Bennington County VT Homes for Sale

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  /45

  $350,000

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft

  19 Royal St, North Bennington, VT 05257

  Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

  Lindsey Martin Maple Leaf Realty

  19 Royal St, North Bennington, VT 05257
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  /4

  $249,000

  • 5 Beds
  • 3 Baths
  • 2,184 Sq Ft

  137 Park St, Bennington, VT 05201

  Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  137 Park St, Bennington, VT 05201
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  /10

  $342,000

  • Land
  • 28.5 Acres
  • $12,000 per Acre

  11 Old County Rd E, Londonderry, VT 05148

  A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  11 Old County Rd E, Londonderry, VT 05148
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  /38

  $1,995,000

  • 5 Beds
  • 3 Baths
  • 6,323 Sq Ft

  2589 W Sandgate Rd, Arlington, VT 05250

  Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons

  Dia Jenks LandVest, Inc/Woodstock

  2589 W Sandgate Rd, Arlington, VT 05250
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  /38

  $980,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
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  /60

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,215 Sq Ft

  92 Coventry Ln, Manchester Center, VT 05255

  Coventry House - Offered For The First Time! Built in 1972, the home was thoughtfully designed by local architect Charles "Bud" Lynch in collaboration with the owners. This custom-built home blends timeless design with natural surroundings. Offering a country kitchen, 4 bedrooms and 3+ vintage baths reflecting the 70’s era focus on color, natural materials, and open floor plans all on one level

  Kristin Comeau TPW Real Estate

  92 Coventry Ln, Manchester Center, VT 05255
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  /6

  $110,000

  • Land
  • 1 Acre
  • $110,000 per Acre

  88A Sylvan Ridge Rd, Winhall, VT 05340

  Wooded lot with hardwoods, evergreens and birch trees. Potential views of Bromley Mountain and beyond. Town maintained road. Close to VAST snowmobile trails. Build your dream home in the Golden Triangle of ski areas, Stratton, Bromley, and Magic Mountains. Only 10 minuets to Manchester. Available on request:Wastewater System and Potable Water Supply PermitSeptic

  Andrew King Stratton Real Estate

  88A Sylvan Ridge Rd, Winhall, VT 05340
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  /23

  $4,000,000

  • 5 Beds
  • 2 Baths
  • 3,347 Sq Ft

  15 Wind Hill Rd, Manchester Center, VT 05255

  At the heart of this remarkable 136-acre property in Manchester Center, Vermont, are two distinct historic homes, each telling a story of the land’s deep roots in the Beattie-Forrest family, who have stewarded it for over a century.The original farmhouse, built circa 1800, offers five bedrooms and two baths, with timeless details including a vintage kitchen and hand-hewn timber framing.

  Paul Carroccio TPW Real Estate

  15 Wind Hill Rd, Manchester Center, VT 05255
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  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street.The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
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  /44

  $69,900

  • 5 Beds
  • 1 Bath
  • 1,952 Sq Ft

  273 Union St, Bennington, VT 05201

  This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

  Catherine Cairns Maple Leaf Realty

  273 Union St, Bennington, VT 05201
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  /34

  $500,000

  • 1 Bed
  • 2 Baths
  • 300 Sq Ft

  417 Maple Hill Rd, Arlington, VT 05250

  Scandinavian Timber Frame Tiny House & Grindbygg! Over 10 acres of privacy and beautiful vistas. 360 degree mountain view from this custom heartfelt build. The property includes a one bedroom tiny house complete with kitchen, gas range, wood stove, movie projector, sleeping loft and so much more. A drilled well, on demand propane hot water heater and water shed for water storage. This cozy

  Margretta Fischer Wohler Realty Group

  417 Maple Hill Rd, Arlington, VT 05250
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  /30

  $1,300,000

  • 11 Beds
  • 9 Baths
  • 9,560 Sq Ft

  3309 3321 Main St, Manchester, VT 05254

  A Rare Opportunity! Introducing a historically significant gem, available for the first time in over 40 years. Set in the picturesque and highly sought after Manchester Village, this timeless estate includes a grand Main House and a charming Carriage House, each situated on its own adjoining 1.27-acre lot, totaling an expansive 2.54 park-like acres. Together, the residences offer 11 bedrooms, 6

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  3309 3321 Main St, Manchester, VT 05254
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  /31

  $150,000

  • 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

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
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  /41

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  245 Southshire Dr, Bennington, VT 05201

  Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /59

  $549,000

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  69 Hillvale Dr, Manchester Center, VT 05255

  This is a wonderful craftsman style ranch in a great location right in the heart of Manchester, in the sunny Hillvale neighborhood. It offers views to Mt. Equinox and is walking access to all Manchester's amenities. Four bedrooms, two full baths, updated kitchen with stainless appliances and granite counter tops, the dining room's french door opens on to an expansive deck for BBQ's and

  Robert Sabol Wohler Realty Group

  69 Hillvale Dr, Manchester Center, VT 05255
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  /27

  $1,250,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  233 Squires Rd, Manchester Center, VT 05255

  Discover a rare opportunity to live and work amidst the serene beauty of Manchester, Vermont. This fully renovated 2-bedroom, 1-bath contemporary ranch, with leased solar array, is nestled on nearly 19 acres, offering a harmonious blend of modern comfort and entrepreneurial potential.The open-concept design features a spacious kitchen and living area, complemented by energy-efficient

  Mark Triller Real Broker LLC

  233 Squires Rd, Manchester Center, VT 05255
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  /9

  $27,500

  • Land
  • 1.2 Acres
  • $22,917 per Acre

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352

  Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

  Kelly Agrillo Southern Vermont Realty Group

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352
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  /49

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  93 Pace Rd, Bennington, VT 05201

  Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

  Harvey Roettinger RE/MAX North Professionals

  93 Pace Rd, Bennington, VT 05201
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  /34

  $475,000

  • 3 Beds
  • 3 Baths
  • 1,696 Sq Ft

  104 Johnny Cake Hill Ln, Readsboro, VT 05350

  If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 22 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock.This serene retreat offers the best of nature — birdsong in the morning, occasional

  Monica Sumner BHG Masiello Brattleboro

  104 Johnny Cake Hill Ln, Readsboro, VT 05350
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  /11

  $179,900

  • 4 Beds
  • 2 Baths
  • 2,643 Sq Ft

  905 County St, Bennington, VT 05201

  Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  905 County St, Bennington, VT 05201
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  /45

  $1,350,000

  • 6 Beds
  • 7 Baths
  • 5,400 Sq Ft

  2001 Depot St, Manchester Center, VT 05255

  LOCATION, LOCATION: 8 minutes from Bromley, 20 minutes to Stratton, yet close to Manchester restaurants, shopping, fishing, Horse Show & golf. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bathroom retreat offers 5,400+ square feet of living space on 3.2 private acres—perfect for use as a primary residence, vacation getaway, or a return to its B&B roots.

  Steven Bryant TPW Real Estate

  2001 Depot St, Manchester Center, VT 05255
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  /50

  $374,900

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

  927 Water St, North Bennington, VT 05257

  Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
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  /42

  $1,950,000

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

  1086 West Rd, Bennington, VT 05201

  Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

  Chris DeFelice Four Seasons Sotheby's Int'l Realty

  1086 West Rd, Bennington, VT 05201
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  /50

  $4,875,000

  • 7 Beds
  • 10 Baths
  • 7,422 Sq Ft

  318 Spring Hill Ln, Dorset, VT 05251

  Welcome to a truly exceptional estate where classic charm and modern craftsmanship unite on 9 secluded acres in the heart of coveted Dorset, Vermont. Meticulously curated with no detail overlooked and no expense spared, this remarkable property features a beautifully renovated 1941 Colonial residence, complemented by a collection of newer luxury companion buildings that together create a one of a

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  318 Spring Hill Ln, Dorset, VT 05251
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  /48

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 3,742 Sq Ft

  34 Southshire Dr, Bennington, VT 05201

  Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

  Kelley Mccarthy Mahar McCarthy Real Estate

  34 Southshire Dr, Bennington, VT 05201
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  /27

  $375,000

  • Land
  • 53 Acres
  • $7,075 per Acre

  0 Rock Bottom Ln, Peru, VT 05152

  Discover the perfect canvas for your dream retreat on this stunning 53-acre parcel in picturesque Peru, Vermont. Tucked away in the Green Mountains, this exceptional property offers expansive views—including a breathtaking sightline to Magic Mountain—and the serenity of true Vermont wilderness.A private driveway is already in place, making access simple and setting the stage for your

  David Shehadi Josiah Allen Real Estate, Inc.

  0 Rock Bottom Ln, Peru, VT 05152
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  /37

  $1,275,000

  • 4 Beds
  • 4 Baths
  • 4,266 Sq Ft

  693 Longview Dr, Manchester, VT 05255

  This four-bedroom, four-bath home offers not only exceptional views and privacy but also the convenience of an in-town location. It's ideally situated in Manchester Village, set on three landscaped acres featuring mature trees, custom stonework, level lawns, and active brook.The interior of the home provides a comfortable living space. On the Main Level, you'll find a spacious living room

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  693 Longview Dr, Manchester, VT 05255
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  /7

  $175,000

  • Land
  • 15.49 Acres
  • $11,298 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
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  /33

  $1,274,999

  • 4 Beds
  • 2.5 Baths
  • 4,620 Sq Ft

  139 Village View Rd, Manchester, VT 05255

  From morning coffee on the deck to cozy evenings by the fire, this Manchester home is designed for comfort, flexibility, and four-season living. The main level features a bright great room, an eat-in kitchen with an adjacent covered porch, a formal dining room, a den with a fireplace, two bedrooms, a full bath, and a primary suite with a walk-in shower and a jetted tub.The finished lower

  Marek Kovac TPW Real Estate

  139 Village View Rd, Manchester, VT 05255
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  /21

  $895,000

  • 4 Beds
  • 5.5 Baths
  • 4,213 Sq Ft

  262 Powderhorn Rd, Manchester Center, VT 05255

  Stunning Contemporary Retreat with Indoor Pool on Nearly 2 AcresWelcome to this beautiful 5-bedroom, 5-bath contemporary home nestled on a sunny 1.9+/- acre lot. Designed for both comfort and style, this expansive residence features a 16' x 32' heated indoor swimming pool, perfect for year-round enjoyment.Originally built in 1973 and extensively renovated in 2000, the home blends timeless

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  262 Powderhorn Rd, Manchester Center, VT 05255
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  /52

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
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  /21

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  6 Deep Woods Rd, Winhall, VT 05255

  Escape to your cozy log ski chalet nestled on a private acre in the charming town of Winhall, Vermont! This delightful 3-bedroom, 1.5-bath home offers 1116 square feet of rustic charm and modern comfort. Imagine returning from a thrilling day on the slopes of nearby Stratton or Bromley, just a short drive away, and unwinding by the crackling outdoor fireplace on your spacious patio, with festive

  Robin Apps Four Seasons Sotheby's Int'l Realty

  6 Deep Woods Rd, Winhall, VT 05255
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  /51

  $970,000

  • 6 Beds
  • 8 Baths
  • 5,764 Sq Ft

  24 Vt Route 11, Londonderry, VT 05148

  Step into a world of potential with this beautiful country retreat, set on the edge of pristine Green Mountain National Forest. Adventure truly begins here, with nearby access to the Catamount Trail and four renowned ski areas just minutes away. Once home to the beloved Nordic Inn, this versatile property carries a rich legacy of hospitality, having once hosted a restaurant and cross-country ski

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  24 Vt Route 11, Londonderry, VT 05148
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  /54

  $1,875,000

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

  2167 Myers Rd, Shaftsbury, VT 05262

  Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub,

  Kelley Mccarthy Mahar McCarthy Real Estate

  2167 Myers Rd, Shaftsbury, VT 05262
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  /42

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft

  516 Oberdorf Rd, Readsboro, VT 05350

  Outdoor lover’s paradise in Alpenwald Village! This beautifully updated 2-bedroom, 2-bath home sits on an ample 2.5 acres and abuts National Forest land—perfect for year-round adventure. Step inside to your open kitchen and a bright family room with cathedral ceilings and a sliding door that opens to a peaceful back porch with stunning mountain views. The spacious mudroom offers plenty of room

  Lindsey Martin Maple Leaf Realty

  516 Oberdorf Rd, Readsboro, VT 05350
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  /27

  $595,000

  • 2 Beds
  • 2 Baths
  • 3,478 Sq Ft

  142 Mount Aeolus Rd, Manchester, VT 05255

  A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income.This well-maintained property

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  142 Mount Aeolus Rd, Manchester, VT 05255
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  /9

  $65,000

  • Land
  • 0.74 Acre
  • $87,838 per Acre

  0 Stratton View Rd, Winhall, VT 05340

  Stratton View Rd Lot # 58 , .74 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition Lot MLS #5036984 available. Own your piece of Vermont.

  Mike England Michael England Real Estate

  0 Stratton View Rd, Winhall, VT 05340
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  /13

  $135,000

  • Land
  • 1.36 Acres
  • $99,265 per Acre

  0 Stratton View Rd, Winhall, VT 05340

  Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

  Mike England Michael England Real Estate

  0 Stratton View Rd, Winhall, VT 05340
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  /8

  $65,000

  • Land
  • 1.02 Acres
  • $63,725 per Acre

  0 Stratton View Rd, Winhall, VT 05340

  Stratton View Rd Lot # 59 , 1.02 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition lot MLS #5036988 available. Own your piece of Vermont.

  Mike England Michael England Real Estate

  0 Stratton View Rd, Winhall, VT 05340
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  /2

  $199,500

  • Land
  • 47 Acres
  • $4,245 per Acre

  TBD Myers Rd, Shaftsbury, VT 05262

  47+/- magical acres of rolling meadows, mountain views, hard woods and wildlife. The acreage affords you the opportunity to build your dream home/mini farm. The expansive acreage invites you to explore the surrounding nature, whether it's a morning walk on the bucolic rural road, greeting the early birds or sitting high on the hillside staring at the stars. Few parcels of this size remain

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  TBD Myers Rd, Shaftsbury, VT 05262

Showing Results 121 - 160, Page 4 of 6