Windham County Real Estate

**Discover the Charm of Windham County, Vermont**

Nestled in the heart of southern Vermont, Windham County is a picturesque region that perfectly blends natural beauty, rich history, and vibrant community life. Known for its rolling hills, lush forests, and pristine waterways, this county is a haven for outdoor enthusiasts and those seeking a serene lifestyle.

Windham County boasts a diverse range of activities year-round. In the warmer months, residents and visitors alike can explore the stunning trails of the Green Mountain National Forest, indulge in kayaking on the Connecticut River, or take in the breathtaking views from the summit of Mount Wantastiquet. As the leaves turn in autumn, the county transforms into a canvas of vibrant colors, making it a prime destination for leaf-peeping and photography.

Culturally rich, Windham County is home to charming towns like Brattleboro, put on the map by its thriving arts scene, eclectic shops, and delightful eateries. The annual Brattleboro Literary Festival and the vibrant local farmers' markets are just a few examples of the community's commitment to celebrating creativity and local culture.

Education and community are at the forefront in Windham County, with a variety of schools and programs that foster lifelong learning. The sense of belonging here is palpable, with friendly neighbors and a welcoming atmosphere that makes everyone feel at home.

Whether you’re looking to settle down, invest in a vacation property, or simply explore a new area, Windham County offers an enchanting blend of nature, culture, and community that is hard to resist. Come and discover why so many have fallen in love with this hidden gem in Vermont!

Newest Listings in Windham County

$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

$314,900

5107035 MLS

Don't miss out on this excellent opportunity to purchase this fully vacant 3-unit Victorian offering immediate cash flow potential with zero tenant transition delays. Built in 1890, featuring gorgeous detailed woodwork and classic styling throughout including 12-foot ceilings, this 4,500 sq ft in-town property combines historic character with income-producing infrastructure already in place. This property offers (3) 2-bed/1-bath units 1 unit on each floor of the home. All Three of the units have fully separated utilities, there are 4 electric meters, 2 individual furnaces, and 3 electric hot water heaters minimizing owner-paid utility exposure. The Lot itself is 0.29-acre in-town lot with a large backyard and on-site parking on both sides of the building a rare combination for a downtown multi-family. Make your appointment today!!

19 Henry St, Rockingham

$479,000

2 Beds ⋅ 2 Baths ⋅ 5107011 MLS

This beautifully refreshed two-bedroom, two-bathroom condo at Seasons on Mount Snow is an ideal mountain retreat. Located just across from Tin Lizzy, you'll have trails practically at your doorstep, ski or ride down to Sundance and catch a lift to the main mountain or over to Carinthia. Inside, the unit strikes a balance between modern style and thoughtful mountain-life functionality. Recent updates include a new boiler (installed 2022), chic contemporary furnishings throughout the living room, dining area, and both bedrooms, and a Samsung Frame TV added just last season. Designed with skiers and riders in mind, the home features smart storage solutions like custom crafted closet systems and a boot bench with helmet cubbies to keep gear organized. A dedicated ski closet with keyless access is also located at the building entrance. The open concept living and dining area centers around a fieldstone, wood-burning fireplace, creating a warm and inviting atmosphere with plenty of room for hosting. Beyond the unit, the Seasons community offers premium amenities including indoor and outdoor pools, a well equipped gym, and a comfortable lounge. With onsite property management for added ease, this property represents mountain living at its finest.

1g Northbrook Village Way Unit D23, Dover

$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. 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

$29,900

2 Beds ⋅ 2 Baths ⋅ 5106781 MLS

Move quickly, and you can own Christmas to New Year's this ski season to use or rent! Enjoy breathtaking mountain views and the ultimate trailside lifestyle with this beautiful two-level, two-bedroom quartershare at the Grand Summit Resort Hotel! Ideally located at the base of Mount Snow, this deeded quartershare offers 13 weeks of vacation ownership each year, with one week every 28 days on a rotating schedule. This mountain-facing unit features an open-concept kitchen and dining area, a spacious living room with a queen sleeper sofa, and a private bedroom with a full bath on the main level. Upstairs, you’ll find a second bedroom with its own ensuite bathroom, providing comfortable accommodations and privacy for family and guests. As a Grand Summit owner, you can use it, rent it, or trade it for stays at other vacation destinations. Enjoy year-round access to an impressive array of resort amenities, including valet parking, a private owners’ lounge, library and deck, full-service fitness center with sauna and steam room, outdoor hot tubs, heated pool, and private owners-only locker rooms for convenient year-round storage of ski or golf equipment. One of the most popular ownership perks is Space A, which provides the opportunity to enjoy additional stays at the hotel outside of your scheduled ownership weeks at a discounted rate; just pay the housekeeping fees, subject to availability. With its prime ski-in/ski-out location, beautiful mountain views, flexible ownership benefits, and exceptional resort amenities, this is a wonderful opportunity to own a piece of the Mount Snow experience. RCI and Interval International affiliated.

309 Qtr 3 Grand Summit Way, Dover

$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

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