Windham County VT Homes for Sale

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  /27

  $475,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,246 Sq Ft

  81 Chapin St, Brattleboro, VT 05301

  Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a

  John Hatton Berkley & Veller Greenwood Country

  81 Chapin St, Brattleboro, VT 05301
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  /27

  $1,450,000

  • Land
  • 201.4 Acres
  • $7,200 per Acre

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360

  Own this large tract of land, over 200 acres that abuts over 1100 additional acres of Green Mountain National Forest. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Currently only 18 of the 200 acres is gravel pit and being reclaimed and closed out on this property. See the Vermont Land Use Permit 2W1316 online for further

  Chris Lowe Lowe's Real Estate, LLC

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360
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  /2

  $55,000

  • Land
  • 21,780 Sq Ft
  • $110,000 per Acre

  404 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

  Sigrid Pickering Chimney Hill Realty

  404 Fox Mountain Rd, Wilmington, VT 05363
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  /37

  $639,000

  • 4 Beds
  • 2.5 Baths
  • 2,573 Sq Ft

  11 Strawberry Hill, Brattleboro, VT 05301

  Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed

  Dan Normandeau Berkley & Veller Greenwood Country

  11 Strawberry Hill, Brattleboro, VT 05301
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  /60

  $999,000

  $89K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 5,828 Sq Ft

  151 Townshend Rd, Grafton, VT 05146

  STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or

  Erin McCormick KW Vermont

  151 Townshend Rd, Grafton, VT 05146
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  /23

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  429 Vt Route 30, Newfane, VT 05345

  Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  429 Vt Route 30, Newfane, VT 05345
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  /32

  $24,500

  • 1 Bed
  • 2 Baths
  • 869 Sq Ft

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356

  This unique style, a sleep six condo, is located on the top floor of the hotel and features two levels, including a loft bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area has a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping four people. The spacious loft bedroom features a king-size bed, a large walk-in closet, and an

  Patricia Fitzpatrick Skihome Realty

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
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  /34

  $609,000

  Open Mon 2PM - 4PM $10K PRICE DROP

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

  556 Sawmill Rd, Wardsboro, VT 05355

  OPEN HOUSE-Monday, May 25 from 2:00 - 4:00. Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with a dedicated office space and attached garage offers over 3,000 square feet of living space. 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

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /8

  $74,900

  • Land
  • 1.1 Acres
  • $68,091 per Acre

  2 Johnson Hill, Dover, VT 05356

  Private 1.10 +/- Acre lot in Dover Hills VT. #WW-2-2888 Permit in place. Trinity Engineering did the engineering and the lot was approved for a three bedroom dwelling.

  Janet Boyd Boyd Real Estate

  2 Johnson Hill, Dover, VT 05356
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  /2

  $25,000

  • Land
  • 26,136 Sq Ft
  • $41,667 per Acre

  28 Upper Howes Way, Wilmington, VT 05363

  Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

  Sigrid Pickering Chimney Hill Realty

  28 Upper Howes Way, Wilmington, VT 05363
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  /23

  $470,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  6D White Oaks Loop Unit 7, Dover, VT 05356

  OPEN HOUSE ~ Memorial Day Weekend ~ Sunday May 24th ~ 12:00-2:00pm ~ Welcome to this spacious end-unit Timber Creek condominium, ideally located directly across from Mount Snow. This highly desirable community offers the perfect blend of mountain convenience and resort-style amenities, making it an exceptional year-round getaway. The main level features a welcoming mudroom entry with built-in

  Monique White Deerfield Valley Real Estate

  6D White Oaks Loop Unit 7, Dover, VT 05356
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  /58

  $720,000

  • 4 Beds
  • 3 Baths
  • 4,379 Sq Ft

  587 Vermont 121, Grafton, VT 05146

  The Woolley House, located at 587 Route 121 East and built around 1818, is a rare and remarkably preserved 2.5 story brick residence in the Federal style. This home, originally constructed for early woolen mill owner John Woolley, features a side-hall layout, blind-arch entryway, and fanlight transom.Original details are beautifully preserved throughout including an original central cooking

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /37

  $795,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /32

  $469,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
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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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  /35

  $399,900

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,488 Sq Ft

  35 School St, Bellows Falls, VT 05101

  This single-family Victorian home located in the village of Bellows Falls has lots of space for family and friends! Four bedrooms, three full baths, a second-floor laundry room, two kitchens, two living rooms, three bonus rooms, and even an area for a potential apartment above the one-car garage! The open-concept updated kitchen/living room offer plenty of storage and seating for everyone and

  Heather Gleim CENTURY 21 North East

  35 School St, Bellows Falls, VT 05101
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  /23

  $159,000

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /19

  $229,000

  $56K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155

  Close to Magic, Bromley and Stratton! This two-bedroom, one bath condo with woodburning fireplace overlooks a beautiful brook and tennis court area. Private deck out back to enjoy some sun. Eat in kitchen with pass through countertop area opens into the living room. Manageable and spacious for a nice weekend getaway or make this your fulltime home. Just minutes to downtown with shopping, fuel,

  Julie Lowe Lowe's Real Estate, LLC

  3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155
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  /22

  $110,000

  • Land
  • 2.5 Acres
  • $44,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Nestled in an idyllic setting at 69 Old Haven Lane, this exceptional building lot offers a rare opportunity to bypass the typical hurdles of new construction and start bringing your vision to life immediately. Located in a sought-after and peaceful pocket of Putney, this property perfectly balances the privacy of a country retreat with the convenience of an excellent location. Much of the

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
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  /15

  $159,500

  • 1 Bed
  • 1 Bath
  • 685 Sq Ft

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
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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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  /8

  $195,000

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  0 Stoney Brook Rd, Londonderry, VT 05148

  Long-range views of Stratton and Bromley define this 4.86 +/- acre offering in Londonderry, where elevation, privacy, and natural beauty come together in a compelling Southern Vermont setting. The access road and future building site are already roughed in, creating a strong foundation for a thoughtfully designed Vermont retreat.Supported by a State of Vermont wastewater permit for a

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  0 Stoney Brook Rd, Londonderry, VT 05148
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  /55

  $490,000

  $35K PRICE DROP

  • 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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  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /60

  $725,000

  • 6 Beds
  • 3 Baths
  • 3,630 Sq Ft

  5 William Mundell Rd, South Newfane, VT 05351

  Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and

  The Malley Group KW Vermont

  5 William Mundell Rd, South Newfane, VT 05351
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  /25

  $369,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  36C N Access Rd Unit 703, Dover, VT 05356

  Spacious Snow Mountain Village townhome adjacent to the upper parking lots at Mount Snow ski resort. This unique large unit is one of only a handful of units with this size for the development. Inside you are greeted by a tiled mudroom area with laundry, and an adjacent large guest room with en suite full bath. The main level has a large open concept living room with wood burning fireplace and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  36C N Access Rd Unit 703, Dover, VT 05356
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  /23

  $189,000

  • Land
  • 3.6 Acres
  • $52,500 per Acre

  00 Lake Hill Rd, Whitingham, VT 05361

  Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing & septic design showing positive results,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd, Whitingham, VT 05361
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  /17

  $339,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  274 Vermont Route 100, Dover, VT 05356

  This storybook log cabin is the kind of place you picture when you think "perfect Vermont getaway." Tucked in the middle of town, everything you want is right here, and Mount Snow resort is just over a mile away. Whether you’re chasing powder days, snowmobile/summer trails, or just a cozy escape, this spot makes it easy to do it ALL. On the MOOver public transportation route to get you around

  Prema Fitzpatrick Real Broker LLC

  274 Vermont Route 100, Dover, VT 05356
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  /27

  $445,000

  • 2 Beds
  • 2 Baths
  • 1,353 Sq Ft

  49 High Point Dr Unit A-14, Stratton, VT 05360

  Embrace the ultimate Stratton lifestyle in this turnkey, one-level 2BR/2BA condo designed for effortless mountain access. Located just moments from the Village and the Stratton training center, this home eliminates the logistics and maximizes the fun with a dedicated gear-ready mudroom and a complimentary shuttle that whisks you straight to the lifts. The interior features a bright, open-concept

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  49 High Point Dr Unit A-14, Stratton, VT 05360
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  /9

  $480,000

  • Land
  • 7.8 Acres
  • $61,538 per Acre

  16 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

  Patricia Fitzpatrick Skihome Realty

  16 Overlook Dr, Dover, VT 05356
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  /8

  $480,000

  • Land
  • 5.08 Acres
  • $94,488 per Acre

  10 Overlook Dr, Dover, VT 05356

  A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

  Patricia Fitzpatrick Skihome Realty

  10 Overlook Dr, Dover, VT 05356
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  /17

  $729,000

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

  778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155

  Ski-In/Ski-Out Perfection: Your Premier Stratton Mountain Retreat! Experience the ultimate Vermont lifestyle in this rare 2-bedroom, 2-bathroom condo, perfectly positioned for true ski-in/ski-out convenience. Located just steps from the Villager Chairlift and the bustling heart of Stratton Village, this residence offers a seamless transition from the slopes to your front door.Designed with

  Robin Apps Four Seasons Sotheby's Int'l Realty

  778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155
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  /43

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  15 Bills Rd, West Wardsboro, VT 05360

  This spacious four-bedroom, three-bath Cape-style home offers a wonderful Vermont retreat, ideally located just minutes from the Stratton Mountain Resort Sun Bowl and the scenic Grout Pond Recreation Area, and only about 10 minutes from Mount Snow Resort. With immediate access to nearby snowmobile trails, it’s perfectly suited for year-round outdoor enthusiasts. Nicely landscaped yard with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  15 Bills Rd, West Wardsboro, VT 05360
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  /60

  $420,000

  • 4 Beds
  • 2 Baths
  • 2,723 Sq Ft

  405 Main St, Wardsboro, VT 05355

  Lovingly shaped over generations of ownership, this is one of those special properties where the setting, charm, and character come together in a way that simply cannot be replicated. Set on 1.10 acres along a woodland creek, this property shines with natural beauty and Vermont charm. A stream-fed pond adds to the tranquil setting, while old stone walls, mature trees, butterfly gardens, and

  Rachel Febbie EXP Realty

  405 Main St, Wardsboro, VT 05355
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  /16

  $275,000

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

  10 Riverfront Dr, Bellows Falls, VT 05101

  This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

  Gale Alger

  10 Riverfront Dr, Bellows Falls, VT 05101
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  /60

  $319,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  3185 Higley Hill Rd, West Marlboro, VT 05363

  Vermont A-Frame Retreat in Marlboro! Escape to this charming 2-bedroom, 2-bath A-frame set on 2.18 wooded acres in scenic Marlboro, Vermont. With a stream, deck, and peaceful natural setting, this property offers the perfect blend of privacy and character. Inside, you’ll find 1,164 square feet of furnished living space featuring natural light, a wood fireplace, first-floor laundry, and a

  Flex Realty Group Flex Realty

  3185 Higley Hill Rd, West Marlboro, VT 05363
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  /27

  $379,000

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  292 Tallwood Cir, Londonderry, VT 05148

  Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal space for preparing meals and

  The Malley Group KW Vermont

  292 Tallwood Cir, Londonderry, VT 05148
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  /48

  $325,000

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  106 Main St Unit 5, Putney, VT 05346

  Bright, airy, and full of personality, this charming two-bedroom, one-bathroom condo in the Village of Putney offers comfort, style, and convenience. Ideally located just minutes from I-91 and close to Putney’s vibrant downtown shops, cafés, and everyday amenities, this condo offers easy access to village life. Inside, natural light fills the thoughtfully designed space, highlighting dreamy

  Rebecca Hiam Southern Vermont Realty Group

  106 Main St Unit 5, Putney, VT 05346
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  /33

  $229,000

  • 1 Bath
  • 475 Sq Ft

  11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

  Discover effortless mountain living in this beautifully updated studio condominium that is walking distance to the slopes and in the desirable Snow Tree community. Perfect for weekend getaways, seasonal escapes, or as a high performing rental investment. This home boasts an extremely strong rental history supported by a documented 3 year history of over $25,000 annually and is being offered fully

  Melissa Ellis Southern Vermont Realty Group

  11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356
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  /33

  $325,000

  $24K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  29 Pikes Falls Rd, Jamaica, VT 05343

  MOTIVATED SELLERS! Bring your offers! Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living.Ideally situated just 15 minutes from Stratton Mountain and 25 minutes

  Carrie Mathews Winhall Real Estate

  29 Pikes Falls Rd, Jamaica, VT 05343

Showing Results 121 - 160, Page 4 of 10