Windham County VT Homes for Sale

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  /41

  $85,000

  • Land
  • 1.02 Acres
  • $83,333 per Acre

  402 Fox Mountain Rd, Wilmington, VT 05363

  Fantastic double lot on top of the Hill with recent soil tests and septic design suitable for your dream home! As Chimney Hill approaches full build out, the number of remaining lots are limited. This is a brand-new cul-de-sac adjoining the National Forest. Of the 5 lots, only two remain available, including this one. Time to stop imagining and start living the dream of your own vacation home.

  Sigrid Pickering Chimney Hill Realty

  402 Fox Mountain Rd, Wilmington, VT 05363
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  /14

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  12 Autumn Gem Dr, Dummerston, VT 05301

  This affordable Dummerston home is tucked away on 11 private acres. Built with personal privacy in mind, the primary bedroom is on one end and the other 2 bedrooms and bath are at the other, eliminating hallways and adding to the living area. Warm yourself and save on fuel with the large pellet stove in the living room. Abundant light with the picture window in the front and skylight over the

  Christine Lewis Brattleboro Area Realty

  12 Autumn Gem Dr, Dummerston, VT 05301
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  /37

  $595,000

  • 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 with ample 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 living

  Thomas Dahlin Berkley & Veller Greenwood Country

  171 Green Meadow, Brattleboro, VT 05301
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  /60

  $1,160,000

  • 5 Beds
  • 4 Baths
  • 3,664 Sq Ft

  82 N Brookwood Rd, Stratton, VT 05360

  Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

  Kim Morgan-Wohler Wohler Realty Group

  82 N Brookwood Rd, Stratton, VT 05360
• 

  

  

  /23

  $135,000

  $5K PRICE INCREASE

  • Land
  • 2.19 Acres
  • $61,644 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

  192 Pingree Park Ln, Londonderry, VT 05148
• 

  

  /23

  $122,000

  $5K PRICE DROP

  • Land
  • 2.07 Acres
  • $58,937 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

  191 Pingree Park Ln, Londonderry, VT 05148
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  /51

  $799,000

  • 4 Beds
  • 5 Baths
  • 3,992 Sq Ft

  1035 Vermont 121, Windham, VT 05359

  Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A

  Jamie Wylie Stratton Real Estate

  1035 Vermont 121, Windham, VT 05359
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  /17

  $319,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  550 S Main St, Brattleboro, VT 05301

  Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways,

  Christine Lewis Brattleboro Area Realty

  550 S Main St, Brattleboro, VT 05301
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  /32

  $475,000

  $75K PRICE DROP

  • 4,116 Sq Ft

  33 Oak St, Brattleboro, VT 05301

  This is a rare opportunity to take over a multi-family redevelopment project in the heart of Brattleboro. Situated on a 0.40-acre site, the property features a vacant three-story building that has already been gutted and fully remediated for lead paint. With municipal zoning approvals already in place to expand from 8 to 13 units and full architectural plans included with the sale, the

  Kate Barry EXP Realty

  33 Oak St, Brattleboro, VT 05301
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  /60

  $535,000

  $25K PRICE DROP

  • 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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  /7

  $65,000

  $10K PRICE DROP

  • Land
  • 20.8 Acres
  • $3,125 per Acre

  0 Hunter Brook Rd, South Newfane, VT 05351

  *Please do not go onto the neighbors driveways.* Deep into Marlboro, on a seasonal rd, set up camp and fall asleep to the white noise of the brook. The campsite is flat, right off the road and then the land slopes upward. At the back there is a shared pond site.Hunter Brook Rd is not maintained in the wintertime, from the Marlboro side; you'll need to snowmobile, ski or walk in.

  Victoria Woods Brattleboro Area Realty

  0 Hunter Brook Rd, South Newfane, VT 05351
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  /31

  $253,000

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  51 Golding Rd, Windham, VT 05359

  This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the

  

  Alison Cummings

  Cummings & Co

  51 Golding Rd, Windham, VT 05359
• 

  

  /39

  $2,900,000

  • 34,419 Sq Ft

  14 Westminster St, Town of Rockingham, VT 05154

  For developers or investors seeking property with stable income and growth potential, the Warner Center campus presents an excellent opportunity. This surveyed 140-acre property comprises 24 residential rental units and 3 commercial spaces within six extensively renovated brick buildings – over 34,000sf altogether. The buildings are situated in a spacious, sunlit field, conveniently located

  Heidi Bernier Berkley & Veller Greenwood Country

  14 Westminster St, Town of Rockingham, VT 05154
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  /44

  $499,000

  $51K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,580 Sq Ft

  1229 Sheldon Hill Rd, Wardsboro, VT 05355

  Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort.The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine

  Jessica Citera Cummings & Co

  1229 Sheldon Hill Rd, Wardsboro, VT 05355
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  /20

  $39,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 530 Sq Ft

  8 Dorf Auf Radar Rd, Wilmington, VT 05363

  Delightful, affordable! Be right in the heart of ski country with access to hiking, boating, fishing and biking! This tidy 2 bedroom home has a 10x16 storage shed for your gear! Big enough for a weekend of fun but small enough to keep the costs reasonable. This is better than renting, and always available when you are! This is an exciting find! The property can only be a vacation/second home only.

  Christine Lewis Brattleboro Area Realty

  8 Dorf Auf Radar Rd, Wilmington, VT 05363
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  /48

  $389,900

  $4K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  9F Brumms Way Unit 9F, Dover, VT 05356

  Beautiful end unit on edge of Bear’s Crossing Condo and Home Community with a stream and the forest as your neighbor. Close to the Ski Home trail. This mixed community is 2 minutes to Mount Snow Ski Resort and to mixed use trails for snowmobiling, xcountry skiing and mountain biking. There is also a shuttle running regularly to the resort and beyond! This unit is “turn key” with 2 bedrooms and a

  Steve Goldfarb Deerfield Valley Real Estate

  9F Brumms Way Unit 9F, Dover, VT 05356
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  /5

  $350,000

  $50K PRICE DROP

  • Land
  • 5.28 Acres
  • $66,288 per Acre

  0 Pond Rd, Town of Rockingham, VT 05346

  Looking for the dream land of your own, in town but outside of it? Look no further! With 5 acres of gently sloped woods there's plenty of space to site multiple building lots if you so wish, and with it abutting Minard's Pond nature area and just minutes from the village, there's plenty to do. Bring your dreams and plans, this might just be for you! Sale is subject to final survey & subdivision

  Courtney Doubleday EXP Realty

  0 Pond Rd, Town of Rockingham, VT 05346
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  /37

  $900,000

  $50K PRICE DROP

  • Land
  • 20.7 Acres
  • $43,478 per Acre

  0 Crotty Dr, Town of Rockingham, VT 05101

  Investors, developers and builders take notice! This large, gently sloped parcel is one the last & largest undeveloped lots of land that fall within the Bellows Falls Village District. Just minutes from downtown and abutting Minard's Pond nature area, this property sits high on the hill with spectacular views available. With dozens of potential building locations and access to town water and

  Courtney Doubleday EXP Realty

  0 Crotty Dr, Town of Rockingham, VT 05101
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  /28

  $52,000

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  274/76Qtr. 1 Grand Summit Way, Dover, VT 05356

  Wake up to the Grand Summit Express and the Bluebird lifts right outside your room. Sleep 10 condo comprises of two units. Unit 276 has a private bedroom with a queen bed, queen sleeper sofa and queen murphy bed in the living area. Kitchenet and a full bath with an extra large covered balcony. Adjoining room 274 has 2 king beds and a full bath. Units are located on the base area side of the

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr. 1 Grand Summit Way, Dover, VT 05356
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  /49

  $399,000

  $96K PRICE DROP

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

  137 Stratton Arlington Rd, West Wardsboro, VT 05360

  Now Offered at $399,000! Exceptional Value Near Mount Snow & Stratton. Classic Vermont Home with Stunning Hilltop Views – Minutes from Mount Snow & Stratton. Set atop a peaceful New England hill, this classic Vermont home offers beautiful local and local mountain views in one of Southern Vermont's most desirable four-season locations. Just six miles from Mount Snow, Stratton Mountain, Grout Pond,

  Donald Koelsch Deerfield Valley Real Estate

  137 Stratton Arlington Rd, West Wardsboro, VT 05360
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  /3

  $125,000

  • Land
  • 1.77 Acres
  • $70,621 per Acre

  997 Stratton Arlington Rd, Stratton, VT 05360

  STRATTON & MOUNT SNOW - Build your dream ski home on this newly subdivided lot with 103' of road frontage and 1.77 private acres located only 10 minutes from both Stratton Mountain Ski Resort and Mount Snow Ski Resort. All the hard work has been done! Survey, septic design, site plan, state of VT wastewater and well approval, and driveway permit have all been approved and filed with the town.

  Derek Greene Derek Greene

  997 Stratton Arlington Rd, Stratton, VT 05360
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  /4

  $37,000

  $22K PRICE DROP

  • Land
  • 3.3 Acres
  • $11,212 per Acre

  0 E Dover Rd Unit 5082739, Wardsboro, VT 05355

  Discover the perfect canvas for your Vermont dream home on this newly created 3.3-acre parcel in Wardsboro. Tucked away in a peaceful, private setting, you’ll enjoy the quiet beauty of the surrounding woods while still being within easy reach of some of Southern Vermont’s most sought-after destinations. Spend your winters skiing at Mount Snow or Stratton Mountain Resort, and take advantage of

  Mike Masters Four Seasons Sotheby's Int'l Realty

  0 E Dover Rd Unit 5082739, Wardsboro, VT 05355
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  /25

  $334,000

  $65K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355
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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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  /39

  $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
• 

  

  /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
• 

  

  /23

  $250,000

  $10K PRICE DROP

  • 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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  /33

  $599,000

  $20K PRICE DROP

  • 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 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 winter skiing and riding to relaxing summer

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /8

  $59,000

  $16K PRICE DROP

  • Land
  • 1.1 Acres
  • $53,636 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
• 

  /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
• 

  

  /23

  $470,000

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

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

  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 bench and cubbies, opening into the dining area that flows seamlessly

  Monique White Deerfield Valley Real Estate

  6D White Oaks Loop Unit 7, Dover, VT 05356
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  /59

  $715,000

  $5K PRICE DROP

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

  587 Vermont 121, Grafton, VT 05146

  Built in 1818 for early woolen mill owner John Woolley, the Woolley House is a rare and beautifully preserved Federal-style brick residence that blends historic character with the demands of contemporary life. Listed on the National Register of Historic Places within the Mechanicsville Historic District, this exceptional property offers unique architectural significance. Classic period details

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /17

  $255,000

  $30K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,320 Sq Ft

  116 Birge St Unit 2, Guilford, VT 05301

  Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

  Christine Lewis Brattleboro Area Realty

  116 Birge St Unit 2, Guilford, VT 05301
• 

  

  /30

  $100,000

  $10K PRICE DROP

  • Land
  • 2.5 Acres
  • $40,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Escape to your own slice of Vermont paradise with this exceptional land offering on Old Haven Lane in highly desirable Putney. This serene, pristine lot offers the perfect canvas for your custom home, tucked away for ultimate privacy yet completely accessible to Putney’s vibrant town center, local schools, and cultural landmarks. Whether you are looking to hold a premium piece of land or break

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
• 

  

  /15

  $135,000

  $25K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 685 Sq Ft

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Welcome to this beautifully refurbished one-bedroom, one-bath condominium in desirable West Brattleboro. Freshly updated with new flooring, fresh interior paint, vanity, and a new oven, this move-in-ready home offers comfortable, low-maintenance living in a convenient location.Ideally situated just minutes from I-91, this condominium provides easy access for commuters while placing you close

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
• 

  

  /53

  $460,000

  $65K 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
• 

  

  /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
• 

  

  /60

  $700,000

  $25K PRICE DROP

  • 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
• 

  

  /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

Showing Results 281 - 320, Page 8 of 12