Homes for Sale near Hiland Hall School

/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
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/15
$545,000
- 6 Beds
- 2 Baths
- 5,878 Sq Ft
972 Vt Route 7a, Shaftsbury, VT 05262

MIXED USE INVESTMENT PROPERTY boasts two rental apartments and first floor retail space. The “Shaftsbury Country Store Building” on Historic Route 7A has stood the test of time. This landmark building dates back to 1850, when 10% of Vermont’s population was destined to serve in the Union Army and fight in the Civil War. The back apartment is on the second and third floors with a large deck

Kristin Comeau

TPW Real Estate

(802) 397-9342

972 Vt Route 7a, Shaftsbury, VT 05262
/32
$189,900
- 3 Beds
- 1 Bath
- 1,576 Sq Ft
7 Scarey Ln, North Bennington, VT 05257

Walking distance to Bennington College! Perfect for college housing. The property has a scenic path alongside the river so students can walk or bike to school without having to be on the road. Currently used as a single family home or can easily be converted to a duplex. This 3 bedroom North Bennington home is set in a quiet location with only ten homes in the little neighborhood with dead end

Lisa Friedman

Great American Dream Realty

(802) 523-3998

7 Scarey Ln, North Bennington, VT 05257
/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
/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
/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
/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
$225,000
- 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
/32
$335,000
- 3 Beds
- 2 Baths
- 1,584 Sq Ft
169 Bard Rd, Bennington, VT 05201

Opportunity awaits with this well-built and meticulously maintained 3-bedroom, 2-bath home nestled on a rare and highly desirable 1.84-acre flat lot in the peaceful countryside—just a short drive to town amenities, shops, and schools, this property features town water, a new roof, nearly new boiler and an attached two-car garage. Set back from the road, this property offers space, privacy, and

Cassie Barbeau Mahar McCarthy Real Estate

169 Bard Rd, Bennington, VT 05201
/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 at the end of a quiet cul-de-sac 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

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
/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
/30
$349,000
- 3 Beds
- 1 Bath
- 2,032 Sq Ft
198 Weeks St, Bennington, VT 05201

Step into this beautiful 1930s classic home, filled with character and endless possibilities. This home offers three bedrooms, one bathroom, and a layout that seamlessly combines classic details with comfortable living spaces. The heart of the home is the large dining area, perfect for hosting gatherings or enjoying quiet family meals. Adjacent, you will find a spacious living room with a

Margretta Fischer Wohler Realty Group

198 Weeks 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
/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
/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
/54
$215,000
- 4 Beds
- 3 Baths
- 2,162 Sq Ft
304 North St Unit 6, Bennington, VT 05201

Great Investment Opportunity! This well-maintained 3-unit property is a fantastic opportunity for savvy investors. Two of the units are currently rented, providing immediate income potential. Situated just a short stroll from downtown, you'll find charming shops, popular restaurants, and close proximity to the Bennington trail system—perfect for outdoor enthusiasts. Just 1 hour from Albany and

Thomas Martins Maple Leaf Realty

304 North St Unit 6, 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 rear

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

927 Water 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
/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 enhanced by

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 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
/21
$179,950
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
3 Farmers Inn Rd, Hoosick Falls, NY 12090

Charming Farmhouse with Endless Potential!This spacious 4-bedroom, 2-bath farmhouse offers 1,728 square feet of living space and is full of character and opportunity. Once configured as a two-family home, it's currently being used as a single-family residenceâ€”providing flexible living arrangements or investment potential. Enjoy quiet mornings or evenings on the large front porch. The property

Kelly Sharifipour Darby Real Estate of New York Inc

3 Farmers Inn Rd, Hoosick Falls, NY 12090
/39
$297,500
- 5 Beds
- 2 Baths
- 2,294 Sq Ft
218 Union St, Bennington, VT 05201

Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

Kelley Mccarthy Mahar McCarthy Real Estate

218 Union St, Bennington, VT 05201
/12
$575,000
- 6 Beds
- 4 Baths
- 15,179 Sq Ft
423 Main St, Bennington, VT 05201

Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

Chris Long BHG Masiello Brattleboro

423 Main St, Bennington, VT 05201
/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
/43
$2,100,000
- 4 Beds
- 3 Baths
- 3,780 Sq Ft
1228 Skiparee Rd, Pownal, VT 05260

Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

Christiane Carroccio TPW Real Estate

1228 Skiparee Rd, Pownal, VT 05260
/5
$2,500,000
- Land
- 0.88 Acre
- $2,840,909 per Acre
113 Depot St, Bennington, VT 05201

Mixed use development site in the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.

Paul Carroccio TPW Real Estate

113 Depot St, Bennington, VT 05201
/8
$59,000
- Land
- 0.29 Acre
- $203,448 per Acre
420 Burgess Rd, Bennington, VT 05201

Level building lot with town sewer and water at the edge of town.Possible owner financing.

Dan Mason Perrott Realty

420 Burgess Rd, Bennington, VT 05201
/2
$49,900
- Land
- 11 Acres
- $4,455 per Acre
0 Mount Anthony Rd, Bennington, VT 05201

A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont—11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds.Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building

Kelley Mccarthy Mahar McCarthy Real Estate

0 Mount Anthony Rd, 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.