Windham County VT Homes for Sale

• 

  

  

  /60

  $674,950

  • 3 Beds
  • 2.5 Baths
  • 2,386 Sq Ft

  56 Whitetail Dr, Vernon, VT 05354

  Buyer could not obtain financing. Properties of this scale and setting are a rare find. Designed with entertaining in mind, the home’s circulation flows effortlessly through a dramatic great room anchored by a striking two-story fireplace. The space opens seamlessly to the dining and kitchen areas and is framed by a wall of windows that lead to an expansive deck overlooking a tranquil pond. A

  

  Mathew Ghafoori

  RE/Max Heritage

  (802) 278-9432

  56 Whitetail Dr, Vernon, VT 05354
• 

  

  

  /23

  $127,000

  • Land
  • 2.07 Acres
  • $61,353 per Acre

  191 Pingree Park Ln, Londonderry, VT 05148

  2.07 acres with 140' riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after mountain

  

  Alison Cummings

  Cummings & Co

  (802) 213-7597

  191 Pingree Park Ln, Londonderry, VT 05148
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  /60

  $4,950,000

  • 4 Beds
  • 8 Baths
  • 16,736 Sq Ft

  1950 Collins Rd, Brattleboro, VT 05301

  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

  

  Margretta Fischer

  Wohler Realty Group

  (802) 317-7158

  1950 Collins Rd, Brattleboro, VT 05301
• 

  

  

  /23

  $142,000

  • Land
  • 2.19 Acres
  • $64,840 per Acre

  192 Pingree Park Ln, Londonderry, VT 05148

  2.17 acres with 199' of riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after

  

  Alison Cummings

  Cummings & Co

  (802) 471-3006

  192 Pingree Park Ln, Londonderry, VT 05148
• 

  

  

  /44

  $789,000

  • 4 Beds
  • 3.5 Baths
  • 2,856 Sq Ft

  15 Sawmill Village Way, Dover, VT 05356

  If you are looking for a quality-built, well-maintained home with modern updates and built-in property maintenance near Mt. Snow, this Village at Sawmill Farms home checks all the boxes. Located just up the hill from the businesses and services of West Dover, near the Mt. Snow golf course, recreational trails, and 2.5 miles from the ski resort, this home is situated perfectly to enjoy the area's

  

  Beth Vickers

  Vermont Real Estate Company

  (802) 341-9969

  15 Sawmill Village Way, Dover, VT 05356
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  /60

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  “Sweet Berry Farm” offers a compelling blend of Vermont character and functional living space, set on 5.7 acres in Jamaica just 12 minutes from Stratton. Originally built in the 1850s and expanded over time, the home delivers a flexible layout suited for both full-time use and weekend living.The main level features an open living and dining area with large windows, complemented by a generous

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /33

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 1,529 Sq Ft

  761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360

  A rare opportunity in Long Trail House, this corner residence has been thoughtfully reimagined from two separate units into a spacious, fully renovated retreat designed for flexible living. The expanded layout now includes multiple sleeping areas and a den/office, offering versatility for guests or remote work. Natural light fills the home thanks to its corner position, while open living space

  Edwin Kevil Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360
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  /33

  $1,760,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360

  This Sun Bowl townhome delivers true ski-in/ski-out access, offering direct connection to Stratton's slopes right from your door. Designed for both comfort and functionality, the home features a bright, open layout with hardwood floors and a striking floor-to-ceiling stone fireplace that defines the main living space. Spanning multiple levels, the layout provides flexibility for hosting and

  Edwin Kevil Stratton Real Estate

  89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
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  /26

  $529,000

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft

  12 Ober Tal Dr Unit C-22, Stratton, VT 05360

  Experience Stratton Mountain living in this well-appointed 1-bedroom, 1-bath condo in the desirable Ober Tal community. Set just off the ski trail with convenient access nearby, this unit offers the benefits of trailside living with a touch more privacy. Inside, the condo has been thoughtfully updated with warm wood and stone accents that create a classic mountain feel, centered around a cozy

  Trent Stephens Wohler Realty Group

  12 Ober Tal Dr Unit C-22, Stratton, VT 05360
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  /79

  $189,900

  • Land
  • 22.32 Acres
  • $8,508 per Acre

  81 Parish Hill Rd Unit 26, Newfane, VT 05345

  Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

  Chad Bruyette Whitetail Properties Real Estate

  81 Parish Hill Rd Unit 26, Newfane, VT 05345
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  /12

  $999,000

  • Land
  • 12.2 Acres
  • $81,885 per Acre

  Higley Hill Rd, Wilmington, VT 05363

  Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

  Community Lands Community Lands

  Higley Hill Rd, Wilmington, VT 05363
• 

  

  /21

  $489,000

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  12 Lilla Ln, Wilmington, VT 05363

  Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

  Adam Palmiter Berkley & Veller Greenwood/Dover

  12 Lilla Ln, Wilmington, VT 05363
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  /51

  $550,000

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

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Optimal Location, Competitively priced, Exceptional property tucked amidst nature with views toward Magic.New Roof, New Septic. Offering Main Residence and a large oversized detached garage/ barn with upstairs finished space and plenty of space for snow mobiles, ATVs and all your mountain vehicles and outdoor toys. Whether you're a weekend warrior looking to enjoy everything the Green Mountains

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /41

  $899,000

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

  9 Windham Way, Dover, VT 05356

  This upgraded new style Greenspring townhome has direct views of Mount Snow and door to door shuttle service to and from the unit and the base area. A well updated 4+ bedroom, 4 bath unit with lots of bonus space, many recent updates and unique features. These include an open concept great room with vaulted ceiling, sunny exposure and sunset/ski trail views, wood burning fireplace unique against

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9 Windham Way, Dover, VT 05356
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  /33

  $495,000

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

  313 S Pine Banks Rd, Putney, VT 05346

  Tucked into the woods of southern Vermont’s most vibrant and artistic village, this thoughtfully updated 25-year-young home offers the perfect blend of modern ease and tranquil privacy amidst natural serenity. Indulge in the pleasures of the region that nourish body and soul – hiking, skiing, dining, local theater and music, and crafts – without the preoccupations and burdens of home renovations

  Thomas Dahlin Berkley & Veller Greenwood Country

  313 S Pine Banks Rd, Putney, VT 05346
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  /60

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,408 Sq Ft

  75 Westminster Rd, Putney, VT 05346

  This charming historic Colonial just moments from Putney Village, blends timeless character with thoughtful updates. This 4-bedroom, 3-bath home features a spacious, open kitchen highlighted by an antique brick hearth, perfect for gathering and entertaining. The flexible floor plan includes a first-floor bedroom with an ensuite full bath and its own separate entrance, offering excellent potential

  Rebecca Hiam Southern Vermont Realty Group

  75 Westminster Rd, Putney, VT 05346
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  /60

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363

  On the Hill, end of the Road, double lot, brand new house with attached garage. If this is what you have been waiting for, wait no more! 2024 modular construction home with 3 bedrooms, 2 baths, one bedroom has an ensuite bath, the other 2 bedrooms share a full bath. Dining area has a slier to the deck out back, and it has a secluded feel of almost complete privacy. Enjoy all the amenities Chimney

  Sigrid Pickering Chimney Hill Realty

  47 Upper Howes Way Unit A-23, Wilmington, VT 05363
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  /37

  $690,000

  • 5 Beds
  • 3 Baths
  • 2,635 Sq Ft

  341 Under the Mountain Rd, Londonderry, VT 05148

  Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

  Andy Reed Four Seasons Sotheby's Int'l Realty

  341 Under the Mountain Rd, Londonderry, VT 05148
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  /40

  $675,000

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

  47 Oak Hill Dr, Dummerston, VT 05301

  Tucked away on a private road, this impeccably maintained 3-bedroom, 2-bathroom home sits on a serene 6-acre lot, offering the perfect blend of privacy and comfort. Set well back from the road, the property provides a peaceful retreat surrounded by nature. Inside, you’ll find a bright and inviting open-concept layout designed for both everyday living and entertaining. The spacious living and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  47 Oak Hill Dr, Dummerston, VT 05301
• 

  

  /54

  $649,000

  • 6 Beds
  • 3 Baths
  • 2,740 Sq Ft

  1161 Little Pond Rd, Londonderry, VT 05148

  Set along a quintessential Vermont country road just moments from the pristine waters of Lowell Lake, this versatile property offers the rare opportunity to enjoy peaceful rural living with flexible multi-family potential. Surrounded by natural beauty and year-round recreation, the setting is both private and convenient to all that Londonderry has to offer. The home features approximately 2,700

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1161 Little Pond Rd, Londonderry, VT 05148
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  /32

  $595,000

  • 5 Beds
  • 2 Baths
  • 2,892 Sq Ft

  238 Hemlock Hill Rd, Wardsboro, VT 05355

  This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the

  Jeffrey Sheehan Cummings & Co

  238 Hemlock Hill Rd, Wardsboro, VT 05355
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  /36

  $529,000

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

  11 Dutchman Ln Unit 4A, Wilmington, VT 05363

  This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  11 Dutchman Ln Unit 4A, Wilmington, VT 05363
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  /42

  $499,990

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  555 Vermont 9, Wilmington, VT 05363

  MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom, two-bath residence blends modern comfort with classic Vermont charm and sits on a desirable double lot, offering both space and privacy. Designed for year-round living or a weekend retreat, the home features a bright, open-concept layout filled with natural light from high-quality Anderson windows and

  Colt Hazell Flex Realty

  555 Vermont 9, Wilmington, VT 05363
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  /60

  $549,000

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft

  794 White Rd, Windham, VT 05359

  Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

  Erica Reynolds Southern Vermont Realty Group

  794 White Rd, Windham, VT 05359
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  /36

  $595,000 Open Sat 10AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  171 Green Meadow, Brattleboro, VT 05301

  Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen featuring lots of counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
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  /34

  $619,000

  • 4 Beds
  • 4 Baths
  • 3,354 Sq Ft

  556 Sawmill Rd, Wardsboro, VT 05355

  Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with an attached garage offers over 3,000 square feet of living space and the perfect blend of comfort, style, and refined Vermont living. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment — from winter

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /55

  $490,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
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  /44

  $525,888

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  37B Kingswood Rd, Dover, VT 05356

  Refined mountain luxury meets effortless four-season living in this impeccable Kingswood townhome, offering direct snowmobile trail access and private shuttle service to Mount Snow. Ideally positioned on the level portion of the development, this exceptional four-bedroom residence enjoys convenient trail access and a more expansive, usable, level rear yard—a rare and highly sought-after offering

  Michelle O'Neil Deerfield Valley Real Estate

  37B Kingswood Rd, Dover, VT 05356
• 

  

  /60

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  3148 Route 11, Londonderry, VT 05148

  Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put their own finishing touches on

  Erin Kendall EXP Realty

  3148 Route 11, Londonderry, VT 05148
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  /43

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,948 Sq Ft

  196 Powder Mill Rd, Londonderry, VT 05148

  Mountain Escape with Multi-Generational Potential in Powder Mill, close to Lowell Lake. Welcome to your 4 season retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible

  Katie Ladue Gilbert BHHS Verani Upper Valley

  196 Powder Mill Rd, Londonderry, VT 05148
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  /60

  $560,000

  • 3 Beds
  • 3 Baths
  • 2,397 Sq Ft

  14 High Top Rd Unit B124, Wilmington, VT 05363

  Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are

  Sigrid Pickering Chimney Hill Realty

  14 High Top Rd Unit B124, Wilmington, VT 05363
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  /27

  $530,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1160 Fowler Rd, Whitingham, VT 05361

  Nestled in the scenic beauty of Whitingham, Vermont, this inviting 3-bedroom, 2-bath home offers the perfect blend of comfort, craftsmanship, and year-round enjoyment. Step inside to discover a bright, open living space highlighted by stunning vaulted ceilings that create an airy, welcoming feel.The home features a finished basement complete with a spacious game room—ideal for entertaining,

  Kristen Breeden Southern Vermont Realty Group

  1160 Fowler Rd, Whitingham, VT 05361
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  /60

  $525,000 Open House 5/17

  • 2 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  4 Newfane Cir Unit 4B, Dover, VT 05356

  LOCATION LOCATION LOCATION!!! Directly across the street from Mt. Show ski resort with shuttle service to and from the mountain. Avoid parking fees and be chauffeured back and forth. Located in the prestigious Greenspring Community, with year round activities. Ski at Mt. Snow, Vermont's closest mountain to NYC, golf in the summer (located with 6 miles of 2 beautiful golf courses, Mt. Snow Golf

  Jason Saphire www.HomeZu.com

  4 Newfane Cir Unit 4B, Dover, VT 05356
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  /26

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft

  68 Ellis Brook Rd, Dover, VT 05341

  Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 Ellis Brook Rd, Dover, VT 05341
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  /60

  $599,000

  • 5 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  673 Vermont 121, Grafton, VT 05146

  Historic Charmer, this c. 1830 farmhouse has been loved and stewarded by its current owners for half a century. It is time to pass this amazing vintage home on to another lucky family. The house has original features including 2 fireplaces, curved plaster walls and beautiful honey colored wide pine floors. The first floor offers an eat-in- kitchen, formal dining room, spacious sunny living room

  Janet Lucier Barrett & Valley Assoc. Inc

  673 Vermont 121, Grafton, VT 05146
• 

  

  /50

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  49 Oles Dr, Guilford, VT 05301

  A picturesque, private home with lovely views from every room. Set back from the road in a pastoral setting, it is quiet and tranquil. The moment you enter through the front covered porch, you are greeted by abundant natural light and breathtaking views. The open floor concept is inviting, and the beautiful timbers were milled from the land. The original owner, who has owned the home for 47

  Kristen Ziter Taylor Brattleboro Area Realty

  49 Oles Dr, Guilford, VT 05301
• 

  

  /24

  $550,000

  • 4,116 Sq Ft

  33 Oak St, Brattleboro, VT 05301

  This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
• 

  

  /31

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

  148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit and hot tub.

  Andrew King Stratton Real Estate

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
• 

  

  /15

  $67,500

  • Land
  • 3.5 Acres
  • $19,286 per Acre

  0 Dover Rd Unit 5054979, Newfane, VT 05345

  Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new home

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  0 Dover Rd Unit 5054979, Newfane, VT 05345
• 

  

  /30

  $749,000

  • Land
  • 2.57 Acres
  • $291,440 per Acre

  Lot 3 Old Mill Ln, Wilmington, VT 05363

  Bring your own builder and discover an exceptional opportunity to own a 2.57 acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 3 Old Mill Ln, Wilmington, VT 05363

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