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Windham County

557 Trager Road Jamaica VT 05343

Jamaica, VT557 Trager Road

Price$8,200,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5076041

  • Residential Single Family
  • Full Bath 6
  • Address 557 Trager Road
  • Bedrooms 6
  • Bathroom 10

Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in its surroundings while still just a short drive to Stratton Mountain Resort and the Stratton Helipad. Step into an open-concept haven where elegance meets comfort. Framed by soaring timber beam ceilings, the main living area echoes the grandeur of the mountains while preserving the warmth and intimacy of a true retreat. Natural materials, handcrafted details, and thoughtful design choices create a home that feels warm, timeless and deeply personal. The estate preserves uninterrupted views across the landscape-ensuring that natural beauty remains the focal point from every vantage point.The grand stone fireplace anchors the living area, drawing the eye to soaring ceilings and expansive windows that frame breathtaking mountain ridges. Sunlight floods the space, highlighting the harmonious blend of natural textures and refined finishes.The gourmet kitchen blends beauty and function with custom wood cabinetry, hand-carved artistic accents, a welcoming breakfast bar, and an expansive island designed for conversation, connection, and effortless entertaining. Every space in this residence has been intentionally designed with a keen eye to detail. While every room blends effortlessly with the home's elevated rustic feel, each one remains extremely unique. Offering six en-suite bedroom in the main residence and 2 bedroom2.5 bath guest quarters. Main Residence with extraordinary gathering rooms and multiple suites, 5 bay barn, guest quarters, pond, miles of maintained trails for mountain biking and winter activities,

Listed by Kim Morgan-Wohler of Wohler Realty Group, Britt Wohler of WOHLER REALTY GROUP

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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$4,999,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5005058

  • Residential Single Family
  • Full Bath 5
  • Address 454 Mountain Road
  • Bedrooms 6
  • Bathroom 8

Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication. A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace. Expansive windows frame breathtaking mountain vistas, filling the space with natural light. The gourmet kitchen features a casual dining area and connects to a separate dining room - ideal for both relaxed and formal gatherings. With six en suite bedrooms, including a luxurious primary suite with a private office, dual walk-in closets, a cedar closet, and a separate storage room, theres plenty of space for all. A custom bunk room with built-in cubbies adds a fun, functional touch for younger guests. Year-round enjoyment continues with a golf simulator, home theatre, and a detached three-car garage with a fully equipped gym. A light-filled hallway connects all levels, creating a seamless flow throughout the home. Outdoors, unwind in the heated gunite pool and hot tub or enjoy tennis, pickleball, or basketball on your private courts. Lush perennial gardens, stonework, and bluestone walkways enhance the natural setting. Whether you're seeking a private escape or a home for generations, this mountaintop retreat is your Vermont dream - just in time for ski season.

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

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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

1950 Collins Road Halifax VT 05358

Halifax, VT1950 Collins Road

Price$3,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5062504

  • Residential Single Family
  • Full Bath 2
  • Address 1950 Collins Road
  • Bedrooms 4
  • Bathroom 8

Exceptional 177+ Acre Estate with Luxury Log Home, Event Venue & Craft Beverage Facilities. Experience unmatched luxury and opportunity on this remarkable 177+ acre estate. Featuring an 8,000+ sq ft timber frame log home, a 7,100 sq ft finished event venue, and on-site winery, craft brewery, and champagne-making facilities, this turn-key property is ideal as a private residence, retreat, or destination business. The custom log home showcases vaulted ceilings, radiant in-floor heating, hardwood and stone flooring, and imported Italian tile. A chef’s kitchen and expansive 800’ wraparound deck offer the perfect space to entertain while enjoying stunning 360-degree mountain, vineyard, and valley views. The boutique vineyard supports in-house wine production, complemented by a dedicated beer brewing system and traditional mthode champenoise champagne facilityperfect for tastings or exclusive label production. The event venue includes a second commercial kitchen, two custom bars, elegant restrooms, and a 7,900 sq ft stone patio with cascading fountainsideal for weddings, retreats, and celebrations. Freshly painted and impeccably maintained, this estate offers total privacy with year-round recreation nearby, including Wilmington’s fine dining, Sunset Lake, and Hermitage Golf Club. A rare opportunityschedule your private tour today.

Listed by Margretta Fischer of Wohler Realty Group

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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

29 Mountain Ridge Drive Wilmington VT 05363

Wilmington, VT29 Mountain Ridge Drive

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

Est. Mortgage: $/month

MLS Number 5068740

  • Residential Single Family
  • Full Bath 4
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 7,000

The Mountain Ridge community is newly developed and this is the first opportunity to enter this new prestigious location. 38 acres with 5 total lots, including a spectacular newly built luxury Timber Frame home being sold as-is near completion, with a builder on board ready to finish, plus 4 separate gorgeous mountain view building sites. Finish this home with the fixtures and finishes already bought and paid for, and be moved in within 4 months according to the builder. The home sits on a 5 acre parcel with stunning ski trail views and direct Haystack golf course access, just down from the Hermitage Club, and 3 miles from Mt Snow. Utter privacy with a great buffer of mature trees, ledge stone patio, large rear deck to take in the scenery, and breathtaking stone walls and landscaping potential. Inside you are treated to a gorgeous open concept floor plan with vaulted great room, exposed post and beam joinery throughout with a Davis Frame custom timber frame kit, a floor to ceiling stone fireplace, gorgeous kitchen dining area with great light, main floor primary suite, main floor mudroom, guest suite and/or office space, dual upstairs suites, a large loft den, lower level theater space, family room, bunk room with attached bath, and spacious bunk room or guest suite over the attached oversized 2 car garage, with large doors and rear door for toys and snowmobiles. No expense has been spared. Then retain the additional lots for privacy, friends, or sell to offset the expense.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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$2,999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4971898

  • Residential Single Family
  • Full Bath 1
  • Address 36 Woffenden Road
  • 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 envision more-the potential to be certified organic or 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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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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

2060 Townshend Road Grafton VT 05146

Grafton, VT2060 Townshend Road

Price$2,895,000The price has recently decreased

Est. Mortgage: $/month

Coming Soon

MLS Number 5092853

  • Residential Single Family
  • Full Bath 4
  • Address 2060 Townshend Road
  • Bedrooms 6
  • Bathroom 4

A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse, where timeless Vermont character meets modern comfort. The residence features six bedrooms, four bathrooms, and two kitchens, complemented by an impressive collection of outbuildings, including a 4,000+ square foot timber frame barn for events, five-bay garage with workshop and offices, seven-bay pole barn, and a three-stall horse barn with heated tack room. Additional accommodations include a separate guest or caretaker residence and two rustic cottages. The substantial acreage includes timberland and open pastures, a half-acre aerated pond, more than two miles of streams, and 6.7 miles of private roads and trails throughout the property. Bordering Mollie Beattie State Forest and the South Branch of the Saxtons River, the land offers opportunities for outdoor recreation, forestry, conservation, maple sugaring, and agricultural pursuits. Three access points to the VAST trail network add to the property's recreational appeal. Meticulously maintained grounds, diverse natural features, and a location near the village of Grafton complete this rare Vermont offering.

Listed by Erin McCormick of KW Vermont

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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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: 6.48% last updated on 2026-06-04

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

56 Handle Road Dover VT 05356

Dover, VT56 Handle Road

Price$2,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5063234

  • Residential Single Family
  • Full Bath 5
  • Address 56 Handle Road
  • Bedrooms 6
  • Bathroom 7

Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler's panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood floors and beautifully tiled baths create a warm refined atmosphere. Upstairs the primary suite offers a fireplace and luxurious bath. An additional en-suite bedroom and three more bedrooms, laundry room, and two full baths provide plenty of space for family and guests. Dual staircases, tiled entry, and both front and back foyers highlight the home's thoughtful design. The grounds are equally impressive with a covered front porch that overlooks the sprawling south facing lawn with winter views of haystack. A serene screened veranda, back deck and stone patio with fire pit invite outdoor gatherings. An oversized-attached two car garage, whimsical children's playhouse and an incredible post and beam barn with full lower level perfect for all your recreational vehicles complete the offering. Exquisite gardens, stone walls and meticulous land scaping surround this rare property, ideally located across from the esteemed Hermitage Inn and exclusive Hermitage Club with easy access to all area activities.

Listed by Richard Caplan of Deerfield Valley Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

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

662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • Full Bath 1
  • Address 662 Howe Farm Road
  • 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 subject to an Act 250 permit and enrolled 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

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

392 Lake Raponda Road Wilmington VT 05363

Wilmington, VT392 Lake Raponda Road

Price$2,195,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089881

  • Residential Single Family
  • Full Bath 4
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,524

A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake - with a private dock - just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats tend to head for the public-access Harriman Reservoir on the southern end of Wilmington, Raponda remains a predominantly owner-enjoyed lake. The result is noticeably less boat noise and wake, making it equally wonderful for kayaking, paddleboarding, and peaceful summer mornings on the water. The property sits on a generous, nicely sized parcel with sweeping level lawn space, a private yard with fire pit, ample parking, kayak racks, and a private dock - which transforms into an ice skating destination come winter. Inside the fully remodeled and expanded vintage four-bedroom, four-bath lake house, an open-concept floor plan invites you in with warm wood floors throughout, a living room anchored by a wood-burning stove set in a stone hearth, and a well-appointed kitchen with stainless appliances and island. A relaxing entertainment area with full bath flows into the heated sunroom addition, with expansive windows framing the lake views and opening onto a wraparound deck. A generous mudroom entry handles gear for every season with ease. Upstairs, the primary suite offers wonderful natural light and a luxurious bath, alongside three spacious guest bedrooms, two additional full baths, custom built-in storage, and a lovely office space. The practical upgrades here are just as impressive: efficient mini-split heating and air conditioning, an attached garage for gear storage, an updated septic system, and a private driveway with ample parking. All of it recently completed, the home is completely turnkey - so all you'll have to worry about is downtime, not upkeep.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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

6 Trail View Lane Dover VT 05356

Dover, VT6 Trail View Lane

Price$2,099,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5072588

  • Residential Single Family
  • Full Bath 5
  • Address 6 Trail View Lane
  • Bedrooms 5
  • Bathroom 6

Enjoy stunning views, privacy, and luxury, 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, tennis courts, game room, on site management company, and direct shuttle service between your home and the base area. This home has been completely renovated and expanded, and features breathtaking views of the ski trails, fireworks displays, and sunsets over the ridgeline, from many of the rooms. The home uniquely features 5 full suites, one of which is on the main floor, as well as a main floor guest bath, an expansive great room with vaulted ceilings, massive stone fireplace with rustic archways, a gorgeous new chefs kitchen with stainless appliances, tile backsplash, farmhouse sink, custom cabinets, island with waterfall counters, amazing natural light and warm lighting schemes, a spacious dining area, media room with built in bookcases, second floor family room with vaulted ceilings, exposed beams, and built in bunk room accessible via barn doors, a vaulted Vermont entry, large mudroom entry with cubbies ideal for winter gear, large new deck overlooking the views, and extensive landscaping. Head to toe renovated with new minisplit a/c. 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

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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: 6.48% last updated on 2026-06-04

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 2026 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 June 9, 2026 9:40 AM EDT

 

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