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Bennington County

r=181-190
364 Oberdorf Road Readsboro VT 05350

Readsboro, VT364 Oberdorf Road, Unit 153

Price$249,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5085074

  • Residential Single Family
  • Full Bath 1
  • Address 364 Oberdorf Road
  • Bedrooms 2
  • Bathroom 1

Charming 2-Bedroom, 1-Bath home with 2 car garage in Alpenwald Village - Your Mountain Escape Awaits! Welcome to this cozy gem nestled in the heart of Alpenwald Village, offering a perfect blend of comfort and adventure. This home is ideal for those seeking privacy, outdoor fun, and a cozy retreat from everyday life. Some of the Key Features include: An oversized 25x26 two-car garage provides ample storage for all your toys, tools, and outdoor equipment. A spacious and airy feel in the open living area, highlighted by an impressive high ceiling, and an energy efficient Mini-Split for comfort all year long. Beautiful stone hearth with a wood stove for those chilly mountain evenings. A 3-Season Sunroom, perfect for relaxing with a good book or enjoying the VT scenery. Set back from the road, this property offers the privacy you've been looking for while still being conveniently located near it all. Enjoy boating, skiing, snowmobiling, and hiking-all just a short drive away. Whether you're searching for a full-time residence or a weekend getaway, this home is your gateway to everything the area has to offer.

Listed by Monique White and Lisa Mirando of Deerfield Valley Real Estate

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

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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.

113 Main Street Bennington VT 05201

Bennington, VT113 Main Street

Price$230,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5068744

  • Residential Single Family
  • Full Bath 1
  • Address 113 Main Street
  • Bedrooms 3
  • Bathroom 1

Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry. Step inside to find gleaming newly upgraded flooring, a warm and inviting layout, and stylish updates throughout, including new kitchen and bathroom cabinetry. The bright kitchen flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. Relax on the covered front porch and enjoy your morning coffee while taking in the neighborhood atmosphere. Outside, the large detached garage offers excellent space for vehicles, hobbies, or additional storage, while solar panels help keep energy costs low. Combining the charm of downtown living with thoughtful modern improvements, this move-in ready home is one you won't want to miss. Schedule your private showing today!

Listed by Lindsey Martin of Maple Leaf Real Estate

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

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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.

99 Coolidge Avenue Bennington VT 05201

Bennington, VT99 Coolidge Avenue

Price$225,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5088016

  • Residential Single Family
  • Full Bath 1
  • Address 99 Coolidge Avenue
  • Bedrooms 3
  • Bathroom 1

This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that add both charm and storage. Conveniently located close to shopping, dining, recreation, and just minutes to the Bennington Recreation Center, this home combines comfort, character, and accessibility in a desirable neighborhood.

Listed by Catherine Cairns of Maple Leaf Real Estate

{$office->Name}

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

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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.

3264 Route 153 Rupert VT 05776

Rupert, VT3264 Route 153

Price$224,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5059970

  • Residential Single Family
  • Full Bath 1
  • Address 3264 Route 153
  • Bedrooms 2
  • Bathroom 1

This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a 200-amp panel, and a generator hook up --move-in ready with nothing left to do. The home features 2 bedrooms, a spacious full bath, an open living and dining room flowing seamlessly into the kitchen, a separate laundry room, and a convenient mudroom entry. Two inviting screened porches extend your living space, while the private fenced backyard provides a perfect retreat. A detached two-car insulated and heated garage/workshop adds versatile space for hobbies or storage. Conveniently located across the street from the D&H Rail Trail, 5 minutes to Merck Forest, and just 10 minutes to Dorset and under 20 minutes to Manchester. Mettawee School District, with school choice for grades 7-12. A turnkey property that blends modern updates with classic comfort-ready to welcome its next owner. THIS PROPERTY IS NOT IN THE FLOOD ZONE, HAS NO HISTORY OF FLOODING AND DOES NOT REQUIRE FLOOD INSURANCE.

Listed by Scott Mcchesney and Robin Chesnut-Tangerman of McChesney RE, Inc.

{$office->Name}

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

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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.

1083 Main Street Bennington VT 05201

Bennington, VT1083 Main Street

Price$219,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5086144

  • Residential Single Family
  • Full Bath 1
  • Address 1083 Main Street
  • Bedrooms 2
  • Bathroom 1

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking.

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

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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.

14 Robinson Avenue Bennington VT 05201

Bennington, VT14 Robinson Avenue

Price$219,500The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5049236

  • Residential Single Family
  • Full Bath 1
  • Address 14 Robinson Avenue
  • Bedrooms 3
  • Bathroom 1

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, Downtown Bennington.

Listed by Timothy Corcoran of Mahar McCarthy Real Estate

{$office->Name}

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

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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.

215 Orchard Street Pownal VT 05261

Pownal, VT215 Orchard Street

Price$219,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5087860

  • Residential Single Family
  • Full Bath 1
  • Address 215 Orchard Street
  • Bedrooms 2
  • Bathroom 1

Welcome to this adorable bungalow in the heart of Pownal the opportunity you've been waiting for! If you've been searching for a home in Pownal but haven't been able to find the right fit or move quickly enough, this charming 2 bedroom, 1 bath home may be exactly what you've been looking for. Featuring an updated kitchen, a cozy pellet stove that primarily heats the home, and a bright enclosed front porch perfect for enjoying all four seasons, this property is full of warmth and character. Step outside to an amazing backyard with beautiful mountain views and plenty of space to entertain, barbecue, garden, or simply enjoy the peaceful setting. Have you been dreaming of starting a small hobby farm? This property offers the flexibility and space to make that vision possible. The detached garage provides endless opportunities whether you're looking for the perfect workshop, man cave, she shed, hobby space, or extra storage. Located close to ATV trail access and outdoor adventures, this home is ideal for someone ready to enjoy country living and Vermont adventures year round. With beautiful cross breezes throughout the home, quiet surroundings, and endless potential, this Pownal gem is truly something special and ready for its next owners to make it their own.

Listed by Brooke Thomson Drew of Mahar McCarthy 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.

20 Sage Street Bennington VT 05257

Bennington, VT20 Sage Street

Price$209,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5083528

  • Residential Single Family
  • Address 20 Sage Street
  • Village North Bennington
  • Bedrooms 4
  • Bathroom 1

Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an excellent opportunity to add your own finishing touches and build equity in a highly desirable location. Enjoy true village living with walkable access to cafs, restaurants, and trails, plus close proximity to Lake Paran and the Park-McCullough House. School choice at the elementary level adds flexibility. Just minutes to downtown Bennington for additional shopping, dining, and amenities, with easy access to multiple ski destinations. Conveniently located approximately one hour to Albany International Airport and about three hours to NYC and Boston. A rare opportunity to own in one of North Bennington’s most sought-after settings.

Listed by Abi Gregorio of eXp 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.

348 Center Street Pownal VT 05261

Pownal, VT348 Center Street

Price$198,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5091890

  • Residential Single Family
  • Full Bath 1
  • Address 348 Center Street
  • Bedrooms 2
  • Bathroom 1

Tucked into the rolling countryside of Pownal, this one-of-a-kind property offers something increasingly hard to find: space, story, and the freedom to make it your own. Set on 4.15 private acres, Once home to a beloved local dairy bar a second cabin and additional outbuildings, all awaiting the right buyer's vision and craftsmanship. Whether you're dreaming of a restored country residence, a primary home with income-producing rental cottages, or a recreational retreat, the bones and the land are here. The wooded acreage has long been a private playground for hiking, hunting, and off-road riding, and that same spirit of outdoor living carries straight through to the front porch. Ideal for investors, contractors, or the adventurous buyer who sees opportunity where others see work. Properties like this, with acreage, multiple structures, and a piece of local Vermont history, rarely come to market at this price point. Conveniently located with easy access to nearby amenities while maintaining that true rural Vermont character.

Listed by Sheryl Morehouse of Bishop West Real Estate, Inc.

{$office->Name}

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

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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.

1138 Main Road Stamford VT 05352

Stamford, VT1138 Main Road

Price$195,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5058792

  • Residential Single Family
  • Full Bath 1
  • Address 1138 Main Road
  • Bedrooms 5
  • Bathroom 2

Stamford, VT - A country drive less than 10 minutes North Adams, MA- home of Mass MoCA. Dating back to 1850 this spacious home boasts 4 bedrooms & 2 baths. 1st floor bedroom, bath, laundry, kitchen, dining, living room, den & sunroom. Nestled on almost and acre of land and bordering a babbling brook this property offers a privacy sanctuary. Come take a look for yourself! Located close to museums such as Mass MoCA & Clark Art Museum, theaters, restaurants, Green Mountain National Forest for hiking, mountain biking, snowshoeing & so much more, boating, down hill skiing in Mass. & VT.

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.

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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 11:39 AM EDT

 

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