Bennington County, VT Homes

• 

  

  

  /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 Real Estate

  889 Overlea Rd, Bennington, VT 05201
• 

  

  

  /35

  Est $673,629

  Not Listed For Sale

  602 Barnumville Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft
  • Built 1960

  602 Barnumville Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /32

  $350,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,196 Sq Ft

  10 Cass Terrace, Manchester Center, VT 05255

  Charming and beautifully updated, this 1920’s home blends timeless character with modern comfort in a desirable Manchester, Vermont setting. Offering 2 bedrooms and 2 baths within 1,200 square feet, this inviting home features an open kitchen flowing seamlessly into the dining area, highlighted by hardwood floors throughout and abundant natural light. A beautiful sunroom off the back of the home

  Kelley Mccarthy Mahar McCarthy Real Estate

  10 Cass Terrace, Manchester Center, VT 05255
• 

  

  

  /53

  $775,000

  Sold Aug 13, 2025

  E12 Rock Ridge Rd, Winhall, VT 05155

  • 3 Beds
  • 3 Baths
  • 1,842 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $421/SF
  • 7 Days On Market

  Last Listing Agent Cheyanne Pugliese

  E12 Rock Ridge Rd, Winhall, VT 05155
• 

  

  

  /31

  Est $531,015

  Not Listed For Sale

  373 Highland Ave, Manchester Center, VT 05255

  • 4 Beds
  • 1.5 Baths
  • 1,830 Sq Ft
  • Built 1905

  373 Highland Ave, Manchester Center, VT 05255

  Last Sold Summary

  • 5 Days On Market
• 

  

  /58

  $1,950,000

  Under Contract

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

  Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
• 

  

  /49

  $1,865,000

  Sold Dec 08, 2025

  380 Partridge Hill Unit 22, Manchester, VT 05254

  • 3 Beds
  • 4.5 Baths
  • 3,874 Sq Ft
  • Built 2008

  Last Sold Summary

  • 1% Below List Price
  • $481/SF
  • 5 Days On Market

  Last Listing Agent Christiane Carroccio TPW Real Estate

  380 Partridge Hill Unit 22, Manchester, VT 05254
• 

  

  /34

  Est $730,187

  Not Listed For Sale

  196 Ways Ln, Manchester Center, VT 05255

  • 4 Beds
  • 3 Baths
  • 2,304 Sq Ft
  • Built 1929

  196 Ways Ln, Manchester Center, VT 05255

  Last Sold Summary

  • 7 Days On Market
• 

  

  /19

  $195,000

  • 3 Beds
  • 1 Bath
  • 1,590 Sq Ft

  176 Glen Ave, Readsboro, VT 05350

  Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

  Cassandra Ehrlich BHG Masiello Brattleboro

  176 Glen Ave, Readsboro, VT 05350
• 

  

  /43

  $180,367

  Sold Nov 06, 2025

  634 Wiley Mountain Dr, Readsboro, VT 05350

  • 1 Bed
  • 400 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $451/SF
  • 40 Days On Market

  Current Estimated Value $178,065

  Last Listing Agent Cyd Scott Cohn & Company

  634 Wiley Mountain Dr, Readsboro, VT 05350
• 

  

  /17

  Est $323,012

  Not Listed For Sale

  1581 E Manchester Rd, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 1952

  1581 E Manchester Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 8 Days On Market
• 

  

  /16

  $495,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

  Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

  Northshire Sales Group Real Broker LLC

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
• 

  

  /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 Real Estate

  150 Fillmore St, Bennington, VT 05201
• 

  

  /28

  Est $248,120

  Not Listed For Sale

  433 Squires Rd, Manchester Center, VT 05255

  • 2 Beds
  • 1 Bath
  • 1,142 Sq Ft
  • Built 1974

  433 Squires Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 9 Days On Market
• 

  

  /37

  $609,000

  $20K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,050 Sq Ft

  1649 E Manchester Rd, Manchester Center, VT 05255

  LOCATION, LOCATION: Privately set just moments from Manchester’s dining, shopping, golf, year-round recreation, and easy access to Bromley and Stratton, this thoughtfully updated 5-bedroom, 2-bath Cape offers 2,050 sq ft on 0.48 acres—ideal as a primary home, Vermont retreat, or long-term investment. Move-in ready and beautifully maintained, the home balances a peaceful setting with exceptional

  Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

  1649 E Manchester Rd, Manchester Center, VT 05255
• 

  

  /40

  $665,000

  Sold May 13, 2026

  134 Monument Ave, Bennington, VT 05201

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft
  • Built 1927

  Last Sold Summary

  • 4% Below List Price
  • $232/SF
  • 178 Days On Market

  Current Estimated Value $679,151

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201
• 

  

  /40

  Est $1,633,544

  Not Listed For Sale

  2894 West Rd, Manchester Center, VT 05255

  • 3 Beds
  • 6 Baths
  • 3,556 Sq Ft
  • Built 1970

  2894 West Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 60 Days On Market
• 

  

  /37

  $575,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  30 Upper Woods and Water Rd, Winhall, VT 05340

  Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest—a daily reminder that some of Southern Vermont’s best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain

  Carrie Mathews Winhall Real Estate

  30 Upper Woods and Water Rd, Winhall, VT 05340
• 

  

  /30

  $80,000

  Sold Aug 13, 2025

  00 Vermont 346, Pownal, VT 05260

  • Land
  • 9.8 Acres
  • $8,163 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 69 Days On Market

  Last Listing Agent Betsy Adamovich Real Broker LLC

  00 Vermont 346, Pownal, VT 05260
• 

  

  /20

  Est $587,018

  Not Listed For Sale

  290 Deer Meadow Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 1,635 Sq Ft
  • Built 1970

  290 Deer Meadow Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 57 Days On Market
• 

  

  /37

  $584,900

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14A Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

  Julie Citron RE/MAX Four Seasons

  14A Marisa Ln, Dorset, VT 05251
• 

  /2

  $400,000

  Sold Mar 09, 2026

  97 N Branch Rd, Winhall, VT 05155

  • Land
  • 1.18 Acres
  • $338,983 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 29 Days On Market

  Last Listing Agent John Sikes Stratton Real Estate

  97 N Branch Rd, Winhall, VT 05155
• 

  

  /29

  Est $701,414

  Not Listed For Sale

  110 Highland Ave, Manchester Center, VT 05255

  • 5 Beds
  • 3.5 Baths
  • 2,912 Sq Ft
  • Built 1890

  110 Highland Ave, Manchester Center, VT 05255

  Last Sold Summary

  • 4 Days On Market
• 

  

  /41

  $1,425,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,931 Sq Ft

  932 Mcnamara Rd, Dorset, VT 05251

  Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality throughout. Soaring

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251
• 

  

  /40

  $185,000

  Sold May 12, 2026

  317 Pleasant St, Bennington, VT 05201

  • 5 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1900

  Last Sold Summary

  • 14% Below List Price
  • $84/SF
  • 125 Days On Market

  Current Estimated Value $192,472

  Last Listing Agent Michael Gilman 3GEN Real Estate Inc

  317 Pleasant St, Bennington, VT 05201
• 

  

  /9

  Est $668,731

  Not Listed For Sale

  207 Hillcrest Rd, Manchester Center, VT 05255

  • 3 Beds
  • 2.5 Baths
  • 2,176 Sq Ft
  • Built 1970

  207 Hillcrest Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 7 Days On Market
• 

  

  /32

  $1,275,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,814 Sq Ft

  19 Maple Hill Rd, Winhall, VT 05340

  Beautifully renovated in 2023, this 4-bedroom, 2-1/2 bathroom contemporary sits on 1.47 wooded acres with a sweeping circular driveway and genuine privacy — while still being on the Stratton shuttle route and just minutes from the base lodge on foot. The interior renovation was done right. Radiant heat floors run through the living room and kitchen, with two wood-burning fireplaces anchoring the

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  19 Maple Hill Rd, Winhall, VT 05340
• 

  

  /56

  $405,000

  Sold Dec 17, 2025

  130 Clark Rd, Pawlet, VT 05761

  • 4 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1790

  Last Sold Summary

  • 3% Above List Price
  • $191/SF
  • 8 Days On Market

  Current Estimated Value $382,062

  Last Listing Agent Scott McChesney McChesney RE, Inc.

  130 Clark Rd, Pawlet, VT 05761
• 

  

  /40

  Est $768,062

  Not Listed For Sale

  521 Barnumville Rd, Manchester Center, VT 05255

  • 3 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1996

  521 Barnumville Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 8 Days On Market
• 

  

  /15

  $299,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  1803 Harwood Hill Rd, Bennington, VT 05201

  Set on a spacious lot and move-in ready raised ranch offers major updates, flexible living space, and excellent value. Recent improvements include a brand-new septic system, new roof, beautifully renovated kitchen, and new deck — giving buyers peace of mind and modern comfort from day one.The versatile lower level provides additional finished space ideal for a home office, family room, guest

  Lori Hurley Four Corner Properties LLC

  1803 Harwood Hill Rd, Bennington, VT 05201
• 

  

  /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 $339,834

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  989 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  /39

  Est $391,852

  Not Listed For Sale

  90 Jennifer Ln, Manchester Center, VT 05255

  • 4 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Built 1970

  90 Jennifer Ln, Manchester Center, VT 05255

  Last Sold Summary

  • 19 Days On Market
• 

  

  /6

  $145,000

  Under Contract

  • Land
  • 3 Acres
  • $48,333 per Acre

  530 Finbars Forest Rd, Manchester Center, VT 05255

  This building lot borders the Manchester Country Club and, with tree clearing, would offer amazing views of the golf course and the Manchester mountains. The location provides easy access to town and everything the area has to offer. This private wooded lot is just minutes away from local highlights, including golf, skiing, hiking, and shopping. Septic permit and design available.

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  530 Finbars Forest Rd, Manchester Center, VT 05255
• 

  

  /60

  $534,000

  Sold Nov 24, 2025

  272 Oak Hill Rd, Shaftsbury, VT 05262

  • 3 Beds
  • 2.5 Baths
  • 3,637 Sq Ft
  • Built 2001

  Last Sold Summary

  • 24% Below List Price
  • $147/SF
  • 111 Days On Market

  Current Estimated Value $557,962

  Last Listing Agent Faith Rhodes Maple Leaf Real Estate

  272 Oak Hill Rd, Shaftsbury, VT 05262
• 

  

  /29

  Est $632,647

  Not Listed For Sale

  36 Boulder Rd, Manchester Center, VT 05255

  • 4 Beds
  • 1.5 Baths
  • 2,512 Sq Ft
  • Built 1825

  36 Boulder Rd, Manchester Center, VT 05255

  Last Sold Summary

  • 7 Days On Market
• 

  

  /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
• 

  

  /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 $290,946

  Last Listing Agent Justine Curry Maple Leaf Real Estate

  4 Rockwood St, Bennington, VT 05201
• 

  

  /29

  Est $567,325

  Not Listed For Sale

  335 Carlen St, Manchester Center, VT 05255

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1987

  335 Carlen St, Manchester Center, VT 05255

  Last Sold Summary

  • 4 Days On Market
• 

  

  /5

  $374,900

  • Land
  • 2.31 Acres
  • $162,294 per Acre

  0 Wall St, Winhall, VT 05340

  Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. The engineering has already been completed, with each lot having a

  Cheyanne Pugliese

  0 Wall St, Winhall, VT 05340
• 

  

  /22

  $795,000

  Sold Sep 17, 2025

  185 Crooked Path Rd, Arlington, VT 05250

  • 4 Beds
  • 5.5 Baths
  • 3,463 Sq Ft
  • Built 2006

  Last Sold Summary

  • $230/SF
  • 9 Days On Market

  Current Estimated Value $792,952

  Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  185 Crooked Path Rd, Arlington, VT 05250

Showing Results 601 - 640, Page 16 of 18