Bennington, VT Homes

• 

  

  

  /47

  $885,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 1,917 Sq Ft

  C1 Meadow Ridge Rd, Winhall, VT 05340

  WELCOME TO YOUR FAMILY'S PERFECT MOUNTAIN RETREAT..WELCOME TO PIPER RIDGE!! This spacious 4 bedroom/4 bath condo is designed for comfort, convenience and offers an exceptional blend of mountain charm and modern amenities! Enjoy two open concept living areas with cozy wood burning fireplaces, fully equipped kitchen, private balcony showcasing winter mountain views...Perfect for entertaining...With

  Sunny Breen Josiah Allen Real Estate, Inc.

  C1 Meadow Ridge Rd, Winhall, VT 05340
• 

  

  

  /30

  $760,000 Sold May 23, 2025

  • 1,600 Sq Ft
  • $475/SF
  • 282 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1978

  15 Tamarack Rd Unit G-2, Stratton, VT 05360

  Discover the perfect blend of adventure and relaxation in this stunning 3-bedroom, 3-bathroom townhome, located on the slopes of Stratton Mountain Resort. Offering the ultimate in convenience, this property features ski-in/ski-out access, allowing you to hit the slopes in seconds and return home with ease.Inside, you'll find a spacious and inviting living area, complete with a cozy

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  15 Tamarack Rd Unit G-2, Stratton, VT 05360
• 

  

  

  /35

  Est $397,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  15 Stratton View Rd, Bondville, VT 05340

  15 Stratton View Rd, Bondville, VT 05340
• 

  

  

  /15

  $485,000

  • 2 Beds
  • 2 Baths
  • 1,353 Sq Ft

  49 High Point Dr Unit A-14, Stratton, VT 05360

  49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

  Andrew King Stratton Real Estate

  49 High Point Dr Unit A-14, Stratton, VT 05360
• 

  

  

  /39

  $405,000 Sold May 16, 2025

  • 1,215 Sq Ft
  • $333/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  5 Red Hickory Rd, Winhall, VT 05340

  The season is not over! Red Hickory 5 at Birch Hill is one of the best values today offered at Stratton. This ready to move into attractively appointed Co-Op townhome is located at the quiet end of popular Birch Hill street with views of the mountain. Three bedrooms, two baths, family room. Winter shuttle service to the base lodge. Brand new in ground pool for your summer enjoyment. This

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  5 Red Hickory Rd, Winhall, VT 05340
• 

  

  /13

  Not Listed For Sale

  234 Mountain Rd, Stratton, VT 05155

  234 Mountain Rd, Stratton, VT 05155
• 

  

  /20

  $495,000

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  374 Winhall Hollow Rd, Winhall, VT 05340

  Tucked away on 9.5 private acres that border the scenic Gale Meadows Pond, this Vermont retreat offers the perfect mix of nature, comfort, and functionality. Whether you're seeking a year-round residence or a seasonal getaway, this property is move-in ready with thoughtful renovations and room to explore. Step inside to a warm and inviting atmosphere where you’ll find brand-new kitchen

  Annette Gallo Real Broker LLC

  374 Winhall Hollow Rd, Winhall, VT 05340
• 

  

  /34

  $338,000 Sold May 16, 2025

  • 1,296 Sq Ft
  • $261/SF
  • 100 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  6217 Vt Route 30, Jamaica, VT 05343

  Perched on a hill above the village of Jamaica, this inviting Cape-style home offers privacy and stunning surroundings just minutes from Stratton Mountain. Sitting on 1.5 acres, the property provides a peaceful retreat with easy access to Winhall, Stratton, and endless outdoor activities. A babbling stream flows nearby, adding to the tranquil setting as you relax on the spacious deck.Despite its

  Trent Stephens Wohler Realty Group

  6217 Vt Route 30, Jamaica, VT 05343
• 

  

  /21

  Est $291,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 320 Sq Ft

  1406 Cole Pond Rd, Jamaica, VT 05343

  1406 Cole Pond Rd, Jamaica, VT 05343
• 

  

  /6

  $84,900

  • Land
  • 1.78 Acres
  • $47,697 per Acre

  0000 Wonder Ln, Jamaica, VT 05343

  Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, this magnificent 1.78-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

  Rachel Febbie EXP Realty

  0000 Wonder Ln, Jamaica, VT 05343
• 

  

  /39

  $2,200,000 Sold May 14, 2025

  • 2,244 Sq Ft
  • $980/SF
  • 10 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  52 Snow Bridge Rd, Stratton, VT 05360

  Exclusive Snowbridge Trailside Retreat — With a premier snowfront location in Stratton’s coveted Snowbridge community, this unit provides true ski-in/ski-out access and walkability to the Stratton Village shops and restaurants. Gear up in the comfort of your home — go from slippers to ski boots, then take the Old Log Trail directly to the Main Base, Gondola, and Ski School. In addition to an

  Cheyanne Pugliese

  52 Snow Bridge Rd, Stratton, VT 05360
• 

  

  /32

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  43 Middle Ridge Rd Unit 120, Winhall, VT 05155

  43 Middle Ridge Rd Unit 120, Winhall, VT 05155
• 

  

  /7

  $74,900

  • Land
  • 2.06 Acres
  • $36,359 per Acre

  000 Wonder Ln, Jamaica, VT 05343

  Prime 2.06-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, this magnificent 2.08-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

  Rachel Febbie EXP Realty

  000 Wonder Ln, Jamaica, VT 05343
• 

  

  /15

  $159,500 Sold May 14, 2025

  • Land
  • 11 Acres
  • $14,395 per Acre

  • 440 Days On Market

  000 Rose Ln, Londonderry, VT 05148

  MOTIVATED SELLERS!!!! This 11 acre parcel is located just off Cole Pond, and is just a few miles to Stratton Mountain Access Road. One lot sits high in the sky with breathtaking views and all the serenity of nature. A well constructed driveway runs approximately halfway up the property where you will find a partial building site with an incredible view of Bromley Mountain, from there if you

  Rachel Febbie EXP Realty

  000 Rose Ln, Londonderry, VT 05148
• 

  

  /37

  Est $318,144 Not Listed For Sale

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

  176 Melendy Hill Rd, South Londonderry, VT 05155

  176 Melendy Hill Rd, South Londonderry, VT 05155
• 

  

  /60

  $710,000

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  3 Short Rd, Bondville, VT 05340

  Reside in a renovated 1800s expanded cape in Vermont, complete with all the country amenities you desire! The presence of a barn with a workshop indicates that the home you are purchasing is well cared for. The eat-in kitchen boasts a soapstone sink, pine flooring, granite countertops, and custom cabinetry. The living room features a wood-burning fireplace, as does the dining room. An addition

  Mike England Michael England Real Estate

  3 Short Rd, Bondville, VT 05340
• 

  

  /29

  $750,000 Sold May 12, 2025

  • 3,084 Sq Ft
  • $243/SF
  • 82 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  12 Jamie Ln, Jamaica, VT 05343

  Showings begin Saturday, February 22, 2025. Set in the heart of Vermont’s stunning landscape, this handcrafted Lincoln Log home offers the perfect blend of privacy and convenience. Surrounded by towering Maples and classic stone walls, it’s just minutes from Stratton’s ski slopes and a short drive to Bromley, Magic Mountain, and Manchester. Inside, a bright, open floor plan features soaring

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  12 Jamie Ln, Jamaica, VT 05343
• 

  

  /34

  Not Listed For Sale

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

  291 Pikes Falls Rd, Stratton, VT 05360

  291 Pikes Falls Rd, Stratton, VT 05360
• 

  

  /36

  $720,000

  • 4 Beds
  • 4 Baths
  • 2,389 Sq Ft

  58 Todd Hill Rd, Bondville, VT 05340

  Escape to your mountain retreat in this spacious 4 bedroom, 4 bath home tucked away in a serene wooden community just minutes away from Stratton Mountain Resort. Perfect for entertaining or relaxing, the home features two cozy wood burning fireplaces that brings warmth and charm throughout the season. Vaulted ceilings in the living room and dining room area provide lots of natural light. Step

  Jamie Wylie Stratton Real Estate

  58 Todd Hill Rd, Bondville, VT 05340
• 

  

  /39

  $1,750,000 Sold May 09, 2025

  • 2,653 Sq Ft
  • $660/SF
  • 87 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1986

  34 Mountain Reach Mews Rd, Stratton, VT 05155

  Incredible opportunity to own a stunning end unit just steps to Stratton Village and the Villager Lift! Walk right out your door and you are next to Stratton's delicious Firetower restaurant! This location cannot be beat. Unit has a young roof and is meticulously maintained. 4 Bedrooms and 4 bathrooms spread out over 4 floors makes for a great ski home that can accommodate sleeping 10-12 with

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  34 Mountain Reach Mews Rd, Stratton, VT 05155
• 

  

  /28

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,014 Sq Ft

  43 Middle Ridge Rd Unit 312, Winhall, VT 05155

  43 Middle Ridge Rd Unit 312, Winhall, VT 05155
• 

  

  /39

  $699,000

  • 6 Beds
  • 3 Baths
  • 2,825 Sq Ft

  95 Melendy Hill Rd, Londonderry, VT 05155

  A fully reimagined 1900’s farmhouse located in the heart of South Londonderry. This six-bedroom, three-bath home has been meticulously remodeled to blend timeless character with contemporary style. Sunlight pours through all-new windows, illuminating generous living spaces. Every detail has been thoughtfully upgraded, from the new heating system, engineered and installed septic, well, and

  Jessica Citera Cummings & Co

  95 Melendy Hill Rd, Londonderry, VT 05155
• 

  

  /30

  $330,000 Sold May 09, 2025

  • 1,088 Sq Ft
  • $303/SF
  • 115 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  21 Stratton Ridge Rd, Winhall, VT 05340

  This charming 3-bedroom, 1.5-bathroom condo is the perfect getaway for ski enthusiasts and nature lovers alike. Conveniently located just minutes from Stratton Mountain, you'll enjoy year-round access to skiing, hiking, and all the village has to offer.Entry has a built-in storage area for all of your gear. The updated kitchen with radiant heat tile floors, features modern appliances, granite

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  21 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  /40

  Est $2,351,978 Not Listed For Sale

  • 7 Beds
  • 9.5 Baths
  • 6,721 Sq Ft

  95 Winhall Hollow Rd, Bondville, VT 05340

  95 Winhall Hollow Rd, Bondville, VT 05340
• 

  

  /20

  $590,000

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

  Experience the best of mountain living at Long Trail House. This light-filled 2-bedroom, 2-bath condo offers comfort, convenience, and an unbeatable location just steps from Stratton’s lifts, shops, and restaurants. The open-concept living area features a gas fireplace, perfect for cozy apres-ski gatherings, and a well-equipped kitchen with a breakfast bar for casual dining. This corner unit has

  Christiane Carroccio TPW Real Estate

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360
• 

  

  /21

  $375,000 Sold May 05, 2025

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

  • 3 Beds
  • 2 Baths
  • Built 1968

  61 Birch Hill Rd Unit 6, Winhall, VT 05340

  This updated 3 bedroom, 2 bathroom Birch Hill unit is decorated with stylish choices, and is offered fully furnished. The mudroom entry has a heated tile floor, and custom ski racks. The first floor has a family room, with laundry closets and newer washer/dryer. The bunkroom is on this first floor along with a bathroom. The middle floor is the living/kitchen/dining room with a fully updated

  Christiane Carroccio TPW Real Estate

  61 Birch Hill Rd Unit 6, Winhall, VT 05340
• 

  

  /30

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,785 Sq Ft

  13 Stratton Rd W Unit 13, Winhall, VT 05340

  13 Stratton Rd W Unit 13, Winhall, VT 05340
• 

  

  /43

  $899,000

  • 4 Beds
  • 3 Baths
  • 3,155 Sq Ft

  460 Stratton Gate Rd, Jamaica, VT 05343

  This exceptional property blends classic post-and-beam farmhouse design with modern craftsmanship. The stunning barn addition is an architectural masterpiece, admired from every angle and flooded with natural light through expansive windows that frame the serene surroundings. Soaring ceilings, rich hardwood floors, and custom finishes create an atmosphere of timeless elegance. An expansive loft

  Helen Nault

  460 Stratton Gate Rd, Jamaica, VT 05343
• 

  

  /25

  $499,000 Sold May 02, 2025

  • 1,096 Sq Ft
  • $455/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  16 Ober Tal Dr Unit E35, Stratton, VT 05360

  This top-floor, 2-bedroom, 2-bath condo in the sought-after E section of Ober Tal offers the ultimate in mountain access. Located just steps from the lifts, it's a true ski-in/ski-out property, and in the warmer months, enjoy hiking and mountain biking directly from your door. Whether you're hitting the slopes, exploring the trails, or biking the mountain, this condo offers the perfect location

  Carrie Mathews Winhall Real Estate

  16 Ober Tal Dr Unit E35, Stratton, VT 05360
• 

  

  /40

  Est $615,417 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  10 Deer St, Bondville, VT 05340

  10 Deer St, Bondville, VT 05340
• 

  

  /34

  $275,000

  • 3 Beds
  • 2 Baths
  • 2,613 Sq Ft

  533 Pratt Bridge Rd, Jamaica, VT 05343

  Nestled in the peaceful and desirable Cole Pond neighborhood, while being merely minutes away from: Stratton Mountain Resort, renowned for its skiing and year-round recreational activities The picturesque landscapes of Southern Vermont – offering hiking, fishing, and various outdoor pursuits Seclusion and serenity on your own 1.6-acre sanctuary. This contemporary 3 bedroom with loft 2 bath,

  Mike England Michael England Real Estate

  533 Pratt Bridge Rd, Jamaica, VT 05343
• 

  

  /35

  $227,000 Sold May 02, 2025

  • 2,072 Sq Ft
  • $110/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1830

  347 Main St, South Londonderry, VT 05155

  Nestled in a peaceful location just 10 minutes from Bromley, Stratton, and Magic Mountains, this 3-bedroom, 2-bathroom home offers the perfect mix of comfort, charm, and functionality. With stunning views in every direction, it’s an ideal spot for both relaxation and entertaining. The spacious living room, featuring a beautiful fireplace, serves as the heart of the home. Large windows frame

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  347 Main St, South Londonderry, VT 05155
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,016 Sq Ft

  12 Quarter Mile Rd, Winhall, VT 05360

  12 Quarter Mile Rd, Winhall, VT 05360
• 

  

  /17

  $399,000

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft

  10 Ober Tal Dr Unit B12, Stratton, VT 05360

  Own at Ober Tal and enjoy Slopeside Living in the heart of Stratton Mountain. Just steps from the Trails and Tamarack Chair Lift, getting on the slopes couldn’t be easier. This updated one-bedroom, one-bath home features an airy open living and dining area with a classic wood-burning fireplace as its centerpiece. A ground-level location offers the bonus of a private patio, while the generous

  Helen Nault

  10 Ober Tal Dr Unit B12, Stratton, VT 05360
• 

  

  /60

  $2,100,000 Sold May 02, 2025

  • 6,195 Sq Ft
  • $339/SF
  • 246 Days On Market

  • 7 Beds
  • 5.5 Baths
  • Built 2007

  18 Rocky Dell Rd, Winhall, VT 05340

  Welcome to this stunning Contemporary Mountain Estate on 26 acres where luxury, privacy and nature converge.Offering more than a home-It's a lifestyle with the perfect blend of sophistication, comfort & natural surroundings. Ideally located just minutes to the Stratton Mountain Resort or the Green Mountain National Forest, easily accessed from Kendall Farm Road. Enjoy the mountains & the outdoors

  Kim Morgan-Wohler Wohler Realty Group

  18 Rocky Dell Rd, Winhall, VT 05340
• 

  

  /40

  Est $912,784 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,872 Sq Ft

  34 Raspberry Hill Rd, Winhall, VT 05340

  34 Raspberry Hill Rd, Winhall, VT 05340
• 

  

  /56

  $3,750,000

  • 7 Beds
  • 7.5 Baths
  • 6,900 Sq Ft

  192 N Brookwood Rd, Stratton, VT 05360

  Perched at the top of Stratton Mountain Resort's most desired destination, this exceptional 7 Bedroom/7.5 Bath retreat is a prime alpine experience. Near the Wanderer ski trail w/ breathtaking views stretching across the Green Mountains, every detail of this property has been designed to offer privacy-capturing the essence of four-season luxury.With a rare blend of refined elegance & natural

  Kim Morgan-Wohler Wohler Realty Group

  192 N Brookwood Rd, Stratton, VT 05360
• 

  

  /53

  $825,000 Sold Apr 29, 2025

  • Land
  • 36 Acres
  • $23,109 per Acre

  • 102 Days On Market

  324 Pikes Falls Rd, South Londonderry, VT 05155

  Extraordinary Stratton Mountain Acreage Opportunity:Discover a rare gem in Stratton Mountain, a 35.7-acre parcel offering breathtaking, commanding views of the resort. Just 5 minutes away from the the Main Base Lodge and less to Sun Bowl. This exceptional property features two building sites, each supported by wastewater systems for a 6-bedroom and a 4-bedroom home.The established driveway leads

  Britt Wohler Wohler Realty Group

  324 Pikes Falls Rd, South Londonderry, VT 05155
• 

  

  /26

  Est $255,076 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 595 Sq Ft

  28 Stratton Rd W Unit 28, Winhall, VT 05340

  28 Stratton Rd W Unit 28, Winhall, VT 05340
• 

  

  /59

  $1,300,000

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  51 Village Square, Stratton, VT 05360

  Experience this Extraordinary Location in the heart of the Stratton Resort Village from this RENOVATED and EXPANDED Village Square 4 bedroom unit where you can walk to everything and be on the lifts in just a few minutes. Nothing compares to trailside living in the VILLAGE where convenience abounds and you won't touch your car until it's time to hit the highway. Ski home for lunch and you'll have

  Kim Morgan-Wohler Wohler Realty Group

  51 Village Square, Stratton, VT 05360

Showing Results 81 - 120, Page 3 of 18