Bennington, VT Homes

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /52

  $800,000 Sold Feb 13, 2025

  • 2,300 Sq Ft
  • $348/SF
  • 47 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  E11 Rock Ridge Rd, Winhall, VT 05155

  SATURDAY DECEMBER 28th 3 - 5 pm Apre' ski time PUBLIC OPEN HOUSE Come take a walk thru Situated in the heart of Stratton, this Piper Ridge condo puts you in the perfect position to enjoy the best of winter sports and mountain recreation. Three floors of living space boast three well placed bedrooms , three baths PLUS family room AND bonus room for your over flow family and guests. Spacious,

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  E11 Rock Ridge Rd, Winhall, 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /57

  $629,000

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

  11 Pond View Rd, Winhall, VT 05340

  The Intervale community has long been popular for affordability and value. This bright and sunny unit boasts an updated kitchen, primary suite on the main level with updated bath. Mini suite on upper level along with a third bedroom and shared bath with the loft area. Heating system replaced with an efficient Buderus boiler. Plenty of room for your weekend guests but a manageable floor plan for

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  11 Pond View Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /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
• 

  

  /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
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  /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
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  /38

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  14 Middle Ridge Rd Unit 19A, Winhall, VT 05155

  14 Middle Ridge Rd Unit 19A, Winhall, VT 05155
• 

  

  /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
• 

  

  /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
• 

  

  /21

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,940 Sq Ft

  38 Quarter Mile Rd, Winhall, VT 05360

  38 Quarter Mile Rd, Winhall, VT 05360
• 

  

  /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
• 

  

  /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
• 

  

  /40

  Est $1,673,393 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 4,551 Sq Ft

  82 High Meadow Rd, Winhall, VT 05340

  82 High Meadow Rd, Winhall, VT 05340
• 

  

  /22

  $665,000

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  43 Middle Ridge Rd Unit 311, Winhall, VT 05155

  Exceptional 2 bedroom /2 bath Rising Bear Unit with Viking Kitchen, propane fireplace and private covered deck. Amenities abound with underground heated parking, year round private outdoor heated pool, sauna and spas. Enjoy private shuttle from the elevator to the Base Lodge during the winter, yet just a short stroll across the Commons into the Village for dining and shopping! Granite

  Kim Morgan-Wohler Wohler Realty Group

  43 Middle Ridge Rd Unit 311, Winhall, 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
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,671 Sq Ft

  13 Old Ridge Rd, Winhall, VT 05155

  13 Old Ridge Rd, Winhall, VT 05155
• 

  

  /54

  $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
• 

  

  /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

  • 5 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  71 Todd Hill Rd, Jamaica, VT 05343

  71 Todd Hill Rd, Jamaica, VT 05343
• 

  

  /31

  $949,000

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  73 Cranberry Hill Rd, Winhall, VT 05340

  Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

  Carrie Mathews Winhall Real Estate

  73 Cranberry Hill Rd, 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
• 

  

  /38

  Not Listed For Sale

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

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
• 

  

  /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
• 

  

  /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
• 

  

  /39

  Est $607,322 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  22 Cranberry Hill Rd, Winhall, VT 05340

  22 Cranberry Hill Rd, Winhall, VT 05340
• 

  

  /48

  $2,999,000

  • 6 Beds
  • 6.5 Baths
  • 6,500 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
• 

  

  /37

  $750,000 Sold Nov 01, 2024

  • 1,372 Sq Ft
  • $547/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  43 Middle Ridge Rd Unit 313, Winhall, VT 05155

  Nestled in the heart of Stratton Mountain, this 3-bedroom, 2-bath condo at Rising Bear Lodge offers the perfect mountain retreat. The primary bedroom, complete with an ensuite bathroom, is conveniently located off the open concept living and dining room, with the kitchen featuring granite counter tops and breakfast bar. Down the hall, you'll find two additional bedrooms, a full bath, and

  Courtney Chase Coldwell Banker Homes Unlimited

  43 Middle Ridge Rd Unit 313, Winhall, VT 05155
• 

  

  /19

  Not Listed For Sale

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

  0 Birch Hill Rd Unit Sugar Maple 5003081, Winhall, VT 05340

  0 Birch Hill Rd Unit Sugar Maple 5003081, Winhall, VT 05340

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