Windham County VT Houses for Sale

/56
$350,000
- 6 Beds
- 4.5 Baths
- 3,042 Sq Ft
2072 N Main St, Londonderry, VT 05148

Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6058

2072 N Main St, Londonderry, VT 05148
/37
$395,000
- 4 Beds
- 2 Baths
- 2,400 Sq Ft
3298 Houghtonville Rd, Grafton, VT 05146

Classic 1800s Farmhouse in Charming Grafton, VermontLocated in Houghtonville, a beautiful part of historic Grafton, this mid-19th century farmhouse offers a rare opportunity to restore and reimagine a true Vermont original. With strong bones and timeless character, the home features wide plank floors, vintage woodwork, and a traditional layout that reflects its heritage. Typical of this

Alison Cummings

Cummings & Co

(802) 317-7411

3298 Houghtonville Rd, Grafton, VT 05146
/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/60
$599,000
- 3 Beds
- 2 Baths
- 3,000 Sq Ft
121 Dover Hill Rd, Dover, VT 05341

Priced to sell! Now priced at $599,000.This is your rare chance to own a versatile 5-acre retreat just minutes from Mount Snow, ready for fall foliage season, winter skiing, or year-round rental income. Whether you're dreaming of a second home, short-term rental, or homestead, this updated Vermont mini-farm delivers. A small barn with paddocks, a classic sugarhouse, vibrant gardens, and raspberry

Nick Sicard EXP Realty

121 Dover Hill Rd, Dover, VT 05341
/48
$680,000
- 4 Beds
- 4 Baths
- 2,590 Sq Ft
196 Old Sawmill Rd, Londonderry, VT 05148

Nestled in the Green Mountains just minutes from Magic Mountain Ski Area, this spacious 4-bedroom retreat offers the perfect Vermont lifestyle. Enjoy easy access to beautiful Lowell Lake, while tucked away on a quiet dead-end road with serene mountain views. Inside, the home features 3 private en suite bedrooms, two of which include cozy loft spaces, plus an additional guest room. A warm and

Lee Brown Four Seasons Sotheby's Int'l Realty

196 Old Sawmill Rd, Londonderry, VT 05148
/37
$849,000
- 4 Beds
- 4 Baths
- 3,600 Sq Ft
5 Hillwinds N, Brattleboro, VT 05301

Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered

Robert Doyle Berkley & Veller Greenwood Country

5 Hillwinds N, Brattleboro, VT 05301
/60
$655,000
- 4 Beds
- 3 Baths
- 2,344 Sq Ft
879 Glebe Mountain Rd, West Townshend, VT 05359

SOARING GLASS, SOARING SPIRITS, SKIING DELIGHTCome see this architecturally dramatic contemporary four bedroom, three bath home replete with glass to the sky, cathedral ceilings, gorgeous mountain views, wood burning fireplace and end of road privacy on almost ten acres. Perched square in the middle of ski country and close to the three charming towns of Londonderry, Grafton and Chester, you

Zachary Zupan EXP Realty

879 Glebe Mountain Rd, West Townshend, VT 05359
/32
$559,000
- 3 Beds
- 3 Baths
- 2,080 Sq Ft
9 Greer Ct, Wilmington, VT 05363

Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Greer Ct, Wilmington, VT 05363
/39
$699,000
- 6 Beds
- 3 Baths
- 2,825 Sq Ft
95 Melendy Hill Rd, Londonderry, VT 05155

A fully reimagined 1900’s farmhouse located in the heart of South Londonderry. This six-bedroom, three-bath home has been meticulously remodeled to blend timeless character with contemporary style. Sunlight pours through all-new windows, illuminating generous living spaces. Every detail has been thoughtfully upgraded, from the new heating system, engineered and installed septic, well, and

Jessica Citera Cummings & Co

95 Melendy Hill Rd, Londonderry, VT 05155
/58
$749,000
- 3 Beds
- 2.5 Baths
- 3,276 Sq Ft
360 Valley View Rd, West Dover, VT 05356

Tucked in the woods just minutes from Mount Snow and The Hermitage Club, this 3-bedroom, 3-bath home blends privacy, comfort, and convenience. Set on a beautifully landscaped lot, the property offers expansive decks surrounded by mature plantings, creating the perfect backdrop for outdoor entertaining or quiet relaxation. Just steps away, Cooper Hill rewards you with breathtaking sunrises, while

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

360 Valley View Rd, West Dover, VT 05356
/37
$925,000
- 7 Beds
- 7.5 Baths
- 6,046 Sq Ft
214 Whites Rd, Wilmington, VT 05363

Experience a rare combination of proximity, privacy, and exposure, from this spectacular 1900s farmhouse nestled on 10+ private pastoral acres off the beautiful Whites Road, just outside the country village of Wilmington, and a short drive to the Mount Snow and Hermitage ski resorts. This home sits at the end of a private drive, with sunny exposure, horse pasture, rolling lawn space, and tennis

Adam Palmiter Berkley & Veller Greenwood/Dover

214 Whites Rd, Wilmington, VT 05363
/43
$899,000
- 4 Beds
- 3 Baths
- 3,155 Sq Ft
460 Stratton Gate Rd, Jamaica, VT 05343

This exceptional property blends classic post-and-beam farmhouse design with modern craftsmanship. The stunning barn addition is an architectural masterpiece, admired from every angle and flooded with natural light through expansive windows that frame the serene surroundings. Soaring ceilings, rich hardwood floors, and custom finishes create an atmosphere of timeless elegance. An expansive loft

Helen Nault

460 Stratton Gate Rd, Jamaica, VT 05343
/47
$570,000
- 4 Beds
- 2 Baths
- 1,937 Sq Ft
149 Dix Ln, Whitingham, VT 05361

Open House Sunday 8/31 10 am to 1:00 - Tucked away on a quiet, town-maintained dead end road this Vermont country homestead offers the perfect blend of charm, privacy, and practicality. Set on 34+ acres, this property has woodlands, pasture and hay fields that have supported a working farm with livestock for the past 5 years. This property is well suited for those seeking a working homestead or a

Sandy Reavill Real Broker LLC

149 Dix Ln, Whitingham, VT 05361
/58
$568,000
- 3 Beds
- 2 Baths
- 2,066 Sq Ft
192 Western Ave, Brattleboro, VT 05301

Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

Claire Renaud Berkley & Veller Greenwood Country

192 Western Ave, Brattleboro, VT 05301
/49
$625,000
- 5 Beds
- 3 Baths
- 4,226 Sq Ft
24 Bluebrook Rd, Dover, VT 05356

Nestled less than two miles from Mount Snow, this spacious 4200 sf private home features 5 Bedrooms (plus a den) and 3 Bathrooms offering the perfect blend of seclusion, convenience, and entertainment.The expansive kitchen and two dining areas will effortlessly accommodate holiday gatherings and cozy Vermont evenings. Even with a full house, the third floor primary suite provides a serene

Melissa Ellis Southern Vermont Realty Group

24 Bluebrook Rd, Dover, VT 05356
/60
$565,000
- 3 Beds
- 3 Baths
- 2,772 Sq Ft
7 Grassy Brook Rd, Brookline, VT 05345

Welcome to The River House—a completely renovated, turn-key escape located directly on the scenic West River, complete with its own private beach. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully updated from top to bottom: all-new flooring,

Flex Realty Group Flex Realty

7 Grassy Brook Rd, Brookline, VT 05345
/31
$556,000
- 3 Beds
- 2 Baths
- 1,522 Sq Ft
174 Whites Hill Rd, Dover, VT 05356

Nestled amidst over 20 acres of pristine land, this Moosehead log home offers the perfect blend of privacy and breathtaking views. Imagine living without the burden of an electric bill, as this property is equipped with a complete solar power system and a backup generator, ensuring you have all the modern conveniences while embracing a sustainable lifestyle.Whether you're working remotely

Regina Perrotto Skihome Realty

174 Whites Hill Rd, Dover, VT 05356
/30
$579,000
- 4 Beds
- 2 Baths
- 2,656 Sq Ft
204 Meeting House Ln, Brattleboro, VT 05301

Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

Desiree Stango Berkley & Veller Greenwood Country

204 Meeting House Ln, Brattleboro, VT 05301
/60
$555,000
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
22 Lower Howe's Rd Unit A89, Wilmington, VT 05363

Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirable features you have been looking for, including a mudroom entry with custom live edge bench, ski, coat and storage racks, three levels of living space, view rail deck, fire pit, family room, laundry, bunk room and full bath on ground level, 2 bedrooms, a full bath and cathedral ceiling open concept living,

Sigrid Pickering Chimney Hill Realty

22 Lower Howe's Rd Unit A89, Wilmington, VT 05363
/41
$579,000
- 4 Beds
- 3 Baths
- 2,948 Sq Ft
196 Powder Mill Rd, Londonderry, VT 05148

Mountain Escape with Multi-Generational Potential in Powder MillWelcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout.The flexible layout offers

Katie Ladue Gilbert KW Vermont Woodstock

196 Powder Mill Rd, Londonderry, VT 05148
/35
$549,000
- 3 Beds
- 2 Baths
- 2,136 Sq Ft
8 Lilla Ln, Wilmington, VT 05363

Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled on a serene wooded lot in the Chimney Hill community. Set back from the road for added privacy, this home offers a perfect blend of comfort and style. As you step inside, a spacious two-room addition, currently used by the seasonal owners for additional sleeping, expands the living space to over 2,100 square feet. The

Patricia Fitzpatrick Skihome Realty

8 Lilla Ln, Wilmington, VT 05363
/41
$574,000
- 3 Beds
- 3 Baths
- 2,704 Sq Ft
4138 W Hill Rd S, Jamaica, VT 05343

This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

Patricia Fitzpatrick Skihome Realty

4138 W Hill Rd S, Jamaica, VT 05343
/60
$645,000
- 3 Beds
- 2.5 Baths
- 3,415 Sq Ft
23 Meeting House Ln, Brattleboro, VT 05301

First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

Bert Inman RE/MAX Town & Country

23 Meeting House Ln, Brattleboro, VT 05301
/17
$625,000
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
9 Cooper Hill Rd, Dover, VT 05341

Welcome to your own private sanctuary, tucked away on six stunning acres of unspoiled natural beauty. This inviting 4-bedroom, 2-bathroom home offers the perfect balance of rustic charm and modern comfort, creating an ideal retreat for those seeking peace, privacy, and outdoor adventure.Surrounded by lush woods and open space, the property features a serene private pond, the soothing sounds

Carrie Mathews Winhall Real Estate

9 Cooper Hill Rd, Dover, VT 05341
/35
$629,000
- 3 Beds
- 2.5 Baths
- 2,033 Sq Ft
64 Gleason Farm Ln, Jamaica, VT 05343

Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner,

Carrie Mathews Winhall Real Estate

64 Gleason Farm Ln, Jamaica, VT 05343
/39
$599,000
- 3 Beds
- 2 Baths
- 1,957 Sq Ft
256 Potter Rd, Wardsboro, VT 05355

Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

Jennifer Hovey-Densmore Deerfield Valley Real Estate

256 Potter Rd, Wardsboro, VT 05355
/29
$625,000
- 4 Beds
- 2 Baths
- 2,137 Sq Ft
72 Colonial Ridge Rd, Dover, VT 05356

This turnkey mountain retreat is ready for you to enjoy! Nestled in the serene Dover Hills, this home is ideally located near Mount Snow, snowmobile trails, shopping, and dining. Featuring four inviting bedrooms and a game room on the lower level, there’s plenty of space for everyone to relax. Cozy up in front of the wood-burning fireplace or breathe in the fresh mountain air while soaking in the

Michelle O'Neil Deerfield Valley Real Estate

72 Colonial Ridge Rd, Dover, VT 05356
/51
$549,000
- 3 Beds
- 2.5 Baths
- 2,494 Sq Ft
63 Cooper Hill Rd, Dover, VT 05356

Welcome to the original Cooper family homestead, a timeless treasure nestled on the highly sought-after Cooper Hill Road. This beautifully preserved antique home seamlessly blends historic character with thoughtful modern updates. A newly added composite deck with sleek cable railing is the perfect place to take in the stunning, long-range mountain views stretching over 100 miles toward NH’s Mt.

Michelle O'Neil Deerfield Valley Real Estate

63 Cooper Hill Rd, Dover, VT 05356
/27
$559,000
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
16 View Rd, Wilmington, VT 05363

Great Chimney Hill vacation home in Lower B section. Super layout where kitchen, counter conversers, dining room folks and living room relaxers can choose to interact as one happy group, or maintain their own separate activities. The pellet stove fireplace & vaulted ceiling in the living room make for such a relaxing space, while the steps that lead to the large loft above provides yet another

Michael Purcell Berkley & Veller Greenwood/Dover

16 View Rd, Wilmington, VT 05363
/22
$415,000
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
275 Sherwood Forest, Londonderry, VT 05148

Offered for the first time! Welcome to 275 Sherwood Forest, an immaculately maintained post-and-beam home tucked away in the heart of Londonderry. This charming property combines timeless craftsmanship with easy upkeep, making it an ideal Vermont getaway or year-round residence. The warm post-and-beam design creates a cozy yet open feel, with natural wood accents and inviting living spaces

Timothy Apps Four Seasons Sotheby's Int'l Realty

275 Sherwood Forest, Londonderry, VT 05148
/19
$399,000
- 4 Beds
- 2 Baths
- 1,830 Sq Ft
4850 Vermont Route 100, Wardsboro, VT 05355

Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

Adam Palmiter Berkley & Veller Greenwood/Dover

4850 Vermont Route 100, Wardsboro, VT 05355
/20
$475,000
- 3 Beds
- 2 Baths
- 1,840 Sq Ft
175 Sherwood Forest, Londonderry, VT 05148

Nestled in the scenic beauty of Londonderry, Vermont, this delightful 3-bedroom, 2-bathroom home offers the perfect blend of comfort, convenience, and outdoor charm. With a thoughtfully designed layout that includes a bedroom and full bath on the main floor, this home is ideal for aging in place or accommodating guests.The heart of the home boasts an open living, dining, and kitchen area,

Christiane Carroccio TPW Real Estate

175 Sherwood Forest, Londonderry, VT 05148
/49
$435,000
- 4 Beds
- 2 Baths
- 1,344 Sq Ft
27 Country Ct, Wilmington, VT 05363

Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous

Janet Boyd Boyd Real Estate

27 Country Ct, Wilmington, VT 05363
/58
$485,000
- 5 Beds
- 3 Baths
- 2,316 Sq Ft
1923 N Hill Rd, Chester, VT 05143

Escape to your own private Vermont retreat in this classic 1980s chalet set on 13+ acres in a serene, park-like setting. Tucked back from the road yet convenient to local amenities, the home offers three levels of living space with five bedrooms and three baths. The lower level features a second kitchen and living area perfect for guests or young adults. In summer, enjoy the best of country

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

1923 N Hill Rd, Chester, VT 05143
/33
$397,777
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
528 Vermont 121, Windham, VT 05155

Nestled alongside a meandering stream, this perfectly private Cape-style home offers an idyllic setting with over 2 acres of lush land, perfect for play, gardening, or entertaining. Built in the late 80's this home features 3 bedrooms and 2 baths blending timeless appeal with modern conveniences. First floor bedroom and a 2 car garage attached with a practical mudroom offers easy living. 5 new

Julie Citron RE/MAX Four Seasons

528 Vermont 121, Windham, VT 05155
/47
$399,000 Open Mon 10AM - 12PM
- 3 Beds
- 2.5 Baths
- 1,900 Sq Ft
398 Vermont 30, Newfane, VT 05345

3BD/3BA true log home on 2 acres with a grand main level that is open and light-filled. Soaring ceilings, wood floors, a country kitchen with farmhouse sink and gas range, dining area, pellet stove, and a half bath with laundry. The main floor also features a spacious primary suite with large closet space and a luxurious bath highlighted by a slate walk-in rain shower. Upstairs are two spacious

Jacki Murano Southern Vermont Realty Group

398 Vermont 30, Newfane, VT 05345
/27
$514,900
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
275 Pams Hill Rd, Wardsboro, VT 05355

Absolutely meticulous and renovated gambrel chalet with private parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to extensive upgrades throughout making it truly turn key. There is a large great room with expansive windows, natural woodwork, great natural light, and efficient gas stove, a beautiful updated

Adam Palmiter Berkley & Veller Greenwood/Dover

275 Pams Hill Rd, Wardsboro, VT 05355
/55
$329,000
- 3 Beds
- 2 Baths
- 2,910 Sq Ft
597 Gates Pond Rd, Jacksonville, VT 05342

Classic Greek Revival Expanded in True New England Farmhouse Fashion w/Studios, Timber-Frame Barn, Workshop, & Greenhouse on 3+ surveyed Acres. This 3-bed, 2-bath offers approximately 3,000 square feet of finished living space w/ flowing layout connecting a series of versatile spaces—all under one roof. From the original formal rooms of the farmhouse, step into a sequence of functional bonus

Jacki Murano Southern Vermont Realty Group

597 Gates Pond Rd, Jacksonville, VT 05342
/20
$285,000
- 3 Beds
- 2 Baths
- 1,710 Sq Ft
172 Franklin Rd, Vernon, VT 05354

Fantastic opportunity! This split level has 3 floors to finish for lots of living! Or, choose to begin with the first floor that has living/dining/kitchen/full bath and bedroom. It needs work, but an easy way to get started. 4 Possible bedrooms (town says 3, appraiser says 4), The basics are here, sheetrock up and partially mudded, good sized bedrooms, lots of windows and kitchen has been

Christine Lewis Brattleboro Area Realty

172 Franklin Rd, Vernon, VT 05354
/44
$475,000
- 4 Beds
- 3 Baths
- 3,314 Sq Ft
76 Spruce St, Brattleboro, VT 05301

Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

Christine Lewis Brattleboro Area Realty

76 Spruce St, Brattleboro, VT 05301

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.