacy, convenience, and Vermont charm. The home features a bright and inviting interior with one bedroom on the main level and two additional bedrooms and a full bath on the lower level. A spacious wraparound porch extends the living space outdoors, providing the perfect spot to relax, entertain, and enjoy the peaceful surroundings. Whether you’re looking for a primary residence, Vermont getaway, or a home base for year-round recreation, this beautifully updated chalet offers easy access to skiing, dining, shopping, hiking, and everything the Woodstock and Killington areas have to offer.

139 Doe Hill Way, Woodstock

264 Blake Hill Rd Unit Z, Woodstock
$749,000
3 Beds ⋅ 3 Baths ⋅ 5113057 MLS
Enjoy expansive views from every level of this beautifully updated, 3-bedroom, 3-full-bath Blake Hill condominium. As a highly desirable end unit, this property welcomes you with a classic bluestone entryway and a large wrap-around porch perfect for outdoor relaxing. Inside, the multi-level floor plan offers exceptional privacy, with an open-concept main level showcasing soaring vaulted ceilings, a dining area, and a living room centered around a cozy wood-burning fireplace with custom built-ins. The large chef's kitchen features stylish appointments, upscale appliances, and a premium Sub-Zero refrigerator. Adjacent the kitchen is a large bedroom with an attached bath, perfect accommodations for friends or family, while a functional mudroom rounds out the main floor. An en suite primary bedroom and sitting area/office serves as a secluded retreat on the entire second level. The fully finished ground level adds significant living space with a sizable third bedroom, full bath, secondary family room with its own fireplace, and massive extra bonus room with dedicated storage. Residents also enjoy access to the community swimming pool, which was completely updated in the summer of 2026. With its proximity to Woodstock Village and the Upper Valley’s many cultural and recreational offerings, this turnkey property is a must-see. Note: Some photos are virtually staged. Public Open House: Sunday, October 11 from 11am-1pm.

264 Blake Hill Rd Unit Z, Woodstock

2687 Garvin Hill Rd, Woodstock
$2,600,000
5 Beds ⋅ 5 Baths ⋅ 5112419 MLS
2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dramatic vaulted great room–showcasing exposed hand-hewn beams and a wood-burning fireplace–as well as a sizable screened porch overlooking the grounds, all of which provide an ideal setting for entertaining family and friends. Adjacent to the kitchen on the other side of the house is a more intimate living room with a second fireplace, an office, and a bedroom with full bath, offering the possibility of one-level living. Upstairs, there is an en suite bedroom and two additional bedrooms that share a full bath. The lower level adds versatile finished space with a 5th bedroom guest suite with recreation space. An attached three-bay garage and barn provide ample room for vehicles, outdoor equipment, and all the gear that comes with four-season Vermont living. The attached barn has two horse stalls. There are two beautiful ponds on the property, the larger is well positioned in the backyard towards the view. Beyond the property, Woodstock’s extensive network of hiking and biking trails, nearby rivers, golf, skiing, and other year-round recreation along with shops, restaurants, and galleries are all within easy reach. Some photos are digitally enhanced.

2687 Garvin Hill Rd, Woodstock

164 Deer Park Dr Unit 175B, Woodstock
$26,000
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

6405 Folding Hills Rd, Woodstock
$1,500,000
3 Beds ⋅ 4 Baths ⋅ 5111623 MLS
SIGNIFICANT PRICE REDUCTION - SOUTH WOODSTOCK - HILLSIDE FARM estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a local master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the heart of the home, the spacious country kitchen features cherry cabinetry, gas cooktop, and an antique Stewart woodstove. The 20’ x 18’ great room offers wide pine floors, exposed framing and a soaring cathedral ceiling, overlooking a lovely 14 foot deep pond and scenic vista. The primary suite includes double closets and an ensuite bath with radiant heat, Jacuzzi tub and shower. Additional bedrooms, dining room, and a home office provide flexible living space. The lower level offers a game room with woodstove and pool table, a small kitchenette, and 3/4 bath. The property is remarkably well equipped with a greenhouse, two-stall horse stable, multiple barns and outbuildings, garage workshop, mechanic’s shop, and a substantial 23’ x 35’ woodworking shop. Tucked into the woods is a delightful rustic cabin complete with kitchenette, woodstove, porch and nearby outhouse; an inviting retreat surrounded by nature and set just above one of two babbling brooks. Located in the heart of South Woodstock’s celebrated horse country, Hillside Farm enjoys proximity to the renowned GMHA and the area’s extensive network of scenic riding trails. This is a rare opportunity to own a gentleman's farm that is move-in ready for a VT homestead or second home. Photos electronically decluttered.

6405 Folding Hills Rd, Woodstock

29 Riverfront Dr Unit 256, Woodstock
$469,900
2 Beds ⋅ 2 Baths ⋅ 5110952 MLS
Have you ever wanted to listen to the river while sitting on your deck, if so then this garden style condo is perfect for you and your family! The entire unit is up to date including granite counter tops, updated kitchen cabinets, new bathroom vanities and all flooring throught the condo. You'll also enjoy the wood burning fireplace on those cold winter nights. When you own at Deer Park you'll have use of the nicest clubhouse in the Loon area. The club features an indoor pool, jacuzzi, weight room, cardio room, game room and a spring fed 5 acre pond with sandy beach for your summer enjoyment. During the winter months Deer Park offers shuttle bus to Loon and an outdoor skating rink. Come see this property for yourself. We know you'll be impressed.

29 Riverfront Dr Unit 256, Woodstock

14 Adams Dr Unit #11, Woodstock
$379,900
3 Beds ⋅ 2 Baths ⋅ 5110667 MLS
This 3 bedroom, 2 bath townhouse in Alpine Village is perfectly located for all of your year-round adventures in the Loon area as well as being a quick minutes drive to Cannon Mountain and Franconia Notch. The restaurants and shops of downtown North Woodstock are just a short walk away. The first level of the house features an open concept living/dining room which has a newer propane fireplace to make those winter nights a little cozier. The kitchen looks out onto a private, grassy backyard which has ample space for a deck to be added. A 3/4 bath and laundry closet are also conveniently located on the main floor. There are three good-sized bedrooms and a full bathroom on the second level. After 2+ decades owned by the current family, this home is ready for the next winter to come make it their own and enjoy for years to come!

14 Adams Dr Unit #11, Woodstock

2033 South Rd, Woodstock
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 5110412 MLS
Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

2033 South Rd, Woodstock

193 Main St Unit Unit 213, Woodstock
$220,000
1 Beds ⋅ 1 Baths ⋅ 5110020 MLS
Nicely updated and move-in ready, this 1-bedroom, 1-bath condo at the Alpine Lodge puts you right in the heart of North Woodstock. The second-floor location offers a comfortable open-concept living and dining area, an updated kitchen, spacious bedroom, full bath, and private front deck with beautiful mountain views. Location is hard to beat! The Pemi River is directly across the street for fishing, swimming, and summer fun, while hiking trails and outdoor adventures are just minutes away. Downtown North Woodstock is an easy two-minute walk, with local restaurants, breweries, shops, and more right at your fingertips. Loon Mountain is about 10 minutes away, Cannon Mountain 20 minutes, and Waterville Valley approximately 30 minutes. Fully furnished and ready to enjoy, this is an ideal White Mountains getaway or year-round home. Just bring your suitcase and settle into North Country living!

193 Main St Unit Unit 213, Woodstock

7 Sundance Rd Unit 4, Woodstock
$400,000
2 Beds ⋅ 3 Baths ⋅ 5104834 MLS
Welcome to your new home or home away from home located in beautiful Woodstock NH. This unique townhome offers a versatile floor plan that is warm and inviting. Cozy up by the fireplace on those cold blister days or read a book in your bright sun room that has two levels of enjoyment. Need an extra space for guest? Utilize the loft for additional sleeping space, privacy, or quiet time. This home has 2 bedrooms and an office that could be used as an additional sleeping space, office, den, or bonus space. The primary bedroom has its own on suite bathroom and two large closets for storage. It opens up to the bright sunrooms lower level making this primary suite the perfect sanctuary. Every inch of this homes space has been utilized for efficiency and functionality. Take advantage of the community amenities that include inground pool, basketball court, and tennis court. This home unlike many townhomes also has a dry functional basement that can be accessed from the interior and exterior. The current owners are using for a workout area. To top it all of this unit comes with a 2 car garage. Home is listed $15,000 below appraised value. Get instant equity! The back deck is brand new. It has been replaced by the HOA since the photos have been taken.

7 Sundance Rd Unit 4, Woodstock

5 & 7 Mountainside Rd, Woodstock
$899,900
5 Beds ⋅ 4 Baths ⋅ 5104119 MLS
Seller is Offering a $10,000 Credit at closing to buy down the interest rate or apply towards closing costs. 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

16 Church St, Woodstock
$1,195,000
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

115 Eastman Rd, Woodstock
$5,350,000
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

2556 Church Hill Rd, Woodstock
$400,000
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

915 Peterkin Hill Rd, Woodstock
$2,300,000
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

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