Windham County VT Homes for Sale

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  /41

  $875,000

  • 7 Beds
  • 6.5 Baths
  • 1,152 Sq Ft

  136 Vermont Route 100, Dover, VT 05356

  Residential Property with Income Potential Near Mount Snow Discover a rare opportunity to own a versatile residential property with multiple income streams, located just minutes from the village of West Dover and the Mount Snow Resort area. Whether used as a primary residence, second home, or investment property, this offering provides exceptional flexibility. The main residence features a

  Cyd Scott Cohn & Company

  136 Vermont Route 100, Dover, VT 05356
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  /15

  $530,000

  • Land
  • 30 Acres
  • $17,667 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343
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  /30

  $139,000

  • Land
  • 20.1 Acres
  • $6,915 per Acre

  251 Phillips Hill Rd, West Halifax, VT 05358

  Discover 20.10 acres of land in Halifax, Vermont, just a short drive to Greenfield, MA, and from skiing at Mount Snow and The Hermitage Club. This property consists of two separately deeded building lots, offering flexibility for two homes or a single retreat. Enjoy seasonal mountain views, peaceful surroundings, and direct access from a quiet country road. In the warmer months, take advantage of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  251 Phillips Hill Rd, West Halifax, VT 05358
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  /30

  $579,000

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft

  204 Meeting House Ln, Brattleboro, VT 05301

  Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

  Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, Brattleboro, VT 05301
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  /32

  $299,000

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

  4106 Vt Route 30, Jamaica, VT 05343

  Built in 1840, this charming home has long been a part of Jamaica’s rich history. Thoughtfully updated for modern living, it features a brand-new septic system, a renovated kitchen with granite countertops, and spacious rooms filled with natural light. Perfectly located just a short walk to town and Jamaica State Park, and only 10 miles from Stratton’s lifts, this property offers the ideal blend

  Carrie Mathews Winhall Real Estate

  4106 Vt Route 30, Jamaica, VT 05343
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  /18

  $1,690,000

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

  34 A or B Boulder Ridge Dr, Dover, VT 05356

  NEW CONSTRUCTION!! The new development team at Boulder Ridge is pleased to announce the next phase of construction at this unique location. Just two minutes to the base of Mount Snow, awe-inspiring year-round views of the slopes of Mount Snow as well as the vast Deerfield Valley, combined with the distinct trails of the Hermitage Club in the distance (a 7 minute drive) are just a few of the many

  John Redd Skihome Realty

  34 A or B Boulder Ridge Dr, Dover, VT 05356
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  /59

  $275,000

  • 2 Beds
  • 1 Bath
  • 715 Sq Ft

  81 Parish Hill Rd, Newfane, VT 05345

  Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

  Chad Bruyette Whitetail Properties Real Estate, LLC

  81 Parish Hill Rd, Newfane, VT 05345
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  /13

  $120,000

  • Land
  • 4.68 Acres
  • $25,641 per Acre

  8559 Vt Route 30, Jamaica, VT 05343

  Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

  TG Glazer Winhall Real Estate

  8559 Vt Route 30, Jamaica, VT 05343
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  /41

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,153 Sq Ft

  487 Vermont Route 100, Londonderry, VT 05148

  Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a

  Jamie Wylie Stratton Real Estate

  487 Vermont Route 100, Londonderry, VT 05148
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  /44

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
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  /28

  $265,000

  • 2 Beds
  • 1 Bath
  • 903 Sq Ft

  1555 W River Rd, Dummerston, VT 05301

  Welcome home to this inviting 2-bedroom, 1-bath Cape on scenic West River Road. Perfectly located just a short drive to downtown Brattleboro’s shops, restaurants, and local conveniences—just over a quarter mile to West River Park and about 30 minutes to Mount Snow—this home offers the ideal blend of country charm and everyday comfort. Set on a beautiful .6-acre lot with mature perennial trees and

  Morriah Adams BHG Masiello Brattleboro

  1555 W River Rd, Dummerston, VT 05301
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  /36

  $98,000

  • Land
  • 10 Acres
  • $9,800 per Acre

  1105 S Hill Rd, Jamaica, VT 05343

  Explore this exciting wooded 10.2+/- acre lot in the desirable town of Jamaica, VT. Jamaica has NO local zoning, making for simplified development, multiple cabins, camping and more. Plenty of road frontage on a year-round town plowed and maintained road. Best of all it is paved all the way to Wardsboro eliminating the difficulties of Vermont Mud Season. Utilities are located across from the

  Curtis Trousdale

  1105 S Hill Rd, Jamaica, VT 05343
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  /24

  $365,000

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft

  85 Stockwell Dr, Brattleboro, VT 05301

  Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride downtown, to Memorial

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
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  /19

  $469,000

  • 2 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363

  Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363
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  /50

  $435,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Country Ct, Wilmington, VT 05363

  Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous

  Janet Boyd Boyd Real Estate

  27 Country Ct, Wilmington, VT 05363
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  /14

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  8 Happy Haven Rd, Wilmington, VT 05363

  Conveniently located to village center, elementary school, lakes and trails. This riverfront home is waiting for a facelift! Three bedrooms, 2 bathrooms, living room, kitchen with a dining area with siders to a deck over looking the Deerfield River. Room downstairs for a hobby or craft room and a family room with a gas fireplace. Newer hot water tank and furnace. Room for gardens and a two car

  Janet Boyd Boyd Real Estate

  8 Happy Haven Rd, Wilmington, VT 05363
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  /44

  $470,000

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  24 Antler Loop, West Dover, VT 05356

  This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  24 Antler Loop, West Dover, VT 05356
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  /3

  $299,000

  • Land
  • 0.84 Acre
  • $355,952 per Acre

  8 B Freestyle Cir, Dover, VT 05356

  Ski in and out at Mount Snow from one of the last two buildable lots on the mountain. If you understand the convenience of slopeside living this could be the location for you to build your dream home. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is the larger of 2 lots

  John Redd Skihome Realty

  8 B Freestyle Cir, Dover, VT 05356
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  /33

  $390,000

  • 3 Beds
  • 1.5 Baths
  • 2,208 Sq Ft

  440 Stratton Arlington Rd, Stratton, VT 05360

  Experience the charm of owning a chalet in Vermont’s sought-after Stratton area, ideally located between Stratton Mountain and Mount Snow for easy ski access. Recent road improvements ensure smooth travel year-round. Outdoor lovers will enjoy nearby trails for hiking, snowmobiling, and snowshoeing, making this an ideal retreat for both relaxation and adventure. The home features a finished

  Mike England Michael England Real Estate

  440 Stratton Arlington Rd, Stratton, VT 05360
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  /9

  $225,000

  • Land
  • 0.73 Acre
  • $308,219 per Acre

  5 Pinnacle View Rd, Dover, VT 05356

  With breathtaking views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  5 Pinnacle View Rd, Dover, VT 05356
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  /38

  $1,075,000

  • 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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  /26

  $199,000

  • 4 Beds
  • 2 Baths
  • 2,470 Sq Ft

  1153 Rockingham Rd, Town of Rockingham, VT 05101

  Calling all investors and handy people! This is your opportunity to bring a classic property back to its former glory. Set on approximately 8.67 acres with frontage along the Williams River and Route 103, the location offers endless potential for a variety of uses. The spacious home appears to have solid bones but will require rehabilitation to restore its charm. A concrete slab is already in

  Chelsea Richardson Barrett and Valley Associates Inc.

  1153 Rockingham Rd, Town of Rockingham, VT 05101
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  /59

  $2,595,000

  • 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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  /14

  $305,000

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

  5 First Ln Unit 1, Wilmington, VT 05363

  Lovely 2 bedroom condo as close as you can get to the 1st tee at the Haystack Golf Club, with winter views over the course to the mountains and sunsets beyond. This practical unit sits conveniently right on one of the best courses in New England, and a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. Inside you are treated to an open concept

  Adam Palmiter Berkley & Veller Greenwood/Dover

  5 First Ln Unit 1, 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

  $529,000

  • 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, is completely dry and waiting to be finished!

  Janet Boyd Boyd Real Estate

  117 Ray Hill Rd, Wilmington, VT 05363
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  /39

  $489,000

  • 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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  /12

  $249,000

  • Land
  • 19.6 Acres
  • $12,704 per Acre

  227 Gault Rd, Wardsboro, VT 05355

  This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

  Victoria Woods Brattleboro Area Realty

  227 Gault Rd, Wardsboro, VT 05355
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  /11

  $39,900

  • Land
  • 1.02 Acres
  • $39,118 per Acre

  12 Buckboard Dr, Dover, VT 05356

  Beautiful wooded one-acre lot located in the Dover Hills development, an established neighborhood of single-family homes. Ideally situated just a short drive to Mount Snow Ski Resort, Mount Snow Golf Course, the Hermitage Club and the villages of Dover and Wilmington, this property offers an excellent balance of privacy and convenience. Enjoy four-season recreation with nearby skiing,

  Donald Koelsch Deerfield Valley Real Estate

  12 Buckboard Dr, Dover, VT 05356
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  /36

  $210,000

  • Land
  • 30.1 Acres
  • $6,977 per Acre

  184 Schoolhouse Rd, Jamaica, VT 05343

  Jamaica, Vermont's hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

  Curtis Trousdale

  184 Schoolhouse Rd, Jamaica, VT 05343
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  /29

  $1,249,000

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

  3F Slalom Dr, Dover, VT 05356

  Just steps from the Mount Snow ski trail, this impeccably maintained 3,500 square foot luxury townhome is located in TrailsEdge, Mount Snow's exclusive ski-on/off community. Never again fight the traffic or pay for parking in the main base area when you can ski to and from your front door! As an end unit, this four-bedroom, 5-bath furnished townhome is a testament to luxury, with radiant heat

  Patricia Fitzpatrick Skihome Realty

  3F Slalom Dr, Dover, VT 05356
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  /26

  $740,000

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

  8 Grouse Ln, Dover, VT 05356

  Escape to 8A Grouse Lane at Mount Snow, where timeless post-and-beam character meets modern comfort in a setting designed for all four seasons. This beautifully reimagined end-unit townhome was thoughtfully redesigned to create an open, inviting living space, complete with a striking wood-burning fireplace—the perfect spot to gather after a day on the mountain.Wake up to ridge-line views,

  Wilkie Bushby TPW Real Estate

  8 Grouse Ln, Dover, VT 05356
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  /26

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  106 Silver Birch Unit 17H, Dover, VT 05356

  Bright 3-Bedroom End Unit at Timber Creek – Across from Mount Snow Ski Area.Welcome to your mountain getaway! This sunny 3-bedroom, 2-bath end unit in the desirable Timber Creek condominium community offers the perfect blend of comfort, convenience, and year-round recreation. Located directly across from Mount Snow and a short drive to the Hermitage Club, you'll enjoy unbeatable access to

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  106 Silver Birch Unit 17H, Dover, VT 05356
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  /2

  $62,000

  • Land
  • 1.03 Acres
  • $60,194 per Acre

  Lot 12 Central Park Estates, Vernon, VT 05354

  1.03 acre building lot in a quiet rural setting in Vernon. Bypass the housing shortage, construct your own dream house. This is near Vernon's popular recreation center, home to a swimming pool, tennis courts, basketball courts, playground, and picnic area. Lily Pond is also nearby, a 40-acre body of quite shallow water with many varieties of birds and plants.

  John Hatton Berkley & Veller Greenwood Country

  Lot 12 Central Park Estates, Vernon, VT 05354
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  /34

  $235,000

  • 2 Beds
  • 1.5 Baths
  • 1,059 Sq Ft

  394 Haystack Rd Unit 2, Wilmington, VT 05363

  Enjoy four-season living in this inviting 2-bedroom, 1.5-bath townhome just a short walk to Haystack Golf Course. Set in a peaceful location with direct Valley Trail and snowmobile access, this well-cared-for home is part of a small HOA with low fees. The main level offers a spacious open layout featuring a cozy wood stove on a slate hearth—perfect for watching the fire roar after a day on the

  Chad Lackey Deerfield Valley Real Estate

  394 Haystack Rd Unit 2, Wilmington, VT 05363
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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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  /34

  $1,395,000

  • 4 Beds
  • 6 Baths
  • 4,072 Sq Ft

  11 E Village Cir, Wilmington, VT 05363

  11 East Village Circle, a beautifully maintained mountain home adjacent to The Hermitage Club in Wilmington, Vermont. This 4-bedroom, ( bonus sleeping room) 6-bath retreat offers a perfect blend of Vermont craftsmanship and modern updates, ideal for year-round living or a turnkey mountain getaway.The open-concept living space features wide-plank wood floors, a stone fireplace, and a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  11 E Village Cir, Wilmington, VT 05363
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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

Showing Results 161 - 200, Page 5 of 10