Bennington County VT Homes for Sale with Garage

/13
$199,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
2017 East Rd, Shaftsbury, VT 05262

3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with new pellet stove, kitchen with modern appliances including newer stove and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches. New carpet.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 798-5968

2017 East Rd, Shaftsbury, VT 05262
/60
$1,795,000
- 17 Beds
- 20 Baths
- 14,861 Sq Ft
3888 Vermont Route 7a, Shaftsbury, VT 05262

The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

Vicki Wilson

Maple Leaf Realty

(802) 444-8317

3888 Vermont Route 7a, Shaftsbury, VT 05262
/38
$595,000
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
359 Hickory Hill Rd, Bennington, VT 05201

Welcome to 359 Hickory Hill! Tucked away at the end of a peaceful cul-de-sac on 2.58 acres, this beautifully updated Center Hall Colonial offers privacy, space, and convivence just minutes from downtown Bennington and major highways to New York City, Boston, and beyond.This three bedroom, two and a half bath home is truly turnkey and move in ready. Inside, you'll find gleaming hardwood and

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 633-6530

359 Hickory Hill Rd, Bennington, VT 05201
/40
$1,450,000
- 4 Beds
- 6 Baths
- 4,272 Sq Ft
1016 West Rd, Manchester Center, VT 05255

Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 357-7462

1016 West Rd, Manchester Center, VT 05255
/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
/60
$1,950,000
- 4 Beds
- 3.5 Baths
- 3,333 Sq Ft
1268 Myers Rd, Shaftsbury, VT 05262

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6014

1268 Myers Rd, Shaftsbury, VT 05262
/36
$499,900
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
1061 Granger Hollow Rd, North Bennington, VT 05257

Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 481-3292

1061 Granger Hollow Rd, North Bennington, VT 05257
/60
$1,600,000
- 5 Beds
- 4.5 Baths
- 4,243 Sq Ft
397 Fern Hill, Dorset, VT 05251

Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 644-3043

397 Fern Hill, Dorset, VT 05251
/60
$1,150,000
- 3 Beds
- 3 Baths
- 2,267 Sq Ft
636 Dexter Rd, Shaftsbury, VT 05262

In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

Kristin Comeau

TPW Real Estate

(802) 520-1220

636 Dexter Rd, Shaftsbury, VT 05262
/4
$249,000
- 5 Beds
- 3 Baths
- 2,184 Sq Ft
137 Park St, Bennington, VT 05201

Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 444-8271

137 Park St, Bennington, VT 05201
/60
$1,100,000
- 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
/43
$699,000
- 4 Beds
- 3.5 Baths
- 5,700 Sq Ft
56 Mending Walls Rd, Manchester Center, VT 05255

Welcome to your next chapter in Manchester, Vermont.Tucked away in the sought-after Mending Walls community, this 4-bedroom, 4-bath home offers over 5,700 square feet of sun-filled space designed for both comfort and connection. Set on a private one-acre lot, it’s clean, unfurnished, and ready for you to make it your own.Inside, you’ll find warm wood floors, a chef’s kitchen with

Trent Stephens

Wohler Realty Group

(802) 215-6507

56 Mending Walls Rd, Manchester Center, VT 05255
/41
$295,000
- 5 Beds
- 2 Baths
- 1,588 Sq Ft
226 North St, Bennington, VT 05201

This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 327-7149

226 North St, Bennington, VT 05201
/36
$4,975,000
- 5 Beds
- 4 Baths
- 5,445 Sq Ft
527 Benson Rd, Manchester Center, VT 05255

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

Story Jenks LandVest, Inc/Woodstock

527 Benson Rd, Manchester Center, VT 05255
/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
/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
/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
/36
$1,790,000
- 4 Beds
- 3 Baths
- 2,139 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
/43
$1,550,000
- 5 Beds
- 4.5 Baths
- 4,219 Sq Ft
7 Timberbrook N, Dorset, VT 05251

Modern Elegance Surrounded by Mountain Serenity. Stunning 5-bedroom, 4.5-bath home nestled on 4.7 acres, just minutes from Dorset Green and Manchester Village. Blending modern design with traditional warmth, the property features energy-efficient geothermal heating & cooling and solar power. Expansive windows and French doors frame mountain views, the deck is perfect for entertaining. The main

Margretta Fischer Wohler Realty Group

7 Timberbrook N, Dorset, VT 05251
/33
$895,000
- 3 Beds
- 3 Baths
- 3,037 Sq Ft
725 Wideawake Rd, Manchester Center, VT 05255

This home offers approximately 3,000 square feet of living space, including three bedrooms plus an additional room for guests, and three bathrooms. The first floor features a spacious master en suite with a walk-in closet, French doors leading to a patio, and a beautifully updated bathroom with radiant flooring and a marble shower. Also on the first floor, you'll find a bright and airy kitchen

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

725 Wideawake Rd, Manchester Center, VT 05255
/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
/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
/37
$995,000
- 5 Beds
- 4.5 Baths
- 3,697 Sq Ft
1589 Richville Rd, Manchester Center, VT 05255

Welcome to your dream Vermont retreat. This classic 3 bedroom Colonial is gracefully set on 9.52 acres of open meadows with direct frontage on the Battenkill River, renowned worldwide for its exceptional trout fishing. With timeless architecture, peaceful privacy, and sweeping Mountain views, this property captures the essence of New England living. Inside, the home blends historic charm with

Carol O`Connor Four Seasons Sotheby's Int'l Realty

1589 Richville Rd, Manchester Center, VT 05255
/27
$1,250,000
- 2 Beds
- 1 Bath
- 1,056 Sq Ft
233 Squires Rd, Manchester Center, VT 05255

Discover a rare opportunity to live and work amidst the serene beauty of Manchester, Vermont. This fully renovated 2-bedroom, 1-bath contemporary ranch, with leased solar array, is nestled on nearly 19 acres, offering a harmonious blend of modern comfort and entrepreneurial potential.The open-concept design features a spacious kitchen and living area, complemented by energy-efficient

Mark Triller Real Broker LLC

233 Squires Rd, Manchester Center, VT 05255
/33
$880,000
- 8 Beds
- 6 Baths
- 4,326 Sq Ft
143 Nichols Rd, Peru, VT 05152

I am writing to share information about a remarkable property in Peru, Vermont, that offers year-round enjoyment.This sun-filled home is situated on 10 acres of land, boasting beautiful mountain views and a private pond complete with a beach, deck, above-ground pool, and a sauna. Imagine swimming, fishing, and hiking in the warmer months, and ice-skating, snowmobiling, and cross-country

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

143 Nichols Rd, Peru, VT 05152
/21
$995,000
- 4 Beds
- 5.5 Baths
- 4,213 Sq Ft
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
/45
$1,150,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
152 Bonnet St, Manchester Center, VT 05255

At 152 Bonnet Street, history holds the walls and craftsmanship tells a story. Built in 1890 and once home to Brewster Antiques, this stately in-town Victorian has stood as a cornerstone of Manchesters architectural heritage for over a century. Thoughtfully renovated from top to bottom, the home honors its vintage soul while embracing modern comfort. Graceful period millwork, preserved original

Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

152 Bonnet St, Manchester Center, VT 05255
/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
/31
$949,000
- 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
/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
/30
$1,250,000
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
77 Fuller Rd W, Bennington, VT 05201

Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

Jason Saphire www.HomeZu.com

77 Fuller Rd W, Bennington, VT 05201
/40
$1,249,000
- 4 Beds
- 6 Baths
- 4,204 Sq Ft
842 Dorset Rd W, Dorset, VT 05251

Spacious luxury contemporary on 15 amazing acres conveniently located on the Dorset West Road. 4 bedrooms including a primary suite on the main floor with adjoining office and huge walk-in closet. Second primary with bath on second floor. Living room with massive stone fireplace and bar area. Well planned and equipped kitchen. Comfortable dining room between living room and kitchen.

Jill Simon Josiah Allen Real Estate, Manchester Branch Office

842 Dorset Rd W, Dorset, VT 05251
/29
$399,000
- 3 Beds
- 1.5 Baths
- 2,831 Sq Ft
535 Red Mountain Rd, Arlington, VT 05250

This beautifully updated farmhouse blends classic charm with modern convenience on a picturesque 3.6-acre lot. Featuring 3 bedrooms and 2 baths, including a first-floor bed and bath, this home offers flexible living space for guests, multigenerational living, or a home office setup. Enjoy the open kitchen/living area with a cozy woodstove (2022), a spacious great room ideal for entertaining, a

Annette Gallo Real Broker LLC

535 Red Mountain Rd, Arlington, VT 05250
/33
$725,000
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
475 Sunrise Ln, Arlington, VT 05250

Discover your private retreat on Beautiful Sunrise Lane! Welcome to "Pine Hollow". This comfortable and inviting home sits on over 6 acres of serene, peaceful landscape, for those seeking a quiet environment and space! Idyllic setting surrounded by pines with complete solitude at the end of a private rd. Enjoy the comfort of generous rooms filled with natural light, ideal for family living

Sunny Breen Josiah Allen Real Estate, Inc.

475 Sunrise Ln, Arlington, VT 05250
/32
$399,900
- 3 Beds
- 2.5 Baths
- 2,162 Sq Ft
364 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

Pam Tworig Bishop West Real Estate, Inc.

364 Bergblume Cir, Stamford, VT 05352
/23
$380,000
- 3 Beds
- 2 Baths
- 1,196 Sq Ft
22 Carlen St, Manchester Center, VT 05255

Discover the charm and value of this affordable starter home 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 features two comfortable bedrooms, a full bath, and a

Andy Reed Four Seasons Sotheby's Int'l Realty

22 Carlen St, Manchester Center, VT 05255
/30
$399,900
- 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
/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
/18
$389,900
- 4 Beds
- 2.5 Baths
- 2,229 Sq Ft
2842 Vermont Route 7a, Shaftsbury, VT 05262

Elegant Country Estate with Panoramic Mountain Views – Shaftsbury, VT.Welcome to 2842 VT-7A — an exceptional single-level luxury residence set on over 5 private, landscaped acres in the tranquil hills of Shaftsbury. This custom-designed ranch-style home blends timeless Vermont charm with modern comfort, offering 2,229± sq ft of refined interior space, thoughtfully crafted for both relaxed

Derek Greene Derek Greene

2842 Vermont Route 7a, Shaftsbury, VT 05262
/44
$499,000 Open Sun 2PM - 4PM
- 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

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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.