Windham Homes for Sale

Welcome to Windham County, Vermont, a picturesque haven nestled in the heart of New England. Known for its stunning natural landscapes, charming small towns, and rich cultural heritage, Windham County offers a unique blend of outdoor adventure and community spirit. Whether you’re seeking a weekend retreat or a permanent residence, this enchanting county is the perfect place to call home.

Windham County is renowned for its breathtaking scenery, with rolling hills, lush forests, and pristine lakes that invite exploration and relaxation alike. Outdoor enthusiasts will delight in the plethora of activities available, from hiking and biking in the warmer months to skiing and snowboarding at nearby resorts during the winter. The county is also home to the historic town of Brattleboro, where you can enjoy vibrant arts, local cuisine, and a bustling farmers’ market that showcases the best of Vermont’s bounty.

When it comes to finding your dream home, Windham County has an array of properties for sale that cater to diverse lifestyles and budgets. From charming Victorian houses and cozy cabins to modern condos with stunning views, there’s something for everyone. Each home is a gateway to the serene beauty and warm community spirit that Windham County embodies.

Imagine waking up to the sound of birds chirping and the sight of stunning mountain vistas, all while being just a stone's throw away from local shops, restaurants, and recreational activities. With homes for sale in this idyllic area, you can turn that dream into a reality. Explore the opportunities that await you in Windham County, where every day feels like a vacation!

Newest Windham Homes for Sale

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 5101689 MLS

10 MINUTES TO STRATTON RESORT | This beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition, and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from Stratton Mountain Resort and less than a mile from Honeypie Restaurant and Rawsonville Market, the location offers easy access to the mountain, local favorites, and everything the area has to offer. High ceilings, generous windows, and two sunrooms fill the interior with natural light, while quality construction and thoughtful details are evident throughout. Recent improvements include a standing-seam metal roof, new Marvin windows, mini-split heating and cooling, new appliances, a large new deck, a new drilled well, a whole-house generator, an EV charger, restored floors and fir doors, updated tile, and custom built-ins. The property has a deep connection to the surrounding land. Beautiful landscaping and stonework complement an open field, apple orchard, raised garden beds built with hemlock milled from the property, and a useful storage shed. The large deck with hot tub creates an inviting place to relax and take in the serene setting. Situated along the Winhall River with direct access to the West River Rail Trail, the property makes it easy to walk, bike, swim, and enjoy the outdoors right from home. A five-bedroom septic system provides flexibility for future expansion. This is the Vermont home you have been looking for-full of character, warmth, and history, yet updated with the level of care and quality that makes ownership easy from day one. A trusted local builder has already done the hard work. Make this your Vermont address. Seller is the listing broker. Neighboring property available 494-498 Goodaleville Road - MLS#5101688. Showings begin 7/24.

564 Goodaleville Rd, Jamaica

$1,450,000

5 Beds ⋅ 4 Baths ⋅ 5101688 MLS

10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit that have long defined it. Thoughtfully renovated by Vermont Country Builders, the home preserves its historic soul while providing quality and efficiency suited for each season. The main house spans three finished levels. An expanded kitchen with soapstone countertops opens to a spacious dining room and cozy sitting area with gas fireplace. Original wide-plank floors, antique doors, and a classic clawfoot tub celebrate the home’s heritage. Extensive improvements include modern insulation, electrical, plumbing, a new foundation, sheetrock, high-efficiency propane boiler, HRV ventilation, mini-splits, Marvin windows, and an improved floor plan. Additional upgrades include standing-seam roofs on all three buildings, custom gutters and snow guards, updated baths, custom built-ins, new appliances, and AZEK decks. A separate guest house, originally Schapiro’s art studio, offers a self-contained one-bedroom apartment with SMEG appliances, in-unit laundry and private hot tub. Below is a large heated storage area and screened porch. The vintage barn has been stabilized and restored with parking and EV charger. Extensive stonework, thoughtful landscaping, gardens, decks, a stone patio, and welcoming front porch complement the setting along the Winhall River. Direct access to the West River Rail Trail makes it easy to walk, bike, swim, and explore right from home. Less than a mile from Honeypie and Rawsonville Market and only minutes from Stratton Mountain Resort. Listing agent is related to seller. See neighboring property MLS # 5101689. Showings begin 7/26.

494-498 Goodaleville Rd, Jamaica

$519,000

3 Beds ⋅ 3 Baths ⋅ 5101601 MLS

A wonderful Colonial home in Dummerston Village Vermont. Classic layout with a huge primary bedroom with double closets, 2 additional generously sized bedrooms and a full bath on the second floor. The first floor has a large family room, dining room, a full bath with laundry, and a lovely 1/2 bath. Freshly updated with a new roof, new Anderson windows, new high efficiency furnace, whole house air conditioning, remodeled kitchen with all new LG appliances, remodeled bathroom with new tile floors. Light and bright! It’s perfect!

56 Park Laughton Rd, Dummerston

$209,900

3 Beds ⋅ 2 Baths ⋅ 5101481 MLS

Here's a 3 bedroom, 2 bath home in Bellows Falls that's been fully renovated and is ready for someone to just move in and enjoy. No projects! All done for you! The front and side porches are a nice touch! The location can't be beat: you're right in town, close enough to walk to shops, restaurants, and everything else downtown Bellows Falls has going on. This one would suit a first time buyer, someone looking to downsize, or anyone who wants a home that's already updated and easy to live in. 7 Underhill Ave is worth a look.

7 Underhill Ave, Rockingham

$235,000

3 Beds ⋅ 2 Baths ⋅ 5101448 MLS

Set on 2.2 wooded acres in Marlboro, this 3-bedroom, 2-bath Cape offers 1,410 square feet of living space and plenty of classic Vermont character. The main level features a spacious kitchen and dining area, a comfortable living room with a brick fireplace and hearth, a first-floor bedroom, full bath, and convenient laundry hookups. Two additional bedrooms and a second full bath are located upstairs. Outside, the level and gently sloping grounds provide room to garden, relax, or enjoy the surrounding woods, a lovely haven for nature and wildlife viewing. A detached two-car garage offers extra-large covered parking with valuable storage space above, ideal for vehicles, toys, or business equipment. Additional highlights include fiber-optic internet availability, a private spring water source, and multiple heating options, including wood and pellet stoves. Conveniently located along Route 9 with easy access to Brattleboro and Wilmington, this residential/commercial property is ready for its second owner to make it their own.

2022 Rte 9, Marlboro

$690,000

5 Beds ⋅ 4 Baths ⋅ 5101430 MLS

Welcome to "Pipe Dream", a cherished family vacation home for nearly two decades. This residence seamlessly blends history, charm, and modern touches to create a truly unique experience. The outdoor space of 3.5 acres is nothing short of magical, featuring stone walls and steps, an inviting in-ground pool, and a tennis court. The expansive level yard offers plenty of room for outdoor fun, while the covered front porch invites you to enjoy your morning coffee, curl up for a lazy afternoon, or take in the Fourth of July fireworks. Additionally, two decks provide ample space for lounging, dining, and more. Inside, the home offers a variety of spaces designed to foster togetherness and relaxation. Gather around the fire in the cozy family room for game nights, or retreat to the den for some quiet time with a good book. The great room is perfect for accommodating the entire gang, while the downstairs recreation space, complete with a pool table/ping pong and foosball, promises endless entertainment. With five bedrooms and several bonus rooms, everyone can enjoy their own private retreat. A Vermont room upon entry to the lower level provides storage for coats, boots, gear, and more. The original structure is complemented by an 840 square-foot permitted addition, which includes a two-car garage, deck, great room, and one of the bedrooms and bathrooms. This home is ideally situated close to town, allowing for easy access to shops, restaurants, village events, and public transportation. It's also just a stone's throw from Harriman’s Reservoir, where you can indulge in boating and swimming. Whether you envision this as your primary residence or vacation getaway, "Pipe Dream" has everything you need. Its prime location offers easy access to Mount Snow Resort and the Hermitage Club for skiing and snowboarding, as well as Mount Snow and Haystack public golf courses. Consider making this extraordinary house your next dream home.

57 Castle Hill Rd, Wilmington

$399,000

2 Beds ⋅ 2 Baths ⋅ 5101312 MLS

Privately nestled at the end of a secluded drive, this quintessential Vermont retreat offers extraordinary privacy and serene mountain views in every direction. Set on a beautifully landscaped parcel with mature trees and an expansive lawn, the property exudes peace and timeless New England charm. The home features 2 bedrooms, 1.5 bathrooms, generous storage, and a detached two-car garage. A classic Vermont barn, currently serving as a recording studio, provides exceptional flexibility for creative pursuits, a workshop, or additional recreational space. Ideally located just minutes from ski areas, shopping, and Grace Cottage Hospital, this is a rare opportunity to enjoy the beauty, serenity, and convenience of Southern Vermont living.

254 Lawrence Dr, Townshend

$299,000

13 Beds ⋅ 8 Baths ⋅ 5101276 MLS

Bring your vision to this unique property filled with opportunity! Offering approximately 13-15 bedrooms, this expansive home was formerly operated as a care facility and has most recently served as a residential property. With the appropriate approvals, it may also offer potential for conversion to a multi-family residence. Many of the bedrooms feature their own attached bathrooms, ranging from private half and full baths to rooms with individual sinks. The home is heated by two oil furnaces, with a propane boiler serving the third floor and two pellet stoves providing supplemental heat on the first floor. Outside, you'll find two spacious decks that are perfect for entertaining, relaxing, or enjoying Bellows Falls' local parades. While the property is in need of TLC and updating, its generous size, flexible layout, and abundance of living space create an exceptional opportunity for investors, developers, or buyers looking to restore a truly distinctive property. Bring your imagination and discover the possibilities!

99 Atkinson St, Rockingham

$167,900

2 Beds ⋅ 1 Baths ⋅ 5101139 MLS

Welcome to this charming 2-bedroom, 1-bath Colonial offering warmth, character, and a convenient location near Bellows Falls and I-91. Inside, you’ll find inviting living spaces filled with natural light, wood flooring, exposed wood accents, and a spacious kitchen featuring an island and plenty of room to gather. The home offers approximately 1,242 square feet of finished living space, first-floor laundry hookups, a wood stove, and two comfortable bedrooms upstairs. Outside, enjoy a covered porch, patio area, landscaped yard, and a wooded backdrop that adds privacy. An attached one-car garage with direct entry and additional driveway parking provides everyday convenience. With public water, high-speed internet availability, and easy access to nearby schools, village amenities, and major travel routes, this character-filled home is ready for its next chapter.

243 Vt Route 121, Westminster

$260,000

4 Beds ⋅ 3 Baths ⋅ 5101087 MLS

Beautiful 1925 stucco Craftsman home needing TLC. Narrow strip oak flooring throughout, brick fireplace with original oak trim, original windows, beautiful oak staircase, arched doorways, dining room with enclosed porch, and a big country kitchen. There are many original features that make this property a great investment. The main house offers 2 sunny bedrooms; the adjacent finished apartment has another two. You could live in the apartment while you work on updating the house. You'll need to budget for insulating the walls, extensive rewiring, renovating 2 bathrooms plus cosmetics. If you have a business or need storage, there is a 24' x 34' barn with electricity and a large concrete parking lot. Once you see all that's here, you'll quickly realize your investment will yield a spacious and comfortable home with reliable income potential in a convenient Guilford location.

106 Coolidge Highway Unit 6-276, Guilford

$330,000

4 Beds ⋅ 2 Baths ⋅ 5101085 MLS

Welcome to a bright, airy home that blends comfort, character, and convenience! Set on 1.26 acres of sunny lawn and wooded privacy, this four-bedroom, two-bath property offers inviting, freshly painted living spaces, central air, and efficient baseboard radiant heat. The living room features a welcoming fireplace, while the kitchen includes a woodstove setup and comes fully applianced with a dishwasher, refrigerator, gas stove, microwave, washer, and dryer. Upstairs, the primary bedroom makes a memorable impression with its vaulted ceiling and exposed brick chimney, adding warmth and architectural charm. Floors are easy to maintain light-toned vinyl planks with carpeted stairs for quiet. Practical features include a drilled well and town sewer, offering ease of ownership in a desirable setting. The location is especially convenient, just a short distance to Exit 1, making it easy to access nearby services, commuting routes, and local amenities. With character-filled details and a 1.26-acre setting, this property is ready to welcome its next owner.

36 Pauls Rd Unit 6-259, Guilford

$489,999

3 Beds ⋅ 2 Baths ⋅ 5100963 MLS

Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and options for a garage. Nice, landscaped level lot with a shed and woodbin, firepit and plenty of parking. Enjoy all the amenities Chimney Hill offers including the exclusive members only clubhouse, located at 2,000' in elevation, it's the perfect spot to enjoy year-round featuring indoor and outdoor heated pools, a brand new hot tub, fitness room, arcade, playroom, lounge, fully-equipped kitchen, playground, community room, table tennis, pickleball, ice skating, hiking, biking and snowmobiling on the 1,200 acre resort campus nestled between the Green Mt National Forest and the town of Wilmington VT. Minutes from world class skiing and shredding at either Vail's Mt Snow or the private Hermitage Club. Discover Southern VT and enjoy outdoor and indoor music, festivals, unique shopping and dining, antiques, flea markets, golf, boating, paddleboarding, and so much more! Owner's list of features and improvements: Two Mini-Split Units for AC/Heat, Replaced all Electric Baseboard Heating Units, Gasoline powered generator hardwired into the electric panel, New Electric Panel, Hardwired Ring Outdoor Cameras, Vapor Barrier Throughout Crawl Space, Flooring throughout the whole house, Window treatments, Furniture, Bedding, Kitchen Appliances, HWH on GMP Rental Program $10 mo., Washer & Dryer, Four Flatscreen TV’s, Safe in MBR, Kitchen Countertops, Both Bathroom Fixtures, Countertops & Toilets, Ceiling Fans & Ceiling Lights, Safety Railings & Wiring on Stairs & Loft, Storage/Woodshed Outside, Firepit.

7 High Top Rd Unit B-117, Wilmington

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