3,783

Middlebury, CT Homes

Section Image Section Image
    • 588 Charcoal Ave, Middlebury, CT 06762

      Est $850,464 Not Listed For Sale

      588 Charcoal Ave, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 4,098 Sq Ft
      • Built 1982
      588 Charcoal Ave, Middlebury, CT 06762

      Last Sold Summary

      • 18% Above List Price
      • $176/SF
      • 270 Days On Market

      Last Sold Price $720,000

      Last Listing Agent Joann Murray Weichert Corporate

  • 0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    /9

    $509,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
  • 6 Ridgewood Dr, Middlebury, CT 06762

    $600,000 Sold Mar 13, 2025

    6 Ridgewood Dr, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,071 Sq Ft
    • Built 2007

    Last Sold Summary

    • $195/SF
    • 71 Days On Market

    Current Estimated Value $619,939

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    6 Ridgewood Dr, Middlebury, CT 06762
    • 13 Hackamore Cir, Middlebury, CT 06762

      Est $533,756 Not Listed For Sale

      13 Hackamore Cir, Middlebury, CT 06762

      • 2 Beds
      • 2.5 Baths
      • 1,917 Sq Ft
      • Built 1998
      13 Hackamore Cir, Middlebury, CT 06762

      Last Sold Summary

      • 9% Above List Price
      • $255/SF
      • 34 Days On Market

      Last Sold Price $489,000

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 0 White Birch Unit 24141986, Middlebury, CT 06762
    0 White Birch Unit 24141986, Middlebury, CT 06762
    0 White Birch Unit 24141986, Middlebury, CT 06762
    /5

    $1,600,000

    • Land
    • 29 Acres
    • $55,172 per Acre

    0 White Birch Unit 24141986, Middlebury, CT 06762

    Attention Builders, Developers, and Investors: fully approved 10 LOT Subdivision for sale in the charming town of Middlebury, CT (29 Acres total) With comprehensive approvals in place including Planning & Zoning, Wetlands, and Health Department clearances, you can get straight to work developing your vision. Each lot is designed to feature a private well and connection to public sewer. Middlebury

    Donna Kennedy Compass Connecticut, LLC

    0 White Birch Unit 24141986, Middlebury, CT 06762
  • 82 Tucker Hill Rd, Middlebury, CT 06762

    $304,150 Sold Oct 24, 2025

    82 Tucker Hill Rd, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 941 Sq Ft
    • Built 1936

    Last Sold Summary

    • 5% Below List Price
    • $323/SF
    • 24 Days On Market

    Current Estimated Value $307,589

    Last Listing Agent Kary Apanovitch Coldwell Banker Realty

    82 Tucker Hill Rd, Middlebury, CT 06762
    • 5 Kimberwick Ct, Middlebury, CT 06762

      Est $521,014 Not Listed For Sale

      5 Kimberwick Ct, Middlebury, CT 06762

      • 2 Beds
      • 2.5 Baths
      • 1,917 Sq Ft
      • Built 1997
      5 Kimberwick Ct, Middlebury, CT 06762

      Last Sold Summary

      • 7% Above List Price
      • $254/SF
      • 55 Days On Market

      Last Sold Price $487,400

      Last Listing Agent Jane Spino Showcase Realty, Inc.

  • 0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
    /9

    $523,920 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
  • 405 Chestnut Cir Unit 77, Middlebury, CT 06762

    $649,500 Sold Jul 25, 2025

    405 Chestnut Cir Unit 77, Middlebury, CT 06762

    • 2 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 99 Days On Market

    Current Estimated Value $660,833

    Last Listing Agent Jodi Dawley Real Estate Two

    405 Chestnut Cir Unit 77, Middlebury, CT 06762
    • 3 Weymouth Way, Middlebury, CT 06762

      Est $296,172 Not Listed For Sale

      3 Weymouth Way, Middlebury, CT 06762

      • 2 Beds
      • 2 Baths
      • 1,136 Sq Ft
      • Built 1997
      3 Weymouth Way, Middlebury, CT 06762

      Last Sold Summary

      • 24% Above List Price
      • $210/SF
      • 22 Days On Market

      Last Sold Price $238,700

      Last Listing Agent Cheryl Grabowski Weichert Corporate

  • 24 Ridgewood Dr, Middlebury, CT 06762
    24 Ridgewood Dr, Middlebury, CT 06762
    24 Ridgewood Dr, Middlebury, CT 06762
    /39

    $574,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,879 Sq Ft

    24 Ridgewood Dr, Middlebury, CT 06762

    Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • 288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    $225,000 Sold Sep 24, 2025

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    • Land
    • 3.32 Acres
    • $67,771 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 330 Days On Market

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762
    • 5 Pommel Ln, Middlebury, CT 06762

      Est $567,547 Not Listed For Sale

      5 Pommel Ln, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,461 Sq Ft
      • Built 1996
      5 Pommel Ln, Middlebury, CT 06762

      Last Sold Summary

      • 15% Above List Price
      • $201/SF
      • 60 Days On Market

      Last Sold Price $495,000

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    /2

    $794,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    15 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    15 Hunting Ridge Rd, Middlebury, CT 06762
  • 1 Independence Cir, Middlebury, CT 06762

    $615,000 Sold Oct 30, 2025

    1 Independence Cir, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,224 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $191/SF
    • 120 Days On Market

    Current Estimated Value $622,060

    Last Listing Agent Carol D'Amato Regency Real Estate, LLC

    1 Independence Cir, Middlebury, CT 06762
    • 9 Caveson Ct, Middlebury, CT 06762

      Est $575,083 Not Listed For Sale

      9 Caveson Ct, Middlebury, CT 06762

      • 2 Beds
      • 2.5 Baths
      • 2,050 Sq Ft
      • Built 1996
      9 Caveson Ct, Middlebury, CT 06762

      Last Sold Summary

      • 3% Above List Price
      • $273/SF
      • 64 Days On Market

      Last Sold Price $560,000

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 61 Sandy Hill Rd, Middlebury, CT 06762
    61 Sandy Hill Rd, Middlebury, CT 06762
    /2

    $529,900

    • 3 Beds
    • 1.5 Baths
    • 1,811 Sq Ft

    61 Sandy Hill Rd, Middlebury, CT 06762

    Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

    Arben Belica William Raveis Real Estate

    61 Sandy Hill Rd, Middlebury, CT 06762
  • 45 E Farms Rd, Middlebury, CT 06762

    $1,100,000 Sold May 19, 2025

    45 E Farms Rd, Middlebury, CT 06762

    • 4 Beds
    • 6 Baths
    • 5,054 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 48 Days On Market

    Current Estimated Value $1,114,883

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    45 E Farms Rd, Middlebury, CT 06762
    • 17 Caveson Ct, Middlebury, CT 06762

      Est $554,539 Not Listed For Sale

      17 Caveson Ct, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,290 Sq Ft
      • Built 1996
      17 Caveson Ct, Middlebury, CT 06762

      Last Sold Summary

      • 15% Above List Price
      • $211/SF
      • 105 Days On Market

      Last Sold Price $482,500

      Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  • 0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
    /9

    $522,128 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
  • 32 Yale Ave, Middlebury, CT 06762

    $390,000 Sold Jan 14, 2026

    32 Yale Ave, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • Built 1925

    Last Sold Summary

    • $210/SF
    • 54 Days On Market

    Current Estimated Value $389,480

    Last Listing Agent Martha Quaratella Coldwell Banker Realty

    32 Yale Ave, Middlebury, CT 06762
    • 130 White Ave, Middlebury, CT 06762

      Est $393,661 Not Listed For Sale

      130 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 1 Bath
      • 1,244 Sq Ft
      • Built 1955
      130 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 12% Above List Price
      • $281/SF
      • 3 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Frank Durante William Raveis Real Estate

  • 292 Park Road Extension, Middlebury, CT 06762
    292 Park Road Extension, Middlebury, CT 06762
    292 Park Road Extension, Middlebury, CT 06762
    /40

    $574,900

    • 5 Beds
    • 2 Baths
    • 1,924 Sq Ft

    292 Park Road Extension, Middlebury, CT 06762

    Discover this classic 5-bedroom, 2-bath Colonial set on a private 1.67-acre lot in desirable Middlebury. This home features hardwood floors, a bright formal living room, and a spacious dining room that opens to a cozy three-season porch overlooking the yard. The kitchen offers brand-new stainless steel appliances and the convenient first-floor bedroom includes laundry for easy main-level living.

    Tammy Ferrauola Eagle Eye Realty PLLC

    292 Park Road Extension, Middlebury, CT 06762
  • 348 Kelly Rd, Middlebury, CT 06762

    $360,000 Sold Jan 30, 2026

    348 Kelly Rd, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1934

    Last Sold Summary

    • 7% Above List Price
    • $469/SF
    • 24 Days On Market

    Current Estimated Value $343,197

    Last Listing Agent Stephanie Oliver Dave Jones Realty, LLC

    348 Kelly Rd, Middlebury, CT 06762
    • 7 Foster St, Middlebury, CT 06762

      Est $373,138 Not Listed For Sale

      7 Foster St, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 724 Sq Ft
      • Built 1950
      7 Foster St, Middlebury, CT 06762

      Last Sold Summary

      • 15% Above List Price
      • $448/SF
      • 6 Days On Market

      Last Sold Price $324,000

      Last Listing Agent Arben Belica William Raveis Real Estate

  • 637 Watertown Rd, Middlebury, CT 06762
    637 Watertown Rd, Middlebury, CT 06762
    637 Watertown Rd, Middlebury, CT 06762
    /40

    $450,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 1,918 Sq Ft

    637 Watertown Rd, Middlebury, CT 06762

    Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home.

    Jonna Dibble BHGRE Gaetano Marra Homes

    637 Watertown Rd, Middlebury, CT 06762
  • 0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    $63,250 Sold Dec 05, 2025

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    • Land
    • 0.76 Acre
    • $83,224 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 80 Days On Market

    Last Listing Agent Rebecca Zandvliet Coldwell Banker Realty 2000

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
    • 700 South St, Middlebury, CT 06762

      Est $1,564,542 Not Listed For Sale

      700 South St, Middlebury, CT 06762

      • 5 Beds
      • 7 Baths
      • 5,811 Sq Ft
      • Built 1980
      700 South St, Middlebury, CT 06762

      Last Sold Summary

      • 11% Below List Price
      • $301/SF
      • 542 Days On Market

      Last Sold Price $1,750,000

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  • 0 N Benson Rd Unit 57, Middlebury, CT 06762
    0 N Benson Rd Unit 57, Middlebury, CT 06762
    0 N Benson Rd Unit 57, Middlebury, CT 06762
    /9

    $561,271 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 57, Middlebury, CT 06762

    An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 57, Middlebury, CT 06762
  • 0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

    $593,360 Sold Oct 10, 2025

    0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2025

    Last Sold Summary

    • 17% Above List Price
    • $304/SF
    • 0 Days On Market

    Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762
    • 133 1/2 Steinmann Ave, Middlebury, CT 06762

      Est $524,687 Not Listed For Sale

      133 1/2 Steinmann Ave, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,083 Sq Ft
      • Built 1941
      133 1/2 Steinmann Ave, Middlebury, CT 06762

      Last Sold Summary

      • 2% Above List Price
      • $247/SF
      • 69 Days On Market

      Last Sold Price $515,000

      Last Listing Agent Karen Griffin Coldwell Banker Realty

  • 116 Yale Ave, Middlebury, CT 06762

    $495,000 Sold Dec 04, 2025

    116 Yale Ave, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,311 Sq Ft
    • Built 1998

    Last Sold Summary

    • 1% Above List Price
    • $214/SF
    • 51 Days On Market

    Current Estimated Value $489,152

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    116 Yale Ave, Middlebury, CT 06762
    • 2056 Straits Turnpike, Middlebury, CT 06762

      Est $287,234 Not Listed For Sale

      2056 Straits Turnpike, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 2,528 Sq Ft
      • Built 1953
      2056 Straits Turnpike, Middlebury, CT 06762

      Last Sold Summary

      • 44% Above List Price
      • $79/SF
      • 10 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  • 0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
    /9

    $603,780 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,706 Sq Ft

    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762

    Last remaining unit! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
  • 396 Watertown Rd, Middlebury, CT 06762

    $790,000 Sold Mar 31, 2025

    396 Watertown Rd, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,935 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $201/SF
    • 64 Days On Market

    Current Estimated Value $810,572

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, Middlebury, CT 06762
    • 346 South St, Middlebury, CT 06762

      Est $1,102,341 Not Listed For Sale

      346 South St, Middlebury, CT 06762

      • 6 Beds
      • 7 Baths
      • 5,938 Sq Ft
      • Built 1958
      346 South St, Middlebury, CT 06762

      Last Sold Summary

      • 38% Above List Price
      • $135/SF
      • 38 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Margaret Muir William Pitt

  • 29 Winding Trail Unit 29, Middlebury, CT 06762

    $520,000 Sold Aug 08, 2025

    29 Winding Trail Unit 29, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $244/SF
    • 117 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    29 Winding Trail Unit 29, Middlebury, CT 06762
    • 53 White Deer Rock Rd, Middlebury, CT 06762

      Est $1,190,844 Not Listed For Sale

      53 White Deer Rock Rd, Middlebury, CT 06762

      • 6 Beds
      • 7 Baths
      • 6,318 Sq Ft
      • Built 2006
      53 White Deer Rock Rd, Middlebury, CT 06762

      Last Sold Summary

      • 23% Above List Price
      • $154/SF
      • 154 Days On Market

      Last Sold Price $970,000

      Last Listing Agent Heather Dever Showcase Realty, Inc.

Showing Results 81 - 120, Page 3 of 18

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