Windham County VT Homes for Sale

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  /11

  $465,000

  • 3,756 Sq Ft

  820 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. Offered at an impressive 10% cap rate, the building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 Western Ave, Brattleboro, VT 05301
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  /45

  $69,500

  • Land
  • 5.57 Acres
  • $12,478 per Acre

  776 Old Route 8, Jamaica, VT 05343

  Tucked away on 5.57 wooded acres, this Vermont property offers the kind of setting that invites you to slow down, breathe deep, and enjoy the outdoors. Located just a few miles from town and everyday essentials, it strikes a rare balance between peaceful seclusion and easy convenience. A portion of the land reaches over to the Norton Pond side of the road, where lake access just across the

  Brandy Goulet Century 21 Farm & Forest/Burke

  776 Old Route 8, Jamaica, VT 05343
• 

  

  

  /40

  $785,000

  • 3 Beds
  • 4 Baths
  • 3,086 Sq Ft

  145 Leon Stocker Dr, Stratton, VT 05360

  Set on two private, wooded acres, this inviting mountain retreat balances classic Vermont warmth with a spacious 3,986-square-foot layout featuring three comfortable bedrooms, a spacious loft area, and four bathrooms. Ideally situated for outdoor enthusiasts, the property offers close proximity to Vermont's VAST trail network, making year-round adventure easily accessible. The heart of the home

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  145 Leon Stocker Dr, Stratton, VT 05360
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  /29

  $115,000

  • Land
  • 5 Acres
  • $23,000 per Acre

  0 Happy Haven Rd Unit 5097175, Wilmington, VT 05363

  Beautiful 5-Acre Vermont Lot with Mountain Views & Potential for Two Home Sites. Discover a rare opportunity to own a stunning 5-acre parcel in southern Vermont, ideally located on Route 100 just north of downtown Wilmington. This exceptional property offers the perfect setting for your dream home—or the potential to build two. Preliminary soil testing supports the potential for two separate

  Monique White Deerfield Valley Real Estate

  0 Happy Haven Rd Unit 5097175, Wilmington, VT 05363
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  /9

  $385,000

  • 7 Beds
  • 4 Baths
  • 3,551 Sq Ft

  1950 N Main St, Londonderry, VT 05148

  It is possible to live rent- or mortgage-free — and here’s your opportunity.This fully rented, three-unit multi-family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with

  Wilkie Bushby TPW Real Estate

  1950 N Main St, Londonderry, VT 05148
• 

  

  /31

  $649,000

  • 5 Beds
  • 3 Baths
  • 2,688 Sq Ft

  7 Tapping Tree Ln, West Dover, VT 05356

  Beautifully maintained and updated expanded chalet in the Dover Hills, just a short drive from the Mount Snow ski resort. The current owners have taken care to keep the original charm of this home while adding rustic features and recent beautiful updates to allow for turn key enjoyment. Off the side of a private cul-de-sac, this home sits on a level double lot with ample parking and pull through

  Adam Palmiter Berkley & Veller Greenwood/Dover

  7 Tapping Tree Ln, West Dover, VT 05356
• 

  

  /27

  $140,000

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  2074 Vt Rt 30, Jamaica, VT 05343

  Some places stop time. River's Edge is one of them.Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River — away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin

  Mike England Michael England Real Estate

  2074 Vt Rt 30, Jamaica, VT 05343
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  /46

  $734,000

  • 3 Beds
  • 5 Baths
  • 4,285 Sq Ft

  258 Chester Rd, Grafton, VT 05146

  Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience.Inside, warm hardwood floors,

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  258 Chester Rd, Grafton, VT 05146
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  /38

  $515,000

  • 4 Beds
  • 3 Baths
  • 2,115 Sq Ft

  367 Stratton Gate Rd, Jamaica, VT 05343

  Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

  

  Alison Cummings

  Cummings & Co

  367 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /43

  $535,000

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft

  176 Brophy Ln, Londonderry, VT 05148

  Discover this charming Vermont log cabin, situated on a quiet, secluded lot just 5 minutes from downtown Londonderry, and 15 minutes to downtown Manchester's restaurants and shopping. This home offers the perfect balance of peaceful mountain living and easy access to local amenities. The first level welcomes you into a large, open-concept living room, dining room, and kitchen area, perfect for

  

  Christopher Cummings

  Cummings & Co

  176 Brophy Ln, Londonderry, VT 05148
• 

  

  /25

  $389,900

  • 2,168 Sq Ft

  88 Happy Haven Rd, Wilmington, VT 05363

  Sweet Country Retreat Near Mount Snow & The Hermitage Club Tucked away on a quiet private road in the heart of Wilmington, this charming country home offers the perfect blend of privacy, comfort, and four-season Vermont living. Just minutes from Mount Snow and the exclusive Hermitage Club, this spacious property is an ideal mountain getaway, full-time residence, or investment opportunity.

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  88 Happy Haven Rd, Wilmington, VT 05363
• 

  

  /54

  $1,249,000

  • 3 Beds
  • 3 Baths
  • 3,654 Sq Ft

  201 Chester Rd, Grafton, VT 05146

  Meticulously maintained and thoughtfully designed, this three-bedroom, three-bath home offers the perfect balance of comfort, functionality, and classic Vermont charm. Set on a picturesque parcel with stunning long-range views, the property is surrounded by mature trees, a small pond, established gardens, and simple, easy-to-maintain landscaping that enhances the natural beauty of the

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  201 Chester Rd, Grafton, VT 05146
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  /34

  $78,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  22 Valley St, Brattleboro, VT 05301

  Welcome to 22 Valley Road, an affordable and easy-to-maintain 2-bedroom, 1-bath mobile home located in Brattleboro’s Tri-Park Cooperative Housing Corporation. This cozy single-level home offers a bright and refreshed interior with natural light, LED lighting, first-floor laundry hookups, and a functional layout that makes great use of the space. The kitchen features an electric range,

  Grayson VanHendrick Flex Realty

  22 Valley St, Brattleboro, VT 05301
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  /16

  $390,000

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  120 Green Mountain Trail, Londonderry, VT 05148

  Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and a full basement providing additional storage and utility space. Recent improvements include a brand-new roof (2026)

  Wilkie Bushby TPW Real Estate

  120 Green Mountain Trail, Londonderry, VT 05148
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  /33

  $339,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  8 Beech Tree Ln, Newfane, VT 05345

  This is just the cutest little cottage you ever did see! It is just the right size not too big, not too small. This charming country cottage would be a wonderful small footprint primary home or would make an ideal weekend getaway! The first floor living space is open with lovely wood floors and a wood stove perfect for those crisp country evenings, tastefully updated kitchen, dining area, and

  Rebecca Seymour Brattleboro Area Realty

  8 Beech Tree Ln, Newfane, VT 05345
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  /60

  $3,995,000

  • 4 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
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  /56

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  136 Yeaw Rd, Dover, VT 05341

  A property that truly must be seen to be appreciated, this exceptional Southern Vermont home offers the perfect balance of privacy and convenience, just minutes from Mount Snow and the village of West Dover. Filled with natural light and hardwood floors, the home offers spaces designed for both comfortable everyday living and entertaining. The beautifully renovated primary suite features a

  Amy Carson Lowe's Real Estate, LLC

  136 Yeaw Rd, Dover, VT 05341
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  /11

  $585,000

  • Land
  • 36.69 Acres
  • $15,944 per Acre

  0 Pine Banks Rd Unit 5096685, Westminster, VT 05158

  Exceptional opportunity to own 36.69 acres of scenic Vermont countryside on desirable Pine Banks Road on the Westminster/Putney border. This beautiful parcel offers a rare combination of expansive open meadows, wooded privacy, and breathtaking long-range views across the Connecticut River Valley and surrounding Green Mountain foothills. The property's rolling landscape provides multiple potential

  Mickey Hipp BHG Masiello Brattleboro

  0 Pine Banks Rd Unit 5096685, Westminster, VT 05158
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  /26

  $1,100,000

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

  48A Hammer Beam Loop Unit 48A, Dover, VT 05356

  Stunning post-and-beam townhome at the base of Mount Snow ski resort. Built in 2007 and completely renovated for turnkey enjoyment, this exceptional unit offers a style and scale rarely found this close to the mountain. Rustic natural woodwork runs throughout, a product of the exposed post-and-beam construction that gives the home its unmistakable character. The open-concept main living level

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48A Hammer Beam Loop Unit 48A, Dover, VT 05356
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  /34

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
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  /48

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  35 Theron Fisher Rd, Grafton, VT 05146

  Nestled along the Saxtons River, moments from historic Grafton, this beautifully restored Colonial farmhouse offers a rare blend of Vermont history, modern luxury, and exceptional curb appeal. Originally built circa 1820, the home has been meticulously reimagined and rebuilt with extraordinary attention to quality and architectural integrity. The renovation includes new plumbing, electrical,

  Gary Coger Four Seasons Sotheby's Int'l Realty

  35 Theron Fisher Rd, Grafton, VT 05146
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  /40

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  152 Our Rd, Putney, VT 05346

  Showings begin Saturday, June 27. Escape to your own Vermont retreat with this charming 2-bedroom, 2-bath log home nestled on 4.7 private acres in Westminster. Set back from the road and surrounded by nature, this property offers the peace and privacy you’ve been searching for while remaining conveniently close to local amenities. A circular driveway welcomes you home, leading to a classic

  Morriah Adams BHG Masiello Brattleboro

  152 Our Rd, Putney, VT 05346
• 

  

  /20

  $239,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft

  1359 Brockways Mills Rd, Rockingham, VT 05143

  Here is your chance to be a homeowner on 4.6 acres of your very own land. This sweet double wide built in 2000 will be easy to heat and maintain for the best of country living on a paved road. This home consists of 3 bedrooms, two baths. The living area is open and spacious with a large living room, dining room and a wonderful functional kitchen. The primary bedroom has its own bath for privacy.

  Monica Sumner BHG Masiello Brattleboro

  1359 Brockways Mills Rd, Rockingham, VT 05143
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  /28

  $675,000

  • 5 Beds
  • 2 Baths
  • 3,144 Sq Ft

  23 Burchard Rd, Dover, VT 05356

  Beautiful contemporary farmhouse with mountain views just a short drive from the Mount Snow ski resort and country village of Wilmington. This home sits conveniently on a level lot with tremendous privacy, but with sewer for peace of mind, high speed internet for easy of use, and shuttle service at the bottom of the street for great mountain access. Thanks to a private lot abutting larger

  Adam Palmiter Berkley & Veller Greenwood/Dover

  23 Burchard Rd, Dover, VT 05356
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  /26

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,136 Sq Ft

  279 North St, East Dover, VT 05341

  Rustic Hunting Cabin on 1+/- Acres. Several sleeping areas including a loft. One full bathroom. Kitchen with stove, ,microwave, refrigerator, stove, pellet stove, wood stove, 2 mini splits, washer & dryer. Plan your weekend runaway now!

  Janet Boyd Boyd Real Estate

  279 North St, East Dover, VT 05341
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  /49

  $979,000

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft

  60 Whites Hill Rd, Dover, VT 05356

  Most people remember the porch first.Floor-to-ceiling panel screens, no handrails, no visual interruption — just a spring-fed pond, a 20-acre hay field, and the Green Mountain ridgeline beyond. The house was positioned to capture this view, and the porch is where it is experienced best.10 private acres in East Dover. Custom-built 1999, expanded 2021, owned and improved by the same family

  Monica Sumner BHG Masiello Brattleboro

  60 Whites Hill Rd, Dover, VT 05356
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  /32

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  14 Mill Rd, West Dover, VT 05356

  Beautifully Maintained 4-Bedroom Home with Spacious Loft Near Mount Snow Ideally located just minutes from Mount Snow, this inviting 4-bedroom, 3-bath home offers the perfect blend of comfort, convenience, and privacy. Nestled in the desirable Sugar Mill Village community, just off Route 100, the property is tucked away in a peaceful wooded setting that feels worlds away while remaining easily

  Joe Castaluccio Winhall Real Estate

  14 Mill Rd, West Dover, VT 05356
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  /36

  $549,000

  • 4 Beds
  • 3 Baths
  • 1,936 Sq Ft

  202 Twin Brook Cir, Londonderry, VT 05148

  Tucked away at the end of a long private driveway on a quiet cul-de-sac, this impeccable 4-bedroom chalet offers the perfect blend of privacy, adventure, and year-round Vermont living in the sought-after Powder Mill community. Set on 1.54 wooded acres, the property is surrounded by nature with access to maintained hiking and snowmobile trails, including connections to the VAST trail network and

  Carrie Mathews Winhall Real Estate

  202 Twin Brook Cir, Londonderry, VT 05148
• 

  

  /38

  $309,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  48 Carriage Hill Rd, Brattleboro, VT 05301

  ***Open House Saturday 6/27 from 11am-2pm** Step into a home that offers the space, privacy, and outdoor lifestyle today's buyers are searching for. With three bedrooms and a comfortable layout, this property blends everyday functionality with room to relax and entertain. The real showstopper is the backyard. Fully fenced and remarkably level, it's a rare find that creates the perfect setting for

  Jonathan Griffus BHG Masiello Keene

  48 Carriage Hill Rd, Brattleboro, VT 05301
• 

  

  /37

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  157 Newfane Hill Rd, Newfane, VT 05345

  Welcome to a home with a story. Originally the 1787 residence of local blacksmith Marshall Newton, this property has been a cherished family retreat for the last fifty years. One of only two original settlements on Newfane Hill that are still there. It’s a place with "old world" charm—like centuries-old wall paneling —but also a new 2025 standing-seam roof and extensive insulation upgrades. This

  Thomas Dahlin Berkley & Veller Greenwood Country

  157 Newfane Hill Rd, Newfane, VT 05345
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  /60

  $795,000

  • 2 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  947 Miller Rd, Brattleboro, VT 05301

  Stunning Southern Vermont home with views, gardens and private pond on 10 acres incoveted Dummerston, Windham County. Entering the circular drive, lush perennial gardens welcome you and the magic begins. This meticulously designed 1600-square-foot home features soaring ceilings and superior craftsmanship throughout. Thespacious kitchen includes custom cabinetry, Sub-Zero and Wolf

  Kristen Ziter Taylor Brattleboro Area Realty

  947 Miller Rd, Brattleboro, VT 05301
• 

  

  /31

  $450,000

  • 4 Beds
  • 3.5 Baths
  • 2,952 Sq Ft

  53 Sugar House Rd, Dover, VT 05301

  Just minutes from Mount Snow, this contemporary chalet offers approximately 3,000 square feet of finished living space and easy access to Southern Vermont's year-round recreation. A cathedral ceiling, floor-to-ceiling windows, abundant natural light, hardwood floors, and a wood-burning fireplace create a warm and inviting atmosphere. The flexible floor plan offers ample space for entertaining,

  Melissa Nebelski Real Broker LLC

  53 Sugar House Rd, Dover, VT 05301
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  /35

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  7 Lightning Ledge Way, Wilmington, VT 05363

  Located in the Chimney Hill community, this four-bedroom, two-bath home offers the perfect Southern Vermont retreat for every season. The open-concept living, kitchen, and dining area creates a welcoming space for gathering with family and friends after a day of skiing, boating, hiking, or exploring the area. Warm wood accents and comfortable living spaces create a relaxed Vermont atmosphere that

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  7 Lightning Ledge Way, Wilmington, VT 05363
• 

  

  /50

  $589,000

  • 3 Beds
  • 3 Baths
  • 2,144 Sq Ft

  596 Four Chimneys Rd, Grafton, VT 05146

  Tucked away near the end of a quiet dead-end country road, this charming vintage rambler offers privacy, natural beauty, and the timeless appeal of rural Vermont living. Set on more than 17 acres of open meadows, woodlands, wildflower fields, aged apple trees and two crystal-clear ponds, the property invites you to reconnect with nature in every season. Summer days are made for exploring the

  Jessica Landers Barrett and Valley Associates Inc.

  596 Four Chimneys Rd, Grafton, VT 05146
• 

  

  /50

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft

  364 Houghtonville Rd, Grafton, VT 05146

  At the beginning of a dirt road just outside the historic village of Grafton VT you will find an exceptional country estate that combines timeless New England charm with modern comfort, privacy, and equestrian amenities. Thoughtfully designed to replicate a classic colonial home and extensively updated by its current owners, this meticulously maintained property offers an extraordinary lifestyle

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  364 Houghtonville Rd, Grafton, VT 05146
• 

  

  /41

  $459,000

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  60 E Brook Crossing, Wilmington, VT 05363

  Tucked among mature trees in the desirable lower section of Chimney Hill, this charming home offers comfort, character, and easy living. A gently sloping gravel driveway and attached garage provide year-round convenience, while beautifully established perennial gardens and a gently sloping yard create an inviting outdoor setting rarely found in the area. Inside, the home exudes warmth and rustic

  Erica Reynolds Southern Vermont Realty Group

  60 E Brook Crossing, Wilmington, VT 05363
• 

  

  /51

  $615,000

  Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  58 Stone Hollow, Londonderry, VT 05148

  Located just under a mile from the center of Londonderry this unique chalet home is crafted with exceptional attention to detail and energy efficiency for year-round comfort. The gourmet kitchen is equipped with professional-grade appliances, contemporary finishes, and a layout designed for everyday living.Adding to the property's unique appeal is a remarkable 480-square-foot treehouse

  Jessica Citera Cummings & Co

  58 Stone Hollow, Londonderry, VT 05148
• 

  

  /34

  $949,000

  • 3 Beds
  • 3.5 Baths
  • 1,800 Sq Ft

  56 Shattarack Rd Unit D6, Stratton, VT 05360

  OPEN HOUSE JULY 4TH 2PM-4PM. Experience ultimate year-round luxury in this tastefully renovated townhome at Slopeside, featuring convenient trail access. Perfectly blending comfort and convenience, this inviting mountain retreat features an updated kitchen and baths, a cozy wood-burning fireplace, and mini-splits for efficient summer cooling. The spacious layout offers three bedrooms plus a

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  56 Shattarack Rd Unit D6, Stratton, VT 05360
• 

  

  /33

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft

  57 Timber Ln, Wardsboro, VT 05360

  Conveniently located between Mount Snow and Stratton Resort you'll find this three-bedroom, two-bathroom home surrounded by lush perennial gardens that thrive in the sun of the one-acre lot's southern exposure within the desirable Snow Mountain Farms community of Wardsboro, Vermont. The main level features an inviting open-concept layout that seamlessly connects the galley kitchen with eat-in

  Kim Meeker Southern Vermont Realty Group

  57 Timber Ln, Wardsboro, VT 05360
• 

  

  /20

  $149,000

  • Land
  • 24 Acres
  • $6,208 per Acre

  381 Whitaker Farm Rd, Marlboro, VT 05344

  24 improved acres in the hills of Marlboro offering a combination of privacy, accessibility, residential, and recreational potential. Recent driveway improvements have created excellent access into the property, leading to a cleared landing and potential building site set back from the road. Existing recreational and old logging trails meander throughout the acreage and are well-suited for

  Jacki Murano Southern Vermont Realty Group

  381 Whitaker Farm Rd, Marlboro, VT 05344

Showing Results 41 - 80, Page 2 of 12