4,310

Bennington, VT Homes

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  • /12

    $995,000

    • 3 Beds
    • 3 Baths
    • 1,501 Sq Ft

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

    Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

    John Sikes Stratton Real Estate

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
  • /39

    $1,455,000 Sold Feb 10, 2025

    • 1,960 Sq Ft
    • $742/SF
    • 180 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2005

    759 Stratton Mountain Access Rd Unit 433, Stratton, VT 05340

    Luxury abounds in this premier Summit Level Hearthstone, boasting direct views of Stratton Mountain from a coveted resort location. Previously leased long-term, this exclusive two-story unit is now on the market, featuring a dramatic cathedral ceiling, majestic beams, and a magnificent stone fireplace. Floor-to-ceiling windows frame year-round sunset vistas over Stratton’s sprawling ski trails,

    Kim Morgan-Wohler Wohler Realty Group

    759 Stratton Mountain Access Rd Unit 433, Stratton, VT 05340
    • /40

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,997 Sq Ft

      926 Dalewood Rd, Jamaica, VT 05343

      926 Dalewood Rd, Jamaica, VT 05343
  • /31

    $400,000

    • 3 Beds
    • 1 Bath
    • 1,338 Sq Ft

    2779 Pikes Falls Rd, Jamaica, VT 05343

    Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no

    Carrie Mathews Winhall Real Estate

    2779 Pikes Falls Rd, Jamaica, VT 05343
  • /41

    $1,225,000 Sold Feb 10, 2025

    • 4,200 Sq Ft
    • $292/SF
    • 182 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1985

    22 Old Ridge Rd, Winhall, VT 05340

    This is a private setting in the High Meadow neighborhood with a spectacular, dead-on view of the Stratton slopes. The snow cat lights twinkle in your windows as they groom your runs for tomorrow’s turns. There is plenty of room for the entire family and friends in the gourmet kitchen, dining room, living room with fire place, family room with wood stove, den, five bedrooms, 3 1/2 baths with

    Dan McKenna Cummings & Co

    22 Old Ridge Rd, Winhall, VT 05340
    • /34

      Est $446,403 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,425 Sq Ft

      162 Upper Bear Ln Unit C-19, Jamaica, VT 05343

      162 Upper Bear Ln Unit C-19, Jamaica, VT 05343
  • /23

    $135,000

    • Land
    • 5 Acres
    • $26,471 per Acre

    1192 Haven Hill Rd, South Londonderry, VT 05155

    This 5+ acre building lot is ready for planning and designing your 5 bedroom dream-home, WW-2-3657 on a quiet country road, and Land Use Permit 2W0032-3. Just minutes to Gale Meadows and Stratton Mountain Resort, there are plenty of summer and winter outdoor adventures to embark on from hiking, kayaking, and fishing in the summer to skiing and snowshoeing in the winter. Only 25-minutes from

    Mike England Michael England Real Estate

    1192 Haven Hill Rd, South Londonderry, VT 05155
  • /22

    $450,000 Sold Jan 31, 2025

    • 850 Sq Ft
    • $529/SF
    • 155 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 1983

    8 Ober Tal Dr Unit A24, Stratton, VT 05360

    Luxury trailside condominium in Stratton Mountain Resort. Completely renovated in 2020 down to the studs! From an all new layout including two new bathrooms featuring heated floors and showers, open gourmet kitchen with oversized granite island, custom cabinets, new high end appliances, new insulation and sound proofing throughout as well as a new modern stone wood burning fireplace. Too many

    Timothy Mich Doddridge Stratton Real Estate

    8 Ober Tal Dr Unit A24, Stratton, VT 05360
    • /27

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft

      5 Oak Rd Unit 5, Winhall, VT 05340

      5 Oak Rd Unit 5, Winhall, VT 05340
  • /20

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 1,044 Sq Ft

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Rare opportunity to own an exceptional ski-in/ski-out Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

    Britt Wohler Wohler Realty Group

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /22

    $208,000 Sold Jan 30, 2025

    • 880 Sq Ft
    • $236/SF
    • 8 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1979

    3389 Vt Route 100 N, Londonderry, VT 05148

    The River House is an iconic gem in South Londonderry that has served as a full time home for several residents since 1979! Beautiful deck in the rear of the property provides privacy. Home has a beautiful dining room with great views towards the West River. There are hiking and snowshoe trails out back that run along the river. Home also has a small studio that has been a great work space for

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    3389 Vt Route 100 N, Londonderry, VT 05148
    • /32

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,268 Sq Ft

      79 Shattarack Rd Unit E7B, Stratton, VT 05360

      79 Shattarack Rd Unit E7B, Stratton, VT 05360
  • /30

    $1,250,000

    • Land
    • 108 Acres
    • $11,574 per Acre

    585 Pleasant Valley Rd, Jamaica, VT 05343

    108 Acres of Pristine Land For Sale – 2 Miles to Stratton Sun Bowl with Panoramic ViewsA rare opportunity to own ~108 acres of stunning land with sweeping views of Stratton’s Sun Bowl and Mount Snow. Just 2 miles to the Sun Bowl base and 15 minutes to Mount Snow, this Jamaica, VT property (on the Stratton line) offers unmatched privacy, no zoning restrictions, and incredible

    Britt Wohler Wohler Realty Group

    585 Pleasant Valley Rd, Jamaica, VT 05343
  • /31

    $765,000 Sold Jan 23, 2025

    • 1,311 Sq Ft
    • $584/SF
    • 210 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1983

    790 Stratton Mountain Access Rd Unit 3415, Stratton, VT 05155

    True Ski-in/Ski-out Bliss Awaits! This rare corner, end-unit condo offers the ultimate convenience of slope-side living. Stairs to two chairlifts (Tamarack and Villager) are right outside the door. This 3-bedroom, 2-bathroom condo is truly turnkey. The recently renovated kitchen and bathrooms feature granite countertops and stainless steel appliances. Unwind by the wood-burning fireplace in the

    Robin Apps Four Seasons Sotheby's Int'l Realty

    790 Stratton Mountain Access Rd Unit 3415, Stratton, VT 05155
    • /37

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,751 Sq Ft

      2418 Vermont Route 100, Londonderry, VT 05148

      2418 Vermont Route 100, Londonderry, VT 05148
  • /39

    $4,300,000

    • 6 Beds
    • 5 Baths
    • 4,715 Sq Ft

    141 W Ridge Rd, Stratton, VT 05360

    Experience the charm of this renovated, ski-in/ski-out 6-bedroom, 5-bathroom retreat, perched as the second-highest home on Stratton’s iconic Lower Wanderer Ski Trail. Immerse yourself in the rustic elegance of this space, where expansive windows invite breathtaking outdoor views inside. This mountain sanctuary seamlessly combines modern comfort, solar technology, and nature’s serene beauty,

    Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    141 W Ridge Rd, Stratton, VT 05360
  • /21

    $327,000 Sold Jan 22, 2025

    • 1,100 Sq Ft
    • $297/SF
    • 35 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1988

    63 Reynolds Ln, Jamaica, VT 05343

    Wonderful secluded hideaway on 5 acres near Stratton Mountain and Mount Snow. This cozy property is minutes away from two major resorts and an abundance of hiking, biking, hunting and more surround this home. Three bedrooms and a loft that can sleep eight. Wood stove to keep you warm during Winter. Also a shed for your tools and barbecue. Come and see this property and enjoy the country drive.

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    63 Reynolds Ln, Jamaica, VT 05343
    • /28

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft

      61 Birch Hill Rd Unit 2 Shagbark HIckory, Winhall, VT 05340

      61 Birch Hill Rd Unit 2 Shagbark HIckory, Winhall, VT 05340
  • /6

    $495,000

    • Land
    • 7 Acres
    • $71,429 per Acre

    lot#2 Margeaux Ln, Stratton, VT 05155

    This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    lot#2 Margeaux Ln, Stratton, VT 05155
  • /48

    $379,000 Sold Jan 15, 2025

    • 2,000 Sq Ft
    • $190/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    3702 Vermont Route 100, Londonderry, VT 05148

    If you are looking for a property in a nice location for a good price, look no further. This single level residence sits off Route 100 in a super convenient neighborhood. Walk into an inviting floor plan beginning with a sunroom/mudroom and second entrance to basement. The eat in country kitchen is well planned for the ambitious cook, including a second sink. The kitchen/dining opens up into

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    3702 Vermont Route 100, Londonderry, VT 05148
    • /9

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft

      16 Styles Branch Rd Unit 208, Stratton, VT 05360

      16 Styles Branch Rd Unit 208, Stratton, VT 05360
  • /5

    $465,000

    • Land
    • 6 Acres
    • $83,935 per Acre

    Lot #4 Margeaux Ln, Stratton, VT 05155

    Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    Lot #4 Margeaux Ln, Stratton, VT 05155
  • /55

    $899,000 Sold Jan 13, 2025

    • 2,900 Sq Ft
    • $310/SF
    • 7 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1996

    45 Hilltop Rd, Winhall, VT 05340

    Our Sellers have certainly raised the bar with this stunning 5 bedroom, 4 bath residence. Taken down to the studs in 2018/19 and lovingly renovated with beautiful custom features in every corner. This mountain modern decor boasts gorgeous wall to wall engineered hardwood white oak floors throughout the entire property softened by inviting area rugs. The attractive kitchen was designed for

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    45 Hilltop Rd, Winhall, VT 05340
    • /40

      Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,923 Sq Ft

      2460 Under the Mountain Rd, Londonderry, VT 05148

      2460 Under the Mountain Rd, Londonderry, VT 05148
  • /4

    $225,000

    • Land
    • 1.99 Acres
    • $113,065 per Acre

    00 Margeaux Ln, Stratton, VT 05155

    This beautiful 1.99-acre parcel, nestled in the woods, offers the perfect setting to build the home of your dreams. With a 5-bedroom septic permit already in place, you’ll be ready to start construction right away. Access is easy via a right-of-way from Margeaux Lane, providing both privacy and convenience. Located just minutes from the Sun Bowl at Stratton. It is close to everything Stratton

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    00 Margeaux Ln, Stratton, VT 05155
  • /36

    $725,000 Sold Jan 03, 2025

    • 1,800 Sq Ft
    • $403/SF
    • 30 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    11 Todd Hill Rd, Winhall, VT 05340

    Move into this pristine 3-bedroom, 2-bath home, just a short drive from Stratton Mountain. The ground floor features a custom-built mudroom with individual lockers and built-in boot warmers—perfect for mountain living. Fully updated with high-end finishes, the home boasts a chef’s kitchen with marble countertops and a spacious center island, seamlessly flowing into the dining area and a large

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    11 Todd Hill Rd, Winhall, VT 05340
    • /15

      Est $450,498 Not Listed For Sale

      • 2 Beds

      300 Vt Route 30, Bondville, VT 05340

      300 Vt Route 30, Bondville, VT 05340
  • /55

    $749,000

    • 3 Beds
    • 3 Baths
    • 2,118 Sq Ft

    A6 Ridge Unit A6, Winhall, VT 05340

    It’s the Premier Location and commanding views that set this Piper Ridge townhome apart. The stunning unobstructed views are central to thetownhomes design, while the southern exposure provides all day sunshine and a light and airy atmosphere. You’ll experience the evening’s magic watching stunning sunsets with the resort lights on full display and will have the premier “front row seats” to

    Karin Hardy Berkshire Hathaway HomeServices Stratton Home

    A6 Ridge Unit A6, Winhall, VT 05340
  • /14

    $370,000 Sold Dec 30, 2024

    • 820 Sq Ft
    • $451/SF
    • 75 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    8 Ober Tal, Stratton, VT 05155

    Nice opportunity to make Stratton Mountain Resort your home away from home. This spacious 1 bedroom, 1 bath is located in close proximity to the Tamarack lift. It features a wood burning fireplace, large living area and dining area. This lower level unit has direct access to the ground floor. Being offered furnished.

    Jamie Wylie Stratton Real Estate

    8 Ober Tal, Stratton, VT 05155
    • /31

      Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,140 Sq Ft

      43 Middle Ridge Rd Unit 410, Winhall, VT 05155

      43 Middle Ridge Rd Unit 410, Winhall, VT 05155
  • /44

    $2,500,000

    • 5 Beds
    • 7 Baths
    • 6,625 Sq Ft

    19 Old Town Rd, Bondville, VT 05340

    Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

    Christiane Carroccio TPW Real Estate

    19 Old Town Rd, Bondville, VT 05340
  • /28

    $550,000 Sold Dec 20, 2024

    • 1,778 Sq Ft
    • $309/SF
    • 72 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1979

    49 Styles Branch Rd Unit 904, Stratton, VT 05360

    Located just 1 mile from the Stratton Base Lodge, this Styles Brook townhome offers three levels of living and a prime location with winter weekend/holiday shuttle service. New owners will delight in the convenience and cozy modern-mountain style of this turn key gem, which is offered fully furnished. On the main level, you’ll find the kitchen, dining and living areas complete with a wood-burning

    Cheyanne Pugliese

    49 Styles Branch Rd Unit 904, Stratton, VT 05360
    • /21

      Est $815,545 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,890 Sq Ft

      24 Shattarack Rd Unit A-1, Stratton, VT 05360

      24 Shattarack Rd Unit A-1, Stratton, VT 05360
  • /35

    $649,000

    • 8 Beds
    • 3.5 Baths
    • 2,520 Sq Ft

    405 Vermont 30, Winhall, VT 05340

    Ski Resort Investment Gem! 2-Family Home Near Stratton & BromleyRare investment opportunity in the heart of Vermont's premier ski region. Located on scenic Vermont Route 30, this property offers unparalleled access to both Stratton Mountain Resort and Bromley Mountain Ski Resort. Whether you're looking to live in one unit and rent the other, or convert it to a single-family home, this

    Robin Apps Four Seasons Sotheby's Int'l Realty

    405 Vermont 30, Winhall, VT 05340
  • /5

    $55,000 Sold Dec 17, 2024

    • Land
    • 1.00 Acre
    • $55,000 per Acre
    • 11 Days On Market

    0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343

    Wooded building lot located at the end of a cul-de-sac near Stratton Mountain and other recreational areas. Perfect site for that primary or second home. The septic Design has been done and approved for a 4 bedroom home.

    Edward Jones Josiah Allen Real Estate, Manchester Branch Office

    0 Karen Dr Unit Lot 12 5021748, Jamaica, VT 05343
    • /6

      Est $131,396 Not Listed For Sale

      122 Blackberry Ln Unit 7, Jamaica, VT 05343

      122 Blackberry Ln Unit 7, Jamaica, VT 05343
  • /13

    $150,000

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

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

    Waaaaait a minute! There’s buildable land just minutes from Stratton Mountain, and it’s already got septic not only approved, but basically installed?!?! I can just build my house on these 4.68 acres and enjoy all of the beauty and convenience of the area? And it's approved for 2 three bedroom houses!!! 2 miles to Stratton and 20 minutes to Manchester. I almost can’t believe this is

    TG Glazer Winhall Real Estate

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

    $817,500 Sold Dec 13, 2024

    • 3,772 Sq Ft
    • $217/SF
    • 30 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1989

    53 Stratton View Rd, Bondville, VT 05340

    This is the mountain house you have been waiting! Just 5 minutes to the Stratton Mountain access road, this spacious residence boasts cathedral ceilings, 2 fireplaces, granite/stainless kitchen and wonderful views of Stratton Mountain trails. Situated on an oversized 2.95 acre parcel with pond, this home has what you are looking for in a Vermont getaway: 4 bedrooms /3.5 baths plus studio, office,

    Kim Morgan-Wohler Wohler Realty Group

    53 Stratton View Rd, Bondville, VT 05340
    • /38

      Est $700,405 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,220 Sq Ft

      28 Redbrook Rd, Winhall, VT 05340

      28 Redbrook Rd, Winhall, VT 05340
  • /56

    $2,999,000

    • 6 Beds
    • 6.5 Baths
    • 6,650 Sq Ft

    25 Mountain Haunts Rd, Winhall, VT 05340

    Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

    Kim Morgan-Wohler Wohler Realty Group

    25 Mountain Haunts Rd, Winhall, VT 05340

Showing Results 201 - 240, Page 6 of 18

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