Bennington, VT Homes

• 

  

  

  /51

  Est $236,303

  Not Listed For Sale

  306 Beech St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1989

  306 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate
• 

  

  

  /38

  $335,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft

  308 Crescent Blvd, Bennington, VT 05201

  Welcome home to this meticulously maintained 3 bedroom, 1.5 bath ranch, perfectly nestled in a highly desirable neighborhood. Offering over 1,400 square feet of single level living space, this home combines classic charm, everyday comfort, and an unbeatable location. Rich hardwood floors flow throughout most of the home creating a warm and inviting atmosphere from the moment you step inside. The

  Angela Bevin Maple Leaf Real Estate

  308 Crescent Blvd, Bennington, VT 05201
• 

  

  

  /35

  $372,000

  Sold May 13, 2026

  303 Prospect St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,463 Sq Ft
  • Built 1949

  Last Sold Summary

  • 1% Above List Price
  • $254/SF
  • 11 Days On Market

  Current Estimated Value $374,432

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  303 Prospect St, Bennington, VT 05201
• 

  

  

  /32

  Est $309,879

  Not Listed For Sale

  17 Tel Rd, Bennington, VT 05201

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

  17 Tel Rd, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  

  /4

  $350,000

  New Construction Pending

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

  526 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 Real Estate

  526 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /18

  $260,000

  Sold Apr 28, 2026

  940 Gage St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft
  • Built 1945

  Last Sold Summary

  • 13% Below List Price
  • $166/SF
  • 58 Days On Market

  Current Estimated Value $272,115

  Last Listing Agent Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
• 

  

  /40

  Est $254,001

  Not Listed For Sale

  316 Beech St, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1948

  316 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Dan Mason Perrott Realty
• 

  

  /46

  $275,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  2867 Chapel Rd, Bennington, VT 05201

  Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the

  Jenifer Prouty Hoffman Hoffman Real Estate

  2867 Chapel Rd, Bennington, VT 05201
• 

  

  /53

  $400,000

  Sold Sep 22, 2025

  495 Fairview St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,309 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $306/SF
  • 12 Days On Market

  Current Estimated Value $409,321

  Last Listing Agent Catherine Cairns Maple Leaf Real Estate

  495 Fairview St, Bennington, VT 05201
• 

  

  /38

  Est $218,567

  Not Listed For Sale

  230 Beech St, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Built 1880

  230 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /16

  $395,000

  Pending

  • 4,646 Sq Ft

  307 North St, Bennington, VT 05201

  Exceptional mixed-use opportunity in Bennington’s MU-2 District offering flexibility for investors, owner-occupants, or live/work configurations. Sale includes both 307 North Street and 307.5 North Street, two separate buildings situated on one 0.70-acre parcel with strong visibility and approximately 150 feet of frontage along North Street (VT Route 7). The front building (c. 1840) offers

  Jeffrey Dorman

  307 North St, Bennington, VT 05201
• 

  

  /19

  $220,000

  Sold Jun 23, 2026

  14 Robinson Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft
  • Built 1927

  Last Sold Summary

  • $175/SF
  • 309 Days On Market

  Current Estimated Value $227,725

  Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
• 

  

  /17

  Est $163,910

  Not Listed For Sale

  224 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,709 Sq Ft
  • Built 1900

  224 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 103 Days On Market

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

  

  /38

  $309,900

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  2 Pine Rd, Bennington, VT 05201

  Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  2 Pine Rd, Bennington, VT 05201
• 

  

  /30

  $277,000

  Sold Jul 10, 2026

  212 Dewey St, Bennington, VT 05201

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft
  • Built 1963

  Last Sold Summary

  • 1% Above List Price
  • $219/SF

  Current Estimated Value $273,244

  Last Listing Agent William Paquin Maple Leaf Real Estate

  212 Dewey St, Bennington, VT 05201
• 

  

  /35

  Est $215,526

  Not Listed For Sale

  218 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft
  • Built 1890

  218 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Thomas Martins Maple Leaf Real Estate
• 

  

  /37

  $264,900

  $24K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  The renovations are done, just move in! Nearly everything is NEW at 109 County Street, including the price! In addition, the seller is offering a $5K credit towards the buyer’s closing costs. This extensively renovated 4BR/2BA home with a fully fenced yard gives you the opportunity to enjoy the benefits of a much newer home without the time, expense, and stress of renovating one yourself.

  Angela Bevin Maple Leaf Real Estate

  109 County St, Bennington, VT 05201
• 

  

  /37

  $256,250

  Sold Sep 03, 2025

  1236 Morgan St, Bennington, VT 05201

  • 2 Beds
  • 1.5 Baths
  • 1,259 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Above List Price
  • $204/SF
  • 7 Days On Market

  Current Estimated Value $267,860

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  1236 Morgan St, Bennington, VT 05201
• 

  

  /32

  Est $231,880

  Not Listed For Sale

  103 Evergreen Dr, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1945

  103 Evergreen Dr, Bennington, VT 05201

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Gabrielle Burdge
• 

  

  /54

  $480,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /45

  $405,000

  Sold Apr 20, 2026

  848 Coleville Rd, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $200/SF
  • 151 Days On Market

  Current Estimated Value $420,047

  Last Listing Agent Beatrice O'Connell Maple Leaf Real Estate

  848 Coleville Rd, Bennington, VT 05201
• 

  

  /40

  Est $261,346

  Not Listed For Sale

  313 Beech St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1960

  313 Beech St, Bennington, VT 05201

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /45

  $269,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  951 Gage St, Bennington, VT 05201

  This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

  Dan Mason Perrott Realty

  951 Gage St, Bennington, VT 05201
• 

  

  /35

  $220,000

  Sold Sep 16, 2025

  115 Jefferson Ave, Bennington, VT 05201

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Built 1930

  Last Sold Summary

  • 18% Below List Price
  • $142/SF
  • 83 Days On Market

  Current Estimated Value $233,375

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  115 Jefferson Ave, Bennington, VT 05201
• 

  

  /17

  Est $384,313

  Not Listed For Sale

  10 Margaret Ln, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,154 Sq Ft
  • Built 1978

  10 Margaret Ln, Bennington, VT 05201

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /7

  $145,000

  $30K PRICE DROP Pending

  • Land
  • 15.49 Acres
  • $9,361 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
• 

  

  /60

  $245,000

  Sold Sep 22, 2025

  19 Robinson Ave, Bennington, VT 05201

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1954

  Last Sold Summary

  • 11% Below List Price
  • $186/SF
  • 3 Days On Market

  Current Estimated Value $261,243

  Last Listing Agent Floyd Amidon Maple Leaf Real Estate

  19 Robinson Ave, Bennington, VT 05201
• 

  

  /45

  Est $416,889

  Not Listed For Sale

  320 Crescent Blvd, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,895 Sq Ft
  • Built 1960

  320 Crescent Blvd, Bennington, VT 05201

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /55

  $209,000

  $16K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,518 Sq Ft

  142 Pine Cir, Bennington, VT 05201

  Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom

  Justine Curry Maple Leaf Real Estate

  142 Pine Cir, Bennington, VT 05201
• 

  

  /12

  $325,000

  Sold Jul 20, 2026

  343 Safford St, Bennington, VT 05201

  • 2,476 Sq Ft
  • Built 1900

  Last Sold Summary

  • $131/SF
  • 34 Days On Market

  Last Listing Agent Lori Hurley Four Corner Properties LLC

  343 Safford St, Bennington, VT 05201
• 

  

  /30

  Est $235,188

  Not Listed For Sale

  101 Coulter St, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,603 Sq Ft
  • Built 1947

  101 Coulter St, Bennington, VT 05201

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  

  /18

  $219,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  420 Gore Rd, Bennington, VT 05201

  Welcome home to this charming 3-bedroom, 2-bath split-level home nestled on a beautiful 1-acre lot with stunning mountain views. Offering the perfect blend of comfort and privacy, this home features an attached garage, a spacious layout, and a peaceful backyard ideal for relaxing or entertaining.Enjoy your morning coffee or evening sunsets from one of two decks overlooking the private yard

  Kelley Mccarthy Mahar McCarthy Real Estate

  420 Gore Rd, Bennington, VT 05201
• 

  

  /23

  $388,800

  Sold Jun 10, 2026

  317 Chester Knoll Dr, Bennington, VT 05201

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2026

  Last Sold Summary

  • $240/SF

  Last Listing Agent Lilli West Maple Leaf Real Estate

  317 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /30

  Est $328,757

  Not Listed For Sale

  402 Jefferson Heights, Bennington, VT 05201

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft
  • Built 1953

  402 Jefferson Heights, Bennington, VT 05201

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Dick Thackston R.H. Thackston & Company
• 

  

  /46

  $259,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,318 Sq Ft

  104 John St, Bennington, VT 05201

  This well-maintained village home located on a dead end rd is move-in ready and filled with inviting features. Set on a desirable corner lot, the property offers an updated bath, spacious covered front and rear porches, and a cozy pellet stove. The kitchen was just updated as well as painted in side and out. The large front entry provides additional usable space, while the one-car insulated and

  Dan Mason Perrott Realty

  104 John St, Bennington, VT 05201
• 

  

  /59

  $408,000

  Sold Jul 27, 2026

  131 Pine Cir, Bennington, VT 05201

  • 4 Beds
  • 3 Baths
  • 2,119 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $193/SF
  • 48 Days On Market

  Current Estimated Value $421,104

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate

  131 Pine Cir, Bennington, VT 05201
• 

  

  /24

  Est $287,597

  Not Listed For Sale

  15 Greenview Dr, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,102 Sq Ft
  • Built 1993

  15 Greenview Dr, Bennington, VT 05201

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  

  /25

  $950,000

  $300K PRICE DROP

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment. The property includes nine guest accommodations, owner's quarters, expansive common areas,

  Marek Kovac TPW Real Estate

  124 Elm St, Bennington, VT 05201
• 

  

  /16

  $130,000

  Sold Jan 28, 2026

  755 Main St, Bennington, VT 05201

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft
  • Built 1890

  Last Sold Summary

  • 10% Below List Price
  • $88/SF
  • 141 Days On Market

  Current Estimated Value $137,803

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

  755 Main St, Bennington, VT 05201
• 

  

  /38

  Est $389,165

  Not Listed For Sale

  150 Pine Cir, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 1,592 Sq Ft
  • Built 2005

  150 Pine Cir, Bennington, VT 05201

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Brandy Lesser

Showing Results 121 - 160, Page 4 of 18