Bennington Homes

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  /35

  $379,900

  • 4 Beds
  • 2.5 Baths
  • 2,530 Sq Ft

  93 Russett Dr, Bennington, VT 05201

  Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 416-3661

  93 Russett Dr, Bennington, VT 05201
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  /4

  $1,350 per month

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  103 County St Unit 1, Bennington, VT 05201

  Property Id: 14887483 bed 1 bath apartment located at first floor.Tenants pay for their utilities:heat electric etc.

  103 County St Unit 1, Bennington, VT 05201
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  $300,000 Sold May 15, 2025

  17 Tel Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 1970

  Last Sold Summary

  • $132/SF
  • 6 Days On Market

  Current Estimated Value $315,917

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  17 Tel Rd, Bennington, VT 05201
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  /51

  Not Listed For Sale

  301 North St Unit 3, Bennington, VT 05201

  • 8 Beds
  • 4 Baths
  • 4,992 Sq Ft
  • Built 1915

  301 North St Unit 3, Bennington, VT 05201

  Last Sold Summary

  • $79/SF
  • 5 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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  /60

  $220,000

  • Land
  • 54 Acres
  • $4,074 per Acre

  399 Bard Rd, Bennington, VT 05201

  Escape to your own private sanctuary on this sprawling 54+/- acre wooded retreat in beautiful Bennington, VT. Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond situated entirely within its southeastern boundary, perfect as a future homestead centerpiece. Enjoy easy access via a paved, town-maintained road leading to level

  Curtis Trousdale Preferred Properties

  399 Bard Rd, Bennington, VT 05201
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  /2

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  165 Benmont Ave, Bennington, VT 05201

  Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

  165 Benmont Ave, Bennington, VT 05201
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  /30

  $345,750 Sold Oct 21, 2025

  374 Overlea Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1948

  Last Sold Summary

  • 5% Below List Price
  • $197/SF
  • 58 Days On Market

  Current Estimated Value $360,867

  Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /27

  Est $183,989 Not Listed For Sale

  731 Main St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft
  • Built 1900

  731 Main St, Bennington, VT 05201

  Last Sold Summary

  • 9% Above List Price
  • $146/SF
  • 7 Days On Market

  Last Sold Price $169,000

  Last Listing Agent Dana Haley Real Broker LLC
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  /35

  $370,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,463 Sq Ft

  303 Prospect St, Bennington, VT 05201

  Nestled on a quiet residential street, this beautifully maintained home effortlessly blends timeless charm with modern convenience, creating a space that is as inviting as it is impressive. From the moment you arrive, you’ll appreciate the character and warmth that set this property apart. At the heart of the home is a thoughtfully designed kitchen featuring modern appliances, rich cherry

  Angela Bevin Maple Leaf Realty

  303 Prospect St, Bennington, VT 05201
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  /20

  $2,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,460 Sq Ft
  • House for Rent

  2509 Skiparee Rd, Bennington, VT 05260

  Welcome to your new home in North Pownal, VT! This charming property offers spectacular views in a serene setting while being just 20mins to Bennington and Williamstown. Ideal for those seeking a peaceful lifestyle while being within reach of local amenities.The spacious floor area provides ample room for relaxation and entertainment, making it a delightful place to call

  2509 Skiparee Rd, Bennington, VT 05260
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  /49

  $435,000 Sold Oct 10, 2025

  458 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 4 Baths
  • 3,040 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $143/SF
  • 7 Days On Market

  Current Estimated Value $457,966

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  458 Fox Hill Rd, Bennington, VT 05201
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  /35

  Est $251,706 Not Listed For Sale

  312 School St Unit 314, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1908

  312 School St Unit 314, Bennington, VT 05201

  Last Sold Summary

  • 6% Above List Price
  • $109/SF
  • 3 Days On Market

  Last Sold Price $237,000

  Last Listing Agent Angela Bevin Maple Leaf Realty
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  /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 access

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
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  /59

  $2,300 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft
  • House for Rent

  212 Dewey St, Bennington, VT 05201

  This property is available now, and is fully furnished. Water/sewer, plowing, and lawn care included. The whole interior of the home has just been repainted in the last couple of years. Wood floors sanded. New stove. New Washer and Dryer, new flooring in the kitchen. Two bedrooms, 2.5 baths. The basement holds huge potential for storage. Small back deck to enjoy the creek. Two car garage. Just

  212 Dewey St, Bennington, VT 05201
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  /28

  $398,350 Sold Sep 04, 2025

  315 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2025

  Last Sold Summary

  • $246/SF
  • 0 Days On Market

  Last Listing Agent Lilli West Maple Leaf Realty

  315 Chester Knoll Dr, Bennington, VT 05201
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  /34

  Est $469,558 Not Listed For Sale

  647 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 2008

  647 Fox Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 9% Above List Price
  • $226/SF
  • 133 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Erika Floriani Hoffman Real Estate
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  /18

  $300,000 Pending

  • 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
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  /10

  $1,200 total monthly price

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

  318 School St Unit 318 School, Bennington, VT 05201

  318 School St Unit 318 School, Bennington, VT 05201
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  /34

  $175,000 Sold May 16, 2025

  106 Park St Unit 8, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1993

  Last Sold Summary

  • $166/SF
  • 9 Days On Market

  Current Estimated Value $181,856

  Last Listing Agent Vicki Wilson Maple Leaf Realty

  106 Park St Unit 8, Bennington, VT 05201
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  /39

  Est $573,613 Not Listed For Sale

  557 Fox Hill Rd, Bennington, VT 05201

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft
  • Built 2009

  557 Fox Hill Rd, Bennington, VT 05201

  Last Sold Summary

  • 12% Above List Price
  • $218/SF
  • 17 Days On Market

  Last Sold Price $510,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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  /53

  $649,000 Under Contract

  • 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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  /18

  $1,400 total monthly price

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

  203 - 205 Union St Unit 2 - Rear Downstairs, Bennington, VT 05201

  203 Union St, Downstairs Back ApartmentIncluded with rent: Heat, Lawncare, Hot Water, Water/SewerFreshly painted first floor unit available at 203 Union St for $1,400 per month.This unit offers a clean, freshly painted living space in a convenient location. The apartment is ready for immediate occupancy. There is a large porch area for extra storage.Rent: $1,400

  203 - 205 Union St Unit 2 - Rear Downstairs, Bennington, VT 05201
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  /28

  $265,000 Sold Dec 15, 2025

  26 Cyr Ct, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 2000

  Last Sold Summary

  • $255/SF
  • 5 Days On Market

  Current Estimated Value $265,594

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  26 Cyr Ct, Bennington, VT 05201
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  /38

  Est $671,901 Not Listed For Sale

  3347 West Rd, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft
  • Built 1969

  3347 West Rd, Bennington, VT 05201

  Last Sold Summary

  • 10% Above List Price
  • $187/SF
  • 20 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Margretta Fischer Wohler Realty Group
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  /45

  $425,000 Pending

  • 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
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  /22

  $995 total monthly price

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

  302 Silver St Unit 304.5, Bennington, VT 05201

  Thiis is a four unit right in town with great considerate tenants.

  302 Silver St Unit 304.5, Bennington, VT 05201
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  /20

  $90,000 Sold Apr 17, 2025

  105 Spring St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1903

  Last Sold Summary

  • 10% Below List Price
  • $59/SF
  • 4 Days On Market

  Current Estimated Value $123,450

  Last Listing Agent Matt Waddington Hoffman Real Estate

  105 Spring St, Bennington, VT 05201
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  /19

  Est $389,677 Not Listed For Sale

  1 Division Place, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft
  • Built 1895

  1 Division Place, Bennington, VT 05201

  Last Sold Summary

  • 212% Above List Price
  • $128/SF
  • 44 Days On Market

  Last Sold Price $125,000

  Last Listing Agent Vicki Wilson Maple Leaf Realty
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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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  /39

  $1,275 total monthly price

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

  18 Main St Unit C, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit C, North Bennington, VT 05257
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  /57

  $190,000 Sold Sep 16, 2025

  100 Webb St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,416 Sq Ft
  • Built 1943

  Last Sold Summary

  • 12% Below List Price
  • $134/SF
  • 75 Days On Market

  Current Estimated Value $193,317

  Last Listing Agent Lindsey Martin Maple Leaf Realty

  100 Webb St, Bennington, VT 05201
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  /21

  Est $170,004 Not Listed For Sale

  106 Park St Unit 16, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1993

  106 Park St Unit 16, Bennington, VT 05201

  Last Sold Summary

  • 10% Above List Price
  • $147/SF
  • 76 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC
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  /36

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,748 Sq Ft

  695 Dermody Rd, Bennington, VT 05201

  This inviting ranch has been thoughtfully cared for and filled with warmth throughout. What truly sets it apart is the location, offering wide, beautiful views you can enjoy everyday. The level lot provides plenty of space for gardening, outdoor gatherings, or simply relaxing on the back deck with a morning cup of coffee, or an evening star gazing. With generous road frontage, the possibilities

  Monique Geannelis Mahar McCarthy Real Estate

  695 Dermody Rd, Bennington, VT 05201
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  /26

  $1,300 total monthly price

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

  178 S Branch St Unit 178, 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

  178 S Branch St Unit 178, Bennington, VT 05201
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  /36

  $300,000 Sold Apr 02, 2026

  318 Chester Knoll Dr, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft
  • Built 2006

  Last Sold Summary

  • $161/SF
  • 5 Days On Market

  Current Estimated Value $298,786

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  318 Chester Knoll Dr, Bennington, VT 05201
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  /30

  Est $450,397 Not Listed For Sale

  414 Matteson Rd, North Bennington, VT 05257

  • 3 Beds
  • 2.5 Baths
  • 1,429 Sq Ft
  • Built 1981

  414 Matteson Rd, North Bennington, VT 05257

  Last Sold Summary

  • 7% Above List Price
  • $294/SF
  • 4 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Lindsey Martin Maple Leaf Realty
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  /33

  $349,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  308 Elm St, Bennington, VT 05201

  Vermont charm meets move-in ready comfort on Elm Street! This inviting 3-bedroom, 2.5-bath Cape offers warm, welcoming spaces throughout. The cozy yet spacious living room features a fireplace — perfect for snowy Vermont evenings — while the generously sized dining room is ideal for hosting holidays and gatherings. The beautifully updated kitchen showcases granite countertops and rich cherry

  Kelley Mccarthy Mahar McCarthy Real Estate

  308 Elm St, Bennington, VT 05201
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  /39

  $1,275 total monthly price

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

  18 Main St Unit C, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit C, North Bennington, VT 05257
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  /41

  $141,000 Sold Apr 01, 2026

  235 Maple St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,060 Sq Ft
  • Built 1915

  Last Sold Summary

  • 5% Below List Price
  • $133/SF
  • 13 Days On Market

  Current Estimated Value $147,691

  Last Listing Agent Lindsey Martin Maple Leaf Realty

  235 Maple St, Bennington, VT 05201
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  Est $332,164 Not Listed For Sale

  19 Royal St, North Bennington, VT 05257

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft
  • Built 2002

  19 Royal St, North Bennington, VT 05257

  Last Sold Summary

  • 2% Above List Price
  • $193/SF
  • 16 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Lindsey Martin Maple Leaf Realty

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