Bennington, VT Homes

• 

  

  

  /32

  $950,000 Sold Dec 06, 2024

  • 3,658 Sq Ft
  • $260/SF
  • 58 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1991

  154 High Meadow Rd Unit C-17, Winhall, VT 05155

  Experience the charm of this updated mountain retreat, nestled in the coveted High Meadow area on Stratton Mountain. This home perfectly blends modern comfort with rustic elegance, featuring a large heated mudroom designed to store all your ski and snowboard gear after a day on the slopes. Inside, unwind in a beautifully maintained contemporary space, complete with two cozy fireplaces and

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  154 High Meadow Rd Unit C-17, Winhall, VT 05155
• 

  

  

  /21

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 820 Sq Ft

  8 Ober Tal Unit A23, Stratton, VT 05155

  8 Ober Tal Unit A23, Stratton, VT 05155
• 

  

  

  /36

  $998,500

  • 4 Beds
  • 3.5 Baths
  • 2,070 Sq Ft

  32 Shattarack Rd Unit B5, Stratton, VT 05360

  They say beauty is only skin deep, but not in the case of this meticulously renovated Slopeside residence, which offers a rare combination of quality, comfort, and location. With more than $500,000 invested, this home delivers far more than surface-level appeal — the kind of work that is not always seen but is most certainly felt. Every system and surface has been thoughtfully addressed. Unlike

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  32 Shattarack Rd Unit B5, Stratton, VT 05360
• 

  

  

  /40

  $810,000 Sold Dec 06, 2024

  • 2,212 Sq Ft
  • $366/SF
  • 145 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  D3 Cobble Ridge Rd, Winhall, VT 05340

  Welcome to D3 Cobble Ridge Road, a beautifully maintained gem nestled in the Piper Ridge Condo community in Winhall, VT. This charming Shelburne design home radiates warmth and elegance, featuring exquisite amenities and impeccable care throughout. The spacious 4-bedroom townhouse offers a perfect blend of comfort and luxury. The interior is adorned with cathedral ceilings that amplify the airy

  Carrie Mathews Winhall Real Estate

  D3 Cobble Ridge Rd, Winhall, VT 05340
• 

  

  

  /40

  Est $956,135 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,017 Sq Ft

  17 Cranberry Hill Rd, Winhall, VT 05340

  17 Cranberry Hill Rd, Winhall, VT 05340
• 

  

  /40

  $1,450,000

  • 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
• 

  

  /33

  $785,000 Sold Dec 04, 2024

  • 1,208 Sq Ft
  • $650/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  792 Stratton Mountain Rd Unit 4527, Stratton, VT 05360

  This Stratton Mountain trailside unit will WOW you! Upscale and tasteful renovation of this top floor Village Watch boasts walls of light, cathedral ceilings, wood burning fireplace and exceptional newly designed kitchen and baths. Designed with contemporary fit and finish, no expense has been spared in creating a most desirable ambiance and spaces for mountain living at its finest.Maximizing

  Kim Morgan-Wohler Wohler Realty Group

  792 Stratton Mountain Rd Unit 4527, Stratton, VT 05360
• 

  

  /26

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,325 Sq Ft

  776 Stratton Mountain Rd Unit 1302, Stratton, VT 05360

  776 Stratton Mountain Rd Unit 1302, Stratton, VT 05360
• 

  

  /46

  $1,350,000

  • 4 Beds
  • 4 Baths
  • 4,640 Sq Ft

  33 Forest Haunts Rd, Winhall, VT 05340

  Discover Your Vermont Retreat Nestled amidst 20.8 private acres of tranquil woods, this French country manor offers an exceptional opportunity to own a piece of Vermont paradise. Situated near the serene North Branch Ball Mountain Brook, enjoy the soothing sounds of cascading water and the breathtaking beauty of nature. Property Highlights: Prime Location: Just minutes from Stratton Resort for

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  33 Forest Haunts Rd, Winhall, VT 05340
• 

  

  /25

  $233,000 Sold Dec 02, 2024

  • Land
  • 5 Acres
  • $45,686 per Acre

  • 4 Days On Market

  84 Lower Taylor Hill Rd, Winhall, VT 05340

  Looking to build near Stratton Mountain? We have THREE - 5 BEDROOM, SINGLE FAMILY HOME WASTEWATER PERMITS! Great opportunity with future flexibility for a new owner! Over FIVE ACRES of beautiful Vermont land, located on the corner of The Stratton Access Road and Lower Taylor Hill Road. State permitted septic designs are already completed and in place, with multiple building sites to choose from!

  Julie Lowe Lowe's Real Estate, LLC

  84 Lower Taylor Hill Rd, Winhall, VT 05340
• 

  

  /38

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  233 Vermont 30, Winhall, VT 05340

  233 Vermont 30, Winhall, VT 05340
• 

  

  /31

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

  148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit

  Andrew King Stratton Real Estate

  148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
• 

  

  /27

  $607,500 Sold Nov 26, 2024

  • 1,071 Sq Ft
  • $567/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  771 Stratton Mnt Access Rd Unit 371, Stratton, VT 05155

  Longtrail House Two bedrooms are some of the most sought after condominiums at the Stratton Mountain Resort. This one will not disappoint! This superior 2 bedroom, 2 bath residence features granite counters in the kitchen and baths, stainless steal appliances, fireplace, new floors throughout, updated fit and finishes are highlighted with beautiful barn style bathroom doors, modern window

  Robert Sabol Wohler Realty Group

  771 Stratton Mnt Access Rd Unit 371, Stratton, VT 05155
• 

  

  /40

  Est $1,741,651 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,609 Sq Ft

  69 W Ridge Rd Unit 365, Winhall, VT 05340

  69 W Ridge Rd Unit 365, Winhall, VT 05340
• 

  

  /50

  $4,999,000

  • 6 Beds
  • 7.5 Baths
  • 8,720 Sq Ft

  454 Mountain Rd, Stratton, VT 05155

  Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication.A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace.

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  454 Mountain Rd, Stratton, VT 05155
• 

  

  /32

  $610,000 Sold Nov 25, 2024

  • 1,408 Sq Ft
  • $433/SF
  • 30 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1965

  22 Loop Rd, Winhall, VT 05340

  Nestled amidst the picturesque landscape of Winhall, Vermont, this visually striking tilt-up home offers the perfect blend of durability, sustainability, and breathtaking beauty. Enjoy the convenience of nearby skiing at Stratton and Bromley, or immerse yourself in outdoor adventures like paddleboarding, fishing, or hiking on the neighboring Swedish Ski Club trails. This two-story residence sits

  Robin Apps Four Seasons Sotheby's Int'l Realty

  22 Loop Rd, Winhall, VT 05340
• 

  

  /14

  Est $560,557 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  68 Sugarbush Dr, Winhall, VT 05340

  68 Sugarbush Dr, Winhall, VT 05340
• 

  

  /8

  $65,000

  • Land
  • 2.00 Acres
  • $32,500 per Acre

  585 Sawmill Rd, Stratton, VT 05360

  Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway.

  Carrie Mathews Winhall Real Estate

  585 Sawmill Rd, Stratton, VT 05360
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  /32

  $375,000 Sold Nov 25, 2024

  • 1,215 Sq Ft
  • $309/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  1 Silver Birch Rd, Winhall, VT 05340

  Mountain Luxury Townhouse: Fully Renovated and in the best location in Birch Hill. Move-In Ready! Experience the ultimate in mountain living in this stunning 3-bedroom, 2-bathroom townhouse, perfect for families and guests alike. Beautifully appointed with top-of-the-line finishes. The kitchen features granite countertops, Stainless Steel KitchenAid and Liebherr appliances. Cozy up to the

  Robin Apps Four Seasons Sotheby's Int'l Realty

  1 Silver Birch Rd, Winhall, VT 05340
• 

  

  /31

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,584 Sq Ft

  56 Sugarbush Rd Unit B-8, Winhall, VT 05155

  56 Sugarbush Rd Unit B-8, Winhall, VT 05155
• 

  

  /21

  $235,000

  • Land
  • 1.30 Acres
  • $180,769 per Acre

  80 the Hollow Rd, Winhall, VT 05340

  We can build it for you. Nestled in the heart of the picturesque **High Meadow at Stratton**, this captivating lot awaits your vision. Embrace the opportunity to own one of the last available parcels in this highly sought-after neighborhood, where extraordinary living blends seamlessly with the tranquility of the Vermont mountains. Enjoy breathtaking views of the iconic **Stratton ski

  Jacek / Realtor Mikolajczyk BHHS Verani Upper Valley

  80 the Hollow Rd, Winhall, VT 05340
• 

  

  /25

  $832,000 Sold Nov 22, 2024

  • 1,383 Sq Ft
  • $602/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  761 Stratton Mountain Access Rd Unit 443 / 444, Stratton, VT 05360

  Great three bedroom home on the top floor, directly across from Stratton’s trailside Village of shops and restaurants. Walk to the ski lifts! This turn-key home has two living spaces and fireplaces, a nice size deck and sweeping views of Stratton Mountain. Park your car in the heated garage and forget it till time to head home! Due to both the location and building amenities, including the

  Andrew King Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 443 / 444, Stratton, VT 05360
• 

  

  /28

  Est $1,117,579 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,806 Sq Ft

  27 Old Ridge Rd, Winhall, VT 05340

  27 Old Ridge Rd, Winhall, VT 05340
• 

  

  /15

  $298,500

  • Land
  • 3.70 Acres
  • $80,676 per Acre

  69 Benson Fuller Dr Unit 29, Winhall, VT 05340

  High dry and spectacular views of the Equinox Mountain range and Bromley Mountain! Oversized building lot with lots of privacy. Approved septic system for a 5 bedroom house!

  Andrea Linkin-Butler Stratton Buyer Brokerage

  69 Benson Fuller Dr Unit 29, Winhall, VT 05340
• 

  

  /37

  $1,700,000 Sold Nov 22, 2024

  • 4,777 Sq Ft
  • $356/SF
  • 114 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1987

  4 Stone House Rd, Winhall, VT 05155

  Nestled among white birch trees within the coveted High Meadow enclave of Stratton Resort, this home boasts breathtaking vistas of the mountain, paired with the convenience of winter shuttle access to the Base Lodge. Recently renovated, this property epitomizes turnkey elegance and tranquility. Step into the post and beam great room, where walls of windows flood the space with natural light. An

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4 Stone House Rd, Winhall, VT 05155
• 

  

  /34

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,712 Sq Ft

  759 Stratton Mountain Access Rd Unit 431, Stratton, VT 05340

  759 Stratton Mountain Access Rd Unit 431, Stratton, VT 05340
• 

  

  /40

  $1,975,000

  • 4 Beds
  • 4 Baths
  • 4,270 Sq Ft

  14 Old Ridge Rd, Winhall, VT 05155

  This mountain home is beautifully furnished with a refined design that perfectly balances comfort and style, offering a seamless move-in ready experience. Located in the sought-after High Meadow neighborhood, this four bedroom, four bathroom property sits high on a perch, with clear views of Stratton’s trails, and a view of Bromley from the front of the house. Rebuilt in 2023/2024, the home is

  Christiane Carroccio TPW Real Estate

  14 Old Ridge Rd, Winhall, VT 05155
• 

  

  /35

  $1,250,000 Sold Nov 18, 2024

  • 2,377 Sq Ft
  • $526/SF
  • 71 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2004

  8 Dogwood Trail Unit 8A Treetop, Stratton, VT 05360

  Treetop at Stratton puts you ski-in/ski-out with the best year round views. This premium trailside location condo has 3 bedrooms and 4 bathrooms spread throughout spacious levels. Family room with gas fireplace has sleeper sofa for guest space, and that second living room that makes a family happy. Cherry floors and cabinets are a warm addition to the classic Adirondack design. Great room with

  Christiane Carroccio TPW Real Estate

  8 Dogwood Trail Unit 8A Treetop, Stratton, VT 05360
• 

  

  /24

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,520 Sq Ft

  76 Shattarack Rd Unit F5D, Stratton, VT 05360

  76 Shattarack Rd Unit F5D, Stratton, VT 05360
• 

  

  /12

  $135,000

  • Land
  • 1.51 Acres
  • $89,404 per Acre

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343

  Discover your dream Vermont escape on this enchanting 1.5-acre wooded lot in Jamaica. Perfectly positioned just minutes from the excitement of Stratton Mountain Resort, this prime parcel offers unparalleled access to world-class skiing, golfing, dining, and shopping.Imagine building your mountain retreat amidst nature's splendor. With a coveted State of Vermont 4-bedroom permit (WW-2-7632) in

  Mike England Michael England Real Estate

  0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
• 

  

  /29

  $480,000 Sold Nov 15, 2024

  • 1,098 Sq Ft
  • $437/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  10 Ober Tal Dr Unit B32, Stratton, VT 05360

  Come make this spacious top floor Stratton Mountain Resort condo your home away from home. Ober Tal is a trailside community at Stratton Mountain Resort adjacent to the Tamarack triple chairlift. Close proximity to the Stratton Village where shops and restaurants await. This turn key two bedroom (one a large loft with bathroom), two bath condominium features new carpet, newer appliances and a

  Jamie Wylie Stratton Real Estate

  10 Ober Tal Dr Unit B32, Stratton, VT 05360
• 

  

  /24

  Est $696,756 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft

  78 Middle Ridge Rd Unit 409, Stratton, VT 05155

  78 Middle Ridge Rd Unit 409, Stratton, VT 05155
• 

  

  /22

  $389,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  7 Wanderer Rd Unit 7, Stratton, VT 05155

  Check out this location! Excellent proximity to the Stratton Base Lodge, Village and the Stratton Training and Fitness Center. This 3 bedroom, 2 bath Wanderer Chalet CO-OP has been beautifully updated. The large open floor plan on the main level is a comfortable gathering space with a fireplace and nicely upgraded kitchen. With fresh paint, renovated baths and new floors throughout this CO-OP is

  Dan McKenna Cummings & Co

  7 Wanderer Rd Unit 7, Stratton, VT 05155
• 

  

  /21

  $810,000 Sold Nov 15, 2024

  • 3,062 Sq Ft
  • $265/SF
  • 49 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1991

  15 Benson Fuller Dr, Winhall, VT 05340

  Indulge in the serenity of the Stratton Mountain Retreat, meticulously designed for your peace and pleasure. Step into this contemporary haven, meticulously planned to reveal breathtaking mountain panoramas from every angle, initiating your immersive experience. Create cherished memories with loved ones in the expansive open-concept living and dining area, where the well-appointed kitchen,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  15 Benson Fuller Dr, Winhall, VT 05340
• 

  

  /34

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft

  3 Stratton Springs Rd Unit 3A, Stratton, VT 05360

  3 Stratton Springs Rd Unit 3A, Stratton, VT 05360
• 

  

  /28

  $825,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  6 Roundtree Rd, Winhall, VT 05340

  Prime Stratton location! This charming 4-bedroom, 2-bathroom retreat offers vaulted ceilings, an open-concept living area with a wood burning fireplace, and a private deck and backyard for relaxing after a day on the slopes. With weekend and holiday shuttle service during ski season, plus easy access to Stratton Village’s shops, dining, and year-round activities, it’s the ideal spot to recharge

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  6 Roundtree Rd, Winhall, VT 05340
• 

  

  /35

  $640,000 Sold Nov 13, 2024

  • 3,280 Sq Ft
  • $195/SF
  • 146 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1996

  660 Dalewood Rd, Jamaica, VT 05343

  Incredible opportunity to have your very own turnkey Stratton Mountain escape! Located on a quiet road, 3.5 miles from the Village, this lovely home has generated a treasure trove of memories for the owner's family for the last several years. Enter from the comfort of the attached garage into a generous mudroom, and head up to the main level where you'll find a well appointed chef's kitchen and

  Christopher Cummings Cummings & Co

  660 Dalewood Rd, Jamaica, VT 05343
• 

  

  /22

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,558 Sq Ft

  776 Stratton Mnt Access Rd Unit 1305, Stratton, VT 05155

  776 Stratton Mnt Access Rd Unit 1305, Stratton, VT 05155
• 

  

  /49

  $795,000 Pending

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

  65 Styles Branch Rd Unit 819, Stratton, VT 05360

  Welcome to Styles Brook 819, an impeccably maintained end unit townhome nestled in the heart of Stratton Mountain Resort. This spacious and light filled 4 bedroom, 3.5 bath residence offers everything you need for four season mountain living, whether you're hitting the slopes in winter or enjoying the cool summer breeze from your private deck. Soak, unwind and recharge after a day on the mtn in

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  65 Styles Branch Rd Unit 819, Stratton, VT 05360
• 

  /2

  $50,000 Sold Nov 08, 2024

  • Land
  • 23 Acres
  • $2,174 per Acre

  • 13 Days On Market

  0 Stratton Gate Rd, Jamaica, VT 05343

  Welcome to an opportunity to own a piece of natural paradise! This expansive piece of land is situated at the end of a town-maintained road, ensuring privacy while remaining easily accessible. One of the highlights of this property is its cascading year-round trout stream that gracefully winds its way, culminating at the breathtaking Angel Falls and Ball Mountain Lake. This property offers an

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 Stratton Gate Rd, Jamaica, VT 05343

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