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Windham County Real Estate

Windham County is located in Southern Vermont and borders Massachusetts.  It is home to some of the finest skiing in New England at Stratton Mountain. Windham County is also home to very well respected institutions such as Marlboro College and the Central Vermont Medical Center. The largest city and towns in Windham County are Brattleboro and Rockingham, which includes Bellows Falls and Saxtons River. Browse available Windham County real estate below. 

Windham County VT Homes for Sale

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169 Silver Lane Wardsboro VT 05355

MLS Number 5028880

  • Residential Single Family
  • Full Bath 2
  • Address 169 Silver Lane
  • Construction Existing
  • Bedrooms 3

This charming 3-br, 2-1/2bath, Moosehead log cabin in Snow Mountain Farms is the ideal Vermont retreat for winter and beyond. Surrounded by a tranquil wooded landscape, the home is perfectly situated between Mount Snow and Stratton Mountain, offering convenient access to skiing, hiking, VAST snowmobile trails, and year-round outdoor adventures. Step inside to discover the warmth and character of natural woodwork throughout, thanks to the home's real log construction. The main floor features a welcoming living room with a stunning fieldstone fireplace, creating a cozy space to unwind after a day outdoors. The open kitchen includes a spacious dining area, stainless steel appliances for entertaining or casual meals. Upstairs, you'll find a generously sized bedroom providing privacy and space for family or visitors. Outdoor living is just as inviting, with a large deck perfect for entertaining, a covered front porch for relaxing, an outdoor hot tub in a gazebo and a private lot surrounded by nature. The home has been thoughtfully built with modern conveniences. Located just down the road from the community amenities, you'll enjoy access to an indoor pool, tennis courts, and nearby snowmobile trails. Whether you're seeking a peaceful mountain escape or an active outdoor lifestyle, this log cabin offers the perfect combination of rustic charm and modern updates in a prime Vermont location.

Listed by Donald Koelsch of Deerfield Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2a Dover Green Loop Dover VT 05356

MLS Number 5028878

  • Condo
  • Square Feet 1,200
  • Bedrooms 3
  • New Contruction Existing
  • Complex Dover Green

Bright updated 3 bed, 2 bath end-unit townhome near Mount Snow with access to the free public shuttle to the slopes, restaurants and beyond. Featuring high ceilings, abundant windows, brick wood burning fireplace and tasteful blend of modern updates while retaining that rustic ski-home feel. Recent updates include new baseboard heating controlled by a Wi-Fi-enabled smart thermostat, fresh interior paint, new plumbing and light fixtures, new low maintenance vinyl flooring. The kitchen also features high end renovations including granite counters, stainless appliances and a large industrial sink with a high-end faucet. The living room has soaring ceilings, fireplace focal point and access to private 2nd floor deck space. The first floor includes a primary suite, full laundry, ample closet space, an additional guest bedroom, and a full bath. A heated airlock mudroom is accessed off the covered front porch and is roomy enough to store your outdoor gear. A spacious lofted third bedroom is a great multipurpose space. Enjoy this corner lot location with a generous yard and ample parking. The building has a new roof and has been well maintained. Highspeed internet, wifi controlled door locks and water heater, reasonable HOA fees. Available for same day showings and a quick closing, imagine finishing out the ski season in your own Vermont getaway.

Listed by Jacki Murano of Southern Vermont Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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106 Silver Birch Dover VT 05356

Dover, VT106 Silver Birch

Price$495,000

Est. Mortgage: $/month

MLS Number 5028874

  • Condo
  • Square Feet 1,900
  • Bedrooms 2
  • New Contruction Existing
  • Address 106 Silver Birch

This 2 bedroom plus bunkroom end unit condo is located across the road from the Mt. Snow ski area. There is a shuttle that will allow you to be free from driving and parking fees. Relax in your private hot tub after or sit on this spacious deck an enjoy the view. A cozy wood-burning fireplace sets the mood for your apre' ski afternoon. On a rainy or cold day, enjoy the Sugar House recreation area with many amenities such as raquet ball, indoor pool, locker rooms, updated work out area and much more. Use as is or personalize it to your liking. Recent updates include new living room and hall way floors, freshly painted walls on the main level and soon to have all new appliances and dining table and chairs just purchased. (after 2/20)

Listed by Regina Perrotto of Skihome Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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49c Greensprings Road Dover VT 05356

Dover, VT49c Greensprings Road

Price$698,000

Est. Mortgage: $/month

MLS Number 5028855

  • Condo
  • Square Feet 2,472
  • Bedrooms 3
  • New Contruction Existing
  • Year Built 1988

Located in the desirable Greensprings neighborhood at Mount Snow Ski Resort, this spacious 3-bedroom, 4-bath townhome offers the perfect blend of mountain charm and modern comfort. The inviting interior features a soaring cathedral ceiling in the living room, anchored by a cozy wood-burning fireplace, creating the perfect apres-ski retreat. A second family room adds flexibility, ideal for gatherings, game nights, or a private media space. The open-concept kitchen and dining area are designed for easy entertaining, while large windows and a private deck with stunning mountain views. Residents enjoy exclusive access to the Greensprings Sports Center, complete with an indoor pool, hot tub, fitness room, and games rooms for year-round relaxation. Outdoor enthusiasts will love the tennis and pickleball courts, while the convenient shuttle service to Mount Snow makes hitting the slopes effortless. For those seeking more adventure, the prestigious Hermitage Club is just a short drive away. Whether you're savoring the warmth of the fireplace, enjoying the panoramic views, or embracing the vibrant outdoor lifestyle, this townhome is the ultimate Vermont getaway.

Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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69 Chapin Lane Jamaica VT 05343

Jamaica, VT69 Chapin Lane

Price$584,000

Est. Mortgage: $/month

MLS Number 5028853

  • Residential Single Family
  • Full Bath 2
  • Address 69 Chapin Lane
  • Construction Existing
  • Bedrooms 4

Welcome to Sugar Chateau- Nestled in the serene landscape of Vermont, this enchanting 4-bedroom log home offers the perfect blend of rustic charm and contemporary comfort. Embrace the warmth and character with exposed beams and a welcoming atmosphere.Enjoy the convenience of modern amenities in a rustic setting, featuring a recently renovated kitchen and bathrooms. Custom new Anderson Windows throughout the home as well. The finished Lower Level is ideal for entertainment or relaxation and provides additional living space with 3/4 bath, laundry room, den area and walk out access. Wonderful Outdoor Living space-unwind on the spacious deck with stunning views of Vermont's natural beauty. Relax in the hot tub after a day of skiing or hiking. Experience the best of both worlds - tranquility and convenience. Located just 15 minutes from Stratton Mountain Resort and a short drive to Jamaica village, offering local shops, dining, and community events. Your Vermont Retreat awaits, whether you're seeking a weekend getaway or a year-round residence, this charming log home offers a unique opportunity to embrace Vermont's lifestyle. See list of updates to this home under Documents.

Listed by Tara van de Velde and Andie Fusco of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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147 Gilbert Road Marlboro VT 05344

Marlboro, VT147 Gilbert Road

Price$499,000

Est. Mortgage: $/month

MLS Number 5028826

  • Residential Single Family
  • Full Bath 1
  • Address 147 Gilbert Road
  • Construction Existing
  • Bedrooms 3

This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past 24 months by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting design. New heat pumps, insulation and septic provide a clean slate for any homebuyer. All brand-new furnishings for an easy transition. A babbling brook runs along one side of the property, leading to the nearby West River. The home is also an easy commute to Brattleboro for unique eateries, farmers markets, gallery walks and so much more. If you are a skier, Mount Snow is nearby! Hikers will have the opportunity to explore the almost 50 acres this property has to offer. Plenty of open space is available for vegetable gardening, as well. This truly is a lovely home waiting for its next chapter to unfold. (Deed says 52.5 plus or minus and tax bill says 49 acres.)

Listed by Monica Sumner of BHG Masiello Brattleboro

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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317 Putney Mountain Road Putney VT 05346

Putney, VT317 Putney Mountain Road

Price$145,000

Est. Mortgage: $/month

MLS Number 5028823

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 1
  • Bathroom 1

Are you looking for a country cottage, off the beaten path but not too far off? A place with tons of potential but needing some TLC to bring it back to full glory? Then this property, located near the top of Putney Mountain, may be just the ticket. As the story goes, the original shepherd's cabin on top of Putney Mountain was moved to this site back in the 60s and the rest of the home was added on in the 70s. Since then it has been enjoyed as a full-time residence. The kitchen area, the original shepherd's cabin, is big enough to accommodate a kitchen/dining arrangement. Just down the hall in the addition is a full bath including washer/dryer hookups, and just beyond is the bright and comfortable living room with hardwood flooring, wrap-around windows, and a door leading to a large deck. Conveniently off the living room is a small den. Upstairs, the bedroom is big and bright as well, and there's a roll-out ladder leading to a loft. Outside you'll find a 2-story outbuilding with multiple possible uses, plus a chicken coop and woodshed. Just up the road there are miles of trails for hiking and biking. Bring your imagination to this country gem in the making and have your Vermont dreams come true.

Listed by Bill Hickok of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19a Kingswood Road Dover VT 05356

Dover, VT19a Kingswood Road

Price$529,000

Est. Mortgage: $/month

MLS Number 5028790

  • Condo
  • Square Feet 1,850
  • Bedrooms 3
  • New Contruction Existing
  • Address 19a Kingswood Road

This three-bedroom plus den townhome boasts an exceptional location only steps from the Kingswood Community Center and an easy shuttle ride to Mount Snow. This townhome features 3 full bathrooms, vaulted ceilings, a wood-burning fireplace, an open-concept living/dining space, and a private deck with wooded views and outdoor hot tub. This home offers a perfect blend of comfort and convenience. The furnace and hot tub have also recently been replaced to ensure efficiency and longevity. For leisure and recreation, the nearby community center, just a quick walk away and offers an array of amenities including an indoor pool, full gym, game room, and community kitchen area. The Kingswood Community is conveniently nestled between the Hermitage Club and Mount Snow. With hiking, snowshoeing, and cross-country skiing all accessible via the Valley Trail System. Outdoor enthusiasts will find endless opportunities for adventure. In addition, as an owner in Kingswood, not only will you possess a slice of Vermont paradise, but you'll also relish the ease and convenience of having maintenance, snow removal, trash service, wood delivery, and any potential issues expertly managed by the friendly and attentive staff at the Community Center. Your Vermont getaway awaits, offering the ideal balance of serenity within a private community setting.

Listed by Melissa Ellis of Southern Vermont Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1105 South Hill Road Jamaica VT 05343

Jamaica, VT1105 South Hill Road

Price$119,000

Est. Mortgage: $/month

MLS Number 5028721

  • Land
  • Address 1105 South Hill Road
  • Acreage 10.2
  • Area VT-Windham
  • PricePerSqFt 11666.67

Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the frontage and high-speed internet is available. Generally mixed hardwoods with large, majestic pines with cedar mixed in. The property slopes slightly to the South and clearing to the south or east may allow for views of the local hills or solar options. Several nice potential building spots, one close to the road and one about 500' back from the road. No septic soil testing has been completed, but the neighbor to the north just received their state septic permit, soils should be similar. There is a small brook at the rear of the property. Easy access to Stratton, Bromley, and Mt. Snow ski resorts.

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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473 Williams Street Brattleboro VT 05301

Brattleboro, VT473 Williams Street

Price$310,000

Est. Mortgage: $/month

MLS Number 5028690

  • Residential Single Family
  • Full Bath 1
  • Address 473 Williams Street
  • Construction Existing
  • Bedrooms 2

Sunny South-Facing End Unit Townhome with Land in Brattleboro, VT. Enjoy the perfect blend of privacy, natural light, and convenience with this unique south-facing end unit townhome. This home is one of three townhomes that share a common wall, has its own land and no HOA fees. Located just minutes from downtown, the Farmers Market and other community events. Versatile! This light filled, well cared for home has ample living and storage space with a first floor bonus room that you could use as a bedroom, office or media room. Open concept living room, dining room & kitchen with first floor half bathroom & pantry. The second floor has 2 bedrooms and a full bathroom. If organizing is your thing you will love the custom organizing systems in each closet. Recent updates include a newer roof, windows, and an efficient Buderus hot water tank. The large, dry basement provides plenty of additional storage space. Step outside to enjoy the pops of color in the established flower beds and the large sprawling deck perfect for relaxing or entertaining guests during the warmer months. Whether you're hosting a gathering or simply enjoying your own private space, this home is a delight. If you are looking for a light filled home that you can move right into and is easy to maintain, convenient to downtown yet private with a flexible layout & storage space - this is the one for you.

Listed by Liz LaVorgna of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

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. Data last updated February 8, 2025 11:07 PM EST