Bennington, VT Homes

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  /50

  $650,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  55 Monument Ave, Bennington, VT 05201

  Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 849-4742

  55 Monument Ave, Bennington, VT 05201
• Explore Bennington

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  /14

  $2,275 per month

  • 2 Baths
  • 1,120 Sq Ft
  • Property for Rent

  343 Dewey St, Bennington, VT 05201

  Well-maintained provider office space available for lease, offering approx. 1,120 sq ft. Layout includes a waiting room with half bath, reception area, 2 operatories (or rooms), private office, and an additional half bath. Shared kitchen with the adjacent unit. Staff enjoy a separate entrance and designated parking, distinct from the public entry and lot. Rent includes electric, heat/AC,

  

  Peter West

  BISHOP WEST REAL ESTATE

  (802) 347-1295

  343 Dewey St, Bennington, VT 05201
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  /33

  $150,000 Sold Oct 31, 2025

  • 1,104 Sq Ft
  • $136/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1880

  229 Division St, Bennington, VT 05201

  Welcome to this charming 1900's cottage, ideally situated in the heart of Bennington Village! This delightful home offers the perfect blend of historic charm and modern convenience, though it is well-loved and awaits your personal touch and some TLC to truly shine. Enjoy easy access to local shopping and schools, making daily errands and commutes a breeze. For outdoor enthusiasts, nearby trails

  Lilli West Maple Leaf Realty

  229 Division St, Bennington, VT 05201
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  /27

  Est $183,154 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  731 Main St, Bennington, VT 05201

  731 Main St, Bennington, VT 05201
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  /36

  $275,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft

  61 Autumn Acres, Bennington, VT 05201

  Welcome home to this charming single level ranch in a peaceful, friendly neighborhood where neighbors still wave hello and lend a cup of sugar. This home offers easy single-level living with three bedrooms, one full bath, and first floor laundry.Step inside to discover beautiful hardwood floors throughout most of the home, currently covered with carpeting that can easily be removed no nails

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 802-8871

  61 Autumn Acres, Bennington, VT 05201
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  /20

  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  201 Division St Unit 201, Bennington, VT 05201

  This freshly painted, recently renovated 2 bedroom unit is now available! 1300/month rent. Washer and Dryer hookups in the unit. Heat pump system with multiple heads handles the heat and cooling. Water/Sewer included in the rent. Owner willing to consider pets with a pet deposit and additional monthly fee. No smoking. First/last/security due at lease signing. Credit and background checks required.

  201 Division St Unit 201, Bennington, VT 05201
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  /44

  $40,000 Sold Oct 31, 2025

  • 1,952 Sq Ft
  • $20/SF
  • 108 Days On Market

  • 5 Beds
  • 1 Bath
  • Built 1910

  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
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  /35

  Est $247,462 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  312 School St Unit 314, Bennington, VT 05201

  312 School St Unit 314, Bennington, VT 05201
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  /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
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  /21

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  124 Albe Dr, Bennington, VT 05201

  Fantastic whole house rental available! This 2 bed, one bath house is a rare rental find. Starting outside it features a large back deck, and a 1 car garage. Moving inside it is all updated! stainless steel appliance, life-proof flooring throughout, ceiling fan in the primary bedroom, and even a finished basement for tons of extra space! There is even a security system if you choose to do a

  124 Albe Dr, Bennington, VT 05201
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  /14

  $20,000 Sold Oct 30, 2025

  • 561 Sq Ft
  • $36/SF
  • 0 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1950

  79 Skytop Dr Unit 6, Bennington, VT 05201

  End unit condo in the Skytop Condominium Association. Needs total rehab, including structural repairs; might be best to teardown and rebuild. Power is on, but water and heat are shut off. Recently connected to town water. There are 8 units in the association that share 3 acres of common land and a paved road. Would make a great long term rental/investment property!

  Jenifer Prouty Hoffman Hoffman Real Estate

  79 Skytop Dr Unit 6, Bennington, VT 05201
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  /34

  Est $444,718 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft

  647 Fox Hill Rd, Bennington, VT 05201

  647 Fox Hill Rd, Bennington, VT 05201
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  /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
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  /18

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft
  • Condo for Rent

  432 South St Unit B4, Bennington, VT 05201

  Discover a delightful living experience at 432 South St. Unit B4, a welcoming 2-bedroom, 1.5-bathroom condo nestled in the highly sought-after Nathaniel Court neighborhood of Bennington, VT. Enjoy a range of amenities, including laundry hookups, a dedicated parking space, lawn care, plowing, and garbage taken care of by the association. Please note that pet will not be considered and smoking

  432 South St Unit B4, Bennington, VT 05201
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  /47

  $304,500 Sold Oct 24, 2025

  • 1,687 Sq Ft
  • $180/SF
  • 10 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  174 Morgan St, Bennington, VT 05201

  Sweet Ranch home that's not too big, not too small, just the right size! Set on 0.52 acres, it's a lovely lot surrounded by trees on 2 sides and has a beautiful mountain view. Attached 1-car garage with built-in storage has an automatic garage door and directly enters the galley kitchen. Refrigerator was removed because it stopped working... you can replace it with the same size, use the

  Jenifer Prouty Hoffman Hoffman Real Estate

  174 Morgan St, Bennington, VT 05201
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  /39

  Est $530,043 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft

  557 Fox Hill Rd, Bennington, VT 05201

  557 Fox Hill Rd, Bennington, VT 05201
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  /41

  $295,000

  • 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
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  /2

  $950 per month

  • 1 Bed
  • 1 Bath
  • 200 Sq Ft
  • Condo for Rent

  106 School St Unit 3, Bennington, VT 05201

  $950/month. First floor one bedroom apartment. Non smoking unit. First/Last/Security required. Credit and background checks required. Sorry, no pets. Heat, hot water, garbage included in rent.

  106 School St Unit 3, Bennington, VT 05201
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  /25

  $285,000 Sold Oct 24, 2025

  • 1,888 Sq Ft
  • $151/SF
  • 47 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  120 Albe Dr, Bennington, VT 05201

  Comfortable, convenient and close to downtown Bennington and all its amenities. Built in 2001, in a quiet neighborhood, the home features 3 bedrooms and 2.5 baths,, which includes a primary suite with its own bath. The first floor offers a spacious eat-in kitchen with washer and dryer efficiently installed in a large closet. The kitchen also has glass doors that open to private deck and a level

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  120 Albe Dr, Bennington, VT 05201
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  /38

  Est $627,586 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft

  3347 West Rd, Bennington, VT 05201

  3347 West Rd, Bennington, VT 05201
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  /26

  $295,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft

  235 Elm St Unit 3, Bennington, VT 05201

  This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

  

  Erica Hale

  Ridgeline Real Estate

  (802) 210-4437

  235 Elm St Unit 3, Bennington, VT 05201
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  /10

  $1,475 per month

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  35 Dudley Place, Bennington, VT 05201

  Please do NOT click the "Request To Apply" button. This will cause a delay in our ability to respond to you. Read below for instructions on how to apply through our website.3br MANUFACTURED HOME for rent!Unit: D-035Apply To: Mountain View CommunityRent: $1475/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog friendly, all animals must be

  35 Dudley Place, Bennington, VT 05201
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  /24

  $42,000 Sold Oct 24, 2025

  • Land
  • 0.48 Acre
  • $87,500 per Acre

  • 55 Days On Market

  26 Asa's Way, Bennington, VT 05257

  Walking trails, a paved road, underground utilities, and water/sewer at the street, what more could you ask for? Situated high on Asa's Way, almost a half acre of slightly sloping and level lot is ready to build on. Over 200 feet of road frontage allows for many home designs; from a hillside house that maximizes the southerly sun, to a modern bungalow perched on a flat landing, bring your ideas!

  Angela Bevin Maple Leaf Realty

  26 Asa's Way, Bennington, VT 05257
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  /19

  Est $150,039 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft

  1 Division Place, Bennington, VT 05201

  1 Division Place, Bennington, VT 05201
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  /17

  $270,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  239 - 241 Elm St, Bennington, VT 05201

  Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

  

  Erica Hale

  Ridgeline Real Estate

  (802) 278-6021

  239 - 241 Elm St, Bennington, VT 05201
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  /44

  $1,350 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Condo for Rent

  254 Union St Unit B, Bennington, VT 05201

  Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,

  254 Union St Unit B, Bennington, VT 05201
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  /30

  $345,750 Sold Oct 21, 2025

  • 1,753 Sq Ft
  • $197/SF
  • 58 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1948

  374 Overlea Rd, North Bennington, VT 05257

  A stunning three bedroom, two bath home on a wooded lot with mountain views and bordered on several sides by serene farm pastures! Just a few minutes from downtown Bennington and even closer to the village of North Bennington! Tons of natural light inside that compliments the updated kitchen and open dining / living room areas. First floor includes enclosed rear sun porch/mudroom, laundry and

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /21

  Est $153,062 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  106 Park St Unit 16, Bennington, VT 05201

  106 Park St Unit 16, Bennington, VT 05201
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  /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
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  /50

  $1,700 per month

  • 4 Beds
  • 1.5 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  129 Grandview St Unit 129, Bennington, VT 05201

  Very large 1,750 square foot apartment (don't hold me to that exact figure)* 9 foot ceilings on both first floor and second floor. Great space, charming* Has the old world feel to it. Building was erected in the late 1800s* It has a living room, dining room (with bay window) and home office on the first floor* It also has a decent sized kitchen on the first floor with fully

  129 Grandview St Unit 129, Bennington, VT 05201
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  /42

  $229,900 Sold Oct 20, 2025

  • 1,274 Sq Ft
  • $180/SF
  • 2 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1860

  414 Park St, Bennington, VT 05201

  Enjoy the beautiful gardens and yard of this 3 bedroom, 1 and a half bath home. Offering country kitchen, formal dining room with built-ins, living room and more. Outside the park like grounds and location make this a must see home. Across the road is the town duck pond and it's a short walk to the high school and ball parks.

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  414 Park St, Bennington, VT 05201
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  /19

  Est $165,198 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  106 Park St Unit 10, Bennington, VT 05201

  106 Park St Unit 10, Bennington, VT 05201
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  /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
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  /24

  $1,100 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  174 S Branch St Unit 174, Bennington, VT 05201

  Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for

  174 S Branch St Unit 174, Bennington, VT 05201
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  /41

  $410,000 Sold Oct 17, 2025

  • 1,792 Sq Ft
  • $229/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  882 East Rd, Bennington, VT 05201

  Welcome to 882 East Road! This spacious first-floor ranch, set on 1.97 acres, offers comfort, convenience, and room to grow. Built in 2002, the home features three bedrooms and two and half baths, all thoughtfully designed for easy single level living.The open kitchen provides plenty of working space, a beautiful pantry, and excellent flow into a large living room, perfect for gathering and

  Brooke Thomson Drew Mahar McCarthy Real Estate

  882 East Rd, Bennington, VT 05201
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  /29

  Est $451,569 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,752 Sq Ft

  9378 Vt Route 9, Bennington, VT 05201

  9378 Vt Route 9, Bennington, VT 05201
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  /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
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  /10

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  130 Union St Unit D, Bennington, VT 05201

  This 1-bedroom, 1-bathroom apartment located within the downtown of Bennington offers 700 square feet of living space. The living room features ample natural light and connects directly to the kitchen, which includes essential appliances. The bedroom provides sufficient space for a queen-sized bed and includes plenty of closet space for storage. The bathroom is equipped with standard fixtures and

  130 Union St Unit D, Bennington, VT 05201
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  /30

  $171,000 Sold Oct 17, 2025

  • 1,724 Sq Ft
  • $99/SF
  • 177 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1979

  14 Pace Rd, Bennington, VT 05201

  One level living on a 1.1 acre level lot. Adequately sized with functional layout, this ranch style home features 3 bedrooms, 1 full bathroom, spacious living area and a full basement!The seller does not accept blind offers or escalation clauses.Cash offers require 10% EMD or $1,000 minimum, whichever is greater, and all financed offers require 1% EMD or $1,000 minimum, whichever is

  Dick Thackston R.H. Thackston & Company

  14 Pace Rd, Bennington, VT 05201
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  /16

  Est $207,905 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,005 Sq Ft

  214 Hickory Rd, Bennington, VT 05201

  214 Hickory Rd, Bennington, VT 05201

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