Homes for Sale near Mt. Anthony Union Middle 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
/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 living

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
/39
$289,000
- 3 Beds
- 1 Bath
- 1,608 Sq Ft
30 Harbour Rd, Bennington, VT 05201

Welcome to the charming ranch home nestled in a desirable and quiet neighborhood! This beautifully maintained three bedroom home offers comfort, style, and fantastic features throughout. The recently renovated full bathroom is a true highlight, featuring a stunning fully tiled walk in shower complete with a built in bench.Enjoy the comfort and efficiency of a brand new mini split, and cook with

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 858-4107

30 Harbour Rd, 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
/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
/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
/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
/36
$575,000
- 4 Beds
- 2 Baths
- 1,982 Sq Ft
556 Mann Hill Rd S, Pownal, VT 05261

The simple two-story Vermont farmhouse with its two original barns enjoys views, privacy, serenity, and all the outdoor space one could need to enjoy farming on a small scale or to allow the adjacent farmer to continue haying the large fields. There majority of the land is wooded and offers all sorts of options from leaving nature alone, to trails, to harvesting timber. The house is relatively

Paul Harsch Harsch Associates

556 Mann Hill Rd S, Pownal, VT 05261
/41
$379,900
- 2 Beds
- 3 Baths
- 1,761 Sq Ft
653 Skyboro Rd E, Pownal, VT 05261

Pristine and perfect. This 2 bedroom, 3 bath home is situated on 2 acres in Pownal. Offering Eat-in Kitchen, living room with fireplace, primary bedroom with private bath, secondary bedroom with private bath, basement family room and laundry room and more. Outside a wonderful sitting deck and patio, a heated 2 car detached garage with shop space, well landscaped yard with garden space and shed.

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

653 Skyboro Rd E, Pownal, VT 05261
/47
$399,000
- 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 gracious

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
/50
$449,000
- 3 Beds
- 2 Baths
- 1,941 Sq Ft
97 Buck Hill Rd, Shaftsbury, VT 05262

Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

97 Buck Hill Rd, Shaftsbury, VT 05262
/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 everything:All

Harvey Roettinger RE/MAX North Professionals

93 Pace Rd, Bennington, VT 05201
/33
$365,000
- 3 Beds
- 1.5 Baths
- 1,666 Sq Ft
379 Swallow Hill Rd, Pownal, VT 05261

Welcome home! Tucked away on over 2.6 private and partially wooded acres in the exclusive and tight-knit Swallow Hill neighborhood, this stunning 3-bedroom, 1.5-bath home offers modern comfort and rustic charm in a serene natural setting in Southern Vermont.Step inside to soaring cathedral ceilings, exposed wood beams, and an abundance of Vermont beauty pouring in through large windows. The heart

Cassie Barbeau Mahar McCarthy Real Estate

379 Swallow Hill Rd, Pownal, VT 05261
/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 rear

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 enhanced by

Kelley Mccarthy Mahar McCarthy Real Estate

34 Southshire Dr, Bennington, VT 05201
/52
$429,000
- 4 Beds
- 2 Baths
- 2,368 Sq Ft
263 Elm St, North Bennington, VT 05257

Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light floods this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining area just off

Margretta Fischer Wohler Realty Group

263 Elm St, North Bennington, VT 05257
/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
/6
$45,900
- Land
- 2.50 Acres
- $18,360 per Acre
0 White Oaks Rd, Pownal, VT 05261

Nature lovers, rejoice! This 2.5-acre secluded lot, nestled up a dirt mountain road, offers unparalleled privacy and a haven for wildlife. Located in Pownal, between Williamstown, MA, and Bennington, VT, this mostly level lot provides a potential ideal building site. You'll be just minutes away from incredible walking trails, including the Dome Trailhead, Agawam Trail, Broad Brook Trailhead,

Matt Waddington Hoffman Real Estate

0 White Oaks Rd, Pownal, VT 05261
/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
/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
/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
/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
/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
/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 are

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
/54
$1,995,000
- 3 Beds
- 3 Baths
- 5,228 Sq Ft
2167 Myers Rd, Shaftsbury, VT 05262

Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub,

Kelley Mccarthy Mahar McCarthy Real Estate

2167 Myers Rd, Shaftsbury, VT 05262
/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
/51
$279,900
- 4 Beds
- 2 Baths
- 1,602 Sq Ft
224 Sycamore Ln, Shaftsbury, VT 05262

This 4 bedroom cape is located on a dead end street in a desirable neighborhood within the village of Shaftsbury. The updated kitchen has a small island and is open to the dining area. The living room has hardwood floors, gas fire place and built-ins along one wall. There is a washer and dryer located on the first floor in the entry hall and a full bath also on this level. There are two

Catherine Cairns Maple Leaf Realty

224 Sycamore Ln, Shaftsbury, VT 05262

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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.