Bennington County VT Homes for Sale

/33
$295,000
- 4 Beds
- 2 Baths
- 1,792 Sq Ft
254 Union St, Bennington, VT 05201

Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

Cassie Barbeau Mahar McCarthy Real Estate

254 Union St, Bennington, VT 05201
/23
$360,000
- 3 Beds
- 2 Baths
- 1,590 Sq Ft
22 Carlen St, Manchester Center, VT 05255

Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

Andy Reed Four Seasons Sotheby's Int'l Realty

22 Carlen St, Manchester Center, VT 05255
/30
$389,900
- 3 Beds
- 2.5 Baths
- 2,162 Sq Ft
64 Bergblume Cir, Stamford, VT 05352

Priced to Sell - Includes Additional Building Lot!This charming 3-bedroom, 3-bath home built in 2007 offers peace, privacy, and natural surroundings. Included in the sale is a second adjoining building lot, adding value and future potential.This home is perfect for those seeking a four-season retreat. The home features abundant natural light through oversized vinyl windows and a cozy wood-burning

Pam Tworig BISHOP WEST REAL ESTATE

64 Bergblume Cir, Stamford, VT 05352
/28
$449,000
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
139 Bergwelt Ln, Readsboro, VT 05350

Charming Country Retreat with Scenic Views and Timeless Character.Welcome to your dream country escape! Nestled on a peaceful, tree-lined lane, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of rustic charm and modern comfort. Set on a spacious 3.6 acre lot, the property boasts serene views, mature gardens, and ample privacy — ideal for relaxing weekends or

Heidi Zizza Four Seasons Sotheby's Int'l Realty

139 Bergwelt Ln, Readsboro, VT 05350
/30
$349,995
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
374 Overlea Rd, North Bennington, VT 05257

A stunning three bedroom, two bath home on a wooded lot with mountain views and bordered on several sides by serene farm pastures! Just a few minutes from downtown Bennington and even closer to the village of North Bennington! Tons of natural light inside that compliments the updated kitchen and open dining / living room areas. First floor includes enclosed rear sun porch/mudroom, laundry and

Gregory Cutler Four Seasons Sotheby's Int'l Realty

374 Overlea Rd, North Bennington, VT 05257
/60
$369,900
- 0.5 Baths
- 4,220 Sq Ft
6828 Main St, Readsboro, VT 05350

Don’t miss your chance to own a piece of Vermont history in the heart of Readsboro. The iconic Readsboro General Store is now available and ready for your vision. Perfectly positioned on Main Street, just steps from the town green, this high-visibility property has long been a favorite stop for locals, visitors, and nearby trail users alike. Currently configured for mixed-use, the building

Flex Realty Group Flex Realty

6828 Main St, Readsboro, VT 05350
/17
$485,000
- 2 Beds
- 1 Bath
- 1,144 Sq Ft
1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

Lori Hurley Four Corner Properties LLC

1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
/44
$499,000
- 4 Beds
- 2 Baths
- 1,708 Sq Ft
144 Oberdorf Rd, Readsboro, VT 05350

Charming 4-Bedroom Chalet on 2 Acres in Scenic Readsboro, VermontEscape to the beauty of southern Vermont. Whether you're looking for a full-time residence or the perfect vacation getaway, this beautifully updated home offers comfort, style, and proximity to all-season recreation.Step inside to discover thoughtful upgrades throughout, including fully renovated bathrooms and a

Evan Russell Real Broker LLC

144 Oberdorf Rd, Readsboro, VT 05350
/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
/36
$399,000
- 5 Beds
- 3 Baths
- 3,118 Sq Ft
100 McCarthy Acres, North Bennington, VT 05257

Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

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
$259,000
- Land
- 18 Acres
- $14,716 per Acre
188 Cedar Ln, Peru, VT 05152

Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

Joe Castaluccio Winhall Real Estate

188 Cedar Ln, Peru, VT 05152
/18
$155,000
- 2 Beds
- 1.5 Baths
- 852 Sq Ft
432 South St Unit C6, Bennington, VT 05201

A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean

Angela Bevin Maple Leaf Realty

432 South St Unit C6, Bennington, VT 05201
/20
$225,000
- 6 Beds
- 1.5 Baths
- 2,082 Sq Ft
266 Robillard Rd, Stamford, VT 05352

SOUTHERN VERMONT!~ Great country location with over a 1/2 acre of beautiful lawns & perennial flower. Sitting porch, large kitchen with pantry opens to dining & living room. Oak hardwood floors on 1st floor. 2nd level has 4 good sized rooms & 3rd level has 2 very nice rooms & a 1/2 bath. Laundry is in basement. Basement appears to be dry. Oil boiler & wood burning furnace in the basement. Lots of

Colleen Zajac Monarch Realty

266 Robillard Rd, Stamford, VT 05352
/21
$249,000
- Land
- 3.42 Acres
- $72,807 per Acre
0 Havoc Hill, Dorset, VT 05253

Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its rugged beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel

Timothy Apps Four Seasons Sotheby's Int'l Realty

0 Havoc Hill, Dorset, VT 05253
/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
/28
$1,700,000
- 4 Beds
- 3.5 Baths
- 2,363 Sq Ft
43 Middle Ridge Rd Unit 415, Winhall, VT 05155

Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

Edwin Kevil Stratton Real Estate

43 Middle Ridge Rd Unit 415, Winhall, VT 05155
/8
$75,000
- Land
- 7 Acres
- $10,534 per Acre
272 Twenty Acre Wood Rd, Arlington, VT 05250

Enjoy views all around on this ready to build on lot of over 7 acres. The views are 180 degrees , but you don't have to drive up a steep hill to get to them. Land has been surveyed house site cleared and septic permit in place.

Andy Reed Four Seasons Sotheby's Int'l Realty

272 Twenty Acre Wood Rd, Arlington, VT 05250
/25
$459,000
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
393 Morse Hill Rd, East Dorset, VT 05253

This beautifully maintained home is now available for the first time in 40 years.On the main level, you will find a generously sized eat-in kitchen with granite countertops that opens to a dining room. There are two additional rooms on the main level: a large living room and a bedroom. The main floor also boasts French door that leads out to a spacious deck, perfect for overlooking the

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

393 Morse Hill Rd, East Dorset, VT 05253
/24
$42,000
- Land
- 0.48 Acre
- $87,500 per Acre
26 Asa's Way, Bennington, VT 05257

Walking trails, a paved road, underground utilities, and water/sewer at the street, what more could you ask for? Situated high on Asa's Way, almost a half acre of slightly sloping and level lot is ready to build on. Over 200 feet of road frontage allows for many home designs; from a hillside house that maximizes the southerly sun, to a modern bungalow perched on a flat landing, bring your ideas!

Angela Bevin Maple Leaf Realty

26 Asa's Way, Bennington, VT 05257
/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
/60
$1,825,000
- 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
/42
$398,500
- 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
/47
$1,895,000
- 5 Beds
- 4.5 Baths
- 3,218 Sq Ft
5491 Vt Route 315, Rupert, VT 05776

Luxury home, move-in ready, on 5+ peaceful acres with protected panoramic mountain views and stream frontage, this fully renovated 1909 Federal offers timeless character with a like-new feel—just 2.5 miles from the Dorset Green and dining but away from the bustle. Every inch of the main home has been meticulously updated with premium materials and workmanship. A custom walnut kitchen with

Annette Gallo Real Broker LLC

5491 Vt Route 315, Rupert, VT 05776
/22
$895,000
- Land
- 24 Acres
- $37,168 per Acre
A Windsor Rd, Manchester, VT 05255

Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

Kim Morgan-Wohler Wohler Realty Group

A Windsor Rd, Manchester, VT 05255
/36
$1,790,000
- 4 Beds
- 3 Baths
- 2,545 Sq Ft
1949 South Rd, Peru, VT 05152

Nestled in a serene and picturesque setting, Berry Hill Farm offers a rare opportunity to own an exceptional Vermont estate blending charm, versatility, and natural beauty. Spanning 15.52 acres across two separately deeded lots, the property combines inspired design with modern comfort. At its heart is a beautifully crafted contemporary home featuring three spacious bedrooms, sunlit living

Kim Morgan-Wohler Wohler Realty Group

1949 South Rd, Peru, VT 05152
/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
/33
$425,000
- 3 Beds
- 2.5 Baths
- 1,777 Sq Ft
8920 Sage Hill Rd Unit 20, Manchester, VT 05255

Nestled amidst the breathtaking scenery, this 3 bedroom condominium offers an idyllic escape. Inside, you're greeted by an open living space on the main floor, featuring high ceilings, natural woodwork and a wood-burning fireplace. The kitchen is spacious and flows into the dining/living area. On the main floor you'll also find the primary bedroom, full bathroom, half bath, and enclosed three

David Halligan Four Seasons Sotheby's Int'l Realty

8920 Sage Hill Rd Unit 20, Manchester, VT 05255
/33
$820,000
- 4 Beds
- 3 Baths
- 2,317 Sq Ft
0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

Carrie Mathews Winhall Real Estate

0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
/38
$525,000
- 4 Beds
- 3 Baths
- 2,073 Sq Ft
2588 Vermont 11, Peru, VT 05152

PRICE ADJUSTMENT: 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

Diana Stugger Four Seasons Sotheby's Int'l Realty

2588 Vermont 11, Peru, VT 05152
/34
$269,900
- 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
/5
$14,500
- Land
- 1.00 Acre
- $14,500 per Acre
0 Lebenschauung Cir Unit 5049439, Stamford, VT 05352

Top-of-the-World Views Await - One Acre in Southern Vermont Discover your own slice of paradise with this beautiful one-acre wooded lot nestled in Southern Vermont. The current owner hand-picked this lot for its ''top of the world'' feel—and with a little clearing, the panoramic views will be nothing short of breathtaking. This is your chance to escape the hustle and build your dream retreat.

Christine Girard Steepleview Realty

0 Lebenschauung Cir Unit 5049439, Stamford, VT 05352
/31
$799,000
- 3 Beds
- 3 Baths
- 2,317 Sq Ft
9 F Cobble Ridge Rd, Winhall, VT 05340

Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

Carrie Mathews Winhall Real Estate

9 F Cobble Ridge Rd, Winhall, VT 05340
/25
$295,000
- 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
/19
$219,500
- 3 Beds
- 1 Bath
- 1,254 Sq Ft
14 Robinson Ave, Bennington, VT 05201

Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

Timothy Corcoran Mahar McCarthy Real Estate

14 Robinson Ave, Bennington, VT 05201
/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
$950,000
- 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

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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.