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Windham County VT Real Estate

Find the latest real estate listings for sale in Windham County, VT. Save your favorites to your account and get email notifications when similar properties hit the market. For more information, any questions you make have & to schedule a show, please feel free to contact us.

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Athens | Brattleboro | Brookline | Dover | Dummerston | Grafton | Guilford | Halifax | Jamaica | Londonderry | Marlboro | Newfane | Putney | Rockingham | Stratton | Townshend | Vernon | Wardsboro | Westminster | Whitingham | Wilmington | Windham

370 Fischer Lane Jamaica VT 05343

Jamaica, VT370 Fischer Lane

Price$9,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5015744

  • Residential Single Family
  • Full Bath 7
  • Address 370 Fischer Lane
  • Construction Existing
  • Bedrooms 6

Accessible, but miles from the everyday. Camp Endo's mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark and stone detailing combined with complete comfort, great light and welcoming spaces. The property was featured in the book Rustic Living by Ralph Kylloe as one of the great rustic style homes in the U.S. The 13,393-square-foot home has an open floor plan, massive stone great room fireplace, chef's kitchen and 6 bedrooms en suite, each with magnificent mountain views. Off the kitchen and great room is a screened-in porch and large deck with an outdoor stone fireplace to soak in the panoramic southerly green mountain views. Smaller gathering spaces include a corner office, gym/spa, meditation room and 22-seat home theater. Camp Endo's extensive trail network provides a daily dose of rugged, natural beauty for mountain biking, walking or snow shoeing and playful options include a paintball course and a six-foot square chessboard. The adjacent barn houses a fully appointed 2 bedroom guest suite, 3-bay garage and half-basketball court with surround sound. Next to the apple orchard is a large swimming pond with views of Stratton Mtn. The property has renewable solar and wind energy.

Listed by Dia Jenks and T Story Jenks of LandVest,Inc/Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

454 Mountain Road Stratton VT 05155

Stratton, VT454 Mountain Road

Price$6,700,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5005058

  • Residential Single Family
  • Full Bath 5
  • Address 454 Mountain Road
  • Construction Existing
  • Bedrooms 6

Luxurious 141 acre mountaintop retreat within Stratton Mountain Resort, stunning views of Stratton, Mt Snow, and Bromley. This architectural masterpiece blends comfort and elegance, with multi level interiors harmonizing living areas and en suite bedrooms. Inspired by the graceful arcs of skiing turns, the design features a dramatic entryway leading to a spacious living room and library. An 18-foot stone fireplace and expansive windows flood the space with natural light and breathtaking views. The entry leads to a gourmet kitchen with a large eat-in dining and a formal dining room, perfect for entertaining. The home boasts 6 en suite bedrooms, an expansive primary suite with an office, two custom walk-in closets and a cedar closet. A custom-built bunk room with locker-style cubbies adds playful sophistication. A light-filled hallway connects the upper and lower levels, linking bedrooms, a home theatre, and living areas, enhancing the open and airy feel. Additional amenities include a golf simulator and a movie theatre. Outdoors enjoy mountain views, perennial gardens, natural stone accents, and a bluestone walkways. In warmer months, luxuriate in the gunite pool and hot tub while soaking in views. A gym in the detached three-car garage is perfect for workouts. Tennis and pickleball courts offer additional outdoor activities. This property is a sanctuary where architectural elegance meets mountain tranquility. Discover the epitome of luxury at this stunning mountain retreat.

Listed by Lisa Sullivan of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

64 Tamarack Road Stratton VT 05155

Stratton, VT64 Tamarack Road

Price$5,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5021231

  • Residential Single Family
  • Full Bath 10
  • Address 64 Tamarack Road
  • Construction Existing
  • Bedrooms 9

Discover this Extraordinary Stratton Mountain Resort Tamarack Heights premier trailside residence. Situated on a sprawling 1.4-acre trailside lot, this property exudes unassuming grandeur from the moment you enter its magnificent great room with a soaring two-story fireplace and floor-to-ceiling windows that frame breathtaking panoramic views of Stratton Village and the surrounding mountains. Architecturally inspired by Vermont's historic covered bridges, the design seamlessly blends with its natural surroundings, snow covered trails and exceptional views from every vantage point. The use of natural materials with custom stonework and woodwork throughout features impeccable craftsmanship. The dining area and gourmet kitchen with stone countertops, oversized island and superior appliances is surrounded by long range views and a front row seat to seasonal fireworks. Expertly designed, this home offers an unrivaled 9+bedroom suite floorplan with unmatched gathering spaces. The primary suite is privately situated with fireplace and substantial walk-in closet, private deck and views, views, views, and remaining suites are located throughout the 7498SF design. Most importantly, you'll ski out onto the trails and back from your own ski lodge room; complete with fireplace, ski lockers, boot dryers, 2nd kitchen and tables for lunch and apres ski! No detail in planning for a mountain lifestyle has been overlooked. This is the epitome of Stratton Mountain living in Vermont's Green Mtns.

Listed by Kim Morgan-Wohler and Britt Wohler of Wohler Realty Group

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

36 Woffenden Road Wilmington VT 05363

Wilmington, VT36 Woffenden Road

Price$3,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4971898

  • Residential Single Family
  • Full Bath 1
  • Address 36 Woffenden Road
  • Construction Existing
  • Bedrooms 6

Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and whimsical and yes it gets even better-this is waterfront property that offers substantial frontage on the North Branch of the Deerfield River, a haven for fly fishing & serenity. For the farmer in you, two livestock barns provide ample space for your animals or hobbies or envision more-the potential to transform these barns into charming event spaces or the farm into a Bed and Breakfast to blend Vermont's rural allure with modern comfort. This property is an opportunity waiting to be realized. With 5 identified potential new home sites, you may consider creating a family compound or explore development possibilities. Additionally, there's a sugar house and sugar lot, operated with modern efficiency for maple syrup production. Historic Wilmington, is only a stone's throw away and Mount Snow and the prestigious Hermitage Club are just a few miles North. Rarely does an opportunity like this arise. While currently part of Vermont's Current Use program, removal is an option upon sale, making your vision even more attainable. Unlock the limitless posibilities at Wheeler Farm!

Listed by Melissa Ellis of Southern Vermont Realty Group

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1324 Middle Road Dummerston VT 05301

Dummerston, VT1324 Middle Road

Price$3,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5023586

  • Residential Single Family
  • Full Bath 7
  • Address 1324 Middle Road
  • Construction Existing
  • Bedrooms 7

Truly a rare and remarkable property. This custom home was lovingly designed and constructed in 2005 with a clear vision for bringing the Vermont scenery in, while maintaining the rustic charm befitting a country estate. The main house features gorgeous exposed timber frame construction throughout, natural wood flooring, paneling, and trim, extensive artisan stonework inside and out, including 3 stone fireplaces, dry laid angular walls, and fountains, high end wrought iron work, extensive soaring glass to take in the gorgeous easterly view, pastoral setting, and perennial gardens, and ample space to explore all your creative outlets including viewing tower, recording studio, library, theater, office, wine cellar, car barn, underground tunnel, multiple primary and guest suites, and more. Situated in the quiet country town of Dummerston, just outside of Brattleboro, with easy access from the highway, and nearby amenities including orchards, farm stands, covered bridges, swimming holes, and extensive hiking, biking, and nature trails. A must see for any discerning buyer looking for a private, one-of-a-kind retreat in Vermont.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 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 December 8, 2024 2:24 PM EST

 

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5 BR, 12,000 sq ft, Almost 70 Acres $6,500,000 Details

465 +/- Woodstock Acres

5BR,  7 Stall Equestrian Barn, $6,750,000 Details

 

22 Acres on Lake Champlain

4BR, Shelburne, $8,475,000 Details