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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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6 River Road Newfane VT 05345

Newfane, VT6 River Road

Price$595,000

Est. Mortgage: $/month

Open House

MLS Number 4972392

  • Residential Single Family
  • Next Open House: Sat 10/7 11:00 am. to 2:00 pm.
  • Bedrooms 3
  • Construction Existing
  • Square Feet 4,268

Magical! This contemporary cedar-sided cape is a hidden gem. In a tranquil and private setting, it is easily accessible to charming Newfane Village and Brattleboro. Tucked away among majestic woods, open garden spaces, and picturesque stone walls, discover a harmonious blend of natural beauty and modern living. Inside you'll be greeted by a large updated kitchen with granite countertops, maple cabinetry, a six-burner stove, and a suite of stainless steel appliances. The open floor plan ensures you'll have a full view of the dining room, living room, and kitchen, making it a perfect hub for gatherings. Windows throughout the main floor provide captivating views of the property's beautiful surroundings. Convenience is paramount with two large first-floor bedrooms, a full bath, an office with built-in desk/shelves, and a level floor plan, ensuring easy access and utility. The fully finished basement offers several additional spaces, including 2 bonus rooms, a bathroom, and a den. On the second floor, you'll find a primary bedroom retreat complete with an en-suite bath featuring a luxurious deep jetted soaking tub. Oversized detached 2-car garage with large 2nd level for storage. And on top of all that, there's an incredible, very private wading/swimming area in Smith Brook! An exceptional property. 2.5 hrs. Boston. 30 Min. To Mount Snow & Stratton. Delayed showings until 10/7/23. Open House Sat. 10/7 & Sun. 10/8 11am-2pm.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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248 Valley View Road Dover VT 05356

Dover, VT248 Valley View Road

Price$675,000

Est. Mortgage: $/month

MLS Number 4972279

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 3,295
  • Bathroom 3

Lovely renovated and expanded chalet in the Dover Hills, just a short drive to the village and Mount Snow ski resort. This home sits nestled on a private double lot with great exposure and natural light. Easy access with a paved driveway off a paved road means you'll never have to worry about getting to your home away from home. Inside you will find a gorgeous open concept floor plan with great room for entertaining, gas fireplace with stone hearth, large upscale kitchen with granite counters and stainless appliances, primary suites on both the main floor and second floor, a guest bedroom and bath on the main floors, a second large family room complete with vaulted ceilings, wood stove, bar area, and gorgeous exposed woodwork, a lower level bunk room and billiard room, laundry, work shop, large mudroom, and a 2 car garage to stay out of the elements. Additionally there is a wraparound deck for fun in the sun, a detached fun hut with hot tub and sauna, ample additional wood and gear storage, direct snowmobile trail access, and ample yard space for enjoying your time in Vermont. Recent updates include energy efficient minisplit a/c throughout, updates to paint and carpet, a new hot tub, and more. A true getaway for entertaining and enjoyment.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • Square Feet 3,569
  • Bathroom 5
  • Bedrooms 4
  • Construction Existing

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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150 Country Lane Wardsboro VT 05355

Wardsboro, VT150 Country Lane

Price$489,000

Est. Mortgage: $/month

MLS Number 4972260

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 1,650
  • Bathroom 3

Lovely well maintained home in Wardsboro, just a short drive to both the Mount Snow and Stratton ski resorts, Grout Pond wilderness area, and other nearby lakes and country villages. Nestled on a private lot in the Snow Mountain Farms community, this home affords lovely privacy without being too remote. There is ample yard space for outdoor enjoyment, an attached garage for toys or keeping your vehicle out of the snow, and a spacious rear deck for entertaining. Inside you are treated to a gorgeous open concept great room with vaulted ceilings and exposed beams, a wood burning fireplace with brick hearth, great natural light thanks to expansive windows, exposed natural woodwork throughout, a large kitchen with solid surface counters and breakfast bar open to the dining area, a main floor primary suite, a main floor guest bath with laundry, 3 spacious upstairs bedrooms including a large room which could make for a tremendous family room or entertainment space, another full bath, and turn key condition throughout for immediate use. This home is just the right amount of space to be able to entertain, without being too much to maintain, affording downtime, not upkeep. The community also has an indoor pool, tennis court, snowmobile trail access, and convenient management services.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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54A Tanglewood Drive Dover VT 05356

MLS Number 4972259

  • Condo
  • Square Feet 2,506
  • New Contruction Existing
  • Bedrooms 4
  • Complex Timber Creek

Recently cleared for a breathtaking view from this Timber Creek townhome. Located directly across from the main entrance to the Mount Snow ski resort, this stunning updated end unit offers all the benefits of a home away from home with almost none of the upkeep. Enjoy amazing views of the ski trails, fireworks displays, groomers, sunsets, and torchlight parade out the windows of your own unit, with direct shuttle service from your front door to the base area, and convenient amenities including an on site management company, exterior maintenance, snow removal, landscaping, and more. Inside you are treated to an open concept living space with a large updated kitchen with granite counters and stainless appliances, wraparound breakfast bar, a wood burning fireplace with stone hearth, gorgeous updated picture windows open to the view, large deck for entertaining, large guest bedroom and full bath with radiant floor, rustic mudroom entry with bench and cubbies, ski locker, and covered front porch. Upstairs is a primary suite, soaking tub and shower. The bright walkout lower level has 2 large bedrooms still with great views, a full guest bath, lower deck ideal for a hot tub spot, large sauna, laundry room, owners closet, and updated floors and barnboard paneling throughout. This is complemented by the Sugar House amenities center including indoor pool, hot tub, gym, racquetball and basketball courts, locker rooms, tennis courts, and cross country ski trail system and warming house.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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482 Pratt Bridge Road Jamaica VT 05343

Jamaica, VT482 Pratt Bridge Road

Price$595,000

Est. Mortgage: $/month

MLS Number 4972214

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,364

Discover the perfect Vermont retreat! This 3-bedroom home, just 10 minutes from Stratton Mountain, near Bromley & Magic Mountain, and a quick half-hour drive to Mount Snow, is your gateway to the Green Mountains. Situated on a generous 1.4-acre lot, this residence offers a spacious mudroom with slate flooring and built-in cubbies for convenience. Upon entering the living room, your eyes will be drawn to the majestic fieldstone fireplace that stretches from floor to ceiling and the vaulted wood ceiling, infusing a rustic charm that's hard to resist. The tastefully renovated kitchen features granite countertops, stainless appliances, ceramic tile and a breakfast bar. The light and bright dining area is open to the kitchen and living room and accesses the private back deck with hot tub. The main level has a primary bedroom for easy living, while the upper level houses two generously sized bedrooms and a full bath. Both bathrooms have been upgraded with elegant granite tops and ceramic tile. The lower level is a haven for family enjoyment, with a den area equipped with built-ins, a perfect spot for kids to hang out, and a versatile office/bonus room and a laundry/utility room. Outside, the house was just painted and the property is professionally landscaped, creating an oasis of natural beauty and enhancing the curb appeal. Stay connected with high-speed internet and explore the nearby Jamaica State Park for hiking and camping adventures. Get it before it's gone.

Listed by Chad Lackey of Deerfield Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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21 Splatter Foot Close Road Wilmington VT 05363

MLS Number 4972160

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,100

Top of the Hill! This house has a lot packed into it. Detached garage for your toys, back-up generator, radiant heat flooring on the main level with plank wood flooring, hot tub room with sliders to the outside, primary suite with its own private balcony and ensuite custom walk-in shower for two, king sized bed and multiple closets. The foyer is welcoming and has a bench to remove gear, and a half bath with laundry closet. The Kitchen with island, and adjacent Dining area have sliders that open to the covered deck, and the layout wraps around to the living room with gas fireplace, and back to the foyer. The lower-level features two bedrooms with double bunks, a family room with a gas fired stove and has an entry door to the Hot Tub Room! Enjoy all the amenities Chimney Hill, the Deerfield Valley, and Southern Vermont offer including year-round swimming in the members-only exclusive Clubhouse located at 2000' in our 1200-acre resort community. The clubhouse features indoor and outdoor heated pools, hot tub, fitness room, arcade, playroom, library, fully-equipped kitchen for members to use, après ski lounge, playground, and outdoor grills. We have3 pickle ball/tennis courts, basketball, fishing pond, an extensive multi-use trail system, and onsite management. The area boasts world class skiing and shredding, festivals, artisans, crafts, music, food, golf, boating, hiking, biking, paddleboarding, lakes, rivers, breweries, wineries, distilleries, and more!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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266 Handle Road Dover VT 05356

Dover, VT266 Handle Road, Unit M

Price$360,000

Est. Mortgage: $/month

MLS Number 4972115

  • Condo
  • New Contruction Existing
  • Square Feet 1,080
  • Bedrooms 2
  • Construction Wood Frame

Modern and updated 2 bedroom, 2 full bath townhome directly across the street from Mount Snow's Carinthia! From your doorstep, walk to the Grommet magic carpet and ride up straight to the lift. No driving or parking necessary! The perfect location to wake up and enjoy your morning coffee on the quiet deck, located on the backside of the building, where you can take in the foliage or winter time mountain views. Three levels of living space, spacious bedrooms and a cozy bonus/family room for overflow sleeping, game nights or movies after a day on the slopes. Beautifully renovated kitchen featuring granite countertops and stainless steel appliances, leading into an open concept dining and living space to enjoy your après-ski, cozied up in front of the wood burning fireplace. A great use of space with ample room to spread out. Turnkey opportunity and tastefully furnished, with rare to find association fees that INCLUDE heat, hot water, sewer, heating system maintenance/replacement, chimney cleaning, snow removal, trash removal, firewood, exterior maintenance, landscaping/grounds maintenance and winter unit checks, all giving you complete peace of mind and taking the worry away. A rarely available Mountaineer unit with a superb location at a fraction of the price! Don't miss out on this perfect getaway spot for year round enjoyment, with amazing rental potential!

Listed by Prema Fitzpatrick of Skihome Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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Lot #5 Beau Ridge Road Wilmington VT 05363

MLS Number 4972089

  • Land
  • Acreage 10.1
  • Utilities None
  • Zoning res

Discover a unique opportunity to own over 10 acres of pristine land nestled in the picturesque beauty of Vermont, near Mount Snow and Lake Raponda. This expansive parcel of land is a haven for nature enthusiasts, offering a perfect blend of serenity and adventure. Situated just a stone's throw away from the renowned Mount Snow ski resort, this community boasts breathtaking views of the mountain, making it an ideal location for outdoor enthusiasts and winter sports aficionados. The property is also conveniently close to the tranquil Lake Raponda, providing endless opportunities for water-based activities, from kayaking to fishing. Accessed via a private, secluded dead-end road, this land offers the utmost privacy and tranquility, ensuring a serene retreat from the hustle and bustle of everyday life. It's worth noting that the property had test pits conducted approximately eight years ago however, the current owners didn't proceed with obtaining a wastewater permit. This is your opportunity to embrace the Vermont lifestyle!

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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102 Qtr. 4,89 Grand Summit Way Dover VT 05356

MLS Number 4971930

  • Condo
  • Bedrooms 1
  • Square Feet 589
  • New Contruction Existing
  • Complex Grand Summit

Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Unit 102 is available as a sleep 4 quartershare with a private location and views of the Deerfield Valley! 589 sq. ft of living space boasts a kitchen, dining/living area with a window looking out to the new Sundance six pack lift, a full bath with double vanities and a private bedroom with balcony. Benefits of Grand Summit ownership include the best ski in/out mountain location available at Mount Snow! Use of the Grand Summit amenities all year-round includes valet parking, owners private lounge and library, fully equipped gym with a sauna, hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year-round storage. A favorite perk for owners participating in the optional rental program is "Space A" which gives you the ability to stay in the hotel even when it's not your ownership week at a discounted rate...just pay housekeeping fees! Resort Condominium International and Interval International affiliated.

Listed by Patricia Fitzpatrick of Skihome Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 2023 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 October 2, 2023 1:12 PM EDT