Windham County VT Homes for Sale

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  $1,997,000

  • 4 Beds
  • 4.5 Baths
  • 3,631 Sq Ft

  14 Talon Dr, Stratton, VT 05360

  Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  14 Talon Dr, Stratton, VT 05360
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  /44

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  85 Browns Rd, Newfane, VT 05345

  Steeped in Vermont history and surrounded by more than 80 acres of fields, woods, and walking trails, this beautifully preserved Newfane farmhouse offers the rare opportunity to own a property where timeless character and modern comfort come together. Whether you're looking for a full-time residence, country retreat, or recreational property, this is a place to slow down and enjoy the beauty of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  85 Browns Rd, Newfane, VT 05345
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  /50

  $599,000

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  24 First Ln Unit 24, Wilmington, VT 05363

  Beautifully updated Country Club Village townhome overlooking the golf course! This move-in-ready property features a remodeled kitchen with granite countertops, stainless steel appliances, and an open-concept kitchen and dining area that's perfect for entertaining. All bathrooms have been tastefully renovated, and new flooring throughout gives the home a fresh, modern feel. Additional upgrades

  Rich Caplan Deerfield Valley Real Estate

  24 First Ln Unit 24, Wilmington, VT 05363
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  /31

  $680,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

  Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

  Timothy Mich Doddridge Stratton Real Estate

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
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  /34

  $175,000

  • 3 Beds
  • 1.5 Baths
  • 1,130 Sq Ft

  58 Scandia Village Rd, West Wardsboro, VT 05360

  Tucked away on 1.20 acres in Wardsboro, this 3-bedroom, 1.5-bath home offers a peaceful Vermont setting with plenty of outdoor space to enjoy. The home features 1,130 finished square feet with a warm, cabin-like interior, wood accents, and an inviting open living area with a wood stove insert for added comfort. The kitchen flows nicely into the main living space, creating an easy layout for

  Grayson VanHendrick Flex Realty

  58 Scandia Village Rd, West Wardsboro, VT 05360
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  /5

  $499,900

  • Land
  • 8.3 Acres
  • $60,229 per Acre

  340 Tyanoga Lot X, Whitingham, VT 05361

  WATERFRONT! WATERFRONT! 756' OF WATERFRONT!!Not only will you enjoy stunning lakefront living- you'll own part of the lake itself with this exceptional 8.3-acre parcel on beautiful Lake Sadawga.Nestled at the end of a quiet cul-de-sac, this private property offers water views and the perfect setting to build your dream home, for full-time living or a second home for quiet enjoyment. Much

  Pauline Green

  340 Tyanoga Lot X, Whitingham, VT 05361
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  /60

  $6,898,000

  New Construction

  • 3 Beds
  • 6 Baths
  • 4,000 Sq Ft

  88 Mann Rd, Wilmington, VT 05363

  A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At

  Rich Caplan Deerfield Valley Real Estate

  88 Mann Rd, Wilmington, VT 05363
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  /24

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 1,730 Sq Ft

  1-C Townhouse Square, Dover, VT 05356

  Experience true ski-in/ski-out living at Mount Snow in the highly sought-after Seasons on Mount Snow community, perfectly situated on Tin Lizzy Trail just seconds from the lift. This spacious 3-bedroom, 3.5-bath townhouse features a thoughtfully designed floor plan, including two private en suite bedrooms that provide exceptional comfort and flexibility for family and guests. Designed for both

  Stephanie Sugden Real Broker LLC

  1-C Townhouse Square, Dover, VT 05356
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  /36

  $525,000

  Open Sat 11AM - 1PM Coming Soon

  • 4 Beds
  • 2 Baths
  • 2,800 Sq Ft

  195 Bellows Falls Rd, Putney, VT 05346

  Charming Putney retreat on 7.8 acres of open and forested land featuring a main house plus an attached in-law suite/apartment with separate entrance—ideal for multi-generational living or aging in place. Enjoy privacy and character with stone walls, abundant fruit trees including peach trees and raspberries, mature lilacs, and five perennial & peony beds. Just 1 mile from the Putney general

  John Hatton Berkley & Veller Greenwood Country

  195 Bellows Falls Rd, Putney, VT 05346
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  /59

  $675,000

  • 3 Beds
  • 2 Baths
  • 2,245 Sq Ft

  442 Josh Rd, Brattleboro, VT 05301

  These spectacular 64 acres are located in one of the area's most romantically pastoral settings with open fields offering a mesmerizing view of Mount Monadnock, all of which is protected by a view easement. Set back at the end of a quiet dirt road and lined by stone walls, with boundary points marked by white quartz boulders, this renovated 1825 post-and-beam farmhouse combines classic

  Neil Goldberg Brattleboro Area Realty

  442 Josh Rd, Brattleboro, VT 05301
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  /20

  $419,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  13 Mill Rd, West Dover, VT 05356

  Three-bedroom, two-bath home on just under a half-acre in Sugar Mill Village offering a functional layout, views of Mount Snow's trails and summit, and a location that puts the area's year-round recreation close at hand. The main level features an open kitchen with breakfast bar, full dining with slider to deck, and living area centered around a wood-burning fireplace, creating a comfortable

  Jacki Murano Southern Vermont Realty Group

  13 Mill Rd, West Dover, VT 05356
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  /22

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you are looking for a second home in the mountains or

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /10

  $129,000

  • Land
  • 2.1 Acres
  • $61,429 per Acre

  179 Oak Hill Rd, Wardsboro, VT 05353

  TWO LOTS, H-4 & H-13, you choose where to build, septic permits in place for both lots! Two, FOUR BEDROOM WASTEWATER PERMITS on file with the state one for each lot! Cleared lot on Maple with driveway installed, the other has been cut and could be ready to go easily! Don't miss this chance to own two abutting lots! Is being offered together or separate! See also MLS#5090072.

  Chris Lowe Lowe's Real Estate, LLC

  179 Oak Hill Rd, Wardsboro, VT 05353
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  /25

  $219,000

  • Land
  • 16.9 Acres
  • $12,959 per Acre

  00 Howe Farm Rd, Jamaica, VT 05343

  Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound,

  Patrice Schneider Southern Vermont Realty Group

  00 Howe Farm Rd, Jamaica, VT 05343
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  /24

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,036 Sq Ft

  456 Route 100, Wilmington, VT 05363

  Light-filled and full of cottage charm, this beautifully updated 2-bedroom, 1-bath home sits on 3.4 level acres with a shared pond, offering a peaceful country setting just minutes from the heart of Wilmington. Originally designed as a 3-bedroom home, the upper level has been roughed in and plumbed, providing an incredible opportunity to create a spacious primary ensuite, additional bedrooms, or

  Patrice Schneider Southern Vermont Realty Group

  456 Route 100, Wilmington, VT 05363
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  /40

  $419,000

  • 3 Beds
  • 1.5 Baths
  • 1,908 Sq Ft

  1408 Hatch School Rd, Brattleboro, VT 05301

  This lovely New England cape is situated on 11 acres, surrounded by beautiful, level land and abundant wildlife. A charming wildlife pond is tucked behind the home, accompanied by a clearing for breathtaking nature scenes. The home has been lovingly cared for by the same family since it was built. Boasting granite countertops and spacious cabinets, the kitchen is well equipped. Two eating areas

  Monica Sumner BHG Masiello Brattleboro

  1408 Hatch School Rd, Brattleboro, VT 05301
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  /47

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  5 Camelot Dr, Wilmington, VT 05363

  Motivated seller! Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the

  Chad Lackey Deerfield Valley Real Estate

  5 Camelot Dr, Wilmington, VT 05363
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  /24

  $255,000

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  23 Robin Way, Brattleboro, VT 05301

  What sets this unit apart is not just that it is an end unit, but it is an end unit with a private deck! You are also right next to the path to Memorial Park for swimming, skiing, skating, baseball games, summer theatre, and so much more! Or head to the popular Saturday Farmer's Market just around the corner. This unit features two bedrooms, one and a half bathrooms, single car garage with

  Rebecca Seymour Brattleboro Area Realty

  23 Robin Way, Brattleboro, VT 05301
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  /36

  $725,000

  • 5 Beds
  • 3 Baths
  • 2,427 Sq Ft

  95 Hemlock Dr, Londonderry, VT 05148

  The smell of woodsmoke on a crisp alpine afternoon, the quiet crunch of fresh powder underfoot, and the sense that the rest of the world has dropped away—this is the reality waiting at the top of Powder Mill Ridge. Tucked into three acres of private Vermont forest, this contemporary retreat is designed less like a standard house and more like a basecamp for a life well-lived.Winters mean

  Robin Apps Four Seasons Sotheby's Int'l Realty

  95 Hemlock Dr, Londonderry, VT 05148
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  /35

  $799,000

  • 5 Beds
  • 3 Baths
  • 2,070 Sq Ft

  24 Snow Vidda Loop, Dover, VT 05356

  Mount Snow Retreat – Walk to the Slopes!Experience the ultimate Vermont mountain getaway in this spacious, fully furnished home, ideally located within walking distance to the Mount Snow slopes. Perfect for large families, groups, or as a vacation retreat, this inviting property features 5 bedrooms and 3 bathrooms, offering plenty of space for everyone.The open-concept living and dining

  Lisa Mirando Deerfield Valley Real Estate

  24 Snow Vidda Loop, Dover, VT 05356
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  /24

  $325,000

  • 2 Beds
  • 2 Baths
  • 2,000 Sq Ft

  239 Harwood Place, Townshend, VT 05359

  Welcome to this one-of-a-kind hexagonal home nestled in the heart of the West River Valley, where thoughtful updates meet Vermont character and a truly special setting. This 2-bedroom, 2-bath residence offers a unique architectural design with vaulted ceilings, abundant natural light, and a layout that feels both open and inviting. The property is very private and also boasts seasonal mountain

  Mike Masters Four Seasons Sotheby's Int'l Realty

  239 Harwood Place, Townshend, VT 05359
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  /40

  $199,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  253 Farnsworth Cir, Putney, VT 05346

  Welcome to 253 Farnsworth Circle in Westminster, VT—a property with beautiful views and plenty of potential to make it your own. The home has already seen several meaningful updates, including a newer metal roof, a refreshed kitchen with new cabinets and countertops, and newer appliances, giving you a great head start on improvements. Step outside onto the spacious deck, the perfect place to

  Kelsey Malloy Keller Williams Realty Metro-Keene

  253 Farnsworth Cir, Putney, VT 05346
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  /60

  $2,290,000

  • 5 Beds
  • 9 Baths
  • 4,400 Sq Ft

  634 Lower Dover Rd, Marlboro, VT 05301

  Discover a once-in-a-generation opportunity to own an extraordinary 745± acre estate in the heart of Southern Vermont. Steeped in centuries of history yet thoughtfully updated for modern living, this remarkable property combines unmatched natural beauty, recreational opportunities, and agricultural potential. The diverse landscape features expansive open fields, mature woodlands, pristine

  Michael Purcell Berkley & Veller Greenwood/Dover

  634 Lower Dover Rd, Marlboro, VT 05301
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  /18

  $409,000

  • 1 Bed
  • 1 Bath
  • 675 Sq Ft

  771 Stratton Mountain Access Rd Unit 468, Stratton, VT 05360

  Perfectly positioned in the heart of Stratton Mountain Resort, this well-maintained fourth-floor Long Trail condominium offers the mountain lifestyle you are looking for. Enjoy partial views of the mountain from your retreat while being just a short walk to Stratton's ski slopes, Village shops, restaurants, year-round events, and outdoor activities. Whether you're heading out for first tracks,

  Carrie Mathews Winhall Real Estate

  771 Stratton Mountain Access Rd Unit 468, Stratton, VT 05360
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  /12

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  455 S Main St, Brattleboro, VT 05301

  Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

  Christine Lewis Brattleboro Area Realty

  455 S Main St, Brattleboro, VT 05301
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  /21

  $160,000

  • Land
  • 11.08 Acres
  • $14,440 per Acre

  0 Rose Ln Unit 5097818, Londonderry, VT 05148

  This 11-acre parcel is situated near Cole Pond, only a few miles from the Stratton Mountain Access Road. The lot offers several potential building sites, including an elevated area that boasts stunning views, as well as a lower option. A driveway extends approximately halfway up the property, providing access to the upper site, which features a remarkable vista of Bromley Mountain. As one

  Mike England Michael England Real Estate

  0 Rose Ln Unit 5097818, Londonderry, VT 05148
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  /21

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,053 Sq Ft

  180 Debbie Higgins Ln, Wardsboro, VT 05355

  Charming, rustic mountain-theme home in excellent turnkey condition located in the peaceful, convenient Snow Mountain Farms in Wardsboro, offering the best of Vermont living. Surrounded by nature and just minutes from scenic hiking trails, outdoor recreation, and year-round adventure, this 3-bedroom, two-story chalet is the perfect mountain retreat. Features include three updated bedrooms, two

  Patrice Schneider Southern Vermont Realty Group

  180 Debbie Higgins Ln, Wardsboro, VT 05355
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  /48

  $975,000

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  412 Hall Ranch Rd, Grafton, VT 05146

  Historic Vermont Hill Farm on 112 Acres Discover the timeless beauty of Vermont country living on this historic hill farm, offering 112 acres of rolling landscapes, open pasture, and wooded privacy. Set among the peaceful hills, this classic property combines the character of a traditional Vermont homestead with the space, versatility, and natural beauty that make rural living so special. The

  Craig Ruggless EXP Realty

  412 Hall Ranch Rd, Grafton, VT 05146
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  /5

  $699,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 3,044 Sq Ft

  661 Wright Orchard Rd, Grafton, VT 05146

  Turn-key, beautifully furnished, and ready to enjoy, this exceptional Vermont property is being offered with all brand-new furnishings included, making it a rare opportunity to step right into the Vermont lifestyle. Set on 20 private acres in the heart of Grafton, this beautifully maintained 3-bedroom, 2-bath home with a custom office offers the perfect blend of comfort, versatility, and modern

  Gail Beardmore Engel & Völkers Okemo

  661 Wright Orchard Rd, Grafton, VT 05146
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  /60

  $1,100,000

  • 3,374 Sq Ft

  85 Route 100, West Dover, VT 05356

  Southern Vermont's fully renovated Mount Snow income compound: five separately metered rentable units across four buildings on 2.57 level acres in West Dover, main-road frontage on VT Route 100, pond on site. About 5 minutes from Mount Snow Resort in the Deerfield Valley, on the ski-bus route from the mountain into Wilmington. Same-road neighbors include Gray Ghost Inn (sold $1,100,000, 2023) and

  Nick Sicard EXP Realty

  85 Route 100, West Dover, VT 05356
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  /19

  $63,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  2022 Route 30, Jamaica, VT 05343

  Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both!Stratton is just 20

  Carrie Mathews Winhall Real Estate

  2022 Route 30, Jamaica, VT 05343
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  /46

  $869,900

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  45 Sawmill Village Way, Dover, VT 05356

  Experience the perfect blend of Vermont charm and modern comfort in this beautifully crafted custom post-and-beam home with a beautiful view, ideally located in the heart of Dover. Just minutes from Mount Snow, local restaurants, shopping, area amenities, and the scenic Valley Trail, this home offers the perfect balance of convenience and privacy in a peaceful wooded setting. Inside, many windows

  Rich Caplan Deerfield Valley Real Estate

  45 Sawmill Village Way, Dover, VT 05356
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  /60

  $1,998,000

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  32 Steep Hill Rd, Wilmington, VT 05363

  Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont’s Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the southern

  Rich Caplan Deerfield Valley Real Estate

  32 Steep Hill Rd, Wilmington, VT 05363
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  $875,000

  • 3 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  482 E Dover Rd, Wardsboro, VT 05355

  Beautiful custom-built log home perched on a hillside in South Wardsboro, offering privacy and a convenient location between Mount Snow and Stratton ski resorts, with easy access to Brattleboro and Manchester. Set on 3 scenic acres, this 3-bedroom, 2 1/2 bath home with a loft blends rustic charm with modern comfort. The inviting covered front porch leads to an open-concept living with fireplace,

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  482 E Dover Rd, Wardsboro, VT 05355
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  /7

  $20,000

  • Land
  • 1.3 Acres
  • $15,385 per Acre

  0 Smead Rd Unit 5097619, Wardsboro, VT 05360

  Affordable opportunities to own land in Southern Vermont are becoming increasingly hard to find. This 1.30+/- acre wooded parcel on Smead Road offers a gradual rise from the road, creating a private, natural setting to enjoy now or explore for the future. Conveniently located between Mount Snow and Stratton, the property is close to year-round recreation, including skiing, snowmobiling, hiking,

  Jacki Murano Southern Vermont Realty Group

  0 Smead Rd Unit 5097619, Wardsboro, VT 05360
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  /29

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 1,993 Sq Ft

  18 High Point Dr Unit 501, Stratton, VT 05360

  Located just one mile from Stratton’s Base Lodge and Village, this 4-bedroom, 3-bath end-unit Styles Brook townhome offers the perfect combination of convenience, comfort, and year-round mountain living. Spanning three levels, Unit 501 enjoys the added privacy, extra windows, and abundant natural light that come with end-unit ownership. The main level is designed for gathering, featuring

  Cheyanne Pugliese

  18 High Point Dr Unit 501, Stratton, VT 05360
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  /31

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  28 Styles Branch Rd Unit 305, Stratton, VT 05360

  Experience the ease of Stratton Mountain living from this inviting three-bedroom Styles Brook condominium, ideally located just moments from the lifts. Hop on the convenient winter shuttle or enjoy a pleasant walk to the base area, with Stratton's Sports Center, fitness facilities, and year-round amenities just a short stroll away.Designed for both comfort and entertaining, the spacious main

  Carrie Mathews Winhall Real Estate

  28 Styles Branch Rd Unit 305, Stratton, VT 05360
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  /28

  $480,000

  • 5 Beds
  • 2 Baths
  • 2,194 Sq Ft

  3327 Route 30, Jamaica, VT 05343

  Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and

  Carrie Mathews Winhall Real Estate

  3327 Route 30, Jamaica, VT 05343
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  /40

  $1,500,000

  • 7 Beds
  • 7.5 Baths
  • 8,364 Sq Ft

  251 Pratt Bridge Rd, Jamaica, VT 05343

  Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

  TG Glazer Winhall Real Estate

  251 Pratt Bridge Rd, Jamaica, VT 05343
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  /13

  $515,000

  • 3,364 Sq Ft

  28 Brook St, Brattleboro, VT 05301

  Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. Offered at an impressive 10% cap rate, the building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  28 Brook St, Brattleboro, VT 05301

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