Windham County VT Homes for Sale with Acreage

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  /32

  $450,000

  • 7 Beds
  • 5 Baths
  • 3,518 Sq Ft

  343 Haystack Rd, Wilmington, VT 05363

  This spacious home is located near Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers Four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a workshop is a great bonus for anyone

  Jessica Citera Cummings & Co

  343 Haystack Rd, Wilmington, VT 05363
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  /28

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  47 Ives Rd, Wilmington, VT 05363

  Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

  Adam Palmiter Berkley & Veller Greenwood/Dover

  47 Ives Rd, Wilmington, VT 05363
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  /46

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,960 Sq Ft

  16 Springhill Rd, Dover, VT 05356

  Experience modern luxury in this stunning contemporary home, less than 10 minutes from Mount Snow and just 15 minutes from The Hermitage Club. This thoughtfully designed retreat offers both sophistication and comfort, with high-end finishes and exceptional craftsmanship throughout. You will be captivated by the soaring freestanding stone fireplace, which serves as the heart of the home, complete

  Patrice Schneider Southern Vermont Realty Group

  16 Springhill Rd, Dover, VT 05356
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  /60

  $4,495,500

  • 4 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  816 Black Bear Rd, Jamaica, VT 05343

  Set atop a scenic Vermont hillside, this five-bedroom custom-built home by The Wadsworth Design Build/Vermont Barns is a stunning example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mount Snow ski resorts, it is the ultimate

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  816 Black Bear Rd, Jamaica, VT 05343
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  /5

  $35,000

  • Land
  • 1.2 Acres
  • $29,167 per Acre

  44 Antler Loop, Dover, VT 05356

  Come and join the nice quiet community of Dover Manor. This lot has road frontage on two sides of the property. There is a small wetland area on the Antler Loop side of the property, about 1/4 of the property. Private roads and close to elementary school, skiing and shopping. Elevation is at about 2000'.Town sewer is available.

  Regina Perrotto Skihome Realty

  44 Antler Loop, Dover, VT 05356
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  /13

  $50,000

  • Land
  • 2 Acres
  • $25,000 per Acre

  667 Hinkley Brook Rd, Grafton, VT 05146

  Nestled along the picturesque Hinkley Brook Road, this 2-acre parcel offers a rare opportunity to build your dream retreat in the charming and historic town of Grafton, Vermont. Just a short walk from the village center, you’ll enjoy the perfect blend of privacy and convenience, surrounded by the beauty of nature and classic New England charm. This peaceful lot boasts a gently wooded landscape

  Jamie Watson BHG Masiello Keene

  667 Hinkley Brook Rd, Grafton, VT 05146
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  /13

  $980,000

  • Land
  • 43.67 Acres
  • $22,441 per Acre

  Lot 10 & 16 Overlook Dr, Dover, VT 05356

  A rare opportunity to own the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 44 acres of land including approximately 0.7 miles of private trails for hiking, ATV, snowmobiling and indirect connection to the VAST trails via Bluebrook Rd. The home site features full panoramic 180-degree mountain and woodland views to the north, east and south,

  Patricia Fitzpatrick Skihome Realty

  Lot 10 & 16 Overlook Dr, Dover, VT 05356
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  /13

  $150,000

  • Land
  • 4.68 Acres
  • $32,051 per Acre

  8559 Vt Route 30 Unit Lots 2 & 3, 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 Unit Lots 2 & 3, Jamaica, VT 05343
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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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  /60

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  1845 Hatch School Rd, Brattleboro, VT 05301

  Welcome to our Contemporary Farmhouse with 100 private acres yet only 5 miles to Wilmington Center and 14 miles to Mount Snow Ski Resort. Harriman Reservoir is close for summer boating, water sports and picnics. Nestled in the heart of nature, the property offers numerous possibilities, including a well-appointed home, a working farm, various business opportunities and/or investment potential. As

  Richard Caplan Deerfield Valley Real Estate

  1845 Hatch School Rd, Brattleboro, VT 05301
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  /24

  $749,000

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

  Lot 3 Old Mill Ln, Wilmington, VT 05363

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

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 3 Old Mill Ln, Wilmington, VT 05363
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  /26

  $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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  /24

  $774,000

  • Land
  • 3.6 Acres
  • $215,000 per Acre

  Lot 5 Old Mill Ln, Wilmington, VT 05363

  Bring. your own builder and discover an exceptional opportunity to own a 3.6 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 with your own builder or to be crafted by the Wadsworth Design Build..

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 5 Old Mill Ln, Wilmington, VT 05363
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  /43

  $2,000,000

  • 6 Beds
  • 4.5 Baths
  • 4,950 Sq Ft

  43 Upton Rd, Dover, VT 05356

  The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end

  Adam Palmiter Berkley & Veller Greenwood/Dover

  43 Upton Rd, Dover, VT 05356
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  /44

  $480,000

  • 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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  /38

  $85,000

  • Land
  • 1.09 Acres
  • $77,982 per Acre

  95 Chimney Hill Rd, Wilmington, VT 05363

  Triple Merged Lot on the Hill! Recent soil tests say this looks good for a 3-bedroom home! Right off the pavement about halfway up the Hill on the plateau. If you've been thinking of building your Dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,100' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season

  Sigrid Pickering Chimney Hill Realty

  95 Chimney Hill Rd, Wilmington, VT 05363
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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

  $999,800

  • 4 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  60 Forest Heights Rd, Stratton, VT 05360

  Spectacular Soaring Post and Beam located on the Dover/Stratton town line. This fabulous home boasts soaring vaulted ceilings in the living room with a wall of windows bringing the view into your home complete with a cozy brick fireplace that sets the perfect ambiance. The kitchen is a chef’s delight, featuring granite countertops with eat in dining, a center island, half bath and easy access to

  Richard Caplan Deerfield Valley Real Estate

  60 Forest Heights Rd, Stratton, VT 05360
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  /49

  $369,000

  • 4 Beds
  • 2 Baths
  • 2,202 Sq Ft

  20 Newell Hill Rd, Wardsboro, VT 05355

  Now offering multiple buyer credits, including a $10,000 credit at closing—ask your agent for full details. Enter through the oversized mudroom, which once served as the town post office, from the attached three-bay garage with automatic doors. This home features generous rooms throughout, starting with a large kitchen and dining area, a living room, two main-level bedrooms, and a full bath.

  Erica Reynolds Southern Vermont Realty Group

  20 Newell Hill Rd, Wardsboro, VT 05355
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  /52

  $999,000

  • 4 Beds
  • 2 Baths
  • 2,741 Sq Ft

  20 Finkel Rd, Wardsboro, VT 05355

  Nestled on nearly 260 acres, this exquisite 18th-century solid post & beam 4 bedroom 2 bath cape offers a harmonious blend of historic charm and modern convenience. Boasting original features like fireplaces, wood flooring, and exposed beams, the home is filled with character. Spacious rooms create a perfect setting for gatherings. Recent updates include a new roof, windows, furnace & oil tank;

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  20 Finkel Rd, Wardsboro, VT 05355
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  /36

  $449,000

  • 3 Beds
  • 3 Baths
  • 2,144 Sq Ft

  44 Villager Loop, Dover, VT 05356

  Mountain Retreat located at 44 Villager Loop, Dover Hills, Dover, VTVery little use and never rented. Upgrades include a freshly painted exterior with a new roof and 3 mini-splits. Large mudroom entry, living room with fireplace, kitchen, dining area, 3 bedrooms, 3 baths, family room and a large deck for entertaining and relaxing. Close to the town center, restaurants, Town Park and Valley

  Janet Boyd Boyd Real Estate

  44 Villager Loop, Dover, VT 05356
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  /2

  $80,000

  • Land
  • 1.97 Acres
  • $40,609 per Acre

  24 Summit Cir, West Brattleboro, VT 05301

  Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

  Claire Renaud Berkley & Veller Greenwood Country

  24 Summit Cir, West Brattleboro, VT 05301
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  /50

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 3,358 Sq Ft

  1917 Stowe Mountain Rd, West Halifax, VT 05358

  Welcome to 1917 Stowe Mountain Rd., a sanctuary of modern elegance nestled in the breathtaking green mountains of Halifax, VT. This luxurious contemporary residence spans 3,358 square feet and seamlessly blends sophisticated design with natural beauty. As you approach this architectural masterpiece, soaring cathedral ceilings create a sense of expansive openness. The glass and Hardie plank

  Monica Sumner BHG Masiello Brattleboro

  1917 Stowe Mountain Rd, West Halifax, VT 05358
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  /37

  $1,700,000

  • 4 Beds
  • 4.5 Baths
  • 3,808 Sq Ft

  15 Stone Ridge Loop, Dover, VT 05356

  A luxurious mountain property with views and acreage, still with great proximity to Mt Snow. This stunning barn style post and beam is nestled on a private 5.97 acre parcel at the rear of the Village at Sawmill Farms. The siting affords gorgeous pastoral views over the common field of the community, views of the peak of Mount Snow, and mountains beyond, with 180 degree winter views, which could

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Stone Ridge Loop, Dover, VT 05356
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  /8

  $65,000

  • Land
  • 2 Acres
  • $32,500 per Acre

  585 Sawmill Rd, Stratton, VT 05360

  Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway.

  Carrie Mathews Winhall Real Estate

  585 Sawmill Rd, Stratton, VT 05360
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  /6

  $45,000

  • Land
  • 1 Acre
  • $45,000 per Acre

  0 Boardman Loop, Wardsboro, VT 05360

  In the Heart of it all! This affordable acre of land is close to skiing, hiking, ponds and all the good stuff Vermont has to offer. Electric poles are across the street and the neighbors are hooked up. Starlink and Xfinity charts say they service the area for at home work, streaming or game playing. There are Covenants attached for the after midnight reading. There is a small stream on the

  Christine Lewis Brattleboro Area Realty

  0 Boardman Loop, Wardsboro, VT 05360
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  /33

  $120,000

  • Land
  • 5 Acres
  • $24,000 per Acre

  0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363

  Beautiful 5-Acre Lot with Mountain Views – Approved for Two Homes!Here’s your chance to own a truly special piece of Vermont! This gorgeous 5-acre parcel on Route 100, just north of Wilmington center, offers the perfect setting for your dream home—or two. Recent soil tests support two single-family homes, each with up to three bedrooms. The land features an open, sun-drenched meadow, gently

  Monique White Deerfield Valley Real Estate

  0 Happy Haven Rd Unit 4998180, Wilmington, VT 05363
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  /40

  $3,250,000

  • 6 Beds
  • 3 Baths
  • 3,309 Sq Ft

  36 Woffenden Rd, Wilmington, VT 05363

  Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds.Boasting a coveted southeast exposure, the home and land are cheerful

  Melissa Ellis Southern Vermont Realty Group

  36 Woffenden Rd, Wilmington, VT 05363
• 

  

  /40

  $1,800,000

  • 9 Beds
  • 9 Baths
  • 8,054 Sq Ft

  207 Brooks Ln, Londonderry, VT 05148

  This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  207 Brooks Ln, Londonderry, VT 05148
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  /9

  $275,000

  • Land
  • 31 Acres
  • $8,871 per Acre

  41 Rice Hill Rd, Dover, VT 05341

  This land has many features. Beautiful large trees (Pines, Birches, Maples, Beech and more!), stone walls, beaver pond, several streams, views with clearing, wild Azalea's, Very private. The land has been perked for a 5 bedroom home in the appropriate area for views. There may be other areas that will perk. Views to the east. Large stream to the west. Some timber may be saleable. Without any

  Regina Perrotto Skihome Realty

  41 Rice Hill Rd, Dover, VT 05341
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  /10

  $84,500

  • Land
  • 5 Acres
  • $16,900 per Acre

  0 Old Ledge Rd Unit 4950217, Westminster, VT 05346

  Private! Surrounded by nature, evergreen Hemlocks and oaks that turn golden in the fall,...but...close to everything you need. Hospitals, Keene, Brattleboro, Dartmouth...3 really good food coops...the one in Putney is 7 minutes away...the interstate just minutes to head north or south. Take a weekend in Boston or NYC for the theater. Shopping...Walpole and Keene in tax free NH, Brattleboro and

  Christine Lewis Brattleboro Area Realty

  0 Old Ledge Rd Unit 4950217, Westminster, VT 05346
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  /17

  $39,900

  • Land
  • 5.66 Acres
  • $7,049 per Acre

  4 Murdock Ln, Whitingham, VT 05361

  Build your dream home on this surveyed 5.66 acre lot with deeded rights to Ryder Pond! A great location for primary or vacation living, situated between down town Wilmington VT and Greenfield MA with easy access to scenic Rt 100. Lakes, ski resorts and out door recreation abound with Mount Snow Resort, Lake Whitingham, Lake Sadawga, Lake Raponda and Molly Stark State Park all close by. To stick

  Jacki Murano Southern Vermont Realty Group

  4 Murdock Ln, Whitingham, VT 05361
• 

  /2

  $199,000

  • 2 Beds
  • 2,710 Sq Ft

  29 Stable Rd, Wilmington, VT 05363

  The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area and Golf Course and The Hermitage Club close to the Coldbrook. Built to sleep 32 People. Features 4 plus acres with ample parking. Building will need an extensive rehab. Not safe to go into the structure.

  Mark Yule BHG Masiello Brattleboro

  29 Stable Rd, Wilmington, VT 05363
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  /2

  $84,900

  • Land
  • 4.27 Acres
  • $19,883 per Acre

  Lot #3 Peachtree Ln, Brattleboro, VT 05301

  Just off desirable Orchard Street is this beautiful 4.27+/- acre building lot. Located at roads end, the site is perfect for a beautiful new home with southerly exposure, stone walls, a gentle rise and privacy. Just minutes from downtown, yet country in feel.

  Desiree Stango Berkley & Veller Greenwood Country

  Lot #3 Peachtree Ln, Brattleboro, VT 05301
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  /2

  $169,900

  • Land
  • 35.4 Acres
  • $4,799 per Acre

  0 Minard Rd, Westminster, VT 05346

  Over 35 wooded acres to call your own. Drive up the winding country road edged with meadows, views and a sense of peace to your own little haven. Spend some time on the land, scouting the views, finding the right site and falling in love with all the potential. Owned by the same family for over 30 years, it has finally come to market in just the right season to experience the golden glow of

  Christine Lewis Brattleboro Area Realty

  0 Minard Rd, Westminster, VT 05346
• 

  /2

  $175,000

  • Land
  • 8.52 Acres
  • $20,540 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
• 

  /2

  $125,000

  • Land
  • 14.91 Acres
  • $8,384 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
• 

  /2

  $225,000

  • Land
  • 9.45 Acres
  • $23,810 per Acre

  0 Higley Hill, Dover, VT 05356

  Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Appointment is required to walk the property.

  Michael Purcell Berkley & Veller Greenwood/Dover

  0 Higley Hill, Dover, VT 05356
• 

  /2

  $64,900

  • Land
  • 3.65 Acres
  • $17,781 per Acre

  Lot 18 Central Park Estates, Vernon, VT 05354

  3.65 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 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 18 Central Park Estates, Vernon, VT 05354
• 

  /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

Showing Results 201 - 240, Page 6 of 7