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
/60
$620,000
- 3 Beds
- 2 Baths
- 2,700 Sq Ft
121 Dover Hill Rd, Dover, VT 05341

Price reduced! Discover this Vermont countryside retreat offering an unbeatable blend of equestrian haven, homestead, and ski getaway, all on 5 private acres in desirable Dover. Enjoy perennial gardens bursting with color, abundant raspberry canes, and asparagus beds for beauty and bounty year-round. Step inside to vaulted ceilings, hardwood floors, and custom inlay bookshelves that add warmth

Nick Sicard EXP Realty

121 Dover Hill Rd, Dover, VT 05341
/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
/40
$720,000
- 3 Beds
- 3.5 Baths
- 1,800 Sq Ft
134 Ellis Brook Rd, Dover, VT 05356

This stunningly renovated 3-bedroom, 3.5-bathroom vacation home with carport, completed in 2021, offers exceptional comfort and style in Dover Hills, near Mount Snow. The remodel includes a brand-new kitchen, bathrooms, flooring, and furniture throughout. Notable upgrades feature an additional 3/4 bathroom, a fully finished basement, and upgraded plumbing, electrical systems, and roof. Modern

Jennifer Hovey-Densmore Deerfield Valley Real Estate

134 Ellis Brook Rd, Dover, VT 05356
/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
/20
$525,000
- 3 Beds
- 2.5 Baths
- 1,120 Sq Ft
4 Sunnyside Rd, West Dover, VT 05356

Location, location, location! This beautifully renovated ski chalet sits just a mile south of the Mount Snow ski resort with public shuttle service to and from the mountain. The home is far more private than you would expect from the small lot size, but that means less to maintain, and more downtime, not upkeep. Thanks to great proximity to amenities you also can easily get to nearby restaurants,

Adam Palmiter Berkley & Veller Greenwood/Dover

4 Sunnyside Rd, West Dover, VT 05356
/33
$550,000
- 3 Beds
- 2 Baths
- 1,688 Sq Ft
19 Titus Farm Rd, Wilmington, VT 05363

The epitome of a Vermont country home, yet just outside the village of Wilmington, down the road from Lake Raponda, and a short drive the Mount Snow ski resort. This lovely 5+ acre property has a beautiful gurgling brook running through it, gorgeous stone work including old walls and an old stone bridge, trails through the pastoral setting, fire pit area, perennial gardens, and utter privacy.

Adam Palmiter Berkley & Veller Greenwood/Dover

19 Titus Farm Rd, Wilmington, VT 05363
/26
$529,000
- 4 Beds
- 2.5 Baths
- 1,864 Sq Ft
1966 Thompsonburg Rd, South Londonderry, VT 05155

A quiet, private sanctuary in a prime location—just minutes from all three local ski areas, Lowell Lake, and the shopping and dining of Londonderry and Manchester. This 4-bedroom retreat is ready to be loved by a new family. Enjoy newly updated bathrooms, appliances, countertops, a new chimney liner, a wood-burning fireplace, and a wood stove insert that makes the family room especially cozy on

Wilkie Bushby TPW Real Estate

1966 Thompsonburg Rd, South Londonderry, VT 05155
/50
$739,000
- 3 Beds
- 3.5 Baths
- 2,050 Sq Ft
52 Spruce Lake Estates, Wilmington, VT 05363

25 private acres with lake frontage, stunning lake & mountain scenery, and a beautifully maintained 3,300+ sq ft home w/ direct-entry 2-car garage. Located in private Spruce Lake Estates—close proximity to Mount Snow & Hermitage Club, State Parks, restaurants, shops and public transportation—this rare property offers 4-season living w/ space, privacy & frontage on a non-motorized lake w/ beach,

Jacki Murano Southern Vermont Realty Group

52 Spruce Lake Estates, Wilmington, VT 05363
/37
$730,000
- 5 Beds
- 3 Baths
- 2,275 Sq Ft
341 Under the Mountain Rd, Londonderry, VT 05148

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

Andy Reed Four Seasons Sotheby's Int'l Realty

341 Under the Mountain Rd, Londonderry, VT 05148
/50
$595,000
- 3 Beds
- 3 Baths
- 1,951 Sq Ft
532 Sherwood Forest, Londonderry, VT 05148

Relax and Reconnect in the Heart of Vermonts Green Mountains.Tucked into a peaceful woodland setting, this warm and welcoming mountain retreat is all about comfort, character, and calm. Surrounded by trees and bathed in filtered natural light, the home blends into its serene landscape with expansive windows, cathedral ceilings, and glowing wood interiors throughout. At its heart, a striking

Nancy Jensen Four Seasons Sotheby's Int'l Realty

532 Sherwood Forest, Londonderry, VT 05148
/60
$695,000
- 4 Beds
- 4 Baths
- 2,978 Sq Ft
23 Brook Rd, Saxtons River, VT 05154

A Distinctive Country Retreat on 6.8± private acres in the heart of the historic village of Saxtons River. This idyllic country estate offers year-round views, exquisite perennial gardens, & two beautifully integrated wings—the timeless Cape & the charming Carriage House. Inside of the Cape wing is a sunlit eat-in kitchen, KraftMaid cherry cabinetry & Silestone quartz countertops —all overlooking

Isabella Luhrs BHG Masiello Keene

23 Brook Rd, Saxtons River, VT 05154
/53
$750,000
- 4 Beds
- 3 Baths
- 1,545 Sq Ft
55 Crosstown Rd, Dover, VT 05356

Tucked alongside the Mount Snow Golf Course on 1.71 park-like acres, this 4-bedroom, 3-bath retreat blends Vermont charm with stylish mid-century flair. The great room makes a bold impression with dramatic vaulted ceilings, exposed beams, a striking floor-to-ceiling brick fireplace, and expansive windows framing the lush landscape. The open layout includes a warm and inviting dining area, cozy

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

55 Crosstown 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
$569,000
- 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
/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
/27
$550,000
- 3 Beds
- 3 Baths
- 3,148 Sq Ft
672 E Orchard St, West Brattleboro, VT 05301

You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

John Hatton Berkley & Veller Greenwood Country

672 E Orchard St, West Brattleboro, VT 05301
/60
$649,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/51
$575,000
- 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
/24
$599,000
- 3 Beds
- 3 Baths
- 2,625 Sq Ft
282 Pams Hill Rd, Wardsboro, VT 05355

As Vermonty as you can get! Located conveniently between Mount Snow and Stratton, for easy access to skiing, shopping, lakes, and summer fun, sits this idyllic log style chalet with tremendous personal use or rental potential. The home sits on a private parcel not far from the Snow Mountain Farms amenities including indoor pool and tennis court. There is ample parking thanks to a cul de sac

Adam Palmiter Berkley & Veller Greenwood/Dover

282 Pams Hill Rd, Wardsboro, VT 05355
/59
$529,000
- 3 Beds
- 2.5 Baths
- 1,736 Sq Ft
30 Big Bend Loop, Wilmington, VT 05363

Escape to the Green Mountains in this beautifully designed 3+ bedroom home with a spacious loft, 2 bonus rooms, and three finished levels in the sought-after Chimney Hill community, fully permitted for short-term rentals with strong income history—ideal for investors or second-home buyers looking to offset costs. Step inside the custom mudroom with built-in cubbies, bench, and closets, and enter

Chad Lackey Deerfield Valley Real Estate

30 Big Bend Loop, Wilmington, VT 05363
/20
$299,000
- 3 Beds
- 1 Bath
- 1,178 Sq Ft
17 Winter Ct, Brattleboro, VT 05301

Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

Liz LaVorgna Berkley & Veller Greenwood Country

17 Winter Ct, Brattleboro, VT 05301
/57
$479,000
- 4 Beds
- 2 Baths
- 1,840 Sq Ft
17 Villager Extension, Dover, VT 05356

Spacious 4-bedroom, 2-bath home located within great proximity to Mount Snow, just over 6 miles away! The inviting living room features a cathedral ceiling and wood-burning fireplace, perfect for apres-ski relaxation. A large mudroom provides ample space for all your gear, and a level driveway makes for nice access. The partially finished basement includes a game room and additional hangout

Erica Reynolds Southern Vermont Realty Group

17 Villager Extension, Dover, VT 05356
/56
$2,595,000
- 4 Beds
- 4 Baths
- 3,585 Sq Ft
127 Fannie Hill Dr, Wilmington, VT 05363

Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

127 Fannie Hill Dr, Wilmington, VT 05363
/44
$400,000
- 2 Beds
- 3 Baths
- 1,696 Sq Ft
399 Laurel Lake Rd, Jacksonville, VT 05342

Turnkey 2-Bedroom Home with Lake Access & Extra Garage – Laurel Lake Living! Welcome to this meticulously maintained 2-bedroom, 3-bathroom home, offering turnkey convenience and year-round comfort just steps from beautiful Laurel Lake. Boasting an open and inviting floor plan, this home features a spacious living area with a cozy pellet stove for energy-efficient warmth, perfect for chilly

Claire Renaud Berkley & Veller Greenwood Country

399 Laurel Lake Rd, Jacksonville, VT 05342
/2
$300,000
- 4 Beds
- 2 Baths
- 1,808 Sq Ft
109 Central St, Brattleboro, VT 05301

Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

Christine Lewis Brattleboro Area Realty

109 Central St, Brattleboro, VT 05301
/53
$450,000 Open Sun 11AM - 1PM
- 4 Beds
- 2.5 Baths
- 2,314 Sq Ft
64 Main St, Putney, VT 05346

Offering an enchanting circa 1830 extended cape with carriage house & office space in Putney Village. Proximal to the Putney Co-Op, General Store, Yellow Barn Music, Putney Public Library, & Putney Farmers Market. Not only aesthetically gorgeous with post & beam construction, it has new sills, beautiful slate roofing, & added energy efficiency. The main house has 4 bedrooms & 1 1⁄2 baths,

Rebecca Seymour Brattleboro Area Realty

64 Main St, Putney, VT 05346
/25
$239,000
- 4 Beds
- 2 Baths
- 1,634 Sq Ft
67 Williams Street Extension, Town of Rockingham, VT 05101

This charming and versatile home is on a double village lot at the end of a dead end road in close proximity to the vibrant village of Bellows Falls. This location allows for wonderful privacy in the heart of town and plenty of room for gardening and entertaining. The second floor has three bedrooms, a 3/4 bath and a kitchen, ideally suited for mother-in-law space or it works as a single family

Oona Madden Berkley & Veller Greenwood Country

67 Williams Street Extension, Town of Rockingham, VT 05101
/34
$299,900 Open Sat 10PM - 11:30PM
- 3 Beds
- 2.5 Baths
- 1,025 Sq Ft
35 Hillcrest Terrace, Brattleboro, VT 05301

Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential

Morriah Adams BHG Masiello Brattleboro

35 Hillcrest Terrace, Brattleboro, VT 05301
/38
$1,499,999
- 3 Beds
- 3.5 Baths
- 3,300 Sq Ft
111 Hughes Ln, Jamaica, VT 05343

Fully renovated in 2022, 450 ft of lake front footage on picturesque Cole Pond. Nestled on nearly 2 acres in Jamaica, VT, this stunning singlefamily home at 111 Hughes Lane was built in 1989 and offers a peaceful retreat for its next owners. With 3 bedrooms, 3 bathrooms, and 1 half bathroom, and 4 built-in adult size bunks for comfortable sleeping of 10, Air-conditioned master bedroom and

Derek Greene Derek Greene

111 Hughes Ln, Jamaica, VT 05343
/27
$263,000
- 2 Beds
- 1 Bath
- 1,440 Sq Ft
637 Wiswall Hill Rd, Townshend, VT 05353

Discover your perfect Vermont escape in this cozy two-story cabin nestled on a sweet, level acre. Whether you're looking for a weekend getaway or a full-time residence, this home offers the ideal blend of rustic charm and everyday functionality. The lower level welcomes you into an open-concept guest or living space, with convenient access to utilities and a fenced-in shaded area—perfect for pets

Jessica Landers Barrett and Valley Associates Inc.

637 Wiswall Hill Rd, Townshend, VT 05353
/32
$369,000
- 2 Beds
- 2 Baths
- 1,020 Sq Ft
53 Hickory Ridge Rd, Putney, VT 05346

Welcome to this charming, well cared for 2 bedroom, 2 bathroom cottage just minutes up the road from Putney village. Step inside to a warm, open living and dining space featuring a handsome wood stove and mantle, and charming exposed beams that add character and a cozy Vermont feel. Follow the hallway past the first cozy bedroom with cathedral ceilings to the spacious and bright primary suite

Rebecca Hiam Southern Vermont Realty Group

53 Hickory Ridge Rd, Putney, VT 05346
/28
$249,000
- 3 Beds
- 1 Bath
- 1,213 Sq Ft
5704 Coolidge Hwy, Guilford, VT 05301

Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor

Dan Normandeau Berkley & Veller Greenwood Country

5704 Coolidge Hwy, Guilford, 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.