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Windham County Real Estate for Sale

Browse the latest real estate for sale in Windham County, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-793-2002 or contact us online.

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370 Fischer Lane Jamaica VT 05343

Jamaica, VT370 Fischer Lane

Price$9,950,000

Est. Mortgage: $/month

MLS Number 5015744

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 10

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

$
$
%
$/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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454 Mountain Road Stratton VT 05155

Stratton, VT454 Mountain Road

Price$6,700,000

Est. Mortgage: $/month

MLS Number 5005058

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 8

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

$
$
%
$/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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64 Tamarack Road Stratton VT 05155

Stratton, VT64 Tamarack Road

Price$5,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5021231

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 11

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

$
$
%
$/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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22 Stags Leap Lane Wilmington VT 05363

Wilmington, VT22 Stags Leap Lane

Price$4,087,000

Est. Mortgage: $/month

MLS Number 5026506

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 7

Spectacular custom home at the base of the Hermitage Club in the Stags Leap community, adjacent to the ski trails at the base of Haystack mountain. This is a rare lot overlooking the trails, with direct ski-on/off and lift access, mountain views, and sunsets beyond, unimpeded by any other homes. Featuring 6 bedrooms, 5 and two half baths, with luxurious high ceiling great room with exposed natural wood beams and stone fireplace, open to a large dining area, a chefs kitchen with large island, quartz counters, stainless appliances, custom bar area with mirrored backsplash, and large windows looking out to the view, a main floor guest bedroom en suite that serves as a great office space with fireplace, a large mudroom entry with half bath, second floor spa like primary suite with large marble bath and stand up shower, walk in closets, stone fireplace, and second office space, two guest bedrooms en suite via a separate guest staircase, both with tiled showers, a full finished walkout lower level with family room, billiard area, and half bath, built in bunk room, guest bedroom, and another full tiled bath, large laundry room, secondary lower mudroom with cubbies for gear, that walks out to the large stone patio wired for hot tub. There is also a spacious wraparound covered porch to entertain, whole home generator, and an oversized 3 door garage for toys, sports cars, or snowmobiles. Thanks to luxury finishes and furnishings, this home is turn key for your immediate enjoyment.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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36 Woffenden Road Wilmington VT 05363

Wilmington, VT36 Woffenden Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 4971898

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 3

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

$
$
%
$/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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168 A And B Sunbowl Ridge Road Stratton VT 05155

MLS Number 4984619

  • Condo
  • County Windham
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 5,660

Listed by Andrew King of Stratton 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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1324 Middle Road Dummerston VT 05301

Dummerston, VT1324 Middle Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 5023586

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 8

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

$
$
%
$/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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19 Stags Leap Lane Wilmington VT 05363

Wilmington, VT19 Stags Leap Lane

Price$3,499,000

Est. Mortgage: $/month

MLS Number 5025323

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6

Stunning new construction at the base of the Hermitage Club in the luxurious Stags Leap community, adjacent to the ski trails at the base of Haystack mountain. Being offered finished for the Winter 25-26 season. The earlier a buyer enters the process the more choice they can have on design and finishes. Presented as a 5 bedroom, 5.5 bath, with a stunning great room and stone fireplace, open to a large kitchen and dining area, a main floor bedroom suite, as well as guest bath, large mudroom entry, and two car garage, second floor primary suite, two guest bedrooms and a guest bath, with open loft to the vaulted main living area, a full finished walkout lower level with family room, theater, and bunk room suite, and luxury finishes throughout. A trusted developer with an extensive local portfolio to afford you peace of mind, ideas for finishes, and consistent delivery timing.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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28 Woodsman Road Extension Dover VT 05356

Dover, VT28 Woodsman Road Extension

Price$3,250,000

Est. Mortgage: $/month

MLS Number 5009495

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 9

Spectacular Adirondack Post and Beam Luxury Estate nestled atop the Dover Hills with stunning long range sunrise views to the east over Southern Vermont and New Hampshire. This breathtaking home enjoys utter privacy and nature thanks to a quiet driveway off a country road with 12+ acres for true Vermont retreat living, yet just a short drive to the Mount Snow ski resort, Hermitage Club, village of Wilmington, and nearby lakes. The idyllic rustic interior boasts gorgeous exposed wood work with post and beam construction and exposed timbers, reclaimed wood floors, vintage barn board paneling, and tremendous natural light to offset the warm wood tones. The 3 story great room has expansive windows, a floor to ceiling stone fireplace, chefs kitchen with stainless appliances and dual entertaining islands, and ample seating. There are two vaulted main floor primary suites, 3 upstairs suites, a large reading loft overlooking the mountain views, stunning timber frame breezeway, and spacious play/bunk room. The lower level has 2 additional suites, a theater, custom wet bar, billiard area, gas fireplace with stone hearth, stone hot tub grotto with it's own full bath, and tremendous owner closets should you choose to offset with the tremendous rentability. There is also a large wraparound deck for taking in the scenery, large mudroom entry for gear, 3 car garage for all your toys, whole home generator, solar array to offset utility costs, ample parking, and four season enjoyment.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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4 Gold Medal Circle Stratton VT 05360

Stratton, VT4 Gold Medal Circle

Price$2,999,000

Est. Mortgage: $/month

MLS Number 4987337

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 7

4 Gold Medal Circle at Stratton, Vermont's newest and most prestigious address, just a 1 minute drive to Stratton's Sun Bowl, with construction coming soon. The 4,845 square foot home boasts expansive views of Stratton's trails along with 6 luxurious bedrooms, 6+ bathrooms, gourmet kitchen complete with high-end appliances and finishes, suspended high efficiency fireplace, and a thoughtfully designed floor plan for a home that promises to be the epitome of modern mountain living. The 2,816 square foot walkout basement with walls of glass and mountain views can be customized and provides easy access to outdoor entertaining space. Gold Medal Circle is an enclave of custom homes, the perfect location for establishing your own retreat with meticulous attention to comfort, style, and elegance. You'll enjoy the adjacent 73 acres of common land deeded for preservation for hiking, snowshoeing, or just basking in the beautiful natural setting. The developer is a master builder with 37 years of experience, specializing in luxury custom homes with superior quality energy efficiency using the latest modern technology, healthy indoor environments, and state of the art thermal protection. Buyers have the option to select finishes and amenities along with working hand-in-hand with the builder and designer to create a spectacular home in which to enjoy a superior mountain lifestyle.

Listed by Deborah Hanst and Jeffrey Sheehan of Cummings & Co

$
$
%
$/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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130 Handle Road Dover VT 05356

Dover, VT130 Handle Road

Price$2,997,000

Est. Mortgage: $/month

MLS Number 5023841

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

Located in between Mount Snow Ski Resort and The Hermitage Club, this stunning farmhouse built in 2016 offers mountain living with a blend of modern amenities and rustic charm. 5 bedrooms and 5 baths, this ski home features an attached garage with epoxy floors,electric car charger, along with a rear door for direct access to VAST trails for the snowmobile enthusiasts. Above the garage, discover a heated and air-conditioned art studio, perfect for creative endeavors. Reclaimed brick floors grace the mudroom, powder room, laundry, and pantry, while warm white oak floors flow throughout the home. The chef's kitchen is equipped with Sub-Zero and Wolf appliances, ideal for culinary enthusiasts. A combined living and dining room showcases a stone wood-burning masonry fireplace, providing both warmth and ambiance. Step outside to the expansive outdoor deck overlooking the wooded landscape. The home has direct access to the hiking, biking, and snowmobile trails adjacent to the property. The primary suite on the first floor boasts cathedral ceilings and ample natural light, along with a luxurious primary bath featuring a steam shower and soaking tub. Upstairs, three additional bedrooms, two baths, an office/study await. The finished lower level offers an additional en suite bedroom and a large playroom, with access to the backyard & hot tub. Brand new detached car storage barn for your special car collection or boat for Lake Whitingham. Could be converted to indoor pickle ball.

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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5402 Vt Route 112 Halifax VT 05358

Halifax, VT5402 Vt Route 112

Price$2,750,000

Est. Mortgage: $/month

MLS Number 5012897

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 6

North River Farm: This is what you imagined Vermont to be. Nestled on over 300 bucolic acres along the stunning North River Gorge in Halifax, this extraordinary country estate offers a once-in-a-lifetime opportunity to own a piece of New England history. The North River compound features completely renovated and expanded 1800's farmhouse, combining classic charm with modern amenities, all while overlooking a cascading mountain river that soothes the soul. The property includes six spacious bedrooms and five luxurious baths, providing ample space for family and guests. Every room has been thoughtfully designed to capture the essence of Vermont living, with hardwood floors, exposed beams, and large windows framing breathtaking views of the surrounding landscape. In addition to the main house, two lovingly restored slate-roof barns add a touch of rustic elegance. One barn has been imaginatively converted into a porch barn, offering a serene spot to relax and enjoy the sights and sounds of the river below. A modern 3,600 sq ft barn/garage awaits your vision, whether it's for additional living space, an artist's studio, or a workshop. Plus, a charming sugar shack gives you the chance to produce your own maple syrup, a true Vermont tradition. This estate offers endless outdoor adventures. Snowmobile, hunt, fish, cross-country ski, ATV, swim, and hike all on your private property, with over half a mile of trails.

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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18 Grenoble Way Wilmington VT 05363

MLS Number 5021484

  • Condo
  • County Windham
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4,338

Welcome to your dream slopeside retreat at the private Hermitage Ski Club! This exceptional 5-bedroom, 6-bathroom townhome has been meticulously designed to offer the perfect balance of luxury and functionality. With direct ski access, the home boasts custom upgrades and elegant interior finishes throughout. Upon entry, you will find a beautifully designed mudroom crafted for an active lifestyle. Weathered grey barn board walls, built-in benches, and organized cubbies create a welcoming space to gear up or wind down. Integrated boot dryers keep your footwear warm and ready for the next adventure.The completely renovated gourmet kitchen is a masterpiece of natural elegance and modern sophistication. Striking black leathered quartzite granite countertops and a matching backsplash make a dramatic statement, while the expansive island provides ample seating for casual dining. The Shou Sugi Ban wood-wrapped hood adds a distinctive, artistic flair. The living room exudes warmth with its open-concept design and stone fireplace stretching up to the vaulted ceiling. High ceilings and expansive windows invite an abundance of natural light and frame picturesque views of the surrounding greenery.Experience year-round comfort with energy-efficient heat pumps and a whole-house steam humidification system. Heated floors in every bathroom.Smart home features like the Control 4 system manage lighting, motorized shades, and Sonos-powered multi-room audio.Townhome is being sold furnished.

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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662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 5

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: 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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9 Lodge Lane Dover VT 05356

Dover, VT9 Lodge Lane

Price$2,299,000

Est. Mortgage: $/month

MLS Number 4999095

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5

Enjoy stunning views, privacy, and access, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, pickleball courts, game room, on site management company, and direct shuttle service from your home to the base area. This spectacular home is nestled on a private 2+ acre lot and features breathtaking views of the ski trails, fireworks displays, and sunsets over the ridgeline, from nearly every room. The home uniquely features 6 bedrooms, one of which is a primary suite on the main floor, an expansive great room with vaulted ceilings, floor to ceiling stone fireplace , an upscale kitchen with island, stainless appliances, and granite counters, amazing natural light and warm lighting schemes, a spacious dining area, lower level family room for entertaining, second floor loft, oversized overflow sleeping and play room ideal for guests, a third floor viewing turret, a vaulted Vermont entry, large mudroom with cubbies ideal for winter gear, spacious rear deck, 2 car garage, and extensive landscaping. New fixtures and appointments, expanded view clearing and lawn space, and more, for amazing personal use or investment. Truly a unique 4 season retreat perfect for entertaining with all the privacy of a home, but all the benefits of community living.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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71 Overlook Drive Dover VT 05356

Dover, VT71 Overlook Drive

Price$2,280,000

Est. Mortgage: $/month

MLS Number 4826276

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 8

This extraordinary property in the prestigious Peaks community has undergone significant renovations with more enhancements on the way, blending contemporary elegance with timeless charm. Perched high above Mount Snow Valley, Pinnacle House offers commanding presence and breathtaking, unobstructed slope views. Inside, soaring vaulted ceilings and exotic African wood paneling frame a solid stone, wood-burning fireplace in the grand living room. A stunning wall of windows captures the picturesque landscape, making nature a centerpiece. Entertain in style in the chef's kitchen, featuring ceruse oak cabinets and top-tier appliances. This six-bedroom masterpiece includes a billiard parlor for hosting friends or unwinding after a day on the slopes. The private master suite is a luxurious retreat with its own fireplace, Juliet balcony, and spa-like bath complete with marble mosaics, a soaking tub, double vanity, and dressing room. The lower level offers a cozy family room with a fireplace, hot tub room, additional bedrooms, marble baths, and a walkout entry. The double laundry room ensures functionality for even the largest gatherings. Guests will appreciate the private suite above the heated two-car garage, offering ample storage and a well-organized mudroom. Outside, a tiered stone patio and private deck provide serene spaces to enjoy panoramic mountain views. Pinnacle House isn't just a home; it's an experience, designed for the discerning buyer who demands the best.

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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0 Tenon Lane Dover VT 05356

Dover, VT0 Tenon Lane

Price$2,250,000

Est. Mortgage: $/month

MLS Number 5017999

  • Land
  • County Windham
  • Square Feet 618,552
  • Acreage 14.2

A unique opportunity to purchase 14 acres in the Mount Snow base area with permits in place for the development of 38 townhouse units, all within walking distance to the Mount Snow ski resort! With the close proximity to the ski area and views of the mountain and surrounding village, this rare opportunity is a developer's dream. Permits and additional information are provided in the document section.

Listed by Patricia Fitzpatrick 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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136 Woodsman Road Extension Dover VT 05356

Dover, VT136 Woodsman Road Extension

Price$2,250,000

Est. Mortgage: $/month

MLS Number 5001708

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

Breathtaking new construction architectural contemporary with a once in a lifetime view being offered for the first time. This extraordinary home was just finished and sits at the crest of the Dover Hills, just below the altitude building cap, with absolutely the best views of the Mount Snow and Haystack ridgeline that I have ever seen, stunning ski trail views, and evening sunsets. The 11 acre end of road parcel has utter privacy, and total uniqueness, yet all the convenience to skiing expected in a luxury mountain escape. The interior boasts a large open floor plan with custom floor to ceiling windows to take in the view, automated sun shades, a large great room area with wood burning fireplace, white oak floors, spectacular chefs kitchen with induction cooktop, exhaust hood, double oven, walk in pantry, wine bar, and island, a spacious dining area, and easy access to the patio and exterior entertaining space. There is an ideal mudroom with cubbies and ample storage, a drive through 3 car garage, EV plug, a guest bedroom with en-suite bath, and an additional full guest bath, both with tiled showers and glass doors. The finished walkout lower level features a primary suite with spa like bath, pedestal tub, tiled shower, walk in closet, and the same dramatic views, two additional guest bedrooms and a full guest bath, a glass office/studio space ideal for working from home, and large laundry room. Exposed wood beams on the exterior, whole home automation, central ac, and more.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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20 West Ridge Road Stratton VT 05155

Stratton, VT20 West Ridge Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 5002928

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

OPEN HOUSE. Friday July 5th, 2-4pm. All Welcome. The exquisite craftsmanship of this stunning Austrian-style chalet evokes the lure of Stratton's early days. A location that was selected for incredible views, and close ski trail access. This true mountain haus has been thoughtfully updated to preserve its charm and authenticity. Imagine waking up to incredible mountain views every morning and enjoying cozy evenings by the fire in your timeless alpine escape. Air conditioned, updated kitchen, updated windows, and a three car garage. Three en suite bedrooms on the second floor, and two additional bedrooms and a full bathroom in another part of the house. The great room is complete with a bar, amazing acoustics, and a breathtaking view. The library has its own fireplace, and secret wine room accessed by a discreet buzzer. The Appalachian/Long Trail crosses nearby for year round hiking and backcountry adventures. This is the place you'll never want to leave.

Listed by Chrissy Carroccio of TPW 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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121 Fannie Hill Road Wilmington VT 05363

Wilmington, VT121 Fannie Hill Road

Price$2,195,000

Est. Mortgage: $/month

MLS Number 5005773

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 4

Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and meticulous maintenance, this home is turn key for immediate enjoyment, with features including an open concept design, large great room with vaulting ceilings and exposed beams, a stone hearth with wood burning fireplace, upscale country kitchen with stainless appliances and granite counters, a secondary wet bar area, sizeable dining table for all your guests, wood floors throughout, a main floor primary suite with walk-in closets and large tiled bath, dual rustic bunk rooms, a lower level guest suite, 7 spacious bedrooms in total, a large family room for great separate entertaining space, movies, and games, as well as an adjacent tv area, and a tremendous mudroom with built in cubbies for all your gear after a day on the trails. There is also a large covered front porch to keep the snow at bay with wood storage, massive hot tub, fenced in dog area, generator, tremendous parking, and nice lawn space without being much to maintain. With proximity like this and creature comforts from home, this makes for a great ski home, as well as a welcome respite from the metropolitan bustle year round.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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52a Snowbridge Road Stratton VT 05155

Stratton, VT52a Snowbridge Road

Price$2,050,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5025685

  • Condo
  • County Windham
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,244

Exclusive Snowbridge Trailside Retreat - With a premier snowfront location in Stratton's coveted Snowbridge community, this unit provides true ski-in/ski-out access and walkability to the Stratton Village shops and restaurants. Gear up in the comfort of your home - go from slippers to ski boots, then take the Old Log Trail directly to the Main Base, Gondola, and Ski School. In addition to an exceptional location, this home offers a layout that is functional and versatile. The open-concept main living area features a cozy floor-to-ceiling wood-burning fireplace, while the den provides an ever-desirable second living space and overflow sleeping area. The home offers two en suite bedrooms, two additional bedrooms, and 3.5 baths, providing ample space for family and guests. Step outside to the deck and enjoy your own private hot tub, ideal for apres-ski relaxation. Walk to dinner and shopping in The Stratton Village. In the warmer months, make the most of your time in Vermont with mountain biking, tennis, and 27 holes of golf located at The Resort. This property unlocks access to the ultimate mountain lifestyle, combining privacy, convenience, and year-round recreation.

Listed by Cheyanne Pugliese of Wohler 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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43 Upton Road Dover VT 05356

Dover, VT43 Upton Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 5026310

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5

The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end chef's kitchen with granite counters, stainless appliances, breakfast bar, pantry, stunning 3 story vaulted great room with stone fireplace that also offsets heating costs, natural wood joinery and exposed beams throughout, beautiful hardwood floors, a large screened-in porch and entertaining deck for 3 season enjoyment, a primary suite on the main level with tiled shower and jacuzzi tub, 3 upstairs guest bedrooms with full bath, spacious loft, and bonus third floor loft room, a full finished basement with family room and full guest suite, as well as ample owner storage, additional guest suite above the garage, and stunning mountain views from almost every room. There is an attached 2 car garage which leads into the oversized mudroom with cubbies for all your gear, hot tub, and numerous recent upgrades including new roof, new paved driveway, all new paint, lighting, wifi thermostats, cameras, and energy monitoring, and furnishings, which are included at the offering price. Direct access to VAST snowmobile trails. Septic sized for 4 bedrooms full time use.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

$
$
%
$/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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92 County Road Stratton VT 05155

Stratton, VT92 County Road

Price$1,995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5015507

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6

This exquisitely-built mountain estate is ready to enjoy and to rent! A mere 3 mins' drive to Stratton's Sun Bowl, 5 mins to the Village and 8 mins to the Golf course. Currently one of the few luxury rental properties near Stratton, this home could be your escape for all seasons. All necessary permits are in place, several rentals are confirmed for 24/25 winter should the buyer want to continue to rent and offset their investment. The property caters to your, or your renters', every whim. The lighted driveway ushers you onto a 5-plus-acre landscaped lot. When you enter the foyer, you are greeted with the soaring 29' old-growth Douglas Fir-beamed ceiling. The living room is highlighted with a stunning two story floor-to-ceiling locally-sourced-stone fireplace, and a wall of windows and French doors. Take in breathtaking views of Pinnacle Peak from the expansive deck. The kitchen is every chef's dream, with plenty of granite counter space, slate backsplashes, custom crafted cherry cabinets, stainless steel appliances, two new double ovens, 5-burner gas cooktop, and a spacious breakfast nook. The first floor primary is an owner's oasis that opens onto the deck. It is appointed with a gas fireplace, sauna, and luxurious marble accented bathroom. Upstairs, you will find 2 ensuite bedrooms, and 2 additional bedrooms with shared bath. The finishes in this self-sufficient solar-powered home are of the highest quality.

Listed by Lauren Niles of Coldwell Banker LIFESTYLES - Quechee

$
$
%
$/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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207 Brooks Lane Londonderry VT 05148

Londonderry, VT207 Brooks Lane

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4971327

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 9

This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it offers ample space for everyone to convene while relishing their individual, private retreats. The main house, steeped in history dating back to 1820, is a delightful 3-bedroom brick farmhouse showcasing a generous 45-foot-long great room that seamlessly extends to a covered patio adorned with an awning, a idyllic setting for outdoor gatherings. The newly renovated kitchen, with granite countertops, serves as the heart of the home, combining modern elegance with timeless charm. The guest cottage features an additional three bedrooms, a cozy living room, and a well-appointed kitchen with an adjoining dining area. Adjacent to the guest cottage, a spa facility awaits, boasting a ground-level private gym, sauna, and an outdoor hot tub. Ascend to the second floor to discover two bedrooms, each with a private bathroom and a shared balcony. Nestled at the property's edge, overlooking the serene swimming pond with a beach, is a rustic cabin complete with a welcoming wood-burning stove and a lofted sleeping area. Ideally suited as a family compound, this retreat offers both separation and privacy

Listed by Timothy Apps 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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16 Mountain Reach Mews Road Stratton VT 05155
Active With Contract

MLS Number 5027413

  • Condo
  • County Windham
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,581

Located just steps from Stratton Village and the lifts, this luxurious slopeside townhouse offers a seamless blend of upscale contemporary design and unbeatable convenience. With gated access and no public roads to cross, this end-unit residence provides a true retreat in the heart of Stratton's trailside community. Step into the bright, open floor plan where modern elegance meets extraordinary design. The main living area is a stunning centerpiece, featuring sleek lines, a wood-burning fireplace, and abundant natural light. The contemporary kitchen boasts designer cabinetry, high-end appliances, and a spacious layout perfect for entertaining. The top floor is dedicated to the private primary suite-a serene escape with a spa-inspired bath, ample dressing space, and panoramic views. Below, the bedroom level features two additional bedrooms, including a cheerful bunk room with a private deck, a suite with an ensuite bath, and a versatile bonus room for office or play. On the entry level, you'll find a flexible secondary family room with a fireplace, a powder room, and a convenient laundry area, all steps from the heated two-car garage. This prime location allows you to walk to ski lifts, restaurants, and shops while enjoying the comfort of a private garage. Showings are subject to availability due to the property's participation in a short term rental program. Experience Stratton's premier lifestyle in this impeccably designed property-call today for more information!

Listed by Trent Stephens of Wohler 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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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 11, 2025 12:37 AM EST