5,296

Bennington, VT Homes

Section Image
  • /48

    $295,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,753 Sq Ft

    166 Cardinal Ln, Bennington, VT 05201

    Discover the charm and potential of this one-of-a-kind mid-century home, offered for sale for the first time. Set on 3.20 private acres with mature, lush landscaping, this spacious property offers a peaceful and serene setting while remaining conveniently close to shopping, schools, restaurants, and the hospital. Originally built in 1964, the home has grown through multiple additions over the

    Monique Geannelis Mahar McCarthy Real Estate

    166 Cardinal Ln, Bennington, VT 05201
  • /8

    $1,100 Per Month

    • 1 Bed
    • 1 Bath
    • 642 Sq Ft
    • 12-16 Sage St.

    12-16-16 Sage St Unit 1, Bennington, VT 05257

    12-16-16 Sage St Unit 1, Bennington, VT 05257
  • /17

    $159,900

    Sold Jun 05, 2026

    432 South St Unit B2, Bennington, VT 05201

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

    Last Sold Summary

    • $188/SF
    • 40 Days On Market

    Current Estimated Value $168,882

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

    432 South St Unit B2, Bennington, VT 05201
    • /44

      Est $330,352

      Not Listed For Sale

      197 Crescent Blvd, Bennington, VT 05201

      • 4 Beds
      • 2.5 Baths
      • 2,248 Sq Ft
      • Built 1958
      197 Crescent Blvd, Bennington, VT 05201

      Last Sold Summary

      • 38 Days On Market

  • /29

    $250,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    103 Jennings Brook Dr, Bennington, VT 05201

    Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

    Kelley Mccarthy Mahar McCarthy Real Estate

    103 Jennings Brook Dr, Bennington, VT 05201
  • /18

    $1,350 Per Month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Putnam Winslow– $1,350 – 1 Bathroom Studio, 300 SQ.FT. – UTILITIES INCLUDED, Available 7/15/26

    341 Main St Unit 309, Bennington, VT 05201

    – Fully renovated studio apartment available for rent in downtown Bennington– Large windows, wood floors, high ceilings– Utilities Included (electric, heat, water and AC)– Off street parking– Free, on-site laundryThis is an income qualifying affordable unit. Annual household income for single occupancy may not exceed $91,440. Income limits increase with additional

    341 Main St Unit 309, Bennington, VT 05201
  • /41

    $410,000

    Sold Oct 17, 2025

    882 East Rd, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Above List Price
    • $229/SF
    • 14 Days On Market

    Current Estimated Value $402,658

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    882 East Rd, Bennington, VT 05201
    • /22

      Not Listed For Sale

      35 West Rd, Bennington, VT 05201

      • 2 Beds
      • 2 Baths
      • 938 Sq Ft
      • Built 1986
      35 West Rd, Bennington, VT 05201

      Last Sold Summary

      • 38 Days On Market

  • /14

    $237,700

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft

    117 Putnam St, Bennington, VT 05201

    This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

    Dan Mason Perrott Realty

    117 Putnam St, Bennington, VT 05201
  • /17

    $1,999 Per Month

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Putnam Hotel – $1,999 – 1 Bedroom/1 Bathroom, 690 SQ.FT. – UTILITIES INCLUDED, Available Immediately

    359 Main St Unit 305, Bennington, VT 05201

    Welcome to Putnam Block, Hotel #305– Beautifully renovated 1 bedroom/1 bathroom apartment available for rent in downtown Bennington– Large windows, wood floors, high ceilings– Granite countertops– Stainless steel appliances– Washer and dryer in unit– Utilities INCLUDED (electric, heat, water and AC)– Elevator– Off street parkingThis is an income

    359 Main St Unit 305, Bennington, VT 05201
  • /19

    $89,499

    Sold Jan 21, 2026

    64 Ethans Way, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 746 Sq Ft
    • Built 2024

    Last Sold Summary

    • $120/SF
    • 238 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    64 Ethans Way, Bennington, VT 05201
    • /42

      Est $320,710

      Not Listed For Sale

      209 Washington Ave, Bennington, VT 05201

      • 4 Beds
      • 4 Baths
      • 3,230 Sq Ft
      • Built 1900
      209 Washington Ave, Bennington, VT 05201

      Last Sold Summary

      • 52 Days On Market

  • /16

    $96,906

    New Construction Under Contract
    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    41 Audrey Ln, Bennington, VT 05201

    Welcome to 41 Audrey 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

    41 Audrey Ln, Bennington, VT 05201
  • /41

    $480,000

    Sold Dec 22, 2025

    245 Southshire Dr, Bennington, VT 05201

    • 4 Beds
    • 2.5 Baths
    • 2,116 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $227/SF
    • 145 Days On Market

    Current Estimated Value $491,421

    Last Listing Agent Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    245 Southshire Dr, Bennington, VT 05201
    • /44

      Est $243,480

      Not Listed For Sale

      16 Browning Place, Bennington, VT 05201

      • 3 Beds
      • 2 Baths
      • 1,366 Sq Ft
      • Built 1900
      16 Browning Place, Bennington, VT 05201

      Last Sold Summary

      • 45 Days On Market

  • /58

    $1,495,000

    Under Contract
    • 7 Beds
    • 5.5 Baths
    • 6,392 Sq Ft

    16 West Rd, Bennington, VT 05201

    Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home’s historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless

    Kelley Mccarthy Mahar McCarthy Real Estate

    16 West Rd, Bennington, VT 05201
  • /40

    $185,000

    Sold Jul 25, 2025

    305 Grove St, Bennington, VT 05201

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Built 2016

    Last Sold Summary

    • 3% Above List Price
    • $231/SF
    • 28 Days On Market

    Current Estimated Value $182,566

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    305 Grove St, Bennington, VT 05201
    • /27

      Est $180,571

      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

      • 7 Days On Market

  • /31

    $90,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    109 Evergreen Dr, Bennington, VT 05201

    House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

    Zachary Zupan EXP Realty

    109 Evergreen Dr, Bennington, VT 05201
  • /15

    $199,900

    Sold Jan 16, 2026

    111 Hicks Ave, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1936

    Last Sold Summary

    • $160/SF
    • 13 Days On Market

    Current Estimated Value $197,903

    Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

    111 Hicks Ave, Bennington, VT 05201
    • /35

      Est $240,320

      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

      • 3 Days On Market

  • /6

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft

    2 Hamlin Ave, Bennington, VT 05201

    2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

    Lori Hurley Four Corner Properties LLC

    2 Hamlin Ave, Bennington, VT 05201
  • /19

    $225,000

    Sold Aug 29, 2025

    1801 S Stream Rd, Bennington, VT 05201

    • Land
    • 16.68 Acres
    • $13,489 per Acre

    Last Sold Summary

    • 34 Days On Market

    Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

    1801 S Stream Rd, Bennington, VT 05201
    • /34

      Est $514,564

      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

      • 133 Days On Market

  • /32

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,443 Sq Ft

    21 Pageant St, Bennington, VT 05201

    This well-maintained ranch-style home offers the convenience of one-level living with 3 bedrooms plus a spacious primary suite. Set on a large lot, the property features two decks, providing plenty of outdoor space for entertaining, relaxing, or enjoying the backyard. An easy walk to the local golf course adds to the appeal of this desirable location. The updated kitchen boasts beautiful granite

    Kelley Mccarthy Mahar McCarthy Real Estate

    21 Pageant St, Bennington, VT 05201
  • /21

    $175,000

    Sold Dec 23, 2025

    2591 Chapel Rd, Bennington, VT 05201

    • 2 Beds
    • 1 Bath
    • 880 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 11 Days On Market

    Current Estimated Value $177,193

    Last Listing Agent Susan Bellville Bellville Realty

    2591 Chapel Rd, Bennington, VT 05201
    • /39

      Est $578,697

      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

      • 17 Days On Market

  • /21

    $215,000

    $20K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 938 Sq Ft

    55 Eden Way Unit 3, Bennington, VT 05201

    Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge community! Meticulously maintained and thoughtfully cared for, this home offers effortless one-level living with nothing left to do but unpack. Step inside to discover a freshly painted interior complemented by new flooring and carpeting throughout. The bright and inviting kitchen features beautiful cabinetry and

    Angela Bevin Maple Leaf Real Estate

    55 Eden Way Unit 3, Bennington, VT 05201
  • /34

    $275,000

    Sold May 22, 2026

    1808 East Rd, Bennington, VT 05201

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Above List Price
    • $260/SF
    • 7 Days On Market

    Current Estimated Value $256,728

    Last Listing Agent Abi Gregorio

    1808 East Rd, Bennington, VT 05201
    • /38

      Est $659,456

      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

      • 20 Days On Market

  • /44

    $269,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,265 Sq Ft

    935 Gage St, Bennington, VT 05201

    Nestled in the Village of Bennington, this charming three-bedroom, two-bath Cape-style home offers comfort, character, and beautiful outdoor living. Step inside to find all fresh flooring, just painted throughout, and inviting spaces filled with natural light. Fireplace in the living room and new glass slider to the deck. Second floor is one large room with spacious closet and full bath-an ideal

    Lilli West Maple Leaf Real Estate

    935 Gage St, Bennington, VT 05201
  • /17

    $140,500

    Sold Feb 24, 2026

    432 South St Unit C6, Bennington, VT 05201

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

    Last Sold Summary

    • 9% Below List Price
    • $165/SF
    • 181 Days On Market

    Current Estimated Value $142,987

    Last Listing Agent Angela Bevin Maple Leaf Real Estate

    432 South St Unit C6, Bennington, VT 05201
    • /19

      Est $369,879

      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

      • 44 Days On Market

  • /15

    $96,906

    New Construction Under Contract
    • 2 Beds
    • 2 Baths
    • 777 Sq Ft

    10 Cassie Ln, Bennington, VT 05201

    Welcome to 10 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

    10 Cassie Ln, Bennington, VT 05201
  • /50

    $640,000

    Sold Dec 22, 2025

    55 Monument Ave, Bennington, VT 05201

    • 3 Beds
    • 2.5 Baths
    • 2,675 Sq Ft
    • Built 1787

    Last Sold Summary

    • 2% Below List Price
    • $239/SF
    • 14 Days On Market

    Current Estimated Value $625,854

    Last Listing Agent Vicki Wilson Maple Leaf Real Estate

    55 Monument Ave, Bennington, VT 05201
    • /21

      Est $175,033

      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

      • 76 Days On Market

  • /52

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    113 Main St, Bennington, VT 05201

    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

    Lindsey Martin Maple Leaf Real Estate

    113 Main St, Bennington, VT 05201
  • /45

    $46,000

    Sold Oct 10, 2025

    109 County St, Bennington, VT 05201

    • 4 Beds
    • 1 Bath
    • 1,146 Sq Ft
    • Built 1900

    Last Sold Summary

    • 42% Below List Price
    • $40/SF
    • 10 Days On Market

    Current Estimated Value $134,254

    Last Listing Agent Justine Curry Maple Leaf Real Estate

    109 County St, Bennington, VT 05201
    • /29

      Est $499,120

      Not Listed For Sale

      9378 Vt Route 9, Bennington, VT 05201

      • 4 Beds
      • 3 Baths
      • 1,752 Sq Ft
      • Built 1985
      9378 Vt Route 9, Bennington, VT 05201

      Last Sold Summary

      • 6 Days On Market

  • /19

    $219,500

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    14 Robinson Ave, Bennington, VT 05201

    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,

    Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home