128

Bennington County VT Homes for Sale with Acreage

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  • /60

    $979,000

    • 4 Beds
    • 3.5 Baths
    • 5,248 Sq Ft

    41-43 Cranberry Hill Rd, Winhall, VT 05340

    This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

    Jamie Luke TPW Real Estate

    41-43 Cranberry Hill Rd, Winhall, VT 05340
  • /51

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 5,228 Sq Ft

    2167 Myers Rd, Shaftsbury, VT 05262

    Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

    Kelley Mccarthy Mahar McCarthy Real Estate

    2167 Myers Rd, Shaftsbury, VT 05262
  • /3

    $79,900

    • Land
    • 10.1 Acres
    • $7,911 per Acre

    0 Old County Ln, Readsboro, VT 05350

    Escape to the tranquil countryside of Readsboro with this stunning 10.10-acre parcel offering exceptional privacy and natural beauty. The property showcases a picturesque mix of open level areas and gentle rolling hills, complemented by mature apple and cherry trees, thriving blueberry bushes, and a charming brook that winds its way through the land.Whether you envision a full-time residence,

    Raelene Robinson-Garrow Real Broker LLC

    0 Old County Ln, Readsboro, VT 05350
  • /8

    $1,900,000

    • Land
    • 199 Acres
    • $9,548 per Acre

    00 Vermont 11, Peru, VT 05152

    199 +/- acre parcel in Peru Vermont bordering Green Mountain National Forest with southern exposure and views of Stratton Mountain and the surrounding Green Mountains. The scale of the land, elevation and orientation provide exceptional privacy, consistent natural light and expansive long range mountain vistas. The property offers a rare combination of direct forest access and proximity to

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152
  • /20

    $600,000

    • Land
    • 28 Acres
    • $21,429 per Acre

    00 Vermont 11, Peru, VT 05152

    28 +/- acre parcel in Peru Vermont with views of Stratton Mountain, Bromley Mountain and Magic Mountain. Rare east, south and westerly exposure provides consistent natural light and excellent solar orientation throughout the day. Positioned across from Johnny Seesaw’s and minutes to Bromley Market and Bromley Mountain Ski Resort, the property offers privacy with immediate access to dining, skiing

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152
  • /46

    $1,550,000

    • 5 Beds
    • 5 Baths
    • 6,129 Sq Ft

    1035 Holy Smoke Rd, Shaftsbury, VT 05262

    Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

    Lori Hurley Four Corner Properties LLC

    1035 Holy Smoke Rd, Shaftsbury, VT 05262
  • /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
  • /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
  • /58

    $1,495,000

    • 7 Beds
    • 5.5 Baths
    • 6,392 Sq Ft

    16 West Rd, Bennington, VT 05201

    Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home’s historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless

    Kelley Mccarthy Mahar McCarthy Real Estate

    16 West Rd, Bennington, VT 05201
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /27

    $290,000

    • 4 Beds
    • 2 Baths
    • 2,190 Sq Ft

    196 Granger Hollow Rd, North Bennington, VT 05257

    Currently being used as a primary home with in-law rental 2nd home, this property could easily transition into a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large

    Steve Schoppmeyer BHG Masiello Brattleboro

    196 Granger Hollow Rd, North Bennington, VT 05257
  • /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
  • /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
  • /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
  • /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
  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /3

    $109,000

    • Land
    • 17 Acres
    • $6,412 per Acre

    00 Bill T Dr, Readsboro, VT 05350

    Escape to the Green Mountains with this beautiful 17-acre parcel located at the end of a town-maintained road in scenic Readsboro, Vermont. This private property offers the perfect mix of seclusion and convenience, surrounded by nature and outdoor recreation opportunities. At the rear of the property, you’ll find a serene beaver pond that attracts moose, birds, and other local wildlife—an ideal

    Samantha Decker Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /24

    $471,000

    • 3 Beds
    • 2 Baths
    • 1,357 Sq Ft

    102 Mccormick Ln, Sunderland, VT 05250

    Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

    Dana Kingsley Josiah Allen Real Estate, Inc.

    102 Mccormick Ln, Sunderland, VT 05250
  • /17

    $65,000

    • Land
    • 2.38 Acres
    • $27,311 per Acre

    0 Sunset Hill Rd Unit B, Pownal, VT 05261

    Motivated sellers welcome you to this gorgeous 2.38+/- acre lot in Pownal, Vermont! Located on a dead end, private road, this lot is nestled on the right hand side when pulling into Sunset Hill Road. Recently flagged for easy access. Mostly level with some vegetation in a quiet neighborhood. Are you dreaming of building your own home or investing in VT real estate? You won’t want to miss this

    Terri Edgerley Edge Realty Vermont

    0 Sunset Hill Rd Unit B, Pownal, VT 05261
  • /60

    $579,900

    • 1 Bed
    • 1 Bath
    • 2,529 Sq Ft

    126 Simeon Dean Rd, Shaftsbury, VT 05262

    Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

    Denise Byers Green Mountain Premiere Properties

    126 Simeon Dean Rd, Shaftsbury, VT 05262
  • /34

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    114 Colebrook Rd, East Arlington, VT 05252

    This is an unfinished home that needs the right owner to complete it to its fullcapacity.Set off on a private road this home is set on a beautiful, secluded, wooded lot.Access to major highways and schools

    David White OwnerEntry.com

    114 Colebrook Rd, East Arlington, VT 05252
  • /6

    $56,900

    • Land
    • 4.2 Acres
    • $13,548 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 4-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

    Flex Realty Group Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /45

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,200 Sq Ft

    9 Lower Taylor Hill Rd, Winhall, VT 05340

    Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

    Timothy Mich Doddridge Stratton Real Estate

    9 Lower Taylor Hill Rd, Winhall, VT 05340
  • /56

    $3,350,000

    • 3 Beds
    • 4.5 Baths
    • 3,059 Sq Ft

    466 3 Maple Dr, Manchester, VT 05254

    Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views. This home features three spacious bedroom suites,

    David Shehadi Josiah Allen Real Estate, Inc.

    466 3 Maple Dr, Manchester, VT 05254

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