Bennington, VT Homes

• 

  

  

  /37

  $219,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,156 Sq Ft

  261 Sycamore Ln, Shaftsbury, VT 05262

  Welcome to 261 Sycamore Lane, Shaftsbury, VT!Nestled in a desirable neighborhood, this charming Cape Cod style home is a perfect fit for first-time homebuyers or those looking to downsize into something more manageable. Set of 0.35 acres, the home offers 3 bedrooms and 1 full bath, with added convenience of a first-floor bedroom and bath.Enjoy a spacious backyard perfect for pets, kids,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 278-9491

  261 Sycamore Ln, Shaftsbury, VT 05262
• 

  

  

  /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

  $290,000 Sold Jul 17, 2025

  • 1,042 Sq Ft
  • $278/SF
  • 75 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1948

  221 Grandview St, Bennington, VT 05201

  Charming renovated cape with mountain views! Perched high on Grandview Street on a spacious and level lot, this beautifully renovated Cape-style home offers comfort, style, and lovely views of Mount Anthony and beyond. Step inside to a bright and welcoming first floor, where an open-concept layout easily accommodates both living and dining areas, enhanced by large windows that fill the space with

  Angela Bevin Maple Leaf Realty

  221 Grandview St, Bennington, VT 05201
• 

  

  

  /18

  Est $221,195 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,012 Sq Ft

  9 Palmer Dr, Pownal, VT 05261

  9 Palmer Dr, Pownal, VT 05261
• 

  

  

  /19

  $225,000 Under Contract

  • Land
  • 17 Acres
  • $13,489 per Acre

  1801 S Stream Rd, Bennington, VT 05201

  Welcome to 1801 South Stream Road a picturesque 16.68 acres of timeless Vermont charm property. This beautiful parcel features two classic Vermont red barns full of character and charm, that offer endless potential. With some repairs, they could be ideal for livestock, storage, or workshop space ready to support your vision for country living. A picturesque pond, in need of a little TLC, offers

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 317-7489

  1801 S Stream Rd, Bennington, VT 05201
• 

  

  /51

  $1,400 per month

  • 1 - 3 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  9 Browning Place, Bennington, VT 05201

  PLEASE READ THIS AD CAREULLY.First floor small three bedroom- New kitchen (cabinets, countertops, appliances - fridge, stove and over the range microwave)- New bathroom, with washer dryer hookups in the bathroom- New recessed lighting- Washer / dryer hookups in bathroom- All the windows are new wood insulated windows.- The apartment will include heat, but not

  9 Browning Place, Bennington, VT 05201
• 

  

  /16

  $25,000 Sold Jul 16, 2025

  • Land
  • 7 Acres
  • $3,571 per Acre

  • 15 Days On Market

  0 Hawley Mountain Rd, Arlington, VT 05250

  Tucked away just off Murray Hollow Road, this 7-acre parcel offers the perfect blend of privacy, natural beauty, and outdoor adventure. Zoned Forest and Recreation, it’s an ideal spot for hunting, hiking, or establishing your own off-grid retreat.Access begins from a town-maintained road, leading you to a trail (locally referred to as Hawley Mountain) after a stream crossing that opens

  Faith Rhodes Maple Leaf Realty

  0 Hawley Mountain Rd, Arlington, VT 05250
• 

  

  /13

  Est $236,611 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  18 Old Route 9, Wilmington, VT 05363

  18 Old Route 9, Wilmington, VT 05363
• 

  

  /11

  $129,000 Under Contract

  • Land
  • 7 Acres
  • $17,223 per Acre

  0 Lois Ln Unit 5045700, Arlington, VT 05250

  Come for the Views—Stay for the Possibilities!Bring Your Architect or Builder.Discover 7.49 exceptional acres across three separate lots, nestled on Lois Lane—a quiet, private dead-end road just off Old West Road in the historic town of Arlington.A driveway is already in place, guiding you to a secluded potential homesite tucked deep into nature.As you enter Lois Lane, Lot #3 sits

  

  Kristin Comeau

  TPW Real Estate

  (802) 613-0403

  0 Lois Ln Unit 5045700, Arlington, VT 05250
• 

  

  /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
• 

  

  /33

  $375,000 Sold Jul 16, 2025

  • 804 Sq Ft
  • $466/SF
  • 53 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1974

  46 Murray Hill Heights Rd Unit 17, Manchester, VT 05255

  Come see this in-town condominium with a garage! This unit features open bright kitchen and a living room with cathedral ceilings and a pellet stove, 2 bedrooms and 3 bathrooms. Enjoy the community amenities, including a pool, playground, and tennis courts. Furniture and appliances are included in the sale. Schedule a visit to see it for yourself. OPEN HOUSE on Memorial day 05/26/2025 from

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  46 Murray Hill Heights Rd Unit 17, Manchester, VT 05255
• 

  

  /35

  Est $254,161 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  312 School St Unit 314, Bennington, VT 05201

  312 School St Unit 314, Bennington, VT 05201
• 

  

  /47

  $379,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  84 Jasper Ln, Arlington, VT 05250

  Fantastic 4 BR meticulously maintained Cape located on a wonderful quiet cul-de-sac, assuring privacy and yet convenient to all Arlington and Manchester amenities. The open concept floorplan lives comfortably with great natural light. Eat in kitchen with all stainless appliances offers great storage, the living room supports ample seating... 4 spacious bedrooms, one with walk in closet, two

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 213-9598

  84 Jasper Ln, Arlington, VT 05250
• 

  

  /51

  $1,001 per month

  • 1 - 3 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  9 Browning Place, Bennington, VT 05201

  PLEASE READ THIS AD CAREULLY.First floor small three bedroom- New kitchen (cabinets, countertops, appliances - fridge, stove and over the range microwave)- New bathroom, with washer dryer hookups in the bathroom- New recessed lighting- Washer / dryer hookups in bathroom- All the windows are new wood insulated windows.- The apartment will include heat, but not

  9 Browning Place, Bennington, VT 05201
• 

  

  /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
• 

  

  /34

  Est $479,893 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft

  647 Fox Hill Rd, Bennington, VT 05201

  647 Fox Hill Rd, Bennington, VT 05201
• 

  

  /38

  $475,000

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft

  1243 Murray Hill Heights Rd Unit 43, Manchester, VT 05255

  Set in the heart of Manchester’s desirable Murray Hill community, this 3-bedroom, 3-bath condo in the Heights offers over 1,700 sq. ft. of comfortable, light-filled living with breathtaking mountain views. Enjoy a spacious three-level layout that offers privacy for guests with one of bedrooms on the top floor. The main living area is perfect for relaxing or entertaining, featuring a

  

  Julie Citron

  RE/MAX Four Seasons

  (802) 402-4782

  1243 Murray Hill Heights Rd Unit 43, Manchester, VT 05255
• 

  

  /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
• 

  

  /41

  $750,000 Sold Jul 14, 2025

  • 1,836 Sq Ft
  • $408/SF
  • 55 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2022

  482 Horton Hill Rd, Shaftsbury, VT 05262

  Built in 2021, this stylish 3 bed, 3 bath modern home sits on 9.8 acres with wide open views from every angle. Large windows and a wraparound Trex deck with sleek cable railing blur the lines between indoors and out, with access from both the living room and primary suite. Inside, the open layout is designed for today's living-featuring a gorgeous kitchen with stainless appliances, granite

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  482 Horton Hill Rd, Shaftsbury, VT 05262
• 

  

  /39

  Est $558,191 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,278 Sq Ft

  557 Fox Hill Rd, Bennington, VT 05201

  557 Fox Hill Rd, Bennington, VT 05201
• 

  

  /28

  $85,000

  • Land
  • 3.75 Acres
  • $22,667 per Acre

  0 High Pine Dr, Arlington, VT 05250

  Just a short walk to the Battenkill River and a stone's throw to the Village of Arlington, this 3.75 acre lot is already permitted for a 5BR house! Partial clearing has already been done and with some additional select clearing you can have lovely views while retaining privacy. A wonderful place for your primary residence or your Vermont getaway!

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 481-3309

  0 High Pine Dr, Arlington, VT 05250
• 

  

  /8

  $1,175 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  166 N Branch St, Bennington, VT 05201

  Please do NOT click the "Request To Apply" button. This will cause a delay in our ability to respond to you. Read below for instructions on how to apply through our website.1br Second Floor Apartment for rent!Unit: 166 BApply To: Mountain View CommunityRent: $1175/moBeds/Baths: 1 beds 1 bathSize: 500 square feetPets: Cat & Dog friendly, all animals must be

  166 N Branch St, Bennington, VT 05201
• 

  

  /20

  $260,000 Sold Jul 14, 2025

  • 1,080 Sq Ft
  • $241/SF
  • 54 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  42 Center St, Bennington, VT 05201

  Charming and cozy 2-Bedroom, 2-Bath Ranch with expansion potential in a quiet, sought-after neighborhood just minutes from downtown and local amenities. With its inviting single-level layout, beautiful hardwood floors, and spacious great room, this home offers comfortable living with timeless appeal.The full walk-out basement adds incredible potential—already partially finished with a

  Faith Rhodes Maple Leaf Realty

  42 Center St, Bennington, VT 05201
• 

  

  /38

  Est $627,715 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft

  3347 West Rd, Bennington, VT 05201

  3347 West Rd, Bennington, VT 05201
• 

  

  /39

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft

  139 Mckinley St, Bennington, VT 05201

  Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (607) 437-6795

  139 Mckinley St, Bennington, VT 05201
• 

  

  /17

  $1,275 per month

  • 2 Beds
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  18 Main St Unit A, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit A, North Bennington, VT 05257
• 

  

  /27

  $1,255,000 Sold Jul 14, 2025

  • 1,799 Sq Ft
  • $698/SF
  • 83 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2015

  1424 West Rd, Manchester Center, VT 05255

  Luxurious Guest House on 16.9 Acres with Unmatched Views and Custom Features. Nestled on nearly 17 acres of pristine land off Manchester West Road, this high-end guest house offers breathtaking panoramic views of the Green Mountains and Mt. Equinox. Designed with a perfect blend of comfort and elegance while you build you dream home, the home features custom carpentry throughout, showcasing

  Andy Reed Four Seasons Sotheby's Int'l Realty

  1424 West Rd, Manchester Center, VT 05255
• 

  

  /37

  Est $557,931 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 2,579 Sq Ft

  70 Flynn Hollow Rd, Sunderland, VT 05250

  70 Flynn Hollow Rd, Sunderland, VT 05250
• 

  

  /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
• 

  

  /20

  $2,900 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  938 Hapgood Pond Rd, Peru, VT 05152

  Property Id: 1458793Bright, 4 BR 2/1/2 ba Spacious House minutes from Bromley Mountain in Peru and Hapgood Pond Recreation Area: Perfect for hiking, with Sandy beach in the State Forest. Close to Manchester, VT Orvis fly-fishing school, shops and restaurants. Vaulted Post and Beam ceilings, open floor plan, mahogany wood floors on private wooded lot along a babbling brook. Main living

  938 Hapgood Pond Rd, Peru, VT 05152
• 

  

  /37

  $895,000 Sold Jul 11, 2025

  • 1,949 Sq Ft
  • $459/SF
  • 40 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  505 Powderhorn Rd, Manchester Center, VT 05255

  THE SECRET IS OUT..... STORY BOOK CHARM ON POWDERHORN ROAD!!Timeless, cozy and elegant mixed with a touch of Vintage allure and just minutes from town/village.Nestled in on over two acres, this stunning home is move-in ready and full of thoughtful updates. Designed by award-winning interior designer Joshua Smith, this home built in the seventies was reimagined to evoke country cottage charm

  Sunny Breen Josiah Allen Real Estate, Inc.

  505 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /33

  Est $475,724 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,020 Sq Ft

  885 Mad Tom Rd, East Dorset, VT 05253

  885 Mad Tom Rd, East Dorset, VT 05253
• 

  

  /16

  $145,000

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  755 Main St, Bennington, VT 05201

  Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 444-8936

  755 Main St, Bennington, VT 05201
• 

  

  /38

  $291,065 Sold Jul 11, 2025

  • 1,736 Sq Ft
  • $168/SF
  • 66 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1946

  121 Fillmore St, Bennington, VT 05201

  Welcome to this newly renovated Cape nestled in a desirable downtown Bennington neighborhood. This spacious home offers four bedrooms and two full bathrooms, including a first floor primary suite for added comfort and convenience.The brand new galley kitchen features gorgeous cabinetry, tile flooring, and energy efficient appliances perfect for modern living. A dedicated dining room

  Brooke Thomson Drew Mahar McCarthy Real Estate

  121 Fillmore St, Bennington, VT 05201
• 

  

  /27

  Est $261,686 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,941 Sq Ft

  239 Breezy Acres Dr, Vernon, VT 05354

  239 Breezy Acres Dr, Vernon, VT 05354
• 

  

  /46

  $895,000

  • 5 Beds
  • 2 Baths
  • 2,424 Sq Ft

  2 Cold Spring Rd, North Bennington, VT 05257

  Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8434

  2 Cold Spring Rd, North Bennington, VT 05257
• 

  

  /39

  $825,000 Sold Jul 11, 2025

  • 3,002 Sq Ft
  • $275/SF
  • 63 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1958

  2844 Main St, Manchester, VT 05254

  Modern Vermont Living in Classic Cape Cod StyleManchester Village | 4 Beds | 3.5 Baths | 3,000 Sq Ft | 9.58 AcresWelcome to your Vermont dream home, a perfect fusion of timeless charm and updated comfort nestled in the heart of Manchester Village. Set on nearly 10 acres with panoramic easterly views of the Green Mountains, this 3,000 sq ft Cape Cod-style home offers the lifestyle

  David Halligan Four Seasons Sotheby's Int'l Realty

  2844 Main St, Manchester, VT 05254
• 

  

  /24

  Est $265,399 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,248 Sq Ft

  382 B Hill Rd, Pownal, VT 05261

  382 B Hill Rd, Pownal, VT 05261
• 

  

  /60

  $2,600,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 5,559 Sq Ft

  1640 3 Maple Dr, Manchester, VT 05255

  Stunning, newly constructed 5,560 SF Architect Designed Cape with attached garage/barn that is Intelligently Efficient in every detail. Views over the open 4 acre parcel frames the idyllic Owls Head, Green Peak, Knee Top, & Dorset Peak in Dorset. Wide Plank flooring transitions beautifully throughout the living areas with porcelain stone tile in the kitchen, mudroom, laundry and baths. The

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 808-6386

  1640 3 Maple Dr, Manchester, VT 05255
• 

  

  /53

  $1,388,000 Sold Jul 11, 2025

  • 3,430 Sq Ft
  • $405/SF
  • 92 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2005

  1325 Barnumville Rd, Manchester Center, VT 05255

  Discover impeccable craftsmanship and contemporary charm at 1325 Barnumville Road in the heart of Manchester, Vermont. This immaculate home is perfectly situated on a spacious lot with sweeping mountain views—offering peace, privacy, and proximity to all the best of Southern Vermont.Step inside to a bright, airy interior filled with natural light, high ceilings, and a thoughtfully

  Christiane Carroccio TPW Real Estate

  1325 Barnumville Rd, Manchester Center, VT 05255

Showing Results 121 - 160, Page 4 of 18