Homes for Sale near Molly Stark School

/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
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/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
/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
/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
/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
/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
/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
/72
$339,000
- 4 Beds
- 2 Baths
- 2,203 Sq Ft
167 Burgess Rd, Hoosick Falls, NY 12090

Step back in time as you arrive at this countryside paradise offering majestic views of Vermont's Green Mountains. This mini farm retains original charm showcasing rare original woodwork, hardwood floors a built-in pass-through and a classic rocking chair front porch with breathtaking views that stretch for miles. Outside, the rolling pastures prime farmland amazes you, and you will also find a

Richard Tinkham Berkshire Hathaway Home Services Blake

167 Burgess Rd, Hoosick Falls, NY 12090
/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
/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
/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
/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
/21
$299,000
- 3 Beds
- 1.5 Baths
- 1,365 Sq Ft
339 Chester Knoll Dr, Bennington, VT 05201

A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

Lori Hurley Four Corner Properties LLC

339 Chester Knoll Dr, Bennington, VT 05201
/26
$289,900
- 3 Beds
- 1.5 Baths
- 1,576 Sq Ft
519 South St, Bennington, VT 05201

Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

Kelley Mccarthy Mahar McCarthy Real Estate

519 South St, Bennington, VT 05201
/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
/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
/47
$299,900
- 4 Beds
- 2.5 Baths
- 2,404 Sq Ft
120 Imperial Ave, Bennington, VT 05201

Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

Kelley Mccarthy Mahar McCarthy Real Estate

120 Imperial Ave, Bennington, VT 05201
/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
/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
/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
/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
/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
/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
/58
$269,000
- 7 Beds
- 4 Baths
- 4,417 Sq Ft
200 Depot St, Bennington, VT 05201

Own a piece of Bennington history! Alex Drysdale House, c. 1850. The grocery store (formerly 138 River Street) operated under the name "A. Drysdale & Son" and was built in 1876. Today this historic property is set up as a four-unit with great income potential. It currently houses three apartments: a freshly renovated four bedroom (used as an Airbnb), three bedroom, and efficiency, along with the

Justine Curry Maple Leaf Realty

200 Depot St, Bennington, VT 05201
/57
$215,000
- 3 Beds
- 1 Bath
- 1,416 Sq Ft
100 Webb St, Bennington, VT 05201

Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the

Lindsey Martin Maple Leaf Realty

100 Webb St, Bennington, VT 05201
/42
$1,950,000
- 9 Beds
- 7 Baths
- 6,956 Sq Ft
1086 West Rd, Bennington, VT 05201

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

Chris DeFelice Four Seasons Sotheby's Int'l Realty

1086 West Rd, Bennington, VT 05201
/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
/35
$264,900
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
115 Jefferson Ave, Bennington, VT 05201

Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

Kelley Mccarthy Mahar McCarthy Real Estate

115 Jefferson Ave, Bennington, VT 05201
/7
$175,000
- Land
- 15 Acres
- $11,298 per Acre
00 Silk Rd, Bennington, VT 05201

Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here

David White OwnerEntry.com

00 Silk Rd, Bennington, VT 05201
/52
$199,000
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
130 Morgan St, Bennington, VT 05201

200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

Dan Mason Perrott Realty

130 Morgan St, 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.