Bennington, VT Homes in ZIP Code 05340

• 

  

  

  /35

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  33 Aspen Ln, Bondville, VT 05340

  Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

  

  Alison Cummings

  Cummings & Co

  (802) 424-9210

  33 Aspen Ln, Bondville, VT 05340
• 

  

  

  /40

  $13,000 per month

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft
  • House for Rent

  21 Valley View Rd, Winhall, VT 05255

  Spectacular 5 bedroom, 5 bathroom house with panoramic mountain views!!! Entry level offers a 2 car garage, laundry room, powder room and large eat in kitchen. Beautiful views out the back sun room! Kitchen opens up to cathedral ceilings in the great room with center stone fireplace, formal dining room, foyer and den. Expansive primary suite on the first floor over looking the back deck with hot

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 328-9426

  21 Valley View Rd, Winhall, VT 05255
• 

  

  

  /28

  $770,000 Sold Jul 18, 2025

  • 3,556 Sq Ft
  • $217/SF
  • 113 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1980

  5 Stratton Ridge Rd, Winhall, VT 05340

  Discover the ultimate Vermont ski retreat, just 2 miles from Stratton Mountain. This captivating home offers breathtaking mountain views across three spacious levels. The upper level features a private primary suite with a newly renovated bath and a cozy loft/office space — your peaceful sanctuary. The heart of the home, the main level, is perfect for gathering, with soaring cathedral ceilings,

  Carrie Mathews Winhall Real Estate

  5 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  

  /31

  Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,888 Sq Ft

  12 Stratton Rd W Unit 12, Winhall, VT 05340

  12 Stratton Rd W Unit 12, Winhall, VT 05340
• 

  

  

  /15

  $115,000

  • Land
  • 2.90 Acres
  • $39,655 per Acre

  Lot 3 Route 11 30, Winhall, VT 05340

  Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 808-6197

  Lot 3 Route 11 30, Winhall, VT 05340
• 

  

  /35

  $3,500 per month

  • 3 Beds
  • 3 Baths
  • 1,312 Sq Ft
  • House for Rent

  3 Bromley Forest Rd, Winhall, VT 05340

  Adorable 3 bed, 3 bath ranch located on desirable Bromley Forest Road in Winhall, just over the border from Manchester. This fully furnished home offers a perfect blend of comfort and convenience in a peaceful, wooded setting. The main level features an open and inviting layout, including a spacious living room, a fully equipped kitchen, and a cozy dining area. The 1st floor primary bedroom

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 300-3940

  3 Bromley Forest Rd, Winhall, VT 05340
• 

  

  /22

  $265,500 Sold Jul 15, 2025

  • 1,332 Sq Ft
  • $199/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  18 Stratton Ridge Rd, Winhall, VT 05340

  Welcome to 18 Stratton West Road – a charming 3-bedroom, 2-bath ski condo located just minutes from Stratton Mountain Resort. This spacious unit features over 1,300 square feet of well-maintained living space, complete with a cozy wood-burning fireplace, updated bathrooms, and generous natural light throughout. The open-concept layout is perfect for entertaining, with a functional kitchen, dining

  Derek Greene Derek Greene

  18 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  /28

  Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 5,896 Sq Ft

  27 Mountain View Rd, Winhall, VT 05360

  27 Mountain View Rd, Winhall, VT 05360
• 

  

  /60

  $1,825,000 Open House 8/30

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

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
• 

  

  /35

  $9,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,908 Sq Ft
  • House for Rent

  43 Cranberry Hill Rd, Winhall, VT 05340

  First time available for a seasonal rental.Call 43 Strattonwald home for your 25-26 ski season. This recently updated modern, yet classic chalet has room for all. With four bedrooms, two of the primary bedrooms with en-suite bathrooms, there is ample room for everyone's comfort. The home has brand new bathrooms, modern decor and state of the art appliances. With several living areas

  Peggy O'neill Cummings & Co

  43 Cranberry Hill Rd, Winhall, VT 05340
• 

  

  /54

  $970,000 Sold Jun 17, 2025

  • 2,672 Sq Ft
  • $363/SF
  • 120 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  13 Windtree Rd, Bondville, VT 05340

  OPEN HOUSE SATURDAY , February 22nd-11:00-3:00.Showings begin 2/20Exceptional Stratton Mountain Resort location on Windtree Road in the desirable North Brookwood neighborhood with Shuttle from your driveway to the Base Lodge! Enjoy this wonderful deck house open floor plan with great winter views, vaulted ceilings, 2 wood burning fireplaces and multiple decks. Well designed for apres ski

  Kim Morgan-Wohler Wohler Realty Group

  13 Windtree Rd, Bondville, VT 05340
• 

  

  /38

  Est $750,833 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,081 Sq Ft

  80 Pond View Rd, Winhall, VT 05340

  80 Pond View Rd, Winhall, VT 05340
• 

  

  /60

  $1,100,000

  • 6 Beds
  • 5 Baths
  • 5,298 Sq Ft

  50 Stratton View Rd, Winhall, VT 05340

  Custom built six-bedroom home on 2 acres with spectacular views of Stratton Mountain. The kitchen has granite countertops and custom cabinets with the dining area nearby with plenty of space to accommodate a large gathering. The living area has a cathedral ceiling with large windows for an abundance of natural light and stunning year-round views of Stratton Mountain, with a lovely stone fireplace

  Mike England Michael England Real Estate

  50 Stratton View Rd, Winhall, VT 05340
• 

  

  /48

  $7,000 per month

  • 5 Beds
  • 3.5 Baths
  • 3,858 Sq Ft
  • House for Rent

  20 Jamie Ln, Winhall, VT 05340

  Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
• 

  

  /29

  $363,825 Sold Jun 06, 2025

  • 1,215 Sq Ft
  • $299/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340

  Discover the ease of Mountain living with the complimentary Birch Hill Shuttle, providing seamless access to winter adventures. This bright and welcoming end-unit townhouse offers plenty of space for family and friends to gather and unwind. With two inviting living areas, three comfortable bedrooms, and two well-appointed bathrooms, there's room for everyone to relax. The spacious entryway is

  Christine Chovan

  30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340
• 

  

  /31

  Not Listed For Sale

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

  6 Black Birch Rd, Winhall, VT 05340

  6 Black Birch Rd, Winhall, VT 05340
• 

  

  /31

  $975,000

  • 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
• 

  

  /46

  $5,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Nearing Rd, Winhall, VT 05340

  Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

  David Powers 42 North LP

  15 Nearing Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /35

  Est $613,960 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,577 Sq Ft

  10 Pond View Rd, Winhall, VT 05340

  10 Pond View Rd, Winhall, VT 05340
• 

  

  /50

  $1,050,000

  • 5 Beds
  • 5.5 Baths
  • 4,729 Sq Ft

  83 Benson Fuller Dr, Bondville, VT 05340

  Just an 8-minute drive to Stratton, 83 Benson Fuller Drive sits atop the beautiful Forest Farms neighborhood, offering both serenity and convenience. This meticulously updated home is ready for you to move in and enjoy the best of Vermont living. Nestled on a quiet dirt road, it’s perfect for morning and evening strolls with the dog before or after a day on the slopes.Inside, this

  Christiane Carroccio TPW Real Estate

  83 Benson Fuller Dr, Bondville, VT 05340
• 

  

  /32

  $14,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  14 Burnt Hill Rd, Winhall, VT 05340

  This modern Strattonwald gem is the ultimate plug-and-play Vermont summer house with location, style, convenience and a lake-side lifestyle to remember. Three living spaces -- one on each floor -- allow for plenty of overflow in the morning and afternoon, with two fireplaces ready for friends and family. Four bedrooms plus sleep loft with its own hang-out space lend space for the whole crew!

  Jamie Luke TPW Real Estate

  14 Burnt Hill Rd, Winhall, VT 05340
• 

  

  /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

  Not Listed For Sale

  • 9 Beds
  • 8 Baths
  • 3,375 Sq Ft

  103 Winhall Hollow Rd, Bondville, VT 05340

  103 Winhall Hollow Rd, Bondville, VT 05340
• 

  

  /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
• 

  

  /17

  $27,500 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Condo for Rent

  5 Byington Ln, Winhall, VT 05340

  A classic Austrian chalet, this outdoors enthusiasts' home is structured for year-round fun! The living and entertaining space encompasses the main floor: The functional open kitchen/dining room is perfect for the gang before and after weekend adventures, with a spacious great room and stone fireplace. A cozy, irresistible loft awaits upstairs for moments curled up with a book, coffee and a thick

  Jamie Luke TPW Real Estate

  5 Byington Ln, Winhall, VT 05340
• 

  

  /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
• 

  

  /40

  Est $788,860 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 4,000 Sq Ft

  386 Winhall Hollow Rd, Bondville, VT 05340

  386 Winhall Hollow Rd, Bondville, VT 05340
• 

  

  /51

  $1,600,000 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 4,541 Sq Ft

  33 Jamie Ln, Bondville, VT 05340

  Exceptional Log Home tucked away in the beautiful Green Mountains of Vermont. Welcome to 33 Jamie Lane a 12 acre sanctuary minutes to Stratton Mountain Resort. This extraordinary property offers true privacy surrounded by woods and nature. Features three finished levels of dramatic living space with floor to ceiling windows , soaring stone fireplace, and cherry floors. Open concept kitchen/dining

  Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

  33 Jamie Ln, Bondville, VT 05340
• 

  

  /29

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  90 Turkey Run Rd, Winhall, VT 05340

  Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

  Christiane Carroccio TPW Real Estate

  90 Turkey Run Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /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
• 

  

  /59

  $1,200,000 Under Contract

  • 3 Beds
  • 3.5 Baths
  • 4,054 Sq Ft

  4 Garden Loop Rd, Winhall, VT 05340

  Your Stratton Mountain retreat awaits! This beautiful turnkey mountain home just off the Stratton Mountain Road is the perfect location for family gatherings, ski trips, hiking and more. This three-bedroom, three-bath home on three levels includes a breathtaking great room with a stone fireplace and vaulted ceilings. Dining room and additional breakfast area next to the kitchen. A large open

  Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

  4 Garden Loop Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /27

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft

  22 Snowflake Ln, Winhall, VT 05340

  22 Snowflake Ln, Winhall, VT 05340
• 

  

  /32

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  35 Glendon Hills Rd, Bondville, VT 05340

  Discover your dream home in Glendon Hills! A truly rare opportunity, this property is the first to become available in this coveted neighborhood in over a decade. Imagine owning a private 1-acre sanctuary with your own picturesque, thriving pond. Inside, experience the joy of cooking in a well-appointed chef's kitchen and the comfort of an open-concept design centered around a charming stacked

  Robin Apps Four Seasons Sotheby's Int'l Realty

  35 Glendon Hills Rd, Bondville, 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
• 

  

  /40

  Est $2,440,535 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
• 

  

  /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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 18