Bennington County VT Houses for Sale

/28
$750,000
- 3 Beds
- 2 Baths
- 2,610 Sq Ft
3622 Dorset West Rd, Dorset, VT 05251

Unique Dorset West Road offering....This rare opportunity beckons creativity, craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts

Sunny Breen Josiah Allen Real Estate, Inc.

3622 Dorset West Rd, Dorset, VT 05251
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/28
$825,000
- 5 Beds
- 2 Baths
- 3,500 Sq Ft
20 Bishop Rd, Searsburg, VT 05363

Absolutely amazing long range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton, from this beautiful 2020 Moosehead log home. This home sits on 7+ acres with easy access to VAST snowmobile trails, as well as your own property to loop on, but still only a short drive to ski resorts, lakes, and other Vermont destinations. The home has a gorgeous open floor

Adam Palmiter Berkley & Veller Greenwood/Dover

20 Bishop Rd, Searsburg, VT 05363
/28
$849,000 New Construction
- 3 Beds
- 2.5 Baths
- 1,980 Sq Ft
40 Jameson Flats Unit D, Manchester, VT 05255

New Construction in the Heart of Manchester – Showings Begin April 15This beautifully designed 3-bedroom, 2.5-bath freestanding home (with potential for a 4th bedroom) offers modern comfort, energy efficiency, and fine craftsmanship just steps from downtown Manchester. The open-concept main level features a chef’s kitchen with an eat-in island, ample storage, stainless steel appliances,

Britt Wohler Wohler Realty Group

40 Jameson Flats Unit D, Manchester, VT 05255
/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
/47
$425,000
- 3 Beds
- 1 Bath
- 1,490 Sq Ft
231 Tudor Rd, Arlington, VT 05250

Perfect weekend getaway or full time home. Private cape cod 1.5 story home with three bedrooms on 8.10 acres, offers mountain views, privacy, and is in excellent condition. Recent Improvements include: thermopane windows and doors, replacement of furnace & hot water heater, kitchen appliances, and added exterior water shut off valves. The home has forced hot air heating (oil), a drilled well,

David Halligan Four Seasons Sotheby's Int'l Realty

231 Tudor Rd, Arlington, VT 05250
/53
$399,000
- 5 Beds
- 3 Baths
- 2,568 Sq Ft
100 McCarthy Acres, North Bennington, VT 05257

Almost lake front! Come for the space, stay for the location! This 2,500+ sq. ft. home offers five bedrooms, three full bathrooms, a large home office in the finished basement, and an additional 250 sq. ft. bonus room off one of the upstairs bedrooms. The owners converted the original garage into a 600 sq. ft. primary bedroom (heated and cooled with an efficient mini-split and separated into a

Nicholas Charest Maple Leaf Realty

100 McCarthy Acres, North Bennington, VT 05257
/32
$398,000
- 3 Beds
- 2 Baths
- 1,337 Sq Ft
78 Carbonti Cir, Arlington, VT 05250

Easy single-level living! Welcome to Arlington's Carbonti Circle. Updated three-bedroom, two-bath ranch nestled in a quiet neighborhood setting just minutes from downtown Arlington and the famous Battenkill River. Set on a .30-acre lot, this home offers the perfect blend of comfort, character and convenience. Experience easy living in this beautifully maintained single-level home! Enjoy a

Margretta Fischer Wohler Realty Group

78 Carbonti Cir, Arlington, VT 05250
/41
$365,000
- 2 Beds
- 2 Baths
- 1,542 Sq Ft
509 Thompson Pond Rd, Pownal, VT 05261

Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

Kelley Mccarthy Mahar McCarthy Real Estate

509 Thompson Pond Rd, Pownal, VT 05261
/23
$595,000
- 4 Beds
- 2 Baths
- 2,139 Sq Ft
62 Dorset Village Ln, Dorset, VT 05251

Charming Home in Quaint Dorset Village SettingNestled on a gentle knoll above the heart of Dorset Village, this delightful home offers the perfect blend of privacy and convenience. Just a short stroll to village amenities and mere moments from the renowned Pinnacle hiking trails, the location is ideal for those seeking both community charm and outdoor adventure.Brimming with

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

62 Dorset Village Ln, Dorset, VT 05251
/37
$2,400,000
- 5 Beds
- 4.5 Baths
- 3,252 Sq Ft
115 Benson Fuller Dr, Jamaica, VT 05343

Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

Carrie Mathews Winhall Real Estate

115 Benson Fuller Dr, Jamaica, VT 05343
/41
$335,000
- 3 Beds
- 1.5 Baths
- 1,682 Sq Ft
23 Robinson Ave, Bennington, VT 05201

Nestled on a quiet street just moments from the golf course, this beautiful two-story brick home offers timeless charm and modern updates. The inviting front porch and lush perennial gardens set the tone for this well-loved property, which also features a fenced-in yard, a small outbuilding, a brand-new shed, and a peaceful backyard water feature. Inside, you'll find 3 bedrooms and 1.5 baths with

Kelley Mccarthy Mahar McCarthy Real Estate

23 Robinson Ave, Bennington, VT 05201
/36
$498,000
- 3 Beds
- 2 Baths
- 1,671 Sq Ft
6 Dwyers Camp Rd, Shaftsbury, VT 05262

Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

Lori Hurley Four Corner Properties LLC

6 Dwyers Camp Rd, Shaftsbury, VT 05262
/37
$395,000
- 2 Beds
- 2 Baths
- 2,248 Sq Ft
106 Millbrook Rd, Arlington, VT 05250

Nestled in the hills of Vermont just 5 minutes from Manchester, this beautifully maintained 2-bedroom, 2-bath home gives off a modern vibe with cedar shake siding and standing seam roof. Set on 2.7 acres of lush, rolling land, the property features mature maple trees and a babbling brook. Dip your toes or cast your line into Mill Brook a year-round mountain stream. The home is set up away from

Margretta Fischer Wohler Realty Group

106 Millbrook Rd, Arlington, VT 05250
/46
$399,500
- 2 Beds
- 2 Baths
- 1,564 Sq Ft
447 Farm Rd, Arlington, VT 05250

Tucked away on a quiet cul-de-sac, this charming cedar shake Cape offers the perfect blend of warmth, character, and privacy. With over 1,500 square feet of finished space, this cottage features wide pine floors, an inviting fireplace, and a rich, soothing color palette. The thoughtfully designed layout includes a spacious living/dining room, kitchen with pantry and unique hardware, and on each

Jenifer Prouty Hoffman Hoffman Real Estate

447 Farm Rd, Arlington, VT 05250
/42
$439,000
- 4 Beds
- 1.5 Baths
- 1,728 Sq Ft
639 Wiley Mountain Rd, Readsboro, VT 05350

Updated mountain home on 13.63 flat, usable acres bordering the Green Mountain National Forest and offering an outdoor paradise in every season. Tucked at the top of a quiet road, this property blends comfort, space, and access to Vermont’s best year-round recreation.Inside, you’ll find new hardwood floors, a renovated kitchen and bathrooms, a main-level bedroom, a full bath, main-level

Melissa Nebelski Skihome Realty

639 Wiley Mountain Rd, Readsboro, VT 05350
/55
$2,225,000
- 4 Beds
- 4.5 Baths
- 5,000 Sq Ft
16 Hunter Ridge Rd, Bondville, VT 05340

Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

16 Hunter Ridge Rd, Bondville, VT 05340
/31
$270,000
- 2 Beds
- 1 Bath
- 836 Sq Ft
473 South Rd, East Arlington, VT 05252

This is an exceptional opportunity at this price point as a starter home for individuals or young families. This quaint craftsman home sits in the town of Sunderland and is the ideal location situated between Manchester and Bennington, Vermont. It is a 2.5 mile drive to the village of Arlington. This location boasts School Choice for families, to include Burr and Burton Academy. A mudroom

Robert Sabol Wohler Realty Group

473 South Rd, East Arlington, VT 05252
/45
$3,600,000
- 4 Beds
- 3.5 Baths
- 2,338 Sq Ft
198 Church St, Dorset, VT 05251

Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems

Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

198 Church St, Dorset, VT 05251
/19
$199,900
- 3 Beds
- 1 Bath
- 952 Sq Ft
42 Colvin Ave, Shaftsbury, VT 05262

Discover comfortable single-level living in this well-maintained ranch-style home, perfectly situated on a 0.16-acre lot. Has 952 square feet, this residence offers three bedrooms and one full bathroom—ideal for families, first-time buyers, or those looking to downsize without compromising on style or functionality.Step inside to be greeted by hardwood floors that flow seamlessly

Timothy Corcoran Mahar McCarthy Real Estate

42 Colvin Ave, Shaftsbury, VT 05262
/38
$565,000
- 4 Beds
- 3 Baths
- 2,073 Sq Ft
2588 Vermont 11, Peru, VT 05152

On a gentle rise surrounded by 7.5 acres of meadows and woodland, this Vermont style ranch subtly blends an appealing rustic charm with contemporary features. The current owners purchased the property in 2021 for family and friends and installed a new wastewater system, new furnace, new roof section, new appliances. The rough sawn clapboard exterior delineates the enduring character of the house.

Diana Stugger Four Seasons Sotheby's Int'l Realty

2588 Vermont 11, Peru, VT 05152
/34
$289,900
- 3 Beds
- 2.5 Baths
- 1,810 Sq Ft
3530 Vt Route 346, Pownal, VT 05261

This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

Matt Waddington Hoffman Real Estate

3530 Vt Route 346, Pownal, VT 05261
/25
$305,000
- 3 Beds
- 2.5 Baths
- 1,888 Sq Ft
120 Albe Dr, Bennington, VT 05201

Comfortable, convenient and close to downtown Bennington and all its amenities. Built in 2001, in a quiet neighborhood, the home features 3 bedrooms and 2.5 baths,, which includes a primary suite with its own bath. The first floor offers a spacious eat-in kitchen with washer and dryer efficiently installed in a large closet. The kitchen also has glass doors that open to private deck and a level

Ann Greenwood Alton + Westall Real Estate Agency, LLC

120 Albe Dr, Bennington, VT 05201
/12
$120,000
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
242 North Rd, East Arlington, VT 05252

Calling all investors! This property is situated on a private 1-acre lot in sought-after Sunderland, featuring a calming stream running behind the property. It includes an oversized detached garage with a second floor above that could be converted into additional living space. Close proximity to Manchester, Bromley Mountain, and Stratton Mountain. Sunderland offers school choice for grades

Matt Waddington Hoffman Real Estate

242 North Rd, East Arlington, VT 05252
/38
$1,200,000
- 5 Beds
- 1 Bath
- 2,228 Sq Ft
395 King Hill Rd, Readsboro, VT 05350

Stunning Mountain & Meadow Views, 135 acres of pristine rolling meadows overlook the Harriman Reservoir, sits a meticulously maintained c. 1770 5 bedroom farmhouse. Welcome to King Hill Farm, this idyllic Vermont homestead has been in the King family for multiple generations. No restrictions, enjoy the peace and quiet of a slight breeze, blue skies and bird songs. Remarkable, one of a kind

Margretta Fischer Wohler Realty Group

395 King Hill Rd, Readsboro, VT 05350
/33
$525,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
3 Strattonwald Rd, Winhall, VT 05340

Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you’ll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

Robin Apps Four Seasons Sotheby's Int'l Realty

3 Strattonwald Rd, Winhall, VT 05340
/22
$995,000
- 4 Beds
- 3 Baths
- 3,659 Sq Ft
445 Canterbury Rd, Manchester Center, VT 05255

Nestled in one of Vermonts most sought-after locations, this exceptional Colonial home boasts sweeping panoramic views of the Green Mountain National Forest and the picturesque Northshire Valley, offering a peaceful and private retreat just minutes from the vibrant town of Manchester. Perfectly oriented to capture stunning morning sunrises, this 2.8-acre property provides the ideal balance of

Andy Reed Four Seasons Sotheby's Int'l Realty

445 Canterbury Rd, Manchester Center, VT 05255
/45
$355,000
- 4 Beds
- 1 Bath
- 1,680 Sq Ft
19 Royal St, North Bennington, VT 05257

Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

Lindsey Martin Maple Leaf Realty

19 Royal St, North Bennington, VT 05257
/26
$255,000
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
2899 W Sandgate Rd, Arlington, VT 05250

Nestled in the green mountains, come enjoy this three-bedroom, two-bath colonial on half an acre. Take in the beautiful meadow and mountain views from the spacious deck. Listen to the sounds of birds and the babbling brook in this lovely private location. The sunny level lot offers plenty of garden space and a generous shed for all your gardening needs. The first floor offers a spacious open

Margretta Fischer Wohler Realty Group

2899 W Sandgate Rd, Arlington, VT 05250
/54
$1,995,000
- 3 Beds
- 2.5 Baths
- 3,451 Sq Ft
139 Prospect St, Manchester, VT 05254

Step into Vermont’s rich history with this beautifully reimagined 3 bedroom, 3,451 sq ft home in the heart of Manchester Village, just steps from over 900 acres of scenic trails at the base of Equinox Mountain. Originally built in 1934 as a historic residence, the home offers a rare blend of timeless character and modern comfort. A marble walkway leads to classic Dutch doors, while a peaceful

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

139 Prospect St, Manchester, VT 05254
/38
$1,995,000
- 5 Beds
- 3 Baths
- 6,323 Sq Ft
2589 W Sandgate Rd, Arlington, VT 05250

Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons

Dia Jenks LandVest, Inc/Woodstock

2589 W Sandgate Rd, Arlington, VT 05250
/38
$980,000
- 4 Beds
- 3.5 Baths
- 4,104 Sq Ft
25 Benson Fuller Dr, Jamaica, VT 05343

Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

Robin Apps Four Seasons Sotheby's Int'l Realty

25 Benson Fuller Dr, Jamaica, VT 05343
/23
$4,000,000
- 5 Beds
- 2 Baths
- 3,347 Sq Ft
15 Wind Hill Rd, Manchester Center, VT 05255

At the heart of this remarkable 136-acre property in Manchester Center, Vermont, are two distinct historic homes, each telling a story of the land’s deep roots in the Beattie-Forrest family, who have stewarded it for over a century.The original farmhouse, built circa 1800, offers five bedrooms and two baths, with timeless details including a vintage kitchen and hand-hewn timber framing.

Paul Carroccio TPW Real Estate

15 Wind Hill Rd, Manchester Center, VT 05255
/44
$100,000
- 5 Beds
- 1 Bath
- 1,952 Sq Ft
273 Union St, Bennington, VT 05201

This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

Catherine Cairns Maple Leaf Realty

273 Union St, Bennington, VT 05201
/34
$500,000
- 1 Bed
- 2 Baths
- 300 Sq Ft
417 Maple Hill Rd, Arlington, VT 05250

Scandinavian Timber Frame Tiny House & Grindbygg! Over 10 acres of privacy and beautiful vistas. 360 degree mountain view from this custom heartfelt build. The property includes a one bedroom tiny house complete with kitchen, gas range, wood stove, movie projector, sleeping loft and so much more. A drilled well, on demand propane hot water heater and water shed for water storage. This cozy

Margretta Fischer Wohler Realty Group

417 Maple Hill Rd, Arlington, VT 05250
/27
$374,000
- 3 Beds
- 2 Baths
- 1,333 Sq Ft
75 Forest Mountain Rd, Peru, VT 05152

Adorable 3-bedroom home on just under 2 acres with a private pond. Full of Vermont charm, this home features open living and dining areas with a cozy wood-burning fireplace and a wall of floor-to-ceiling sliders that bring in beautiful natural light. Whip up your favorite meals in the beautifully updated kitchen. Covered porches on both levels offer relaxing spots to take in the tranquil pond

Carrie Mathews Winhall Real Estate

75 Forest Mountain Rd, Peru, VT 05152
/30
$1,300,000
- 11 Beds
- 9 Baths
- 9,560 Sq Ft
3309 3321 Main St, Manchester, VT 05254

A Rare Opportunity! Introducing a historically significant gem, available for the first time in over 40 years. Set in the picturesque and highly sought after Manchester Village, this timeless estate includes a grand Main House and a charming Carriage House, each situated on its own adjoining 1.27-acre lot, totaling an expansive 2.54 park-like acres. Together, the residences offer 11 bedrooms, 6

Gregory Cutler Four Seasons Sotheby's Int'l Realty

3309 3321 Main St, Manchester, VT 05254
/43
$445,000
- 3 Beds
- 2.5 Baths
- 3,924 Sq Ft
410 Tudor Rd, Arlington, VT 05250

Triple Mountain Views! The wrap-around decks and expansive views will impress any nature lover. This home offers hardwood floors, Vermont marble countertops, and an abundance of windows and light paired with interesting architectural design. Around every turn, you will be surprised by space and contemporary architecture. Re-built in 2011, offering two bedrooms and three baths with a walk-out

Margretta Fischer Wohler Realty Group

410 Tudor Rd, Arlington, VT 05250
/31
$150,000
- 3 Beds
- 1 Bath
- 1,508 Sq Ft
109 Evergreen Dr, Bennington, VT 05201

House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

Zachary Zupan EXP Realty

109 Evergreen Dr, Bennington, VT 05201
/22
$139,000
- 4 Beds
- 1 Bath
- 1,262 Sq Ft
101 Morgan St, Bennington, VT 05201

Motivated seller.!!! Move in asd add your finishing touches to this Antique House located in Downtown on a generous corner. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being

Dan Mason Perrott Realty

101 Morgan St, Bennington, VT 05201
/41
$524,900
- 4 Beds
- 2.5 Baths
- 2,116 Sq Ft
245 Southshire Dr, Bennington, VT 05201

Nestled in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS).The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a

Ann Greenwood Alton + Westall Real Estate Agency, LLC

245 Southshire Dr, Bennington, VT 05201

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.