3,768

Middlebury, CT Homes

Section Image
    • 34 Breakneck Hill Rd, Middlebury, CT 06762

      Est $869,027

      Not Listed For Sale

      34 Breakneck Hill Rd, Middlebury, CT 06762

      • 5 Beds
      • 3 Baths
      • 4,551 Sq Ft
      • Built 2006
      34 Breakneck Hill Rd, Middlebury, CT 06762

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Arben Belica William Raveis Real Estate

  • 42 White Ave, Middlebury, CT 06762
    42 White Ave, Middlebury, CT 06762
    42 White Ave, Middlebury, CT 06762
    /25

    $449,900

    $30K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    42 White Ave, Middlebury, CT 06762

    Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan,

    Justin Cabral West View Properties, LLC

    42 White Ave, Middlebury, CT 06762
  • 27 Winding Trail Unit 27, Middlebury, CT 06762

    $565,000

    Sold Jan 14, 2026

    27 Winding Trail Unit 27, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,680 Sq Ft
    • Built 2014

    Last Sold Summary

    • $211/SF
    • 89 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    27 Winding Trail Unit 27, Middlebury, CT 06762
    • 1600 Straits Turnpike, Middlebury, CT 06762

      Est $534,861

      Not Listed For Sale

      1600 Straits Turnpike, Middlebury, CT 06762

      • 3 Beds
      • 1.5 Baths
      • 1,932 Sq Ft
      • Built 1950
      1600 Straits Turnpike, Middlebury, CT 06762

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Lauren Cavallo Lauren Ashley Homes LLC

  • 66 Artillery Rd, Middlebury, CT 06762
    66 Artillery Rd, Middlebury, CT 06762
    66 Artillery Rd, Middlebury, CT 06762
    /25

    $585,000

    • 4 Beds
    • 3.5 Baths
    • 2,691 Sq Ft

    66 Artillery Rd, Middlebury, CT 06762

    Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The

    Maria Taylor Klemm Real Estate Inc

    66 Artillery Rd, Middlebury, CT 06762
  • 111 Dwyer Rd, Middlebury, CT 06762

    $710,000

    Sold Dec 18, 2025

    111 Dwyer Rd, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 3,212 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Below List Price
    • $221/SF
    • 162 Days On Market

    Current Estimated Value $709,907

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    111 Dwyer Rd, Middlebury, CT 06762
    • 530 Whittemore Rd, Middlebury, CT 06762

      Est $498,357

      Not Listed For Sale

      530 Whittemore Rd, Middlebury, CT 06762

      • 3 Beds
      • 3 Baths
      • 2,973 Sq Ft
      • Built 1940
      530 Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Monique Jacobs Lamacchia Realty

  • 75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    /36

    $249,900

    $20K PRICE INCREASE
    • Land
    • 4.67 Acres
    • $53,512 per Acre

    75 Gleneagle Rd, Middlebury, CT 06762

    SHOVEL READY! LAST AVAILABLE HOMESITE IN THIS UPSCALE SUBDIVISION OF FINER HOMES. PUBLIC WATER & SEWER LATERALS ALREADY EXTENDED TO PROPERTY. CLOSE TO EVERYTHING, BUT EXTREMELY PRIVATE. MINIMUM SQ FOOTAGE 2800SF.

    Scott Tedesco Tedesco Real Estate

    75 Gleneagle Rd, Middlebury, CT 06762
  • 863 Whittemore Rd, Middlebury, CT 06762

    $444,000

    Sold May 29, 2026

    863 Whittemore Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,456 Sq Ft
    • Built 1954

    Last Sold Summary

    • 11% Above List Price
    • $305/SF
    • 26 Days On Market

    Current Estimated Value $432,320

    Last Listing Agent Marisela Agelvis West View Properties, LLC

    863 Whittemore Rd, Middlebury, CT 06762
    • 783 Whittemore Rd, Middlebury, CT 06762

      Est $729,588

      Not Listed For Sale

      783 Whittemore Rd, Middlebury, CT 06762

      • 5 Beds
      • 3 Baths
      • 3,728 Sq Ft
      • Built 1953
      783 Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 182 Days On Market

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 323 Watertown Rd, Middlebury, CT 06762
    323 Watertown Rd, Middlebury, CT 06762
    323 Watertown Rd, Middlebury, CT 06762
    /23

    $539,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,067 Sq Ft

    323 Watertown Rd, Middlebury, CT 06762

    Looking for a 4 bedroom home in a prime location? Here it is. This classic home sits on just over one acre of property with gorgeous gardens and a lush lawn. On the interior, a spacious updated kitchen with granite counters, an island, plenty of room for dining and wonderful storage. For easy entertaining, the living room and dining room adjoin and allow for a great flow. Enjoy a cozy family room

    Donna Bannon BHGRE Gaetano Marra Homes

    323 Watertown Rd, Middlebury, CT 06762
  • 82 Mirey Dam Rd, Middlebury, CT 06762

    $975,000

    Sold Nov 17, 2025

    82 Mirey Dam Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,471 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $281/SF
    • 4 Days On Market

    Current Estimated Value $970,803

    Last Listing Agent Jetlir Kulla Coldwell Banker Realty

    82 Mirey Dam Rd, Middlebury, CT 06762
    • 312 Three Mile Hill Rd, Middlebury, CT 06762

      Est $524,715

      Not Listed For Sale

      312 Three Mile Hill Rd, Middlebury, CT 06762

      • 5 Beds
      • 2.5 Baths
      • 3,030 Sq Ft
      • Built 1950
      312 Three Mile Hill Rd, Middlebury, CT 06762

      Last Sold Summary

      • 186 Days On Market

      Last Listing Agent Marian Van Egas Berkshire Hathaway NE Prop.

  • 0 N Benson Rd Unit 58, Middlebury, CT 06762
    0 N Benson Rd Unit 58, Middlebury, CT 06762
    0 N Benson Rd Unit 58, Middlebury, CT 06762
    /9

    $608,000

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,582 Sq Ft

    0 N Benson Rd Unit 58, 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 58, Middlebury, CT 06762
  • 200 N Farm Rd, Middlebury, CT 06762

    $728,000

    Sold May 08, 2026

    200 N Farm Rd, Middlebury, CT 06762

    • 4 Beds
    • 4 Baths
    • 3,360 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $217/SF
    • 17 Days On Market

    Current Estimated Value $738,103

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    200 N Farm Rd, Middlebury, CT 06762
    • 588 Charcoal Ave, Middlebury, CT 06762

      Est $849,223

      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

      • 270 Days On Market

      Last Listing Agent Joann Murray Weichert REALTORS Briotti Group

  • 106 Steinmann Ave, Middlebury, CT 06762
    106 Steinmann Ave, Middlebury, CT 06762
    106 Steinmann Ave, Middlebury, CT 06762
    /29

    $479,900

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,630 Sq Ft

    106 Steinmann Ave, Middlebury, CT 06762

    Welcome Home to this nicely updated New England Cape style home with a comfortable and convenient layout. This move-in ready home offers 4 bedrooms and 2 full bathrooms. An inviting living room showcases a fireplace creating a warm and cozy gathering space for the whole family, adjoining dining area leads to The large kitchen includes ample workspace, lots of cabinets and tile flooring, with easy

    Tammi Ligouri Independent Realty Group

    106 Steinmann Ave, Middlebury, CT 06762
  • 58 Shadduck Rd, Middlebury, CT 06762

    $499,900

    Sold Aug 26, 2025

    58 Shadduck Rd, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,360 Sq Ft
    • Built 1934

    Last Sold Summary

    • 23% Below List Price
    • $212/SF
    • 150 Days On Market

    Current Estimated Value $502,847

    Last Listing Agent Amber Segetti RE/MAX RISE

    58 Shadduck Rd, Middlebury, CT 06762
    • 13 Hackamore Cir, Middlebury, CT 06762

      Est $546,662

      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

      • 34 Days On Market

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    /9

    $509,900

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

    0 N Benson Rd Unit 47 24099635, 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
  • 7 Sandy Beach Rd, Middlebury, CT 06762

    $4,050,000

    Sold Jan 15, 2026

    7 Sandy Beach Rd, Middlebury, CT 06762

    • 6 Beds
    • 4 Baths
    • 5,816 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Below List Price
    • $696/SF
    • 35 Days On Market

    Last Listing Agent Beverly Mosch William Pitt Sotheby's Int'l

    7 Sandy Beach Rd, Middlebury, CT 06762
    • 5 Kimberwick Ct, Middlebury, CT 06762

      Est $526,496

      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

      • 55 Days On Market

      Last Listing Agent Jane Spino Showcase Realty, Inc.

  • 0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
    /9

    $519,900

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 53 24086541, 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 53 24086541, Middlebury, CT 06762
  • 2 Dogwood Ct, Middlebury, CT 06762

    $545,000

    Sold Feb 26, 2026

    2 Dogwood Ct, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 3,103 Sq Ft
    • Built 2007

    Last Sold Summary

    • 8% Below List Price
    • $176/SF
    • 202 Days On Market

    Current Estimated Value $553,937

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    2 Dogwood Ct, Middlebury, CT 06762
    • 5 Pommel Ln, Middlebury, CT 06762

      Est $584,134

      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

      • 60 Days On Market

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 24 Steinmann Ave, Middlebury, CT 06762
    24 Steinmann Ave, Middlebury, CT 06762
    24 Steinmann Ave, Middlebury, CT 06762
    /40

    $449,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft

    24 Steinmann Ave, Middlebury, CT 06762

    *Please submit your offers by Monday July 20th at 2:00pm.* Welcome to 24 Steinmann Avenue, where charm, thoughtful updates, and exceptional outdoor living come together in one of Middlebury's most desirable locations. This inviting Cape offers a flexible layout that lives larger than expected. The renovated kitchen features butcher block countertops, updated appliances, hardwood floors, recessed

    Michael Mastronardi Keller Williams Realty

    24 Steinmann Ave, Middlebury, CT 06762
  • 64 Watertown Rd, Middlebury, CT 06762

    $759,900

    Sold Jun 30, 2026

    64 Watertown Rd, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 4,094 Sq Ft
    • Built 1987

    Last Sold Summary

    • $186/SF
    • 73 Days On Market

    Current Estimated Value $755,077

    Last Listing Agent Olivia Bueno William Raveis Real Estate

    64 Watertown Rd, Middlebury, CT 06762
    • 9 Caveson Ct, Middlebury, CT 06762

      Est $573,332

      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

      • 64 Days On Market

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • 555 Whittemore Rd, Middlebury, CT 06762
    555 Whittemore Rd, Middlebury, CT 06762
    555 Whittemore Rd, Middlebury, CT 06762
    /12

    $449,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 1,855 Sq Ft

    555 Whittemore Rd, Middlebury, CT 06762

    Welcome to this charming Cape Cod home, situated on a 0.34-acre corner lot in the highly desirable town of Middlebury. This home offers 1,855 square feet of comfortable living space with 4 bedrooms and 2.5 baths. The heart of the home features updated oversized country kitchen, with cabinets galore, stainless steel refrigerator, dishwaher and microwave and a gas range. Formal Living Room and

    Deb Smolley Dave Jones Realty, LLC

    555 Whittemore Rd, 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 $317,087

    Last Listing Agent Kary Apanovitch Coldwell Banker Realty

    82 Tucker Hill Rd, Middlebury, CT 06762
    • 17 Caveson Ct, Middlebury, CT 06762

      Est $575,863

      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

      • 105 Days On Market

      Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  • 0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
    /9

    $560,753

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

    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762

    5 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 52 24100213, Middlebury, CT 06762
  • 851 South St, Middlebury, CT 06762

    $937,500

    Sold Jun 30, 2026

    851 South St, Middlebury, CT 06762

    • 5 Beds
    • 2.5 Baths
    • 3,301 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Below List Price
    • $284/SF
    • 68 Days On Market

    Current Estimated Value $945,975

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    851 South St, Middlebury, CT 06762
    • 130 White Ave, Middlebury, CT 06762

      Est $390,155

      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

      • 3 Days On Market

      Last Listing Agent Frank Durante William Raveis Real Estate

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

    $729,900

    New Construction $30K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,466 Sq Ft

    28 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ sq ft 4 bedroom colonial. 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

    28 Hunting Ridge Rd, 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
    • 7 Foster St, Middlebury, CT 06762

      Est $365,593

      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

      • 6 Days On Market

      Last Listing Agent Arben Belica William Raveis Real Estate

  • 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

    New Construction 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 50 24118969, 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 $616,142

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

    1 Independence Cir, Middlebury, CT 06762
    • 700 South St, Middlebury, CT 06762

      Est $1,655,749

      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

      • 542 Days On Market

      Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

Showing Results 41 - 80, Page 2 of 18

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