Homes for Sale near Mt. Anthony Union High School

/4
$199,900
- 5 Beds
- 2 Baths
- 1,478 Sq Ft
32-34 Sage St, Bennington, VT 05257

Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 402-4994

32-34 Sage St, Bennington, VT 05257
/20
$750,000
- 4 Beds
- 5 Baths
- 6,650 Sq Ft
338 Main St, Bennington, VT 05201

Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 347-6655

338 Main St, Bennington, VT 05201
/21
$175,000
- Land
- 18 Acres
- $9,749 per Acre
0 U S 7, Pownal, VT 05261

Beautiful Pownal Valley views from almost wherever you stand on this 17.95 acre parcel. Zoned for commercial use along the road frontage and rural residential in back creates opportunities for different types of development.

Vicki Wilson

Maple Leaf Realty

(802) 327-8230

0 U S 7, Pownal, VT 05261
/4
$279,000
- 4 Beds
- 4 Baths
- 2,080 Sq Ft
123 Bradford St, Bennington, VT 05201

4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Showings to begin 6/10/2024

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 210-1728

123 Bradford St, Bennington, VT 05201
/43
$119,900
- Land
- 26 Acres
- $4,665 per Acre
0000 Skiparee Rd, Pownal, VT 05261

Gorgeous 25.7 acre parcel on a dead end road in Pownal, Vermont. This wooded lot offers many possibilities for a home site. Across a stream and up the logging road there is a large clearing that would offer great privacy, with the mountain behind you and great views to the south and east. A lot of opportunity for outdoors activities, homesteading, livestock and gardening. This lot makes the world

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 392-2133

0000 Skiparee Rd, Pownal, VT 05261
/2
$225,000
- 6 Beds
- 2 Baths
- 2,112 Sq Ft
303-305 Gage St, Bennington, VT 05201

Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 471-3314

303-305 Gage St, Bennington, VT 05201
/59
$1,150,000
- 3 Beds
- 3 Baths
- 2,462 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
/19
$225,000
- 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
/41
$320,000
- 5 Beds
- 2 Baths
- 2,418 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
/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
/38
$695,000
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
359 Hickory Hill Rd, Bennington, VT 05201

Welcome to this beautifully updated Center Hall Colonial, privately set on 2.58 wooded acres at the end of a peaceful cul-de-sac just minutes from downtown and major highways. The three bedroom, two and half bath home is truly move in ready, offering the perfect balance of comfort, style, and privacy. Step inside to an open concept main level where the kitchen flows seamlessly into the

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 633-6530

359 Hickory Hill Rd, Bennington, VT 05201
/31
$399,900
- 4 Beds
- 2 Baths
- 2,229 Sq Ft
2842 Vermont Route 7a, Shaftsbury, VT 05262

Prime Shaftsbury Real Estate. Large 4 bedroom, 2 bath home situated on 1.16 acres outside of town. Offering kitchen with dining area, living room, family room with pellet stove, primary suite with media nook and spacious closets, exercise room or workshop and so much more. Space for a home business or entertaining. Large yard and convenient location. 10 minutes to either Bennington or Arlington

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 882-6672

2842 Vermont Route 7a, Shaftsbury, VT 05262
/11
$185,000
- 4 Beds
- 2 Baths
- 2,643 Sq Ft
905 County St, Bennington, VT 05201

Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 204-5943

905 County St, Bennington, VT 05201
/49
$38,000
- Land
- 7 Acres
- $5,429 per Acre
170 Gore Rd, Bennington, VT 05201

Come Explore this 7 +/- acre wooded lot located among a rural residential neighborhood in Bennington VT. This is the lot Behind the Homes and is accessed by a deeded and surveyed 50’ ROW off the paved and town-maintained Gore Road. Power and services are at the road frontage. The property contains a mature hardwood forest primarily of Oak and Maple. Ever so slightly sloping, with a

Curtis Trousdale

170 Gore Rd, Bennington, VT 05201
/59
$699,000
- 3 Beds
- 2.5 Baths
- 3,637 Sq Ft
272 Oak Hill Rd, Shaftsbury, VT 05262

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 dedicated home office—perfect for remote work or

Faith Rhodes Maple Leaf Realty

272 Oak Hill Rd, Shaftsbury, VT 05262
/33
$355,000
- 4 Beds
- 2 Baths
- 2,072 Sq Ft
60 Knoll Crest Ln, Bennington, VT 05201

Step into this well maintained brick and clapboard residence, perfectly nestled in a lovely neighborhood. Just minutes from the hospital and a short, pleasant walk to downtown, this home offers the best of both convenience and community.Bathed in natural light, the interior boasts an inviting and functional layout highlighted by gleaming hardwood floors and timeless character throughout.

Moira Spivey Four Seasons Sotheby's Int'l Realty

60 Knoll Crest Ln, Bennington, VT 05201
/31
$395,000
- 2 Beds
- 1 Bath
- 1,624 Sq Ft
2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

Escape to peace and privacy in this beautiful 2-bedroom, 1 bath getaway home set on 7.15 picturesque acres, complete with your own private pond and surrounded by majestic mountains. Step inside to an open-concept kitchen, dining, and living area-perfect for entertaining or simply soaking in the serenity. The space is filled with natural light thanks to large windows that frame the stunning views.

Kelley Mccarthy Mahar McCarthy Real Estate

2374 Shaftsbury Hollow Rd, North Bennington, VT 05257
/45
$365,000
- 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
/47
$389,000
- 5 Beds
- 3.5 Baths
- 3,600 Sq Ft
46 Duffy Dr, Bennington, VT 05201

This spacious 5-bedroom, 4-bath Colonial in Bennington's sought-after Maplewood neighborhood offers over 3,600 sq ft of flexible living space, including a finished walk-out in-law suite with full kitchen and private entry. Thoughtfully updated with granite counters, stainless steel appliances, and a smart home system including ADT security, glass break sensors, and a smart thermostat. The vaulted

Nick Sicard EXP Realty

46 Duffy Dr, 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
/53
$595,000
- 4 Beds
- 2.5 Baths
- 2,456 Sq Ft
23 Mechanic St, North Bennington, VT 05257

Modern Comfort Meets Historic Charm in North Bennington, VermontNestled within the heart of North Bennington's National Historic District, this thoroughly modern and light-filled home offers the perfect blend of timeless character and contemporary living. Situated on a beautifully landscaped 0.69-acre lot, the property includes a private backyard with ample space for perennial and vegetable

Kelley Mccarthy Mahar McCarthy Real Estate

23 Mechanic St, North Bennington, VT 05257
/46
$425,000
- 3 Beds
- 3 Baths
- 1,728 Sq Ft
4 Bank St, Bennington, VT 05201

Across from the 5th Fairway of the Mount Anthony Country Club you’ll find this charming, meticulously maintained 3 bedroom 2 bath home. The spacious open layout, custom kitchen, and expansive deck are warm and inviting. Relax on your front porch and enjoy the scenic mountain vistas of Mount Anthony and the Bennington Monument. Fabulous, convenient location! The home began as a bungalow, the

Margretta Fischer Wohler Realty Group

4 Bank St, Bennington, VT 05201
/55
$325,000
- 3 Beds
- 1.5 Baths
- 1,664 Sq Ft
93 Pace Rd, Bennington, VT 05201

Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

Harvey Roettinger RE/MAX North Professionals

93 Pace Rd, Bennington, VT 05201
/50
$398,900
- 5 Beds
- 4 Baths
- 3,400 Sq Ft
927 Water St, North Bennington, VT 05257

Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

927 Water St, North Bennington, VT 05257
/48
$599,900
- 4 Beds
- 3.5 Baths
- 3,742 Sq Ft
34 Southshire Dr, Bennington, VT 05201

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

Kelley Mccarthy Mahar McCarthy Real Estate

34 Southshire Dr, Bennington, VT 05201
/48
$685,000
- 3 Beds
- 2.5 Baths
- 1,738 Sq Ft
1516 W Mountain Rd, Shaftsbury, VT 05262

Discover your dream retreat in this immaculate 3-bedroom, 3-bath, single level home, nestled on over 4 acres of breathtaking landscape. Enjoy expansive mountain views of the Taconic range, Bennington Monument, and Mount Graylock. Relax on the spacious deck or in the screened-in porch, soaking in the stunning vistas. This updated one-level home, features hardwood floors throughout and an open

Margretta Fischer Wohler Realty Group

1516 W Mountain Rd, Shaftsbury, VT 05262
/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
/57
$250,000
- 3 Beds
- 1 Bath
- 1,224 Sq Ft
153 Spur Rd Unit PVT, Bennington, VT 05201

Simplify life in this charming one-story home nestled on 2 peaceful acres, offering the perfect blend of privacy and convenience just minutes from town. Thoughtfully designed for comfort and accessibility, this cozy 3-bedroom property features an open-concept kitchen, dining, and living area centered around a classic brick fireplace—ideal for Vermont’s cozy seasons.Enjoy the warmth of a bonus

Lindsey Martin Maple Leaf Realty

153 Spur Rd Unit PVT, Bennington, VT 05201
/34
$299,900
- 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
$319,000
- 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
/27
$119,000
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
318 Skyboro Rd, Pownal, VT 05261

Nice 1 acre lot with older mobile home in need of renovations or remove the current home and replace it with a new mobile home. Maybe you have been renting in a park and want to move your home to this lot. It would also make a nice building lot with the drilled well and underground power already in place.The possibilities are endless.

Dan Mason Perrott Realty

318 Skyboro Rd, Pownal, VT 05261
/56
$249,000
- 3 Beds
- 1 Bath
- 1,660 Sq Ft
174 Cleveland Ave, Shaftsbury, VT 05262

Fresh clean ranch ready for your finish touched. This house was just painted and the roof was replaced. Large fenced back yard for pets. The deck id ready for a new pool or just access the backyard for games or leisure. Easy to show and move in ready.

Dan Mason Perrott Realty

174 Cleveland Ave, Shaftsbury, VT 05262
/59
$920,000
- 4 Beds
- 5 Baths
- 3,974 Sq Ft
145 White Farm Ln, Shaftsbury, VT 05262

Located in a desirable subdivision, this beautifully maintained home offers a perfect balance of seclusion and convenience, just minutes from shopping and amenities in both Bennington and Manchester. This home offers two newly renovated primary en-suites, with hardwood floors throughout and a multitude of updates and renovations making this a true turn key property. The first floor primary

Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

145 White Farm Ln, Shaftsbury, VT 05262
/37
$239,900
- 6 Beds
- 2 Baths
- 2,288 Sq Ft
215 Dewey St, Bennington, VT 05201

Beautifully situated in the heart of Bennington, this spacious and sunlit 2,288 sq ft duplex (1,144 sq ft per unit) is the perfect blend of comfort, character, and income potential. Each unit features three generous bedrooms, one full bath, in-unit laundry, and charming hardwood floors in the main living areas. An abundance of windows fills the space with natural light, creating a bright and

Jeffrey Dorman EXP Realty

215 Dewey St, Bennington, VT 05201
/40
$225,000
- 3 Beds
- 1 Bath
- 1,538 Sq Ft
721 Vt Route 7a, Shaftsbury, VT 05262

Located in the downtown neighborhood of Shaftsbury. Walking distance to school, town offices, country stores, parks and playgrounds. A first-floor bedroom with French doors leading outside - as well as a first-floor family room, laundry room, new kitchen and den. Two bedrooms upstairs. There's plenty of room in this home. A one car garage and fully fenced in lot for your privacy.

Wendy Larson Maple Leaf Realty

721 Vt Route 7a, Shaftsbury, VT 05262
/49
$255,000
- 2 Beds
- 1 Bath
- 864 Sq Ft
130 Sycamore Ln, Shaftsbury, VT 05262

Looking for easy living on a quiet, dead-end street in a desirable neighborhood? Look no further! This one level ranch has all you need. Sitting on a nice-sized yet manageable lot, this two bedroom home has been meticulously maintained from top to bottom. The furnace was replaced only a year ago, so heating costs have been low for the current owners. Great news for Vermont winters! The bedrooms

Justine Curry Maple Leaf Realty

130 Sycamore Ln, Shaftsbury, VT 05262
/9
$1,950,000
- Land
- 7 Acres
- $278,571 per Acre
720 N Branch St, Bennington, VT 05201

Prime redevelopment opportunity in Bennington. 720 North Branch Street offers 6 acres of level land with frontage and easy access—ideal for residential or mixed-use development. Included in the sale is 702 North Branch Street, a two-unit duplex with a 3-bedroom apartment on the first floor and a 2-bedroom unit upstairs. Recent improvements include a new boiler, oil tank, and hot water heater.

Paul Carroccio TPW Real Estate

720 N Branch St, Bennington, VT 05201
/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

Showing Results 1 - 40, Page 1 of 2

Vermont Bennington Mt. Anthony Union High School

How to Buy a Home How to Finance a Home How to Sell a Home

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.