3,768

Middlebury, CT Homes

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  • 1252 Straits Turnpike, Middlebury, CT 06762
    1252 Straits Turnpike, Middlebury, CT 06762
    /2

    $299,900

    Pending
    • 4 Beds
    • 1 Bath
    • 1,848 Sq Ft

    1252 Straits Turnpike, Middlebury, CT 06762

    SUBJECT TO PROBATE APPROVAL, AS-IS, WHERE-IS CONDITION NO FHA, CHFA OR VA LENDING AVAILABLE. NEEDS WORK. LOTS OF HARDWOOD FLOORS, DETACHED 2 CAR GARAGE WORKSHOP AND STORAGE LOFT. LARGE ROOMS, SHARED DRIVEWAY 24 HOUR NOTICE SHOWINGTIME. SUBJECT TO PROBATE APPROVAL. AS-IS, WHERE-IS CONDITION. NO FHA, CHFA OR VA LENDING AVAILABLE. MAKE DEPOSIT CHECK(s) TO: ATTORNEY ANDREW PIANKA TRUSTEE 315 CENTER

    Gianna Alberti ALBERTI REALTY ASSOCIATES, LLC

    1252 Straits Turnpike, 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 $405,153

    Last Listing Agent Martha Quaratella Coldwell Banker Realty

    32 Yale Ave, Middlebury, CT 06762
    • 133 1/2 Steinmann Ave, Middlebury, CT 06762

      Est $526,923

      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

      • 69 Days On Market

      Last Listing Agent Karen Griffin Coldwell Banker Realty

  • 0 N Benson Rd Unit 62, Middlebury, CT 06762
    0 N Benson Rd Unit 62, Middlebury, CT 06762
    0 N Benson Rd Unit 62, Middlebury, CT 06762
    /9

    $545,400

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 62, 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 62, Middlebury, CT 06762
  • 1 Arrowwood Ct Unit 1, Middlebury, CT 06762

    $569,500

    Sold Jun 12, 2026

    1 Arrowwood Ct Unit 1, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,295 Sq Ft
    • Built 2019

    Last Sold Summary

    • $248/SF
    • 36 Days On Market

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    1 Arrowwood Ct Unit 1, Middlebury, CT 06762
    • 2056 Straits Turnpike, Middlebury, CT 06762

      Est $294,997

      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

      • 10 Days On Market

      Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  • 130 Fairhaven Dr, Middlebury, CT 06762
    130 Fairhaven Dr, Middlebury, CT 06762
    130 Fairhaven Dr, Middlebury, CT 06762
    /39

    $649,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,654 Sq Ft

    130 Fairhaven Dr, Middlebury, CT 06762

    Ideal location! Beautiful 3-bedroom, 3.5-bath colonial situated at the end of a private cul-de-sac in desirable Middlebury, just minutes from the highway. This bright, sun-filled home features hardwood floors throughout, a spacious family room, custom kitchen with quartz countertops, stainless steel gas range, plus a formal dining room with a brick fireplace. Relax in the skylit sunroom or enjoy

    Tom Dorso Mapleridge Realty

    130 Fairhaven Dr, Middlebury, CT 06762
  • 13 Caveson Ct, Middlebury, CT 06762

    $530,000

    Sold Mar 24, 2026

    13 Caveson Ct, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 2,011 Sq Ft
    • Built 1996

    Last Sold Summary

    • $264/SF
    • 129 Days On Market

    Current Estimated Value $513,969

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    13 Caveson Ct, Middlebury, CT 06762
    • 346 South St, Middlebury, CT 06762

      Est $1,257,990

      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 Days On Market

      Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l

  • 36 Independence Cir, Middlebury, CT 06762
    36 Independence Cir, Middlebury, CT 06762
    36 Independence Cir, Middlebury, CT 06762
    /40

    $650,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    36 Independence Cir, Middlebury, CT 06762

    Welcome to this impressive 3,512-square-foot Colonial offering 10 spacious rooms 4 bedrooms 3.5 baths and a 2 car attached garage. Thoughtfully maintained and updated this home features newer mechanicals installed in 2023 including a furnace and water heater. Large deck for convenient outdoor grilling The elegant interior showcases hardwood flooring throughout crown molding and chair rail

    David Hughes Century 21 AllPoints Realty

    36 Independence Cir, Middlebury, CT 06762
  • 286 Mirey Dam Rd, Middlebury, CT 06762

    $900,000

    Sold Jul 09, 2026

    286 Mirey Dam Rd, Middlebury, CT 06762

    • 4 Beds
    • 3 Baths
    • 4,451 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $202/SF
    • 14 Days On Market

    Current Estimated Value $984,472

    Last Listing Agent Pam Famiglietti William Raveis Real Estate

    286 Mirey Dam Rd, Middlebury, CT 06762
    • 116 Bronson Dr, Middlebury, CT 06762

      Est $624,753

      Not Listed For Sale

      116 Bronson Dr, Middlebury, CT 06762

      • 3 Beds
      • 3 Baths
      • 2,262 Sq Ft
      • Built 1963
      116 Bronson Dr, Middlebury, CT 06762

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Tracie Mormile Paiva Higgins Group Real Estate

  • 0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
    /9

    $555,888

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762

    Only 3 Units Remaining! 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 44 24109951, 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 $354,860

    Last Listing Agent Stephanie Oliver Dave Jones Realty, LLC

    348 Kelly Rd, Middlebury, CT 06762
    • 11 Strathmore Rd, Middlebury, CT 06762

      Est $679,926

      Not Listed For Sale

      11 Strathmore Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,722 Sq Ft
      • Built 1984
      11 Strathmore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 77 Crest Rd, Middlebury, CT 06762
    77 Crest Rd, Middlebury, CT 06762
    77 Crest Rd, Middlebury, CT 06762
    /37

    $749,900

    • 4 Beds
    • 3.5 Baths
    • 2,674 Sq Ft

    77 Crest Rd, Middlebury, CT 06762

    Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters,

    Michael Vartolone William Raveis Real Estate

    77 Crest 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
    • 33,105 Sq Ft
    • $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
    • 36 Richardson Dr, Middlebury, CT 06762

      Est $356,399

      Not Listed For Sale

      36 Richardson Dr, Middlebury, CT 06762

      • 3 Beds
      • 1.5 Baths
      • 1,398 Sq Ft
      • Built 1920
      36 Richardson Dr, Middlebury, CT 06762

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Susan Woodfield Showcase Realty, Inc.

  • 168 N Farm Rd, Middlebury, CT 06762
    168 N Farm Rd, Middlebury, CT 06762
    168 N Farm Rd, Middlebury, CT 06762
    /40

    $699,900

    $65K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,302 Sq Ft

    168 N Farm Rd, Middlebury, CT 06762

    Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath Colonial is beautifully situated on 2.34 private acres offering the perfect blend of classic charm and comfortable living. A generous entry foyer welcomes you into a thoughtfully designed home featuring a formal living room with fireplace, elegant formal dining room and a spacious eat-in kitchen complete

    Karen Stanco Showcase Realty, Inc.

    168 N Farm Rd, 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 Lovley Century 21 AllPoints Realty

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

      Est $489,200

      Not Listed For Sale

      130 Christian Rd, Middlebury, CT 06762

      • 4 Beds
      • 2 Baths
      • 1,958 Sq Ft
      • Built 1940
      130 Christian Rd, Middlebury, CT 06762

      Last Sold Summary

      • 139 Days On Market

      Last Listing Agent Joseph Conforti West View Properties, LLC

  • 3 Pine Ridge Unit 23, Middlebury, CT 06762
    3 Pine Ridge Unit 23, Middlebury, CT 06762
    3 Pine Ridge Unit 23, Middlebury, CT 06762
    /28

    $721,000

    New Construction Pending
    • 2 Beds
    • 2.5 Baths
    • 2,290 Sq Ft

    3 Pine Ridge Unit 23, Middlebury, CT 06762

    Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

    Robert Michaud Michaud Real Estate

    3 Pine Ridge Unit 23, Middlebury, CT 06762
  • 18 Deer Run Rd, Middlebury, CT 06762

    $810,000

    Sold May 08, 2026

    18 Deer Run Rd, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $370/SF
    • 29 Days On Market

    Current Estimated Value $804,185

    Last Listing Agent Jodi Dawley Real Estate Two

    18 Deer Run Rd, Middlebury, CT 06762
    • 222 Crest Rd, Middlebury, CT 06762

      Est $736,194

      Not Listed For Sale

      222 Crest Rd, Middlebury, CT 06762

      • 5 Beds
      • 2.5 Baths
      • 2,442 Sq Ft
      • Built 1941
      222 Crest Rd, Middlebury, CT 06762

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Jackie Desmarais 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

    New Construction 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 51 24117506, Middlebury, CT 06762
  • 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 $499,106

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    116 Yale Ave, Middlebury, CT 06762
    • 70 Steinmann Ave, Middlebury, CT 06762

      Est $409,353

      Not Listed For Sale

      70 Steinmann Ave, Middlebury, CT 06762

      • 4 Beds
      • 2 Baths
      • 1,486 Sq Ft
      • Built 1971
      70 Steinmann Ave, Middlebury, CT 06762

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Heather Crabtree RE/MAX RISE

  • 6 Deer Run Rd, Middlebury, CT 06762
    6 Deer Run Rd, Middlebury, CT 06762
    /2

    $849,900

    New Construction $40K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    6 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) 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

    6 Deer Run Rd, Middlebury, CT 06762
  • 16 Winding Trail, Middlebury, CT 06762

    $625,000

    Sold Apr 10, 2026

    16 Winding Trail, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,646 Sq Ft
    • Built 2014

    Last Sold Summary

    • $236/SF
    • 29 Days On Market

    Last Listing Agent Georgieanna Fisher Home Selling Team

    16 Winding Trail, Middlebury, CT 06762
    • 1232 Straits Turnpike, Middlebury, CT 06762

      Est $335,469

      Not Listed For Sale

      1232 Straits Turnpike, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 1,708 Sq Ft
      • Built 1920
      1232 Straits Turnpike, Middlebury, CT 06762

      Last Sold Summary

      • 144 Days On Market

      Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

  • 85 Blueberry Knolls, Middlebury, CT 06762
    85 Blueberry Knolls, Middlebury, CT 06762
    85 Blueberry Knolls, Middlebury, CT 06762
    /22

    $550,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2 Baths
    • 2,156 Sq Ft

    85 Blueberry Knolls, Middlebury, CT 06762

    Welcome to a truly special property! This beautifully updated 7-room ranch is tucked away at the end of a private cul-de-sac and set on stunning, parklike grounds that offer exceptional privacy and tranquility. Meticulously maintained and thoughtfully updated, this home features newer mechanicals throughout for added comfort and peace of mind-see the attached upgrade list for details. The

    Lynn LaForme Regency Real Estate, LLC

    85 Blueberry Knolls, Middlebury, CT 06762
  • 93 Fenn Rd, Middlebury, CT 06762

    $420,000

    Sold Oct 09, 2025

    93 Fenn Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,636 Sq Ft
    • Built 1951

    Last Sold Summary

    • 1% Below List Price
    • $257/SF
    • 62 Days On Market

    Current Estimated Value $422,964

    Last Listing Agent Rob Marucci Better Living Realty, LLC

    93 Fenn Rd, Middlebury, CT 06762
    • 524 Charcoal Ave, Middlebury, CT 06762

      Est $773,013

      Not Listed For Sale

      524 Charcoal Ave, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 3,030 Sq Ft
      • Built 1999
      524 Charcoal Ave, Middlebury, CT 06762

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Jill Taylor RE/MAX Right Choice

  • 880 Whittemore Rd, Middlebury, CT 06762
    880 Whittemore Rd, Middlebury, CT 06762
    880 Whittemore Rd, Middlebury, CT 06762
    /40

    $499,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,157 Sq Ft

    880 Whittemore Rd, Middlebury, CT 06762

    Highest and Best by Tuesday, the 21st, 5pm. Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city sewer. This light and bright home combines timeless character with important modern updates, including a DeGiorgi roof with a transferable warranty, a new driveway, updated electrical panel, and a newer boiler.

    Christina Zainc BHGRE Gaetano Marra Homes

    880 Whittemore Rd, Middlebury, CT 06762
  • 28 Maple Dr, Middlebury, CT 06762

    $435,000

    Sold Oct 14, 2025

    28 Maple Dr, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft
    • Built 1950

    Last Sold Summary

    • 17% Below List Price
    • $273/SF
    • 233 Days On Market

    Current Estimated Value $450,699

    Last Listing Agent Dean Giatas Fiorelli Realty, LLC

    28 Maple Dr, Middlebury, CT 06762
    • 695 Whittemore Rd, Middlebury, CT 06762

      Est $673,206

      Not Listed For Sale

      695 Whittemore Rd, Middlebury, CT 06762

      • 3 Beds
      • 4.5 Baths
      • 2,813 Sq Ft
      • Built 1978
      695 Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent rob raad Better Living Realty, LLC

  • 15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    /38

    $834,900

    New Construction $75K PRICE INCREASE
    • 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
  • 0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762

    $505,834

    Sold Oct 17, 2025

    0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762

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

    Last Sold Summary

    • $259/SF
    • 0 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762
    • 36 Middlebury Terrace, Middlebury, CT 06762

      Est $423,642

      Not Listed For Sale

      36 Middlebury Terrace, Middlebury, CT 06762

      • 3 Beds
      • 1.5 Baths
      • 1,849 Sq Ft
      • Built 1933
      36 Middlebury Terrace, Middlebury, CT 06762

      Last Sold Summary

      • 177 Days On Market

      Last Listing Agent Frank Durante William Raveis Real Estate

  • 25 Avalon Dr, Middlebury, CT 06762
    25 Avalon Dr, Middlebury, CT 06762
    25 Avalon Dr, Middlebury, CT 06762
    /39

    $879,900

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 3,494 Sq Ft

    25 Avalon Dr, Middlebury, CT 06762

    Located in one of Middlebury's most desirable and beautifully maintained subdivisions Avalon Farms with streetlights and Belgian block lined streets, this impressive 3 bedroom, 3 full and 1 half bath Colonial offers 3,494 square feet of refined and flexible living. Set on a premium, fully usable flat lot surrounded by mature pines for year round privacy, the home features Hardie Plank siding and

    Connie Widmann William Raveis Real Estate

    25 Avalon Dr, Middlebury, CT 06762

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