Windham County VT Homes for Sale

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  /45

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  1033 Burrington Hill Rd, Whitingham, VT 05361

  Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

  Monique White Deerfield Valley Real Estate

  1033 Burrington Hill Rd, Whitingham, VT 05361
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  /39

  $895,000

  • 5 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3715 Route 11, Londonderry, VT 05148

  Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

  Cheyanne Pugliese

  3715 Route 11, Londonderry, VT 05148
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  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301
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  /59

  $2,398,000

  • 4 Beds
  • 4 Baths
  • 3,585 Sq Ft

  127 Fannie Hill Dr, Wilmington, VT 05363

  Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  127 Fannie Hill Dr, Wilmington, VT 05363
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  /38

  $749,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  717 Horsenail Hill Rd, Chester, VT 05143

  Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

  Robin Apps Four Seasons Sotheby's Int'l Realty

  717 Horsenail Hill Rd, Chester, VT 05143
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  /15

  $459,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  117 Ray Hill Rd, Wilmington, VT 05363

  This wonderful home boast 10.5 +/- acres, plenty of room for gardening, a pond and is only moments to the village center! Beautiful hard wood floors throughout, Livingroom with gas fireplace a a beautiful view, dining area and kitchen, 3 bedrooms, 2 bathrooms, 2 decks and a simple 1 car garage. The lower level boasts a walk- out, that is waiting to be finished!

  Janet Boyd Boyd Real Estate

  117 Ray Hill Rd, Wilmington, VT 05363
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  /39

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  156 Mountain View Rd, Wilmington, VT 05363

  This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  156 Mountain View Rd, Wilmington, VT 05363
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  /31

  $33,500

  • 1 Bed
  • 2 Baths
  • 709 Sq Ft

  145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

  Kelly Agrillo Southern Vermont Realty Group

  145/47 Qtr.1,89 Grand Summit Way, 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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  /20

  $205,000

  • 2 Beds
  • 1.5 Baths
  • 955 Sq Ft

  10 Morningside Commons, Guilford, VT 05301

  Why rent when you can own this beautifully updated townhouse in a welcoming multi-generational community, ideally located near shops, restaurants public transportation, and all the conveniences you need? The bright open-concept kitchen, dining living area has been thoughtfully renovated with fresh paint, newer cabinets and appliances. First-floor laundry adds everyday ease, featuring a newer

  Kerry Mulverhill

  10 Morningside Commons, Guilford, VT 05301
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  /18

  $190,000

  • Land
  • 12.74 Acres
  • $14,914 per Acre

  Lot 1 Faraway (Jones) Rd, Putney, VT 05346

  Properties in this area don’t come up often, so don’t miss out. This land is located just off a privately maintained road on the Putney-Dummerston line. There are stonewalls bordering the land and an excellent mix of hardwoods including some majestic maples. The land features a gentle easterly slope and there are walking trails around the property as well as many others nearby. Soils evaluation

  Bill Hickok Berkley & Veller Greenwood Country

  Lot 1 Faraway (Jones) Rd, Putney, VT 05346
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  /5

  $50,000

  • 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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  /37

  $36,500

  • 2 Beds
  • 2 Baths
  • 878 Sq Ft

  313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room and queen sleeper sofa as well as a king bed in private bedroom on the first floor. Full bath with double sink vanity on the first floor. Lofted bedroom also has a king bed and a 3/4 bath . Benefits of Grand Summit ownership include the best

  Kelly Agrillo Southern Vermont Realty Group

  313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
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  /39

  $399,900 Open Sat 10AM - 12PM

  • 3 Beds
  • 1.5 Baths
  • 1,339 Sq Ft

  16 Willow St, Brattleboro, VT 05301

  Tucked away on a quiet dead-end street just moments from downtown Brattleboro, this bright and inviting 3 bedroom, 1.5 bath Colonial offers the perfect blend of comfort, character, and convenience. A spacious mudroom provides a practical and welcoming entry, leading to a thoughtfully laid out interior featuring first-floor laundry, a large living room with flexible space for a home office, and a

  Jamie Watson BHG Masiello Keene

  16 Willow St, Brattleboro, VT 05301
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  /2

  $59,900

  • Land
  • 1 Acre
  • $59,900 per Acre

  Lot 37 Woodsman Rd, Dover, VT 05356

  Super building lots up near the Dover Elementary School. Gentle sloping lots, with municipal sewer and underground telephone & electric. Prices reflect the quality of the view(s). Some with ski area(s) to the west and others with local ridgelines to south. Only moments from West Dover dining, shopping, and skiing. The Elementary School provides a fun campus for younger recreational fun. How many

  Michael Purcell Berkley & Veller Greenwood/Dover

  Lot 37 Woodsman Rd, Dover, VT 05356
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  /10

  $88,000

  • Land
  • 10.05 Acres
  • $8,756 per Acre

  Lot 3 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 3 North St, Dover, VT 05431
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  /31

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  68 E Brook Crossing, Wilmington, VT 05363

  Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 E Brook Crossing, Wilmington, VT 05363
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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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  /31

  $699,000

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

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

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

  Timothy Mich Doddridge Stratton Real Estate

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
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  /32

  $749,000

  • Land
  • 1.22 Acres
  • $613,934 per Acre

  Lot 2 Old Mill Ln, Wilmington, VT 05363

  Bring your own builder and discover an exceptional opportunity to own a 1.22-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 2 Old Mill Ln, Wilmington, VT 05363
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  /31

  $37,500

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft

  311 Qtr 3 Grand Summit Way, Dover, VT 05356

  Beautiful mountain view from this two-level, two-bedroom loft quartershare in the Grand Summit Resort Hotel! This trailside condo can be used, rented, or traded for stays at other vacation destinations! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This mountain-side unit features an open-concept kitchen/dining

  Patricia Fitzpatrick Skihome Realty

  311 Qtr 3 Grand Summit Way, Dover, VT 05356
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  /16

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  39 Atwood St, Brattleboro, VT 05301

  First time offered, EVER... built and loved by the current family, it is time to pass the keys to a new generation of owners ready to put their own love and dreams into this sweet home. Just across from the high and middle schools, around the corner from Oak Grove grade school, and down the street from the hospital and shopping. There is a first floor bed and bath for aging in place, but 2 big

  Christine Lewis Brattleboro Area Realty

  39 Atwood St, Brattleboro, VT 05301
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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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  /48

  $294,000

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

  5 Reynolds Dr, Brattleboro, VT 05301

  Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers a rare "move-in ready" opportunity for both savvy investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. With new toilets and stainless/modern

  Kate Barry EXP Realty

  5 Reynolds Dr, Brattleboro, VT 05301
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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 four elegant Regency

  Mendi Michael Engel & Völkers Okemo

  587 Vermont 121, Grafton, VT 05146
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  /37

  $399,000

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  44 Howes Loop, Wilmington, VT 05363

  Thoughtfully maintained 4-bedroom, 2-bath Chimney Hill chalet offering a warm, inviting feel with natural wood finishes, open-concept design, woodstove and features that capture the essence of Vermont living. The main living areas are bright, comfortable and welcoming, with easy flow to a deck overlooking surrounding mountain ridgelines—an ideal setting for both quiet mornings and relaxed

  Jacki Murano Southern Vermont Realty Group

  44 Howes Loop, Wilmington, VT 05363
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  /27

  $949,000

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

  15 Boulder Ridge Dr, Dover, VT 05356

  Spectacular ski trail and half pipe views from this beautiful 2008 4 bedroom townhome across from the Mount Snow ski resort with easy shuttle access. This immaculate unit and is truly ready for turn key enjoyment. Inside you are treated to a vaulted great room with floor to ceiling stone fireplace, tremendous natural light, south facing exposure, and direct ski area views with sunsets beyond, an

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Boulder Ridge Dr, Dover, VT 05356
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  /10

  $299,000

  • Land
  • 7.08 Acres
  • $42,232 per Acre

  103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

  Located between Chester and Bellows Falls, just a mile from exit 6 off I-91, the opportunity for development awaits your ideas. Easy access, level parcel for either commercial ventures, gardens, or home. Land consists of two parcels separated by School Bus Depot Road totaling 7.08 acres. The island parcel gives excellent exposure to Route 103 for terrific signage. 103 is a high traffic corridor

  Heidi Bernier Berkley & Veller Greenwood Country

  103 Schoolbus Depot Rd, Town of Rockingham, VT 05101
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  /49

  $380,000

  • 3 Beds
  • 3 Baths
  • 2,307 Sq Ft

  30 Back St, Newfane, VT 05345

  Affording you an easy stroll to the center of historic Newfane, this vintage cape combines idyllic charm and modernized, upgraded comfort. Bright & expansive, the country kitchen is bathed in natural light. The open design of the first-floor flows from the kitchen with accents of artistic tiling, to the dining/ living room. The natural beauty of this setting is drawn within by the continuous wall

  Randi Ziter Brattleboro Area Realty

  30 Back St, Newfane, VT 05345
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  /51

  $915,000

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

  33 Carinthia Rd, Dover, VT 05356

  LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

  Jacki Murano Southern Vermont Realty Group

  33 Carinthia Rd, Dover, VT 05356
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  /12

  $235,000

  • Land
  • 18.93 Acres
  • $12,414 per Acre

  0 Forest Heights Rd, West Dover, VT 05356

  Are you ready to turn your dream home into a reality? This expansive parcel of land, located just 2 miles from the slopes of Mount Snow, is waiting for your vision. The property offers an ideal combination of privacy and seclusion and with some clearing, you can unveil extraordinary views of the Mount Snow ski slopes, creating the perfect backdrop for your dream home. The property boasts

  Michelle O'Neil Deerfield Valley Real Estate

  0 Forest Heights Rd, West Dover, VT 05356
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  /45

  $437,000

  • 4 Beds
  • 3.5 Baths
  • 2,015 Sq Ft

  29 First Unit 17, Wilmington, VT 05363

  Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sited on the 1st fairway at the Haystack Golf Course. An oversized deck invites outdoor dining and entertaining, with sunsets over Haystack Mountain as your backdrop. Inside, natural light pours through windows and skylights into the open floor plan featuring vaulted ceilings, a fieldstone wood-burning

  Monique White Deerfield Valley Real Estate

  29 First Unit 17, Wilmington, VT 05363
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  /55

  $859,000

  • 6 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  5825 Vermont 30, Townshend, VT 05353

  6+ bed, 5 bath 21± Acre Equestrian Estate in West Townshend VT Distinctive property combines the charm of a private equestrian estate w/tastefully finished and versatile living space & top horse facilities. On ~21 acres, including a 3-bed main home plus attached 1-bed accessory unit—ideal for guests, staff, or flex living. Metal roof, drilled well, whole-house generator. Main Barn: 8 box stalls,

  Jacki Murano Southern Vermont Realty Group

  5825 Vermont 30, Townshend, VT 05353
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  /15

  $20,000

  • 1 Bath
  • 407 Sq Ft

  152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356

  Quarter share (deeded interval 3) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This first floor (Unit 152) with a sleep four studio is 407 sq ft and has a Murphy bed in the living area, a kitchen/dining area, and a full bath. This unit is located on

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  152 - Qtr 3 89 Grand Summit Way Unit 152, Dover, VT 05356
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  /48

  $350,000

  • 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
• 

  

  /14

  $995,000

  • Land
  • 10,890 Sq Ft
  • $3,980,000 per Acre

  19 Sundance Village Loop, Dover, VT 05356

  A unique opportunity to build slopeside on Mount Snow with building plans already in place! This .25 acre lot is the only available parcel in a 14-lot subdivision located trailside to the Sundance ski trail. The Seller has incurred expenses and performed extensive work to provide the building plans included in the sale price. There are design guidelines and an architectural review committee to

  Patricia Fitzpatrick Skihome Realty

  19 Sundance Village Loop, Dover, VT 05356
• 

  

  /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
• 

  

  /5

  $185,000

  • Land
  • 36,590 Sq Ft
  • $220,238 per Acre

  1 Pinnacle View Ln, Dover, VT 05356

  If it's close proximity you want to skiing Mt. Snow then this is your place to build your dream home. Just off a paved road in a small 5 lot subdivision. Underground utilities and sewer hookup available. Convenient to lakes, golf and restaurants, a diamond in the rough. Winter views of Mt. Snow (says owner)

  Regina Perrotto Skihome Realty

  1 Pinnacle View Ln, Dover, VT 05356
• 

  

  /28

  $52,000

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

  274/76Qtr. 2 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 two units. Unit 276 has a private bedroom with a queen bed, a queen sleeper sofa, and a queen Murphy bed in the living area, a kitchenette, and a full bath with an extra-large covered balcony. The adjoining room, 274, has 2 king beds and a full bath. Units are located on the base area side

  Kelly Agrillo Southern Vermont Realty Group

  274/76Qtr. 2 Grand Summit Way, Dover, VT 05356
• 

  

  /60

  $429,000

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft

  26 N Wind Rd, Wilmington, VT 05363

  Rustic Country Home This inviting rustic country home features a spacious great room with a vaulted ceiling and a beautiful fieldstone fireplace with a buckstove—perfect for cozy winter nights. A large dining area offers plenty of space for gathering with family and friends, complemented by an awesome bar ideal for entertaining. The first floor includes a generously sized bedroom, while the

  Rich Caplan Deerfield Valley Real Estate

  26 N Wind Rd, Wilmington, VT 05363

Showing Results 161 - 200, Page 5 of 9