3,798

Middlebury, CT Homes

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

    $585,000

    Pending
    • 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
  • 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
  • 152 Glenwood Ave, Middlebury, CT 06762
    152 Glenwood Ave, Middlebury, CT 06762
    152 Glenwood Ave, Middlebury, CT 06762
    /19

    $224,900

    $75K PRICE DROP Pending
    • 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
  • 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 $701,447

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    111 Dwyer Rd, Middlebury, CT 06762
  • 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 $424,444

    Last Listing Agent Marisela Agelvis West View Properties, LLC

    863 Whittemore Rd, Middlebury, CT 06762
  • 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 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 47 24099635, 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 $963,246

    Last Listing Agent Jetlir Kulla Coldwell Banker Realty

    82 Mirey Dam Rd, Middlebury, CT 06762
  • 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
  • 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 $766,386

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    200 N Farm Rd, Middlebury, CT 06762
  • 555 Whittemore Rd, Middlebury, CT 06762
    555 Whittemore Rd, Middlebury, CT 06762
    555 Whittemore Rd, Middlebury, CT 06762
    /13

    $449,000

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

    555 Whittemore Rd, Middlebury, CT 06762

    Welcome to this charming Cape Cod home, ideally situated on a spacious .34-acre corner lot in the highly desirable town of Middlebury. Built in 1946, this home offers 1,855 square feet of comfortable living space with four bedrooms and two-and-a-half bathrooms. The heart of the home features an oversized country kitchen, including stainless steel appliances,.... plenty of space for cooking,

    Deb Smolley Dave Jones Realty, LLC

    555 Whittemore Rd, 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 $493,495

    Last Listing Agent Amber Segetti RE/MAX RISE

    58 Shadduck Rd, Middlebury, CT 06762
  • 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
  • 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 $765,596

    Last Listing Agent Connie Widmann William Raveis Real Estate

    34 Avalon Dr, Middlebury, CT 06762
  • 28 Hunting Ridge Rd, Middlebury, CT 06762
    28 Hunting Ridge Rd, Middlebury, CT 06762
    28 Hunting Ridge Rd, Middlebury, CT 06762
    /38

    $759,900

    New Construction
    • 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
  • 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
  • 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
  • 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 $554,565

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

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

    $299,900

    • 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

    Gianna Alberti ALBERTI REALTY ASSOCIATES, LLC

    1252 Straits Turnpike, 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 $304,054

    Last Listing Agent Kary Apanovitch Coldwell Banker Realty

    82 Tucker Hill Rd, Middlebury, CT 06762
  • 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
  • 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 $946,286

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    851 South St, Middlebury, CT 06762
  • 36 Independence Cir, Middlebury, CT 06762
    36 Independence Cir, Middlebury, CT 06762
    36 Independence Cir, Middlebury, CT 06762
    /40

    $650,000

    • 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
  • 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 $650,984

    Last Listing Agent Jodi Dawley Real Estate Two

    405 Chestnut Cir Unit 77, Middlebury, CT 06762
  • 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
  • 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

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