Bennington County VT Homes for Sale

• 

  

  /2

  $125,000

  • Land
  • 1.45 Acres
  • $86,207 per Acre

  L/O River Rd, Winhall, VT 05340

  This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

  Cheyanne Pugliese

  L/O River Rd, Winhall, VT 05340
• 

  

  

  /45

  $995,000

  • 13 Beds
  • 12 Baths
  • 8,594 Sq Ft

  2759 Vt Route 11, Peru, VT 05152

  Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2759 Vt Route 11, Peru, VT 05152
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  /60

  $5,600,000

  • 5 Beds
  • 5.5 Baths
  • 4,674 Sq Ft

  1060 Upper Hollow Rd, Dorset, VT 05251

  'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy

  Sunny Breen Josiah Allen Real Estate, Inc.

  1060 Upper Hollow Rd, Dorset, VT 05251
• 

  

  

  /16

  $205,000

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  40 Bourn Brook Rd Unit 50, Manchester, VT 05255

  Modern In-Town Living and Fully Renovated Bourn Brook Condo. Experience the best of Manchester Center in this meticulously renovated end-unit at Bourn Brook. Whether you are looking for an affordable primary residence or a sleek "lock-and-leave" weekend getaway, this condo delivers modern style in a prime, walkable location.Interior HighlightsNo detail was spared in this top-to-bottom

  Robin Apps Four Seasons Sotheby's Int'l Realty

  40 Bourn Brook Rd Unit 50, Manchester, VT 05255
• 

  

  

  /23

  $120,000

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  818 Old Depot Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway, vacation rental, or full-time home. New vinyl siding, a recent metal roof, and newer furnace. Enjoy

  Lisa Friedman Great American Dream Realty

  818 Old Depot Rd, Shaftsbury, VT 05262
• 

  

  /37

  $829,000

  • 4 Beds
  • 3 Baths
  • 2,797 Sq Ft

  13 Betty Johnson Ln, Bondville, VT 05340

  Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  13 Betty Johnson Ln, Bondville, VT 05340
• 

  

  /31

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  109 Evergreen Dr, Bennington, VT 05201

  House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
• 

  

  /15

  $500,000

  • Land
  • 21.2 Acres
  • $23,585 per Acre

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
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  /36

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2092 N Bennington Rd, North Bennington, VT 05257

  Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  2092 N Bennington Rd, North Bennington, VT 05257
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  /58

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

  Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
• 

  

  /40

  $305,000

  • 3 Beds
  • 2.5 Baths
  • 1,378 Sq Ft

  61 E Branch Farms Unit 1, Manchester Center, VT 05255

  East Branch Farms is in the most convenient location! This 3 bedroom and 2 and a half bath condo is ready for its next owners. Wood floors on the main level and new granite countertops in the kitchen. Full basement with both interior and exterior access for workshop space or extra storage. Located at the edge of lovely Manchester VT it is privately screened from the road with views of soaring

  

  Alison Cummings

  Cummings & Co

  (802) 300-4136

  61 E Branch Farms Unit 1, Manchester Center, VT 05255
• 

  

  /50

  $750,000

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

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340

  WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340
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  /40

  $475,000

  • 4 Beds
  • 3 Baths
  • 1,680 Sq Ft

  7 Stratton West Rd Unit 7, Winhall, VT 05340

  This recently renovated 4/5 bedroom Stratton West home is located minutes to Stratton Resort for skiing, golf, and all your recreation activities. The new, custom-built kitchen offers an open layout with beautiful granite countertops. Front and back decks provides places to grill and relax on warm summer nights, or you can cozy up with the Harman pellet stove in the winter months. The first level

  Mike England Michael England Real Estate

  7 Stratton West Rd Unit 7, Winhall, VT 05340
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  /51

  $1,650,000

  • 3 Beds
  • 2.5 Baths
  • 3,368 Sq Ft

  276 Wilcox Hollow Rd, Sandgate, VT 05250

  Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid

  

  Margretta Fischer

  Wohler Realty Group

  (802) 521-2796

  276 Wilcox Hollow Rd, Sandgate, VT 05250
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  /25

  $98,999 New Construction

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft

  78 Ethans Way, Bennington, VT 05201

  Welcome to 78 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polomodel manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

  Kate Barry EXP Realty

  78 Ethans Way, Bennington, VT 05201
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  /38

  $375,000

  • Land
  • 1.23 Acres
  • $304,878 per Acre

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

  Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

  Kim Morgan-Wohler Wohler Realty Group

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
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  /12

  $450,000

  • Land
  • 10.26 Acres
  • $43,860 per Acre

  4.1 Pearl Buck Dr, Winhall, VT 05340

  One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

  Kim Morgan-Wohler Wohler Realty Group

  4.1 Pearl Buck Dr, Winhall, VT 05340
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  /39

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  38 Oak Ridge Ln, Bennington, VT 05201

  Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

  Matt Waddington Hoffman Real Estate

  38 Oak Ridge Ln, Bennington, VT 05201
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  /8

  $35,000

  • Land
  • 1 Acre
  • $35,000 per Acre

  0 Barber Pond Rd, Pownal, VT 05261

  Tucked into the scenic rural landscape of Pownal, Vermont, this approximate one-acre parcel of raw land offers a blend of natural privacy and water frontage on Barber Pond. Ideal for recreational use or future development, subject to local zoning and permitting. Enjoy the charm of the southern Vermont countryside while remaining within easy reach of nearby towns and outdoor amenities. Known for

  Vicki Wilson Maple Leaf Realty

  0 Barber Pond Rd, Pownal, VT 05261
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  /25

  $1,425,000

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  1058 Granger Hollow Rd, North Bennington, VT 05257

  A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, North Bennington, VT 05257
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  /14

  $2,500,000

  • Land
  • 227 Acres
  • $11,013 per Acre

  00 Vermont 11, Peru, VT 05152

  227 acre offering in Peru Vermont combining a 199 acre parcel bordering Green Mountain National Forest and a 28 acre parcel with views of Stratton, Bromley and Magic Mountains. Southern exposure and varied terrain provide excellent natural light, privacy and long range Green Mountain vistas. The property offers exceptional scale and flexibility suitable for a private estate, family compound or

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /8

  $150,000

  • Land
  • 2.26 Acres
  • $66,372 per Acre

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

  Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
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  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
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  /51

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  281 Old County Ln, Readsboro, VT 05350

  Nestled on more than two acres of beautifully maintained countryside and mature forest, this renovated 1892 farmhouse blends New England charm with peaceful seclusion and easy access to local attractions. Just 15 minutes from Mass MoCA, 25 minutes from Mount Snow, and close to hiking and ATV trails, it’s perfect for outdoor enthusiasts. Inside, you’ll find a warm and thoughtfully updated home

  Melissa Nebelski Real Broker LLC

  281 Old County Ln, Readsboro, VT 05350
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  /16

  $139,000

  • Land
  • 1.62 Acres
  • $85,802 per Acre

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

  wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

  Mike England Michael England Real Estate

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
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  /3

  $219,000

  • 2 Beds
  • 1 Bath
  • 1,872 Sq Ft

  17 Henry Hill, Stamford, VT 05352

  Sean Taylor Moresi Real Estate Partners

  17 Henry Hill, Stamford, VT 05352
• 

  

  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
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  /32

  $295,000

  • 1 Bed
  • 1.5 Baths
  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /52

  $675,000

  • 3 Beds
  • 4 Baths
  • 2,274 Sq Ft

  490 Barnumville Rd, Manchester Center, VT 05255

  490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries,

  David Shehadi Josiah Allen Real Estate, Inc.

  490 Barnumville Rd, Manchester Center, VT 05255
• 

  

  /12

  $95,000

  • Land
  • 1 Acre
  • $95,000 per Acre

  41 Moose Hollow Rd, Winhall, VT 05340

  Build your dream home on this ready-to-go 1-acre lot in the Green Mountains. Located on a private gravel road in Winhall, this mostly cleared parcel offers a gentle slope, power at the road, a nearby stream, and a state-issued 4-bedroom septic permit already in place. The setting provides a peaceful, natural feel while keeping you close to the best of Southern Vermont. Bromley Mountain is about

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  41 Moose Hollow Rd, Winhall, VT 05340
• 

  

  /58

  $299,000

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

  207 Silver St, Bennington, VT 05201

  Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a

  Dan Mason Perrott Realty

  207 Silver St, Bennington, VT 05201
• 

  

  /23

  $125,000

  • Land
  • 2.9 Acres
  • $43,103 per Acre

  311 Beechwood Ln, Peru, VT 05152

  This lovely, nearly 3 acre parcel of land is located on Beechwood Lane, about 1 mile from the Town center of Peru. There is approximately 353' frontage on Beechwood Lane and approximately 271' frontage on Beechnut Drive. The land is gently sloped and nicely wooded for privacy. Xfinity high speed internet available. Peru features the J.J. Hapgood General store, Peru Congregational Church, Hapgood

  Dylan Gage Bromley Real Estate

  311 Beechwood Ln, Peru, VT 05152
• 

  

  /20

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  1180 North Rd, East Arlington, VT 05252

  Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

  Jason Saphire www.HomeZu.com

  1180 North Rd, East Arlington, VT 05252
• 

  

  /42

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262

  Welcome to Rod and Gun Club Rd. Offering 1748 sq ft, with a full useable basement, sitting on 4.43 acres of land, with a 3-bay garage with carport as well as, an attached 2-car garage, a barn with stalls if you want to have some animals. This newly renovated ranch style home with thoughtful design offers 3B,2Bath, with a spacious and flexible layout with a fireplace with a gas insert in the

  

  Wendy Larson

  Hooscik Realty

  (802) 526-6197

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262
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  /55

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 2,321 Sq Ft

  24 N Branch Rd, Winhall, VT 05340

  Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite-

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340
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  /36

  $699,000

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

  682 E Manchester Rd, Manchester Center, VT 05255

  Welcome to a private Vermont retreat that blends rustic post-and-beam charm with modern versatility. Nestled above the serene Bourne Brook, this property offers the perfect balance of privacy, natural beauty and convenience. The main house exudes warmth and craftmanship, and is complemented by an income producing apartment above the 2 car garage, adding flexibility for extra guests, long term

  

  Christopher Cummings

  Cummings & Co

  (802) 441-7038

  682 E Manchester Rd, Manchester Center, VT 05255
• 

  

  /40

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  11 Founders Hill Rd, Winhall, VT 05360

  Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  11 Founders Hill Rd, Winhall, VT 05360
• 

  

  /17

  $160,000

  • Land
  • 2.9 Acres
  • $55,172 per Acre

  Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250

  This scenic undeveloped lot in Sunderland, Vermont, offers an exceptional opportunity to build in a peaceful yet convenient location. Set along a picturesque bike route, the property features level terrain that makes it ideal for easy construction and design flexibility. The land is already cleared, opening up the possibility for lovely mountain views and allowing you to envision your home

  Andy Reed Four Seasons Sotheby's Int'l Realty

  Lot 21 Sunderland Hill Rd, West Arlingtn, VT 05250
• 

  

  /4

  $27,999

  • Land
  • 2.4 Acres
  • $11,666 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2.4-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /4

  $28,000

  • Land
  • 2.3 Acres
  • $12,174 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350

Showing Results 81 - 120, Page 3 of 5