3,783

Middlebury, CT Homes

Section Image
  • 73 Yale Ave, Middlebury, CT 06762

    $300,000 Sold Jan 16, 2026

    73 Yale Ave, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 1,099 Sq Ft
    • Built 1945

    Last Sold Summary

    • 14% Below List Price
    • $273/SF
    • 50 Days On Market

    Current Estimated Value $344,291

    Last Listing Agent Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, Middlebury, CT 06762
    • 40 Winthrop Dr, Middlebury, CT 06762

      Est $1,754,971 Not Listed For Sale

      40 Winthrop Dr, Middlebury, CT 06762

      • 4 Beds
      • 6.5 Baths
      • 4,954 Sq Ft
      • Built 2001
      40 Winthrop Dr, Middlebury, CT 06762

      Last Sold Summary

      • $353/SF
      • 94 Days On Market

      Last Sold Price $1,750,000

      Last Listing Agent John Donato Jr Showcase Realty Tristate

  • /38

    $659,900

    • 4 Beds
    • 4 Baths
    • 4,200 Sq Ft

    3 Brookside Dr, Middlebury, CT 06762

    Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the

    Shagufta Zahid S Factor Realty Group LLC

    3 Brookside Dr, Middlebury, CT 06762
  • 94 Upper Whittemore Rd, Middlebury, CT 06762

    $555,000 Sold Jul 02, 2025

    94 Upper Whittemore Rd, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft
    • Built 1944

    Last Sold Summary

    • 3% Above List Price
    • $274/SF
    • 47 Days On Market

    Current Estimated Value $561,483

    Last Listing Agent Gina Williams Preston Gray Real Estate

    94 Upper Whittemore Rd, Middlebury, CT 06762
    • 740 Whittemore Rd, Middlebury, CT 06762

      Est $622,469 Not Listed For Sale

      740 Whittemore Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,830 Sq Ft
      • Built 1981
      740 Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 6% Above List Price
      • $208/SF
      • 27 Days On Market

      Last Sold Price $590,000

      Last Listing Agent Adrian Cote William Raveis Real Estate

  • /2

    $729,990 Open House 3/15

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    321 Artillery Rd, Middlebury, CT 06762

    Coming SOON!!! Large Colonial with charm and character is ready to call home! Offering privacy on its fabulous 4 acres with magical views and abundant sunlight. The home offers four large bedrooms with ample light that will surely please you. The formal living room with complete with a alrge picture window and marble fireplace will serve as a great oplace to relax at the end of a long day. The

    Frank Durante William Raveis Real Estate

    321 Artillery Rd, Middlebury, CT 06762
  • 400 Long Meadow Rd, Middlebury, CT 06762

    $675,000 Sold Jun 06, 2025

    400 Long Meadow Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,778 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Above List Price
    • $243/SF
    • 44 Days On Market

    Current Estimated Value $684,042

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    400 Long Meadow Rd, Middlebury, CT 06762
    • 108 White Ave, Middlebury, CT 06762

      Est $609,551 Not Listed For Sale

      108 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1953
      108 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 16% Above List Price
      • $250/SF
      • 7 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  • /40

    $689,000 Pending

    • 4 Beds
    • 5 Baths
    • 3,254 Sq Ft

    84 Munson Rd, Middlebury, CT 06762

    Experience comfort, space, and scenic surroundings at 84 Munson Road, Middlebury, CT 06762, a well-situated home set in a peaceful and desirable community. This inviting property offers a thoughtfully designed layout with generous living areas filled with natural light, creating a bright and welcoming atmosphere. The main level provides ideal flow for everyday living and entertaining, while the

    Thomas Mele Dorrance Realty

    84 Munson Rd, Middlebury, CT 06762
  • 69 Nick Rd, Middlebury, CT 06762

    $440,000 Sold Jun 24, 2025

    69 Nick Rd, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,414 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Above List Price
    • $311/SF
    • 38 Days On Market

    Current Estimated Value $437,066

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    69 Nick Rd, Middlebury, CT 06762
    • 28 Jensen Dr, Middlebury, CT 06762

      Est $479,641 Not Listed For Sale

      28 Jensen Dr, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,552 Sq Ft
      • Built 1970
      28 Jensen Dr, Middlebury, CT 06762

      Last Sold Summary

      • 9% Above List Price
      • $172/SF
      • 4 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  • /37

    $759,000

    • 4 Beds
    • 2.5 Baths
    • 2,753 Sq Ft

    117 Crest Rd, Middlebury, CT 06762

    Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the

    Lori Geraci BHGRE Gaetano Marra Homes

    117 Crest Rd, Middlebury, CT 06762
  • 30 Nick Rd, Middlebury, CT 06762

    $480,000 Sold Nov 07, 2025

    30 Nick Rd, Middlebury, CT 06762

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2011

    Last Sold Summary

    • 9% Below List Price
    • $192/SF
    • 113 Days On Market

    Current Estimated Value $485,610

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    30 Nick Rd, Middlebury, CT 06762
    • 18 Jericho Rd, Middlebury, CT 06762

      Est $553,762 Not Listed For Sale

      18 Jericho Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,908 Sq Ft
      • Built 1978
      18 Jericho Rd, Middlebury, CT 06762

      Last Sold Summary

      • 4% Above List Price
      • $182/SF
      • 61 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Michael Bachmann HomeSmart Homes and Estates

  • /2

    $709,900 Pending

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

    2 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) 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

    2 Deer Run Rd, Middlebury, CT 06762
  • 180 Ridgewood Dr Unit 219, Middlebury, CT 06762

    $565,000 Sold Jun 18, 2025

    180 Ridgewood Dr Unit 219, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $300/SF
    • 71 Days On Market

    Current Estimated Value $572,219

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    180 Ridgewood Dr Unit 219, Middlebury, CT 06762
    • 150 Carriage Dr, Middlebury, CT 06762

      Est $646,777 Not Listed For Sale

      150 Carriage Dr, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 1963
      150 Carriage Dr, Middlebury, CT 06762

      Last Sold Summary

      • 4% Above List Price
      • $249/SF
      • 4 Days On Market

      Last Sold Price $620,000

      Last Listing Agent Colleen Burne Coldwell Banker Realty

  • /9

    $545,400 Pending

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

    0 N Benson Rd Unit 64 24077175, 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 64 24077175, 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 $577,929 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

      • 54% Above List Price
      • $194/SF
      • 51 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Lauren Cavallo Lauren Ashley Homes LLC

  • /2

    $699,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,877 Sq Ft

    14 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run Rd(aka Lot 19) 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

    14 Deer Run 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 $701,441

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    111 Dwyer Rd, Middlebury, CT 06762
    • 410 Charcoal Ave, Middlebury, CT 06762

      Est $959,699 Not Listed For Sale

      410 Charcoal Ave, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 3,172 Sq Ft
      • Built 2006
      410 Charcoal Ave, Middlebury, CT 06762

      Last Sold Summary

      • 16% Above List Price
      • $260/SF
      • 19 Days On Market

      Last Sold Price $825,000

      Last Listing Agent Blair Patterson William Raveis Real Estate

  • /9

    $548,828 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,462 Sq Ft

    0 N Benson Rd Unit 55 24086408, 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 55 24086408, 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 $969,835

    Last Listing Agent Jetlir Kulla Coldwell Banker Realty

    82 Mirey Dam Rd, Middlebury, CT 06762
    • 261 Sandy Hill Rd, Middlebury, CT 06762

      Est $782,793 Not Listed For Sale

      261 Sandy Hill Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 3,750 Sq Ft
      • Built 1997
      261 Sandy Hill Rd, Middlebury, CT 06762

      Last Sold Summary

      • 12% Above List Price
      • $187/SF
      • 34 Days On Market

      Last Sold Price $699,900

      Last Listing Agent Karen Berwick Real Estate Two

  • /6

    $200,000 Pending

    • Land
    • 1.13 Acres
    • $176,991 per Acre

    288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

    Gorgeous 1.13 acre lot in a brand new subdivision. Level and on a private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD. Shared maintenance for private driveway. Flood

    John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 5, 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 $494,952

    Last Listing Agent Amber Segetti RE/MAX RISE

    58 Shadduck Rd, Middlebury, CT 06762
    • 109 Marney Dr, Middlebury, CT 06762

      Est $507,110 Not Listed For Sale

      109 Marney Dr, Middlebury, CT 06762

      • 5 Beds
      • 2.5 Baths
      • 2,696 Sq Ft
      • Built 1966
      109 Marney Dr, Middlebury, CT 06762

      Last Sold Summary

      • 24% Above List Price
      • $152/SF
      • 37 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Karen Griffin Coldwell Banker Realty

  • /19

    $259,900

    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft

    152 Glenwood Ave, Middlebury, CT 06762

    2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your

    Don Orsini West View Properties, LLC

    152 Glenwood Ave, Middlebury, CT 06762
  • 34 Avalon Dr, Middlebury, CT 06762

    $750,000 Sold Jul 23, 2025

    34 Avalon Dr, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 3,374 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $222/SF
    • 62 Days On Market

    Current Estimated Value $766,618

    Last Listing Agent Connie Widmann William Raveis Real Estate

    34 Avalon Dr, Middlebury, CT 06762
    • 530 Whittemore Rd, Middlebury, CT 06762

      Est $506,593 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

      • 6% Above List Price
      • $161/SF
      • 85 Days On Market

      Last Sold Price $480,000

      Last Listing Agent Monique Jacobs RE/MAX

  • /24

    $229,900

    • Land
    • 4.67 Acres
    • $49,229 per Acre

    75 Gleneagle Rd, Middlebury, CT 06762

    LOCATION, LOCATION, LOCATION!!! ONLY LOT FOR SALE IN THIS PRIVATE, 11 LOT SUBDIVISION OF QUALITY-BUILT HIGH END HOMES. SUBDIVISION HAS THE UNIQUE BONUSES OF PUBLIC WATER & SEWER (ALREADY EXTENDED TO LOT) AND CLOSE PROXIMITY TO LOCAL RETAIL AND HIGHWAYS. 4.67 ACRE SITE TUCKED AWAY AT THE END OF A TURN-AROUND TO THE LEFT OF THE ELABORATE GAZEEBO AND LAND TRUST PROPERTY.

    Scott Tedesco Tedesco Real Estate

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

      Est $705,149 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

      • 4% Above List Price
      • $181/SF
      • 182 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • /9

    $509,900 Under Contract

    • 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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 47 24099635, 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 $600,029

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    2 Dogwood Ct, Middlebury, CT 06762
    • 312 Three Mile Hill Rd, Middlebury, CT 06762

      Est $520,902 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

      • 2% Above List Price
      • $168/SF
      • 186 Days On Market

      Last Sold Price $508,500

      Last Listing Agent Marian Van Egas Berkshire Hathaway Home Services

  • /9

    $519,900 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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 53 24086541, Middlebury, CT 06762
  • 713 Whittemore Rd, Middlebury, CT 06762

    $505,000 Sold May 23, 2025

    713 Whittemore Rd, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1916

    Last Sold Summary

    • 1% Above List Price
    • $342/SF
    • 2 Days On Market

    Current Estimated Value $502,261

    Last Listing Agent Robert Vignola Coldwell Banker Realty

    713 Whittemore Rd, Middlebury, CT 06762

Showing Results 41 - 80, Page 2 of 18

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