Bennington, VT Homes

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  /26

  $290,000 Sold Mar 26, 2026

  235 Elm St Unit 3, Bennington, VT 05201

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft
  • Built 1880

  Last Sold Summary

  • 2% Below List Price
  • $110/SF
  • 8 Days On Market

  Current Estimated Value $288,000

  Last Listing Agent Erica Hale Ridgeline Real Estate

  235 Elm St Unit 3, Bennington, VT 05201
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  /30

  Est $213,361 Not Listed For Sale

  110 Booth Terrace, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,114 Sq Ft
  • Built 1924

  110 Booth Terrace, Bennington, VT 05201

  Last Sold Summary

  • 2% Above List Price
  • $189/SF
  • 6 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Abi Gregorio
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  /44

  $450,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  32 Cortland Ln, Bennington, VT 05201

  This well-maintained 1999 Colonial offers the perfect blend of timeless design, functional space, and peaceful surroundings in a desirable neighborhood just outside of town. Set on a wooded lot with a wrap-around covered front porch, this home invites you to slow down and enjoy the best of Vermont living. Inside, you’ll find over 2,100 square feet of thoughtfully designed living space with a

  Jenifer Prouty Hoffman Hoffman Real Estate

  32 Cortland Ln, Bennington, VT 05201
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  /26

  $193,500 Sold Aug 06, 2025

  305 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1937

  Last Sold Summary

  • 3% Below List Price
  • $119/SF
  • 17 Days On Market

  Current Estimated Value $199,608

  Last Listing Agent Matt Waddington Hoffman Real Estate

  305 Weeks St, Bennington, VT 05201
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  /30

  Est $325,580 Not Listed For Sale

  233 Grandview St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft
  • Built 1950

  233 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • $158/SF
  • 5 Days On Market

  Last Sold Price $324,000

  Last Listing Agent Thomas Martins Maple Leaf Realty
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  /21

  $75,000 Pending

  • Land
  • 0.45 Acre
  • $166,667 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
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  /38

  $291,065 Sold Jul 11, 2025

  121 Fillmore St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1946

  Last Sold Summary

  • 1% Above List Price
  • $168/SF
  • 66 Days On Market

  Current Estimated Value $301,774

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  121 Fillmore St, Bennington, VT 05201
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  /33

  Est $168,643 Not Listed For Sale

  105 Booth Terrace, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 1880

  105 Booth Terrace, Bennington, VT 05201

  Last Sold Summary

  • 25% Above List Price
  • $161/SF
  • 68 Days On Market

  Last Sold Price $135,000

  Last Listing Agent Dan Mason Perrott Realty
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  /15

  $269,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft

  626 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

  626 Main St, Bennington, VT 05201
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  /14

  $20,000 Sold Oct 30, 2025

  79 Skytop Dr Unit 6, Bennington, VT 05201

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • Built 1950

  Last Sold Summary

  • 27% Below List Price
  • $36/SF
  • 0 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  79 Skytop Dr Unit 6, Bennington, VT 05201
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  /40

  Est $286,335 Not Listed For Sale

  100 Booth Terrace, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 1905

  100 Booth Terrace, Bennington, VT 05201

  Last Sold Summary

  • 4% Above List Price
  • $175/SF
  • 54 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Justine Curry Maple Leaf Realty
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  /16

  $96,406 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  32 Cassie Ln, Bennington, VT 05201

  Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  32 Cassie Ln, Bennington, VT 05201
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  /54

  $80,000 Sold Dec 09, 2025

  889 Overlea Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $87/SF
  • 4 Days On Market

  Last Listing Agent Catherine Cairns Maple Leaf Realty

  889 Overlea Rd, Bennington, VT 05201
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  /23

  Est $252,759 Not Listed For Sale

  101 Barber St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,574 Sq Ft
  • Built 1920

  101 Barber St, Bennington, VT 05201

  Last Sold Summary

  • 20% Above List Price
  • $133/SF
  • 34 Days On Market

  Last Sold Price $210,000

  Last Listing Agent William Paquin Maple Leaf Realty
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  /39

  $359,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  38 Oak Ridge Ln, Bennington, VT 05201

  Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

  Matt Waddington Hoffman Real Estate

  38 Oak Ridge Ln, Bennington, VT 05201
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  /60

  $285,000 Sold Feb 18, 2026

  150 Fillmore St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $203/SF
  • 54 Days On Market

  Last Listing Agent Justine Curry Maple Leaf Realty

  150 Fillmore St, Bennington, VT 05201
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  /34

  Est $243,669 Not Listed For Sale

  99 Barber St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1965

  99 Barber St, Bennington, VT 05201

  Last Sold Summary

  • 4% Above List Price
  • $251/SF
  • 14 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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  /4

  $350,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  527 Jennings Brook Dr, Bennington, VT 05201

  Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

  Lilli West Maple Leaf Realty

  527 Jennings Brook Dr, Bennington, VT 05201
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  /44

  $340,000 Sold Jan 23, 2026

  989 Carpenter Hill Rd, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $205/SF
  • 85 Days On Market

  Current Estimated Value $326,642

  Last Listing Agent Angela Bevin Maple Leaf Realty

  989 Carpenter Hill Rd, Bennington, VT 05201
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  /30

  Est $267,544 Not Listed For Sale

  228 Grandview St, Bennington, VT 05201

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft
  • Built 1933

  228 Grandview St, Bennington, VT 05201

  Last Sold Summary

  • $245/SF
  • 108 Days On Market

  Last Sold Price $267,000

  Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty
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  /17

  $65,000

  • Land
  • 5.6 Acres
  • $11,607 per Acre

  80 Crossover Rd, Bennington, VT 05201

  This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.

  Dan Mason Perrott Realty

  80 Crossover Rd, Bennington, VT 05201
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  /48

  $296,500 Sold Nov 21, 2025

  4 Rockwood St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $156/SF
  • 6 Days On Market

  Current Estimated Value $296,910

  Last Listing Agent Justine Curry Maple Leaf Realty

  4 Rockwood St, Bennington, VT 05201
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  /32

  Est $325,909 Not Listed For Sale

  214 Silver St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,466 Sq Ft
  • Built 1860

  214 Silver St, Bennington, VT 05201

  Last Sold Summary

  • 9% Above List Price
  • $122/SF
  • 2 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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  /30

  $290,000 Sold Jul 17, 2025

  221 Grandview St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft
  • Built 1948

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 75 Days On Market

  Current Estimated Value $289,477

  Last Listing Agent Angela Bevin Maple Leaf Realty

  221 Grandview St, Bennington, VT 05201
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  /31

  Est $300,217 Not Listed For Sale

  325 Silver St, Bennington, VT 05201

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft
  • Built 1956

  325 Silver St, Bennington, VT 05201

  Last Sold Summary

  • 13% Above List Price
  • $144/SF
  • 10 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Derek Greene Derek Greene
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  /48

  $239,900 Sold Jun 06, 2025

  213 Maple St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • Built 1910

  Last Sold Summary

  • $166/SF
  • 2 Days On Market

  Current Estimated Value $250,345

  Last Listing Agent Matt Waddington Hoffman Real Estate

  213 Maple St, Bennington, VT 05201
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  /11

  Est $144,522 Not Listed For Sale

  432 South St Unit C5, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft
  • Built 1989

  432 South St Unit C5, Bennington, VT 05201

  Last Sold Summary

  • 6% Above List Price
  • $144/SF
  • 10 Days On Market

  Last Sold Price $136,500

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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  /21

  $120,000 Sold Mar 09, 2026

  1319 Vail Rd, Bennington, VT 05201

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

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
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  /36

  Est $163,170 Not Listed For Sale

  432 South St Unit B5, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft
  • Built 1989

  432 South St Unit B5, Bennington, VT 05201

  Last Sold Summary

  • 2% Above List Price
  • $169/SF
  • 5 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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  /34

  $335,000 Sold Jun 09, 2025

  290 Springhill Rd, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,354 Sq Ft
  • Built 1980

  Last Sold Summary

  • 13% Below List Price
  • $142/SF
  • 208 Days On Market

  Current Estimated Value $349,657

  Last Listing Agent Vicki Wilson Maple Leaf Realty

  290 Springhill Rd, Bennington, VT 05201
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  /26

  Est $164,652 Not Listed For Sale

  432 South St Unit A2, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft
  • Built 1989

  432 South St Unit A2, Bennington, VT 05201

  Last Sold Summary

  • 3% Above List Price
  • $169/SF
  • 142 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Lilli West Maple Leaf Realty
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  /44

  $315,000 Sold Jun 20, 2025

  197 Crescent Blvd, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1958

  Last Sold Summary

  • 7% Below List Price
  • $140/SF
  • 38 Days On Market

  Current Estimated Value $331,793

  Last Listing Agent Cassie Barbeau Mahar McCarthy Real Estate

  197 Crescent Blvd, Bennington, VT 05201
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  /4

  Not Listed For Sale

  406 South St, Bennington, VT 05201

  • 6 Beds
  • 6 Baths
  • 2,690 Sq Ft
  • Built 1900

  406 South St, Bennington, VT 05201

  Last Sold Summary

  • $132/SF
  • 27 Days On Market

  Last Sold Price $355,500

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group
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  /47

  $240,000 Sold Sep 24, 2025

  120 Imperial Ave, Bennington, VT 05201

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 1895

  Last Sold Summary

  • 20% Below List Price
  • $100/SF
  • 114 Days On Market

  Current Estimated Value $263,141

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
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  /32

  Est $243,990 Not Listed For Sale

  402 South St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 2,262 Sq Ft
  • Built 1940

  402 South St, Bennington, VT 05201

  Last Sold Summary

  • 32% Above List Price
  • $82/SF
  • 721 Days On Market

  Last Sold Price $185,000

  Last Listing Agent Phil Lewis Mahar McCarthy Real Estate
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  /47

  $160,000 Sold Jun 18, 2025

  136 Mccall St, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,094 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $76/SF
  • 39 Days On Market

  Current Estimated Value $167,443

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  136 Mccall St, Bennington, VT 05201
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  /19

  Est $309,027 Not Listed For Sale

  314 South St, Bennington, VT 05201

  • 6 Beds
  • 2 Baths
  • 2,452 Sq Ft
  • Built 1880

  314 South St, Bennington, VT 05201

  Last Sold Summary

  • 24% Above List Price
  • $102/SF
  • 288 Days On Market

  Last Sold Price $249,500

  Last Listing Agent David White OwnerEntry.com
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  /44

  $249,000 Sold Jun 20, 2025

  16 Browning Place, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 1900

  Last Sold Summary

  • $182/SF
  • 45 Days On Market

  Current Estimated Value $250,703

  Last Listing Agent Lilli West Maple Leaf Realty

  16 Browning Place, Bennington, VT 05201
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  /38

  Est $157,988 Not Listed For Sale

  314 Weeks St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,301 Sq Ft
  • Built 1920

  314 Weeks St, Bennington, VT 05201

  Last Sold Summary

  • 33% Above List Price
  • $91/SF
  • 14 Days On Market

  Last Sold Price $119,000

  Last Listing Agent Floyd Amidon Maple Leaf Realty
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  /46

  $280,000 Sold Jun 30, 2025

  4 Pine Rd, Bennington, VT 05201

  • 4 Beds
  • 1 Bath
  • 1,875 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $149/SF
  • 73 Days On Market

  Current Estimated Value $297,683

  Last Listing Agent Dan Mason Perrott Realty

  4 Pine Rd, Bennington, VT 05201

Showing Results 161 - 200, Page 5 of 18