Bennington County, VT Homes

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  /50

  $650,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  55 Monument Ave, Bennington, VT 05201

  Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 849-4742

  55 Monument Ave, Bennington, VT 05201
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  /40

  $11,300 per month

  • 5 Beds
  • 3 Baths
  • 4,432 Sq Ft
  • House for Rent

  303 W View Estates, Manchester, VT 05255

  Gorgeous 4,432 Square Foot - 5 bedroom, 3 bath Log Home in the Heart of Manchester and the Green Mountains! You won't find a better equipped, more spacious and luxury home, located in one of the best Winter and Summer vacation spots in Vermont. 1st Floor boasts a beautiful great room with cathedral ceiling, stone fireplace seamlessly flows into an open-concept kitchen/dining area. Great for

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 300-4671

  303 W View Estates, Manchester, VT 05255
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  /54

  $460,000 Sold Dec 03, 2025

  • 1,394 Sq Ft
  • $330/SF
  • 4 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  78 Farm Rd Unit A3, Peru, VT 05152

  SLOPESIDE at Bromley Village...Ski-in/Ski-out to and from the Bennington House or take the Plaza chairlift to this coveted location! This 3-Level, 2 Bedroom + Loft, 1-1/2 Bathroom Townhouse is bright and cheery w/ vaulted ceilings in the Living room w/ a brick, wood-burning Fireplace, which steps out to the sun-filled Deck! The combination Main Living area also features an updated Kitchen w/ bar

  Dylan Gage Bromley Real Estate

  78 Farm Rd Unit A3, Peru, VT 05152
• 

  

  

  /22

  Est $278,890 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,048 Sq Ft

  494 Atwood Dr, Pownal, VT 05261

  494 Atwood Dr, Pownal, VT 05261
• 

  

  

  /39

  $299,000 Pending

  • 2 Beds
  • 1 Bath
  • 989 Sq Ft

  78 Farm Rd Unit E, Peru, VT 05152

  Beautifully updated two bedroom TRAILSIDE condo in the Bennington House in Bromley Village. Ski on and off from your backyard with direct access to the Plaza chairlift! Summertime activities abound at Bromley Adventure Park and in all directions from your very own jumping off point in the heart of "Manchester and the Mountains." Enjoy local dining and Apres Ski just moments away at the revamped

  

  Beth Vickers

  Vermont Real Estate Company

  (802) 481-3679

  78 Farm Rd Unit E, Peru, VT 05152
• 

  

  /25

  $3,200 per month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  78 Franklin Rd, Manchester, VT 05255

  AVAILABLE NOW! WINTER RENTAL: '25/'26 As the seasons change, this charming older home in the heart of Manchester Village is ready to welcome you. With its unique traditional elements, this fully furnished home is a perfect retreat for the Winter Season.Bon appetit! Located just a couple of blocks from Manchester's Restaurant Row...Available November 15th '25, through

  

  Kristin Comeau

  TPW Real Estate

  (802) 300-3752

  78 Franklin Rd, Manchester, VT 05255
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  /7

  $120,000 Sold Dec 01, 2025

  • Land
  • 46.89 Acres
  • $2,559 per Acre

  • 49 Days On Market

  0 Klondike Rd Unit 5062056, Stamford, VT 05352

  If you are looking for a big beautiful private piece of Vermont where you can build your getaway camp, where you can cut trails in, ride, hunt, shoot, have your friends over for a bonfire and a few brews, this may be the place for you. This is a rectangular nearly 46 acre piece waiting for your creative genius and some hard work and sweat - in the invigorating Vermont woods!. This is in a forest

  Duncan Honig Maple Leaf Realty

  0 Klondike Rd Unit 5062056, Stamford, VT 05352
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  /40

  Est $999,019 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,031 Sq Ft

  276 Wilcox Hollow Rd, Sandgate, VT 05250

  276 Wilcox Hollow Rd, Sandgate, VT 05250
• 

  

  /26

  $295,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft

  235 Elm St Unit 3, Bennington, VT 05201

  This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

  

  Erica Hale

  Ridgeline Real Estate

  (802) 210-4437

  235 Elm St Unit 3, Bennington, VT 05201
• 

  

  /16

  $5,500 per month

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Townhouse for Rent

  556 Equinox On the Battenkill Unit J-11, Manchester, VT 05254

  SUMMER RENTAL 2026 - EQUINOX ON THE BATTENKILL There is so much to offer! This sought-after four-bedroom EOB townhome is now available for a summer seasonal rental. EOB amenities include tennis, pickleball, pool, and clubhouse privileges. Enjoy all that Manchester and the Mountains have to offer. We have the Manchester Music Festival, The Vermont Summer Festival, the Dorset Theatre, the

  

  Kristin Comeau

  TPW Real Estate

  (802) 348-2094

  556 Equinox On the Battenkill Unit J-11, Manchester, VT 05254
• 

  

  /21

  $815,000 Sold Dec 01, 2025

  • 4,213 Sq Ft
  • $193/SF
  • 152 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1973

  262 Powderhorn Rd, Manchester Center, VT 05255

  Stunning Contemporary Retreat with Indoor Pool on Nearly 2 AcresWelcome to this beautiful 5-bedroom, 5-bath contemporary home nestled on a sunny 1.9+/- acre lot. Designed for both comfort and style, this expansive residence features a 16' x 32' heated indoor swimming pool, perfect for year-round enjoyment.Originally built in 1973 and extensively renovated in 2000, the home blends timeless

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  262 Powderhorn Rd, Manchester Center, VT 05255
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  /32

  Est $1,319,653 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,507 Sq Ft

  40 Nims, Dorset, VT 05251

  40 Nims, Dorset, VT 05251
• 

  

  /17

  $270,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  239 - 241 Elm St, Bennington, VT 05201

  Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

  

  Erica Hale

  Ridgeline Real Estate

  (802) 278-6021

  239 - 241 Elm St, Bennington, VT 05201
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  /17

  $2,300 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  3789 Dorset West Rd, Dorset, VT 05251

  YEAR ROUND Rental - Unfurnished One-Bedroom Super cool one-bedroom unfurnished renovated Carriage House perched high above the Dorset West Road. Just a short distance from the Dorset Inn, the Dorset Theatre, the Dorset Field Club, and the beloved Dorset Union Store. UTILITIES INCLUDED. Use of the 1-car GARAGE also included in the rent. The Landlord requires references, background, and

  

  Kristin Comeau

  TPW Real Estate

  (802) 423-3173

  3789 Dorset West Rd, Dorset, VT 05251
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  /59

  $489,105 Sold Dec 01, 2025

  • 1,828 Sq Ft
  • $268/SF
  • 127 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  69 Hillvale Dr, Manchester Center, VT 05255

  This is a wonderful craftsman style ranch in a great location right in the heart of Manchester, in the sunny Hillvale neighborhood. It offers views to Mt. Equinox and is walking access to all Manchester's amenities. Four bedrooms, two full baths, updated kitchen with stainless appliances and granite counter tops, the dining room's french door opens on to an expansive deck for BBQ's and

  Robert Sabol Wohler Realty Group

  69 Hillvale Dr, Manchester Center, VT 05255
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  /40

  Est $897,833 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,774 Sq Ft

  67 Coventry Ln, Manchester Center, VT 05255

  67 Coventry Ln, Manchester Center, VT 05255
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  /33

  $239,000 Under Contract

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

  2460 East Rd, Shaftsbury, VT 05262

  Well-maintained 3-bedroom, 2-bath ranch-style home on a 1-acre lot at the outskirts of town. Offering 1,120 square feet of single-level living space, this property features an efficient floor plan with an eat-in kitchen, comfortable living room, and three bedrooms including a primary with half bath. The home is clean and functional, with an opportunity for cosmetic updates to suit your style.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 474-4448

  2460 East Rd, Shaftsbury, VT 05262
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  /38

  $2,995 per month

  • 2 Beds
  • 2.5 Baths
  • 1,875 Sq Ft
  • House for Rent

  5451 River Rd, Arlington, VT 05250

  LUXURY HOUSE RENTAL ABOVE THE BATTENKILL!Winter Ski Season (starting 01/03/26) or 6 months, through 06/30/26 Experience the timeless beauty of Southern Vermont in this exceptional rental perched above the scenic Battenkill. Just six miles to Arlington village along Route 313, the peaceful Battenkill Valley unfolds a rare, unspoiled gem that captures the essence of the Vermont lifestyle.

  

  Kristin Comeau

  TPW Real Estate

  (802) 689-8318

  5451 River Rd, Arlington, VT 05250
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  /58

  $975,000 Sold Nov 27, 2025

  • 3,500 Sq Ft
  • $279/SF
  • 38 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1987

  20 Jamie Ln, Winhall, VT 05340

  Get ready for ski season! Plenty of space for the whole family. Set up for fun with two living rooms, a hot tub and barrel sauna. Great rental history. Owner is Listing Broker.

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
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  /34

  Est $521,913 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,586 Sq Ft

  32 County Rd, Stamford, VT 05352

  32 County Rd, Stamford, VT 05352
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  /36

  $275,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft

  61 Autumn Acres, Bennington, VT 05201

  Welcome home to this charming single level ranch in a peaceful, friendly neighborhood where neighbors still wave hello and lend a cup of sugar. This home offers easy single-level living with three bedrooms, one full bath, and first floor laundry.Step inside to discover beautiful hardwood floors throughout most of the home, currently covered with carpeting that can easily be removed no nails

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 802-8871

  61 Autumn Acres, Bennington, VT 05201
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  /14

  $2,275 per month

  • 2 Baths
  • 1,120 Sq Ft
  • Property for Rent

  343 Dewey St, Bennington, VT 05201

  Well-maintained provider office space available for lease, offering approx. 1,120 sq ft. Layout includes a waiting room with half bath, reception area, 2 operatories (or rooms), private office, and an additional half bath. Shared kitchen with the adjacent unit. Staff enjoy a separate entrance and designated parking, distinct from the public entry and lot. Rent includes electric, heat/AC,

  

  Peter West

  BISHOP WEST REAL ESTATE

  (802) 347-1295

  343 Dewey St, Bennington, VT 05201
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  /20

  $500,000 Sold Nov 26, 2025

  • 1,920 Sq Ft
  • $260/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1986

  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
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  /40

  Est $2,791,500 Not Listed For Sale

  • 5 Beds
  • 7.5 Baths
  • 8,700 Sq Ft

  440 Marcia Ln, Dorset, VT 05251

  440 Marcia Ln, Dorset, VT 05251
• 

  

  /15

  $915,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,898 Sq Ft

  3343 Main St, Manchester, VT 05255

  Steps from the heart of Manchester Village private 5 pastoral acres offer an unique opportunity while enjoying exceptional privacy and sweeping views of Equinox Mountain to the west. The Village, with marble walkways, underground power and electrified gas lanterns, undeniably creates a peaceful approach from a lengthy driveway back to this special residence buffered from the busy world, yet

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 808-6127

  3343 Main St, Manchester, VT 05255
• 

  

  /56

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • House for Rent

  397 Powderhorn Rd, Manchester Center, VT 05255

  SPRING/SUMMER RENTAL: Charming newly renovated ranch with 3 bedrooms, 2 baths is the perfect summer rental, offering a cozy and inviting atmosphere! Conveniently located close to town for easy access to shops and dining. Enjoy a fenced-in backyard with a deck, perfect for grilling and outdoor relaxation. The kitchen and living room are located on the first floor, along with the spacious primary

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 729-7527

  397 Powderhorn Rd, Manchester Center, VT 05255
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  /60

  $625,000 Sold Nov 26, 2025

  • 2,034 Sq Ft
  • $307/SF
  • 56 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1885

  3 Short Rd, Bondville, VT 05340

  Charming Vermont Homestead: Ideal for Ski Lovers or Those Seeking a Homesteading Lifestyle Modern Updates Meet Classic Vermont Charm: Extensive updates over the years, including improved heating, plumbing and septic systems, radiant floors in the great room, renovated kitchen, new appliances, and updated bathrooms. Experience convenience and comfort while preserving the character of this original

  Mike England Michael England Real Estate

  3 Short Rd, Bondville, VT 05340
• 

  

  /22

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,708 Sq Ft

  16 Clark Rd, Rupert, VT 05776

  16 Clark Rd, Rupert, VT 05776
• 

  

  /60

  $985,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,215 Sq Ft

  92 Coventry Ln, Manchester Center, VT 05255

  Coventry House - Offered For The First Time! Built in 1972, the home was thoughtfully designed by local architect Charles "Bud" Lynch in collaboration with the owners. This custom-built home blends timeless design with natural surroundings. Offering a country kitchen, 4 bedrooms and 3+ vintage baths reflecting the 70’s era focus on color, natural materials, and open floor plans all on one level

  

  Kristin Comeau

  TPW Real Estate

  (802) 424-8410

  92 Coventry Ln, Manchester Center, VT 05255
• 

  

  /31

  $6,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  294 Green Peak Orchard S, Dorset, VT 05253

  Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-7034

  294 Green Peak Orchard S, Dorset, VT 05253
• 

  

  /16

  $130,000 Sold Nov 25, 2025

  • 1,290 Sq Ft
  • $101/SF
  • 45 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1966

  76 Harvest Hills Dr, North Bennington, VT 05257

  Single level living with 3 bedrooms and 1 bath home. Attached 2 car garage with direct access to the house. Nice level yard for outdoor activities and gardening. Full basement has great storage and possible additional living space. Spend quiet evening in the screened back porch that looks out over open field.

  Susan Bellville Bellville Realty

  76 Harvest Hills Dr, North Bennington, VT 05257
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  /26

  Est $355,974 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  629 Glen Rd, Peru, VT 05152

  629 Glen Rd, Peru, VT 05152
• 

  

  /28

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  72 Sawmill Rd, Pownal, VT 05261

  Experience the perfect blend of comfort and functionality in this modern doublewide, built in 2022, offering easy one-level living with upgraded insulation for energy efficiency. Features newer sitework with a drilled well and engineered septic system designed and permitted for 2 bedrooms, meaning 4-person occupancy. This spacious home features three bedrooms, allowing for versatile options using

  

  Gary Fuls Jr

  RE/MAX Transitions

  (802) 722-7730

  72 Sawmill Rd, Pownal, VT 05261
• 

  

  /18

  $4,500 per month

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  191 Forest Mountain Rd, Peru, VT 05152

  WELCOME TO PERU MOUNTAIN LODGE... Now Available For Your Vermont Summer '25 Vacation! Don't Let This One Get away... Cozy open living area with four Bedrooms. Two bedrooms on the main level, the Main Suite in the loft above, and a fourth bedroom in the finished walk-out basement. This home boasts a cathedral ceiling, an updated cooks kitchen, and a striking stone fireplace with two

  

  Kristin Comeau

  TPW Real Estate

  (802) 889-8948

  191 Forest Mountain Rd, Peru, VT 05152
• 

  

  /60

  $534,000 Sold Nov 24, 2025

  • 3,637 Sq Ft
  • $147/SF
  • 111 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  272 Oak Hill Rd, Shaftsbury, VT 05262

  BRAND NEW ROOF!! RECENT PRICE REDUCTION TOO! Built in 2001, this stunning contemporary home sits on just under 8 peaceful acres and offers a perfect blend of space, light, and comfort. The grand two-story living room features soaring ceilings and a cozy pellet stove, creating an impressive focal point. The first floor offers a spacious primary suite for ultimate convenience, along with a

  Faith Rhodes Maple Leaf Realty

  272 Oak Hill Rd, Shaftsbury, VT 05262
• 

  

  /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
• 

  

  /58

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,284 Sq Ft

  1098 W Sandgate Rd, Arlington, VT 05250

  Private, Quiet, and Solidly built timeless Post & Beam 2,200 SF residence on 10.05 acres offering South and Westerly sunlight all day long ending with lovely sunsets! Overlooking a spring fed pond and a mix of open terrain and deciduous slope side forest with trails. The house offers main level all open 40' X 32' great room living / dining/ kitchen with a massive center 2.5 story stone fireplace.

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 992-1723

  1098 W Sandgate Rd, Arlington, VT 05250
• 

  

  /37

  $8,000 per month

  • 3 Beds
  • 3 Baths
  • 1,980 Sq Ft
  • House for Rent

  3093 Route 30, Dorset, VT 05251

  Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 255-8729

  3093 Route 30, Dorset, VT 05251
• 

  

  /29

  $535,000 Sold Nov 24, 2025

  • 1,850 Sq Ft
  • $289/SF
  • 72 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  93 Mountain Ridge Rd, Peru, VT 05152

  Looking for a cozy Cape-style home near skiing, top-rated schools, and year-round outdoor activities? This charming yet modern residence, just minutes from Bromley, Magic, and Stratton Mountains and close to Londonderry and Manchester, offers the perfect blend of solid construction and timeless character. Built from the ground up in 2002, it features wide pine floors with radiant heat throughout,

  Andy Reed Four Seasons Sotheby's Int'l Realty

  93 Mountain Ridge Rd, Peru, VT 05152
• 

  

  /36

  Est $732,832 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,104 Sq Ft

  469 Laclair Rd, Shaftsbury, VT 05262

  469 Laclair Rd, Shaftsbury, VT 05262

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