Homes for Sale near Hiland Hall School

• 

  

  

  /22

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside Dr, Bennington, VT 05201
• 

  

  

  /29

  $415,000

  • 6 Beds
  • 3 Baths
  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 266-4364

  126 Washington Ave, Bennington, VT 05201
• 

  

  

  /34

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,067 Sq Ft

  258 Harvest Hills Dr, North Bennington, VT 05257

  Welcome to this beautifully maintained ranch-style home offering 2000+ finished SF of living space. Located on one of North Bennington’s most desired streets, close to the village school, market and restaurants, and the Mile Around Woods trail. Nestled on a quiet cul-de-sac, this home offers a perfect combination of space, lovely mountain views and a welcoming neighborhood including a large pond

  Mary Beth French Hoffman Real Estate

  258 Harvest Hills Dr, North Bennington, VT 05257
• 

  

  

  /18

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  940 Gage St, Bennington, VT 05201

  Classic cape with a twist! The eat-in kitchen has plenty of cooking area plus an eat-in area in a windowed alcove. The dining room is large enough for sit downs and the living room is the whole length of the house so movie nights are a go! In the entry side of the house you have a wonderful enclosed porch to serve as a mud room and a sweet sitting porch out front. AND!!!!... there is a fenced in

  Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
• 

  

  

  /54

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
• 

  

  /40

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  134 Monument Ave, Bennington, VT 05201

  Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary

  Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  /58

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,934 Sq Ft

  508 Barney Rd, Bennington, VT 05201

  WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area.

  Dan Mason Perrott Realty

  508 Barney Rd, Bennington, VT 05201
• 

  

  /45

  $450,000

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft

  848 Coleville Rd, Bennington, VT 05201

  The House that Love Built-Multigenerational Comfort &Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude.Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways,

  Beatrice O'Connell Maple Leaf Realty

  848 Coleville Rd, Bennington, VT 05201
• 

  

  /31

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /44

  $365,000

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft

  989 Carpenter Hill Rd, Bennington, VT 05201

  Country charm meets modern comfort... Welcome to your perfect slice of paradise! This lovingly updated ranch home is nestled on a peaceful country road and sits on a generous 2.6 acre lot, offering the ideal blend of privacy, space, and style. Step inside to discover a bright, refreshed interior featuring new vinyl plank flooring, freshly painted walls in a neutral palate, and updated lighting

  Angela Bevin Maple Leaf Realty

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  /43

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
• 

  

  /45

  $345,000

  • 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
• 

  

  /50

  $374,900

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  927 Water St, North Bennington, VT 05257

  Charming Historic Home with Garden, Barn & Flexible Living Spaces This beautiful 100+ year-old home offers over 3,400 sq. ft. of warmth, character, and room to grow. Flooded with natural light, this home on 2+ acres has three sunny upstairs bedrooms and three baths. In addition to a large living room and full dining room, the main floor has a laundry/mudroom and front and rear parlors that can

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
• 

  

  /52

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  263 Elm St, North Bennington, VT 05257

  New Price! 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 graces 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

  Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257
• 

  

  /35

  $575,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  704 Fox Hill Rd, Bennington, VT 05201

  House hunting in Vermont and can't find what you want? Or it sold before you had time to tour or think it through? This brand new custom built home could be the answer. Desirable neighborhood with paved town roads, close to SVMC hospital, Bennington College, downtown restaurants and events, and one hour from Albany Int'l Airport. Nestled at the base of Mount Anthony, there's direct access to

  Jenifer Prouty Hoffman Hoffman Real Estate

  704 Fox Hill Rd, Bennington, VT 05201
• 

  

  /47

  $625,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  682 Fox Hill Rd, Bennington, VT 05201

  Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
• 

  

  /21

  $257,900

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  905 Vt Route 9, Woodford, VT 05201

  Just east of downtown Bennington, this well-maintained 3-bedroom, 1-bath ranch offers easy single-level living in a desirable Woodford location with quick access to nearby amenities, southern Vermont destinations, and major routes into neighboring states. Recent improvements over the past five years include newer windows, doors, roof, appliances, and a renovated kitchen and bath, making the home

  Jeffrey Dorman

  905 Vt Route 9, Woodford, VT 05201
• 

  

  /39

  $269,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  77 Mcguire St, North Bennington, VT 05257

  Charming Ranch in the sought-after Paran Acres neighborhood, this tidy 3BR/1BA is a blank slate waiting for your personal touches. Photos have been virtually staged to help you visualize just how sweet this home can be. Step inside to find sun-filled rooms and an easy, open layout designed for comfortable, low-maintenance living. A clean, dry basement offers endless possibilities: create a cozy

  Angela Bevin Maple Leaf Realty

  77 Mcguire St, North Bennington, VT 05257
• 

  

  /50

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining

  Lindsey Martin Maple Leaf Realty

  113 Main St, Bennington, VT 05201
• 

  

  /22

  $249,900

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft

  107 Coolidge Ave, Bennington, VT 05201

  Discover this beautifully updated home set directly on the Walloomsac River, offering 123 feet of peaceful river frontage. Enjoy fishing right from your own backyard, hosting gatherings by the water, or simply relaxing to the soothing sounds of the flowing river. Ideally located within walking distance of Main Street, the Rec Center (featuring a gym, sauna, indoor pool, and tennis and basketball

  Matt Waddington Hoffman Real Estate

  107 Coolidge Ave, Bennington, VT 05201
• 

  

  /40

  $215,000

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft

  317 Pleasant St, Bennington, VT 05201

  Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400).

  Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /21

  $105,000

  • Land
  • 0.45 Acre
  • $233,333 per Acre

  236-240 Grandview St, Bennington, VT 05201

  Call your builder! This double lot is ready to build on. Public water, sewer, and electricity are at the street on a town-maintained, paved village residential road. The lot is ideally situated close to essential amenities, including the hospital and a vibrant Main Street boasting diverse shops, restaurants, breweries, and groceries. Enjoy exceptional access to the outdoors with the nearby Green

  Lori Hurley Four Corner Properties LLC

  236-240 Grandview St, Bennington, VT 05201
• 

  

  /21

  $120,000

  • Land
  • 20 Acres
  • $6,000 per Acre

  1319 Vail Rd, Bennington, VT 05201

  Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

  Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
• 

  

  /15

  $269,000

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft

  624 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  624 Main St, Bennington, VT 05201
• 

  

  /26

  $199,900

  • 4 Beds
  • 2 Baths
  • 1,278 Sq Ft

  215 Maple St, Bennington, VT 05201

  Huge Price Reduction. Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor

  Matt Waddington Hoffman Real Estate

  215 Maple 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
• 

  

  /10

  $245,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  209 Grove St Unit 11, Bennington, VT 05201

  Well-maintained 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, an eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice backyard, 2 covered parking spaces

  Julie Glover Mahar McCarthy Real Estate

  209 Grove St Unit 11, Bennington, VT 05201
• 

  

  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
• 

  

  /17

  $145,000

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  432 South St Unit C6, Bennington, VT 05201

  A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean

  Angela Bevin Maple Leaf Realty

  432 South St Unit C6, Bennington, VT 05201
• 

  

  /16

  $145,000

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  755 Main St, Bennington, VT 05201

  Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  755 Main St, 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
• 

  /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

  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

  137 Park St, Bennington, VT 05201
• 

  

  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street.The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
• 

  

  /31

  $135,000

  • 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
• 

  

  /11

  $169,900

  • 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 with a lot of square footage.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  905 County 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
• 

  

  /7

  $175,000

  • Land
  • 15.49 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
• 

  

  /39

  $279,900

  • 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

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