Bennington County VT Homes for Sale

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  $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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  /17

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 1,368 Sq Ft

  21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255

  THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction:Eligibility Requirements: * Vermont Residency or Residency at time of Purchase * First Time Vermont Homebuyer * Household Income at or Below $178,735* * Qualify for a Bank Mortgage * 10% Down Payment The developer will offer Gifted Equity and Paid Points at closing that will reduce the purchase price of the real estate and

  Britt Wohler

  21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
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  /39

  $895,000

  • 4 Beds
  • 4 Baths
  • 2,673 Sq Ft

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

  Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

  Mike England Michael England Real Estate

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
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  /31

  $235,000

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  67 Bourn Brook Rd Unit 53, Manchester Center, VT 05255

  Ideally located in the heart of Manchester Vermont, this 2 Bedroom, 1 Bath townhouse is just minutes from Shopping, Dining, Schools, the Town Recreation area which features Walking Paths, Community Pool, Tennis, Pickle Ball, Basketball, and Athletic Fields. On the main level is a very comfortable living area, dining space, and the kitchen, all with hardwood floors. The kitchen has updated

  Robert Sabol Wohler Realty Group

  67 Bourn Brook Rd Unit 53, Manchester Center, VT 05255
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  /40

  $179,000

  • Land
  • 0.2 Acre
  • $895,000 per Acre

  10 Partridge Hill, Manchester, VT 05255

  One of the last remaining lots in the exceptional Partridge Hill Association. This beautiful lot is situated to capture wonderful views and abbuts common land and a huge undeveloped land parcel on it's boundaries- offering a private outdoor space. The building envelope benefits from the ability to approach the parcel through the adjacent common land. Underground power and cable at the lot.

  Kim Morgan-Wohler Wohler Realty Group

  10 Partridge Hill, Manchester, VT 05255
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  /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
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  /21

  $235,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  209 Grove St Unit 11, Bennington, VT 05201

  A must see, well-kept 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, a spacious eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice, level backyard, 2

  Julie Glover Mahar McCarthy Real Estate

  209 Grove St Unit 11, 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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  /34

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,343 Sq Ft

  760 W Mountain Rd, Shaftsbury, VT 05262

  Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

  Kelley Mccarthy Mahar McCarthy Real Estate

  760 W Mountain Rd, Shaftsbury, VT 05262
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  /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
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  /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
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  $1,550,000

  • 5 Beds
  • 5 Baths
  • 4,650 Sq Ft

  20 Blackberry Ln, Peru, VT 05152

  Welcome to Bromley Village. This spacious 5 bedroom, 5 bath house offers everything you need to ensure the comfort of your group whether it’s large or small. The heart of this home is the magnificent great room with 20 foot ceilings, wood burning fireplace, slate floors, dining area and corner bar. The gourmet kitchen with red cabinets, soapstone counters, and top of the line appliances (Sub

  David Citron RE/MAX Four Seasons

  20 Blackberry Ln, 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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  /29

  $250,000

  • 9 Beds
  • 5 Baths
  • 3,810 Sq Ft

  6982 Main St, Readsboro, VT 05350

  Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  6982 Main St, Readsboro, VT 05350
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  /22

  $895,000

  • Land
  • 24.08 Acres
  • $37,168 per Acre

  A Windsor Rd, Manchester, VT 05255

  Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

  Kim Morgan-Wohler Wohler Realty Group

  A Windsor Rd, Manchester, VT 05255
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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
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  /25

  $289,000

  • 7 Beds
  • 6 Baths
  • 5,712 Sq Ft

  136 North St, Bennington, VT 05201

  Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail,

  Jeffrey Dorman

  136 North St, Bennington, VT 05201
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  /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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  /45

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  145 Oberdorf Rd, Readsboro, VT 05350

  Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4-bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

  Evan Russell Real Broker LLC

  145 Oberdorf Rd, Readsboro, VT 05350
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  /26

  $199,000

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  210 Division St, Bennington, VT 05201

  Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

  Lilli West Maple Leaf Realty

  210 Division St, Bennington, VT 05201
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  /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
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  /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
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  /48

  $3,285,000

  • 5 Beds
  • 6 Baths
  • 6,900 Sq Ft

  68 Green Peak Orchard S, East Dorset, VT 05253

  Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry.

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

  68 Green Peak Orchard S, East Dorset, VT 05253
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  /15

  $825,000

  • Land
  • 77.6 Acres
  • $10,631 per Acre

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

  Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

  Trent Stephens Wohler Realty Group

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
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  /4

  $190,000

  • 5 Beds
  • 2 Baths
  • 1,478 Sq Ft

  32-34 Sage St, Bennington, VT 05257

  Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer. Current tenants keep their units up well.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  32-34 Sage St, Bennington, VT 05257
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  /8

  $65,000

  • Land
  • 1.24 Acres
  • $52,419 per Acre

  2041 East Rd, Bennington, VT 05201

  Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life.

  Dan Mason Perrott Realty

  2041 East Rd, Bennington, VT 05201
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  /40

  $289,000

  • 6 Beds
  • 4 Baths
  • 2,520 Sq Ft

  111 Booth Terrace, Bennington, VT 05201

  Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout.

  Abi Gregorio

  111 Booth Terrace, Bennington, VT 05201
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  /41

  $394,000

  • 3 Beds
  • 3 Baths
  • 2,038 Sq Ft

  43 Bergblume Cir, Readsboro, VT 05350

  Outdoor Enthusiasts’ Paradise!Tucked into the hills of southern Vermont, this newer updated, and well-maintained home is built for the buyer who lives for the outdoors and wants space for toys and more. Access to major snowmobiling and ATV trails puts you at the trailhead before your coffee gets cold, while skiing, kayaking, boating, fishing, and hiking are all just minutes away. Deer, bear,

  Pam Tworig Bishop West Real Estate, Inc.

  43 Bergblume Cir, Readsboro, VT 05350
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  /60

  $1,595,000

  • 17 Beds
  • 20 Baths
  • 14,861 Sq Ft

  3888 Vermont Route 7a, Shaftsbury, VT 05262

  The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

  Vicki Wilson Maple Leaf Realty

  3888 Vermont Route 7a, Shaftsbury, VT 05262
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  /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
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  /27

  $609,000

  • 4 Beds
  • 3 Baths
  • 1,650 Sq Ft

  60 Hilltop Rd Unit 60, Winhall, VT 05340

  Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  60 Hilltop Rd Unit 60, Winhall, VT 05340
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  /23

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  22 Carlen St, Manchester Center, VT 05255

  Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

  Andy Reed Four Seasons Sotheby's Int'l Realty

  22 Carlen St, Manchester Center, VT 05255
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
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  /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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  /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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  /6

  $99,000

  • Land
  • 1 Acre
  • $99,000 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 Site PlanCovenants

  Andrew King Stratton Real Estate

  88A Sylvan Ridge Rd, Winhall, VT 05340
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  /57

  $2,275,000

  • 9 Beds
  • 8 Baths
  • 5,512 Sq Ft

  288 Cedar Ln, Peru, VT 05152

  Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

  Jessica Citera Cummings & Co

  288 Cedar Ln, Peru, VT 05152
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  /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
• 

  /2

  $249,000

  • Land
  • 29.9 Acres
  • $8,328 per Acre

  0 North Rd Unit 5079306, East Arlington, VT 05252

  Once you locate this quiet parcel there is a lovely wooded setting which offers a potential for a family compound or a possible subdivision. See Directions.There utilities along the extensive road frontage of North Road and Bacon Hollow Road which is a dead end... No soils or engineering value completed and must be processed with new zoning and state permitting.

  Charles Mauro Josiah Allen Real Estate, Inc.

  0 North Rd Unit 5079306, East Arlington, VT 05252

Showing Results 121 - 160, Page 4 of 5