4,310

Bennington, VT Homes

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  • /37

    $454,000 Sold Apr 28, 2025

    • 1,760 Sq Ft
    • $258/SF
    • 315 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    400 Edie Ln, Jamaica, VT 05343

    Welcome to Hot Toddy Hill. your perfect Vermont Getaway! Nestled minutes away from Stratton, this cozy contemporary home in the charming town of Jamaica, Vermont, is ideal for gatherings and retreats with friends. The living room boasts vaulted ceilings with wood slat detail, its ideal for relaxing in front of the wood-burning fireplace apres ski. The fully equipped eat-in kitchen boasts brand

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    400 Edie Ln, Jamaica, VT 05343
    • /35

      Est $498,006 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,470 Sq Ft

      383 Winhall Hollow Rd, Bondville, VT 05340

      383 Winhall Hollow Rd, Bondville, VT 05340
  • /38

    $789,000

    • 4 Beds
    • 4 Baths
    • 2,997 Sq Ft

    44 Hilltop Rd, Winhall, VT 05340

    Four bedroom, four bathroom Intervale townhouse has all the space you need in a Stratton home. This is the largest Intervale floor plan, with a second living room and wet bar on the lower, walk out floor. The main floor has a mud room entry, living room with wood burning fireplace, and dining room open to kitchen. The primary suite is on the main floor, secondary suite is upstairs, and an

    Christiane Carroccio TPW Real Estate

    44 Hilltop Rd, Winhall, VT 05340
  • /44

    $640,000 Sold Apr 25, 2025

    • 3,988 Sq Ft
    • $160/SF
    • 52 Days On Market
    • 7 Beds
    • 4 Baths
    • Built 1942

    13 Winhall Station Rd, Londonderry, VT 05155

    Solid six-bedroom home with detached one bedroom apartment being offered fully furnished on 3.4 acres of land! Surrounded by mature maples and beautiful local views of Stratton Mountain. This property sits on the corner of Winhall Station Road and Route 100 in Londonderry Vermont. Winhall Station Road will lead out a dead-end road to the Winhall Campground and the West River area with wonderful

    Julie Lowe Lowe's Real Estate, LLC

    13 Winhall Station Rd, Londonderry, VT 05155
    • /40

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,212 Sq Ft

      74 N Brookwood, Stratton, VT 05155

      74 N Brookwood, Stratton, VT 05155
  • /44

    $495,000

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

    486 Windy Rise Ln E, Londonderry, VT 05148

    Contemporary Ski-Style Retreat in Southern Vermont – A Home for All Seasons!Escape to the mountains in this 3-bedroom, 3-bath home, nestled in the heart of Southern Vermont—just minutes from Stratton, Bromley, and Magic Mountain ski resorts.This home has rustic charm, features multiple living spaces and a bathroom on each floor. The relaxed dining/living space is open and inviting so

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    486 Windy Rise Ln E, Londonderry, VT 05148
  • /6

    $122,500 Sold Apr 18, 2025

    • Land
    • 2.20 Acres
    • $55,682 per Acre
    • 53 Days On Market

    10 Little Brook Rd, Winhall, VT 05340

    Prime 2.2-acre building lot in the desirable Vermont Ventures community! Conveniently located less than 15 minutes from Stratton Resort and Bromley, just 20 minutes from Manchester. This property includes a wastewater permit for a 5-bedroom home, with power available at the road, Little Brook is a town-maintained road, there is a ROW for access to the lot. With some clearing, the property offers

    Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    10 Little Brook Rd, Winhall, VT 05340
    • /36

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,244 Sq Ft

      22 Upper Glades Unit 22, Stratton, VT 05360

      22 Upper Glades Unit 22, Stratton, VT 05360
  • /59

    $2,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,938 Sq Ft

    23 Valley View Rd, Winhall, VT 05340

    Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

    Kim Morgan-Wohler Wohler Realty Group

    23 Valley View Rd, Winhall, VT 05340
  • /37

    $615,000 Sold Apr 15, 2025

    • 1,500 Sq Ft
    • $410/SF
    • 39 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    29 Burnt Hill Rd, Winhall, VT 05340

    Discover your dream chalet in the heart of Strattonwald—a stunningly renovated retreat designed for year-round mountain adventures and modern comfort! Beautifully renovated 3-bedroom, 2-bathroom home in Winhall offers the perfect blend of convenience and recreation. Just a quick drive to Stratton Mountain, this property provides easy access to winter slopes and summer fun. The community amenities

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    29 Burnt Hill Rd, Winhall, VT 05340
    • /39

      Est $1,294,947 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,814 Sq Ft

      19 Maple Hill Rd, Winhall, VT 05340

      19 Maple Hill Rd, Winhall, VT 05340
  • /44

    $729,000

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft

    86 Benson Fuller Dr, Bondville, VT 05340

    OPEN HOUSE Saturday August 30 11-1. Great opportunity! Your Ultimate Getaway Escape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces.Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    86 Benson Fuller Dr, Bondville, VT 05340
  • /40

    $850,000 Sold Apr 04, 2025

    • 3,119 Sq Ft
    • $273/SF
    • 168 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1996

    36 Road To Millbrook, Winhall, VT 05340

    This impeccably maintained home sits on 5.28 acres of beautifully landscaped land adjacent to the National Forest. Featuring a spacious interior with a stone wood-burning fireplace and vaulted cathedral ceilings, this home is move-in ready. Recent upgrades include two newly renovated bathrooms. The first floor offers an open living layout, while the lower level boasts a cozy den/family room.

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    36 Road To Millbrook, Winhall, VT 05340
    • /26

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 1,993 Sq Ft

      47 Styles Branch Rd Unit 907, Stratton, VT 05360

      47 Styles Branch Rd Unit 907, Stratton, VT 05360
  • /37

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 3,252 Sq Ft

    115 Benson Fuller Dr, Jamaica, VT 05343

    Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

    Carrie Mathews Winhall Real Estate

    115 Benson Fuller Dr, Jamaica, VT 05343
  • /41

    $2,100,000 Sold Apr 04, 2025

    • 5,300 Sq Ft
    • $396/SF
    • 248 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1974

    20 W Ridge Rd, Stratton, VT 05360

    OPEN HOUSE. Friday July 5th, 2-4pm. All Welcome.The exquisite craftsmanship of this stunning Austrian-style chalet evokes the lure of Stratton's early days. A location that was selected for incredible views, and close ski trail access. This true mountain haus has been thoughtfully updated to preserve its charm and authenticity. Imagine waking up to incredible mountain views every morning and

    Christiane Carroccio TPW Real Estate

    20 W Ridge Rd, Stratton, VT 05360
    • /26

      Est $515,000 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,763 Sq Ft

      121 Stratton Gate Rd, Jamaica, VT 05343

      121 Stratton Gate Rd, Jamaica, VT 05343
  • /28

    $1,700,000

    • 4 Beds
    • 3.5 Baths
    • 2,363 Sq Ft

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155

    Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

    Edwin Kevil Stratton Real Estate

    43 Middle Ridge Rd Unit 415, Winhall, VT 05155
  • /39

    $1,250,000 Sold Apr 02, 2025

    • 2,625 Sq Ft
    • $476/SF
    • 32 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2003

    6 Cranberry Ct, Stratton, VT 05360

    Designed for mountain living, this expansive 4-bedroom, 4-bathroom townhome is the largest floor plan in Tree Top, offering unparalleledsquare footage and luxurious features. The property includes a total of 4 bedrooms, 3 are spacious primary suites with private baths, a cozy lower-level family room, and an open-concept great room adorned with a stone fireplace, soaring cathedral ceilings, and

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    6 Cranberry Ct, Stratton, VT 05360
    • /40

      Est $922,245 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,196 Sq Ft

      40 Loop Rd, Winhall, VT 05340

      40 Loop Rd, Winhall, VT 05340
  • /35

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft

    5 Linscott Rd Unit 56, Jamaica, VT 05343

    This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances,

    Diana Stugger Four Seasons Sotheby's Int'l Realty

    5 Linscott Rd Unit 56, Jamaica, VT 05343
  • /35

    $1,900,000 Sold Apr 01, 2025

    • 2,581 Sq Ft
    • $736/SF
    • 14 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1986

    16 Mountain Reach Mews Rd, Stratton, VT 05155

    Located just steps from Stratton Village and the lifts, this luxurious slopeside townhouse offers a seamless blend of upscale contemporary design and unbeatable convenience. With gated access and no public roads to cross, this end-unit residence provides a true retreat in the heart of Stratton’s trailside community.Step into the bright, open floor plan where modern elegance meets extraordinary

    Trent Stephens Wohler Realty Group

    16 Mountain Reach Mews Rd, Stratton, VT 05155
    • /40

      Est $634,186 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,024 Sq Ft

      381 Winhall Hollow Rd, Bondville, VT 05340

      381 Winhall Hollow Rd, Bondville, VT 05340
  • /36

    $1,790,000

    • 4 Beds
    • 3 Baths
    • 2,545 Sq Ft

    1949 South Rd, Peru, VT 05152

    Nestled in a serene and picturesque setting, Berry Hill Farm offers a rare opportunity to own an exceptional Vermont estate blending charm, versatility, and natural beauty. Spanning 15.52 acres across two separately deeded lots, the property combines inspired design with modern comfort. At its heart is a beautifully crafted contemporary home featuring three spacious bedrooms, sunlit living

    Kim Morgan-Wohler Wohler Realty Group

    1949 South Rd, Peru, VT 05152
  • /19

    $585,000 Sold Apr 01, 2025

    • 1,811 Sq Ft
    • $323/SF
    • 180 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1986

    47 High Point Dr Unit B21, Stratton, VT 05360

    This top-floor, end-unit 3-bedroom, 3-bath Crown Point condominium offers the ideal balance of comfort and convenience. Located just a short walk from the Stratton Sports Center and Stratton Village, it's perfectly situated for both relaxation and adventure. The shuttle provides easy access to the slopes and all that Stratton has to offer. Inside, the open floor plan features cathedral ceilings

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    47 High Point Dr Unit B21, Stratton, VT 05360
    • /27

      Est $651,196 Not Listed For Sale

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

      2 Chad Cir, Winhall, VT 05340

      2 Chad Cir, Winhall, VT 05340
  • /41

    $574,000

    • 3 Beds
    • 3 Baths
    • 2,704 Sq Ft

    4138 W Hill Rd S, Jamaica, VT 05343

    This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

    Patricia Fitzpatrick Skihome Realty

    4138 W Hill Rd S, Jamaica, VT 05343
  • /14

    $1,050,000 Sold Mar 29, 2025

    • 1,780 Sq Ft
    • $590/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340

    Incredible opportunity to own in one of Stratton Mountain Resort's most desirable communities! One of the largest three bedroom floor plans in all of Hearthstone Lodge. This home boasts three bedroom and two and half bathrooms, corner location directly off the elevator, open floor plan with mountain views, cozy gas fireplace, air conditioning for Summer use and two assigned underground parking

    Timothy Mich Doddridge Stratton Real Estate

    759 Stratton Mountain Access Rd Unit 331, Stratton, VT 05340
    • /25

      Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,900 Sq Ft

      8 Hardwood Hill Unit 8B, Stratton, VT 05360

      8 Hardwood Hill Unit 8B, Stratton, VT 05360
  • /33

    $820,000

    • 4 Beds
    • 3 Baths
    • 2,317 Sq Ft

    0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

    Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

    Carrie Mathews Winhall Real Estate

    0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
  • /29

    $455,000 Sold Mar 28, 2025

    • 1,570 Sq Ft
    • $290/SF
    • 53 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    2 Byington Ln Unit 5, Winhall, VT 05340

    Welcome to this stunning, modern townhome overlooking the pool, just a short walk to Winhall shops and restaurants and only minutes from the renowned Stratton Resort. This three-bedroom, two-bathroom townhome offers the perfect Vermont retreat for all seasons, with a layout designed to maximize mountain views and convenience.Spread across three levels, the home’s second floor boasts an

    Robin Apps Four Seasons Sotheby's Int'l Realty

    2 Byington Ln Unit 5, Winhall, VT 05340
    • /31

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,817 Sq Ft

      22 Mountain View Rd, Winhall, VT 05360

      22 Mountain View Rd, Winhall, VT 05360
  • /40

    $1,695,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /29

    $550,000 Sold Mar 28, 2025

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

    43 Styles Branch Rd Unit 1008, Stratton, VT 05360

    Nestled in the desirable Styles Brook community, this inviting 3-bedroom, 2.5-bath townhome offers the perfect blend of privacy and convenience. With a sought-after location just steps away from the pool and paddle tennis court, this property provides the ideal setting for relaxation and recreation. Enjoy a private and serene atmosphere while being part of a vibrant neighborhood, with easy access

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    43 Styles Branch Rd Unit 1008, Stratton, VT 05360
    • /36

      Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,271 Sq Ft

      43 Middle Ridge Rd Unit 416, Winhall, VT 05155

      43 Middle Ridge Rd Unit 416, Winhall, VT 05155
  • /31

    $799,000

    • 3 Beds
    • 3 Baths
    • 2,317 Sq Ft

    9 F Cobble Ridge Rd, Winhall, VT 05340

    Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

    Carrie Mathews Winhall Real Estate

    9 F Cobble Ridge Rd, Winhall, VT 05340
  • /24

    $430,000 Sold Mar 26, 2025

    • 1,716 Sq Ft
    • $251/SF
    • 26 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1967

    13 Lower Taylor Hill Rd, Winhall, VT 05340

    This beautifully updated home near Stratton Mountain blends classic charm with modern updates. As you enter, you'll find a mudroom with a convenient storage closet and a half bath. The spacious living and dining area features a striking fieldstone fireplace and sliding doors that open to a large deck, perfect for hosting guests. The custom kitchen offers hardwood floors, a pantry, and a laundry

    Carrie Mathews Winhall Real Estate

    13 Lower Taylor Hill Rd, Winhall, VT 05340
    • /39

      Est $746,026 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,300 Sq Ft

      28 W Branch Rd, Winhall, VT 05340

      28 W Branch Rd, Winhall, VT 05340
  • /28

    $749,000

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft

    21 Burnt Hill Rd, Winhall, VT 05341

    Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont!This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    21 Burnt Hill Rd, Winhall, VT 05341
  • /13

    $150,000 Sold Mar 26, 2025

    • Land
    • 13 Acres
    • $11,811 per Acre
    • 111 Days On Market

    0 Pikes Falls Rd Unit 4993566, Stratton, VT 05360

    Embrace the allure of Vermont living with this exceptional parcel of land located just moments from Stratton Resort. This 12.7-acre parcel boasts a prime location to build your Vermont dream home with the perfect blend of seclusion and accessibility. Located across from the Golf School with frontage on Pikes Falls (Upper Taylor Hill ) and North Rd. and on the border of Winhall and Stratton town

    Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

    0 Pikes Falls Rd Unit 4993566, Stratton, VT 05360

Showing Results 121 - 160, Page 4 of 18

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