Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

and narrow your search. If you have fewer than 200 results, you can save your search.

Bennington County

r=171-180
302 Prospect Street Bennington VT 05201

Bennington, VT302 Prospect Street

Price$275,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5086287

  • Residential Single Family
  • Full Bath 1
  • Address 302 Prospect Street
  • Bedrooms 3
  • Bathroom 2

Welcome to this lovely Colonial home, formerly a charming carriage house, nestled in one of Bennington's most desirable walkable neighborhoods. Offering over 1,500 square feet of inviting living space, this well maintained home features 3 bedrooms, 2 bathrooms, and a versatile bonus room perfect for a home office or potential fourth bedroom. Inside, you'll find beautiful wood floors and trim, rustic beams, and newly installed plush carpeting. The sunny interior is filled with natural light thanks to large windows that flood the home with brightness. The kitchen offers stainless steel appliances direct access to the back deck. Updated bathrooms and ample closet space blend modern convenience with the timeless charm of the home. Step outside to enjoy the beautifully landscaped yard, complete with a newly painted deck ideal for entertaining and gatherings, as well as stunning mountain views. The level, usable yard offers plenty of space for outdoor enjoyment, room for a garden, and a large paved driveway accommodates up to six vehicles. A generously sized shed offers perfect storage for your outdoor items. Additional highlights include low-maintenance vinyl siding, replacement tilt-out windows for easy cleaning, and an updated metal roof. In the basement you will find a finished rec room, laundry area and extra storage with peg wall for your tools and a sump pump. Connected to town water and sewer, this home offers added ease of maintenance. Enjoy the peace and comfort of this quiet neighborhood while being just minutes from the hospital, shopping, and vibrant downtown Bennington. An hour from Albany International Airport, close to all Southern Vermont and the tri-state area has to offer. A true gem in the heart of town-you won't want to miss this one!

Listed by Mary Beth French of Hoffman Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1384 Route 153 Rupert VT 05776

Rupert, VT1384 Route 153

Price$275,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089545

  • Residential Single Family
  • Full Bath 1
  • Address 1384 Route 153
  • Bedrooms 3
  • Bathroom 1

Beautiful country farmhouse with meadow views. Come see this 3 bedroom one bath home on half an acre surrounded by country views and meadows. Built in 1865 this Vermont homestead has a wonderful sunny garden area and attached one car garage. The main level has everything you need; a generous first floor bedroom and large bathroom, spacious living and dining areas and eat in kitchen with newer appliances. Oversized bonus room with separate enterance perfect for a home office or workshop. The second floor features two additional bedrooms and space enough for a second bathroom. Don't miss the famous Sugar Shed and Come make this well maintained property your home. General Store, post office and the rail trail are all close by. Only 15 minutes to Dorset Green and 10 minuted to Salem NY for all your shopping needs. Priced to sell! Grades 7-12 School Choice! Call today! Don't let this affordable option get away.

Listed by Margretta Fischer of Wohler Realty Group

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

212 Dewey Street Bennington VT 05201

Bennington, VT212 Dewey Street

Price$275,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5090068

  • Residential Single Family
  • Address 212 Dewey Street
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,265

Move right in or continue operating as a short-term rental-this fully furnished 2-bedroom, 2.5-bath ranch offers comfort, convenience, and flexibility all in one package. Currently used as an Airbnb, all contents are included, making this a true turnkey opportunity. Inside, you'll find recently refinished hardwood floors, and skylights that fill the home with natural light. A pellet stove for ambiance (main heat is hot water baseboard) adds warmth and character, while the central cooling system keeps the home comfortable year-round. The large heated basement offers excellent ceiling height and endless possibilities for storage, workshop space, or future finishing. Efficient Buderus boiler with multiple heating zones adds to the home's quality and functionality. Additional features include an attached 2-car garage, small rear deck for relaxing outdoors, and a peaceful stream running through the property for a tranquil setting. This property checks all the boxes.

Listed by Will Paquin of Maple Leaf Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

26 Knoll Crest Lane Bennington VT 05201

Bennington, VT26 Knoll Crest Lane

Price$274,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5089377

  • Residential Single Family
  • Full Bath 1
  • Address 26 Knoll Crest Lane
  • Bedrooms 3
  • Bathroom 1

Beautifully updated Cape-style home nestled in a quiet, sought-after neighborhood with picturesque views of Mount Anthony. Full of charm and character, this move-in-ready home perfectly blends comfort, style, and convenience. Tucked away on a dead-end street, it's ideally located near SVMC hospital, public transportation, scenic hiking trails, and Bennington's vibrant Main Street, which offers shops, restaurants, and year-round community events. The main level features a spacious great room with beautifully refinished hardwood floors (2024), an updated kitchen with new cabinetry, butcher block countertops, and new appliances (refrigerator and dishwasher, 2024), along with a convenient first-floor bedroom and a full bath with a beautifully tiled shower surround. Upstairs, you'll find two additional bedrooms with ample storage, including charming custom hallway built-ins that add both timeless character and functionality. The full basement provides excellent potential for additional living space, with one side open and ready to be finished, while the other is currently configured as a workshop/hobby area along with the laundry and mechanical systems. Step outside onto the expansive 20ft x 15ft back deck and take in the scenic mountain views-the perfect setting for relaxing or entertaining guests while overlooking the backyard. The yard offers ample space to enjoy without being overwhelming to maintain, providing the perfect balance of open outdoor living and easy upkeep. It's a blank canvas ready for new owners to add their own gardens, landscaping, and personal touches to truly make it their own. Additional recent upgrades include a 200-amp electrical panel (2024), a heat pump hot water heater (2024), foam insulation throughout with new sheetrock upstairs following insulation (2023), seamless edge gutters (2024), and a complete interior repaint in 2024. Truly move in condition and ready for its new owners to start making their own memories.

Listed by Matt Waddington of Hoffman Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2092 N Bennington Road Bennington VT 05257

Bennington, VT2092 N Bennington Road

Price$269,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5074418

  • Residential Single Family
  • Village North Bennington
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 900

Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front living room with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has panoramic view of the Hoosic River. The front living room has a fireplace option (has a chimney and fireplace structure but just needs updating) and it has enough space to use as a living room and dining room combo. There is plenty of storage in the full-size, walkout basement where the washer and dryer are located. This house also has 2 sheds, 2 car ports and 2 driveways. This house is cozy indoors and offers dreamlike outdoor living with walkout access to the river where you can raft, go inner tubing, boating and fishing. Two spacious decks for outdoor dining, grilling, entertaining, hosting a wedding, bird watching or just relaxing and enjoying the view. In the very large backyard, you can pitch a tent, for camping, or gardening. The possibilities for this house are endless. Great for those who love the outdoors. This house is close to ski resorts, hiking trails, schools, shops, places for dining, parks, gas station (is just down the road), Movie theater and a short drive to the Highway. You're 10 minutes away from downtown Bennington. Close to Lake Paran, a short 15 minutes ride to Ny and 30minutes ride to Massachusetts. There are not a lot of houses like this one. And in such a prime location. Don't miss out on this once in a lifetime opportunity!

Listed by Max Squiers of KW Vermont - Brenda Jones Real Estate Group

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

86 Mill Road Stamford VT 05352

Stamford, VT86 Mill Road

Price$269,900The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5087723

  • Residential Single Family
  • Full Bath 1
  • Address 86 Mill Road
  • Bedrooms 2
  • Bathroom 1

Southern VT - Only 10 minutes to North Adams, MA - home of Mass MoCA - Discover this charming 2-bedroom, 1-bath ranch nestled in a peaceful and picturesque setting in Stamford. This well-maintained home features a nicely updated kitchen with dining area, a spacious living room with fireplace. Enjoy the beauty of the outdoors from the fantastic sunroom overlooking the backyard, along with an additional breezeway designed for seasonal relaxation and entertaining. A unique bonus feature awaits just outside -- your own backyard bunkhouse, complete with bunk beds and a cozy sitting area, perfect for guests or a fun retreat. Continue beyond to enjoy private river access surrounded by nature and tranquility. All of this is set in a serene rural location, while still being conveniently located 10-15 min from North Adams, offering easy access to local attractions!

Listed by Colleen Zajac and Susan Colvin of Monarch Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

508 Barney Road Bennington VT 05201

Bennington, VT508 Barney Road

Price$269,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5084270

  • Residential Single Family
  • Full Bath 1
  • Address 508 Barney Road
  • Bedrooms 3
  • Bathroom 2

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. The septic was just serviced.

Listed by Dan Mason of Perrott Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

935 Gage Street Bennington VT 05201

Bennington, VT935 Gage Street

Price$269,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5088129

  • Residential Single Family
  • Full Bath 2
  • Address 935 Gage Street
  • Bedrooms 3
  • Bathroom 2

Nestled in the Village of Bennington, this charming three-bedroom, two-bath Cape-style home offers comfort, character, and beautiful outdoor living. Step inside to find all fresh flooring, just painted throughout, and inviting spaces filled with natural light. Fireplace in the living room and new glass slider to the deck. Second floor is one large room with spacious closet and full bath-an ideal primary suite. Outside, perennial gardens add color and charm while the brand-new back deck creates the perfect place to relax or entertain. Spend your summer evenings gathered around the fire pit, listening to the peaceful sounds of the nearby creek in your shaded backyard retreat. Conveniently located close to downtown shops, dining, schools, and local amenities, this move-in-ready home combines village convenience with the tranquility of Vermont living.

Listed by Lillian West of Maple Leaf Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

895 Barber Pond Road Pownal VT 05261

Pownal, VT895 Barber Pond Road

Price$259,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5083987

  • Residential Single Family
  • Full Bath 1
  • Address 895 Barber Pond Road
  • Bedrooms 3
  • Bathroom 1

Turnkey and impeccably maintained, this charming 3-bedroom, 1-bath ranch offers effortless single-level living on a picturesque 1.3-acre lot. Inside, you'll find gleaming hardwood floors and a thoughtfully updated interior, highlighted by a fully renovated kitchen and bathroom that blend modern finishes with everyday functionality. The home is truly “neat as a pin,” reflecting pride of ownership throughout. Mini-split systems provide efficient heating and cooling, complemented by a cozy woodstove for added warmth and character. Step outside to enjoy your own private retreat, complete with an above-ground pool and spacious deck-perfect for summer entertaining or relaxing in a peaceful setting. Set in a beautiful location with room to roam, this move-in-ready home offers comfort, style, and convenience in one inviting package.

Listed by Faith Rhodes of Maple Leaf Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

569 Buck Hill Road Arlington VT 05250

Arlington, VT569 Buck Hill Road

Price$250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5080009

  • Residential Single Family
  • Full Bath 2
  • Address 569 Buck Hill Road
  • Bedrooms 5
  • Bathroom 2

Amazing 1850s farmhouse rich in old-world charm and character. Gleaming hardwood floors, large sun-filled rooms, and timeless architectural details throughout. Distinctive features include an elegant arched doorway, a unique library with octagonal bookshelves, and a striking turret that enhances the home's historic appeal. The spacious primary bedroom stretches 25 feet and offers two separate sections-ideal for creating a private suite with a sitting area and generous closet space. Massive walk up attic is ready for finishing and the full basement with concrete floor is perfect for storage. Additional highlights include a gorgeous slate roof and multiple porches. A detached two-car garage with loft and side storage area provides excellent options. Set in a highly convenient location just 0.15 mile to Arlington schools and the library, with easy access to area destinations, hiking, and skiing. 10 miles to vibrant downtown Manchester's shops and restaurants and 15 miles to Bennington. A rare opportunity to own a classic Vermont farmhouse with enduring character for an almost too good to be true price!

Listed by Lisa Friedman of Great American Dream Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2026 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. Data last updated June 9, 2026 1:40 PM EDT

 

You Can Edit This Text

Custom Search

Luxury Home Guide