Windham Homes for Sale

Welcome to Windham County, Vermont – a hidden gem nestled in the heart of New England, where picturesque landscapes meet a rich tapestry of history and culture. Known for its stunning natural beauty, this charming county is home to rolling hills, tranquil lakes, and vibrant forests that change with the seasons, offering a breathtaking backdrop for outdoor enthusiasts and nature lovers alike.

Windham County boasts a diverse array of towns, each with its unique character and charm. From the quaint village of Brattleboro, known for its bustling arts scene and community spirit, to the serene beauty of Putney and its welcoming atmosphere, there’s a perfect spot for everyone. The county is also home to a variety of recreational activities, including hiking, skiing, and kayaking, making it an ideal location for those who appreciate an active lifestyle.

For those looking to call Windham County home, there are numerous homes for sale that cater to a wide range of tastes and budgets. Whether you’re seeking a cozy cabin tucked away in the woods, a historic farmhouse with character, or a modern home with stunning views, the real estate options here are as diverse as the landscape itself. The local real estate market is thriving, with properties that offer not just a place to live, but a lifestyle steeped in community and natural beauty.

Explore the charm of Windham County and discover the perfect home that reflects your dreams and aspirations. Your Vermont adventure awaits!

Newest Windham Homes for Sale

$269,000

2 Beds ⋅ 1 Baths ⋅ 5107073 MLS

If you've been waiting for that sweet little property in Putney to come along, here is your chance! Properties in Putney, in this condition, in this price range, don't come along too often and this one is a little gem. This extremely well maintained home is ready to go and comes fully furnished, perfect for that starter home! The property features two bedrooms, a tastefully updated eat-in kitchen, a living room with picture window, a full bathroom, and an attached single-car garage with extra space for a workshop and storage. Outside, you will find a nice front deck, a large front yard, and a backyard with a concrete patio offering plenty of room for gatherings, gardening, and play! Showings begin with an open house on Sunday the 30th from 10:00-12:00.

101 Cemetery Rd, Putney

$529,000

4 Beds ⋅ 2 Baths ⋅ 5106956 MLS

Beautifully updated 4 bedroom, 2 bathroom home located in the heart of Grafton along Main Street. Brand new kitchen with all new cabinetry, appliances and quartz countertops. All new windows throughout, 2 brand new bathrooms, new paint both interior and exterior, and newly sanded floors. Old world charm with the amenities of today. Very easy to maintain home. Airbnb Rental Income of $4,000 per month.

152 Main St, Grafton

$499,000

2 Beds ⋅ 2 Baths ⋅ 5106916 MLS

Celebrate! You have earned it! A gentle neighborhood for 55 and more, mowing, plowing and shoveling included in the HOA.. Leave the tough stuff for the young at heart! Sit snug as a bug in the sun room and watch it snow, without a care or worry, or run off to play pickle ball in the warm seasons....Want to be snow birding? Perfect set up as the home is easy care inside and out. Park a car in the garage for the winter and forget about it till spring. Comfort is what you deserve and have earned. This is it.

171 Buttonwood Dr, Brattleboro

$525,000

3 Beds ⋅ 3 Baths ⋅ 5106903 MLS

Just what you have been waiting for! The perfect spot in the perfect neighborhood! Watch the moon rise over Wantastiquet and the seasons change from your back yard! Listen for spring...when the ice cracks on the river and lets go...and watch the shoots pop to greet a new warm and beautiful summer season. This contemporary raised ranch has a wall of windows to the garden, a lovely little wood stove for chilly evenings and a cook's kitchen. The Star Trek elevator allows you to age in place, drive in to the garage, step on the elevator and zoom to the main floor so every inch of the house is accessible. Recently renovated, this is worth seeing. Possession on 11/6/26. Join us at the Open House 8/30/26, 11-1.

205 Wantastiquet Dr, Brattleboro

$349,000

4 Beds ⋅ 3 Baths ⋅ 5106862 MLS

Woodsy and charming ski chalet just a short drive from the village of Wilmington and Harriman Reservoir, and 10 minutes to the Mount Snow ski resort. This home sits on a private wooded lot, nestled in the Chimney Hill community with easy access thanks to a circular driveway, and just down the hill from the amenities building. The home has been partially updated and cared for and features a large living room with exposed woodwork, great natural light from the large windows, a wood burning stove and brick hearth, spacious dining area which leads into the large kitchen, media room which could serve as a main floor bedroom, large mudroom entry with ample gear storage and full bath, and spacious deck for entertaining. The upper level has 4 vaulted bedrooms as well as a second full bathroom. There is a full walkout lower level for tremendous expansion potential. Featuring the tremendous Chimney Hill amenities including indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep.

3 Woodchuck Ln, Wilmington

$325,000

3 Beds ⋅ 1 Baths ⋅ 5106844 MLS

Enjoy the best of Vermont country living in this bright, 3-bedroom, 1-bath home set on 2+/- mostly wooded level acres just off Route 100. The property offers plenty of room to relax, play, garden, and enjoy the outdoors. A covered porch provides a welcoming spot to take in the peaceful surroundings. Inside, the home features a spacious open kitchen, living, and dining area with a large primary bedroom, Its own private deck with hot tub. Two additional bedrooms, and a full basement offering plenty of storage. Recent improvements include fresh interior paint. Outdoor enthusiasts will love the location, with nearby VAST snowmobile trails, Lake Whitingham/Harriman Reservoir just minutes away for boating and fishing, and Mount Snow approximately 20 minutes away for skiing, snowboarding, hiking, mountain biking, and golf. Downtown Wilmington, with its shopping, dining, and local amenities, is only about 10 minutes away. Only 30 minutes to MASS MoCA. The oversized detached 2-car garage offers plenty of room for vehicles, recreational equipment, and toys, plus a full upper level for storage or future use. With easy access from Massachusetts, Connecticut, New York, and southern Vermont, this property makes an excellent year-round residence, vacation getaway, or Vermont retreat. Move-in ready and priced to sell. Come enjoy everything Mount Snow, Deerfield Valley has to offer!

639 Wilmington Cross Rd, Whitingham

$299,000

3 Beds ⋅ 1 Baths ⋅ 5106777 MLS

OPEN HOUSE: Saturday, 8/29, 11-2pm. This charming 3 bedroom, 1 bath Vermont home is full of personality, character, and vintage charm, offering inviting spaces both inside and out! Situated on 1 acre, with part of the land offering direct frontage on the Rock River, you'll enjoy your own little summer time paradise. Inside, warm wood floors, and unique architectural details give the home a character all its own. With a first floor bedroom, bathroom and two bedrooms upstairs, this home can work well for most lifestyles and stages of life. The whimsical finished attic offers possibilities for a studio, reading retreat, additional bathroom or creative space. The layout of the home offers enough space to spread out. A detached shed adds even more versatility. The covered front porch is perfect for morning coffee or lazy afternoons, while gardens, flowering hydrangeas, a sweet picket fence, and a spacious lawn create a storybook setting surrounded by the woods and just across the street the beautiful Rock River, for a personal swimming spot or fishing hole. Recent improvements include a new leach field, spray foam insulated attic and crawlspace, and some exterior painting. Colorful, cozy, and full of soul, this is a home with character and a lovely setting, just minutes from the quaint village of Newfane, just 12 miles from both Mount Snow ski resort and in the other direction, the vibrant town of Brattleboro.

311 Dover Rd, Newfane

$465,000

4 Beds ⋅ 3 Baths ⋅ 5106736 MLS

This spacious Londonderry contemporary house sits on a sunny, level one-acre lot and is conveniently located at the base of Glebe Mountain and mere minutes from Magic Mountain for snow sports and Lowell Lake for summer hikes, kayaking and keeping an eye on the native loons that nest there. The layout offers three levels of bright and roomy living spaces with a comfortable floorplan and lots of room for gathering or finding private quiet time. The main level features a large kitchen and dining area, living room with fireplace and vaulted ceilings, and two bedrooms including an expansive primary suite with a fireplace, walk-in closet and private bathroom. Above is large loft, partially open to the area below and suitable for almost any use (home office, library, play space) with lots of attic space for storage. A partially finished lower level (above grade at the rear of the house with full walk-out and regular windows) has a large rec room with pellet stove and hearth, two additional bedrooms, laundry, full bathroom, bonus room, and a large workshop in the mechanical and utility area. The two-car garage with workshop and upper level, and a garden shed complete the offering. Renovations were in progress but incomplete, and the house needs work (mostly cosmetic) and updating, and it is priced to reflect that need. Londonderry is a dynamic community with a good mix of primary and vacation homes with access to great schools, shopping and dining, four-season recreation in any direction, arts and music through the year, and a fantastic farmers market in the summer and fall. The location and community will support your investment, so come take a look!

2855 Thompsonburg Rd, Londonderry

$435,000

4 Beds ⋅ 2 Baths ⋅ 5106611 MLS

This four bedroom, 2 bath home sits on 10 acres with 2 streams. The house features a large country kitchen, living room with upper level office or play room loft, solid wood doors, bluestone entry floor. There is a large concrete basement under under the bedroom wing. Additional features include: full house generator and a large 3 bay garage. There is direct access to snowmobile trails. The house is sold unfurnished...the photos showing furniture are virtually staged.

1752 E Dover Rd, Dover

$629,000

5 Beds ⋅ 3 Baths ⋅ 5106583 MLS

Perfectly positioned for enjoying all that the Mount Snow area has to offer, this beautifully updated home is located just 1.5 miles from Mount Snow Ski Resort and approximately 1 mile from the Mount Snow Golf Course. Step inside to a bright and inviting interior featuring vaulted ceilings, beautiful wood floors, mini-splits for year-round comfort, and a cozy woodstove the perfect place to warm up after a day on the slopes. The completely remodeled kitchen is a standout, offering stainless steel appliances, a farmhouse sink, and a charming dining nook ideal for casual meals and gatherings. The main level features warm wood flooring throughout the living spaces, complemented by tiled bathrooms. The home is being offered mostly furnished, making it easy to settle in and start enjoying your Vermont getaway. The finished lower level provides additional living space with a spacious family room and convenient walkout access, offering plenty of room for guests, recreation, or relaxing after a day of outdoor adventures. Outside, enjoy the peaceful setting from the deck overlooking the beautiful property, along with the added convenience of a detached two-car garage for vehicles, recreational gear, and storage. With its extensive updates, comfortable and welcoming interior, beautiful setting, and exceptional proximity to Mount Snow skiing, golf, dining, and year-round recreation, this property is an ideal choice for a primary residence, vacation retreat, or Vermont mountain getaway.

13 Circle View Dr, Dover

$479,000

2 Beds ⋅ 2 Baths ⋅ 5106580 MLS

It has all you wanted! Shiny wood floors to celebrate New England building, plenty of windows to capture every inch of light possible, granite tops on a multitude of cabinets, a step in shower but also a tub for long soaks or the little ones who visit....total one floor living, so rare locally, even no stairs to the direct entry garage. A service that plows, shovels and mows.....a playground for adults with pickle ball, dedicated exercise room, meeting room and kitchen, and a cozy place by the fire to sit and visit. If you are at an age when you can appreciate an easier lifestyle, come take a look and see if this is your next adventure. This property is being subdivided from a larger parcel.

162 Buttonwood Dr, Brattleboro

$449,000

3 Beds ⋅ 2 Baths ⋅ 5106545 MLS

Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready! Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse located at 2,000' on the Hill, featuring year-round swimming, new hot tub, fitness room, arcade room, playroom, community room, fully equipped members kitchen, reading nook, après ski lounge, 3 tennis court areas plus basketball court, extensive multi-use trail system, snowmobiling, ice skating, pickleball and tennis, stocked fishing pond, hiking, biking, and more! Plus, the Deerfield Valley offers world class skiing and shredding literally minutes away, fine and casual dining, unique shopping, escape room, mini, disk, and traditional golf, kayaking, canoeing, pontoon and sail boating, paddleboarding, the Green Mt National forest, antiques, flea markets, breweries, wineries, distilleries, music, theater, equestrian events, and so much more!

47 Upper Howes Rd Unit A-23, Wilmington

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