3,802

Homes in ZIP Code 06762

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

    $729,900

    $35K PRICE DROP Under Contract
    • 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
  • 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 $394,191

    Last Listing Agent Martha Quaratella Coldwell Banker Realty

    32 Yale Ave, Middlebury, CT 06762
  • 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
  • 541 Benson Rd, Middlebury, CT 06762

    $465,000

    Sold Jun 17, 2026

    541 Benson Rd, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1942

    Last Sold Summary

    • 11% Below List Price
    • $291/SF
    • 25 Days On Market

    Current Estimated Value $518,914

    Last Listing Agent Joseph Martino Joseph Martino Real Estate

    541 Benson Rd, Middlebury, CT 06762
  • 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
  • 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
  • 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
  • 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 $517,387

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    13 Caveson Ct, Middlebury, CT 06762
  • 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
  • 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 $348,913

    Last Listing Agent Stephanie Oliver Dave Jones Realty, LLC

    348 Kelly Rd, Middlebury, CT 06762
  • 25 Avalon Dr, Middlebury, CT 06762
    25 Avalon Dr, Middlebury, CT 06762
    25 Avalon Dr, Middlebury, CT 06762
    /39

    $879,900

    • 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
  • 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
  • 0 N Benson Rd Unit 66, Middlebury, CT 06762
    0 N Benson Rd Unit 66, Middlebury, CT 06762
    0 N Benson Rd Unit 66, Middlebury, CT 06762
    /9

    $562,350

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

    0 N Benson Rd Unit 66, 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 66, 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
  • 1140 Southford Rd, Middlebury, CT 06762
    1140 Southford Rd, Middlebury, CT 06762
    1140 Southford Rd, Middlebury, CT 06762
    /13

    $399,000

    • Land
    • 1.5 Acres
    • $266,000 per Acre

    1140 Southford Rd, Middlebury, CT 06762

    Exceptional opportunity to acquire a 1.5-acre industrial development parcel located along the highly visible Southford Road corridor in Middlebury. Situated within the IG-40 (Gateway Industrial Design District), this property is ideally suited for flex industrial, contractor headquarters, light manufacturing, or office-warehouse development. The site benefits from access to public water and

    Robert Ghent Ghent Realty Advisors

    1140 Southford Rd, 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 $763,333

    Last Listing Agent Jodi Dawley Real Estate Two

    18 Deer Run Rd, Middlebury, CT 06762
  • 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

    New Construction 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 46 24097231, 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 $493,590

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    116 Yale Ave, Middlebury, CT 06762
  • 122 Crest Rd, Middlebury, CT 06762
    122 Crest Rd, Middlebury, CT 06762
    122 Crest Rd, Middlebury, CT 06762
    /37

    $825,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 3,253 Sq Ft

    122 Crest Rd, Middlebury, CT 06762

    Welcome to your own private retreat at 122 Crest Road-where timeless charm meets thoughtful modern updates. This beautifully maintained 3-bedroom, 2.5-bath Cape Cod-style home is just moments from town, the library, green, and local dining. Designed with both everyday living and entertaining in mind, the home features a custom sunken great room with a dramatic wall of windows that floods the

    Heather Dever Showcase Realty, Inc.

    122 Crest 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
  • 80 Pine Hollow Dr, Middlebury, CT 06762
    80 Pine Hollow Dr, Middlebury, CT 06762
    80 Pine Hollow Dr, Middlebury, CT 06762
    /31

    $749,900

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,806 Sq Ft

    80 Pine Hollow Dr, Middlebury, CT 06762

    Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

    Gina Farra Keller Williams Realty

    80 Pine Hollow Dr, Middlebury, CT 06762
  • 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
  • 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

    New Construction 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 57, 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 $417,727

    Last Listing Agent Rob Marucci Better Living Realty, LLC

    93 Fenn Rd, Middlebury, CT 06762
  • 3 Brookside Dr, Middlebury, CT 06762
    3 Brookside Dr, Middlebury, CT 06762
    3 Brookside Dr, Middlebury, CT 06762
    /36

    $599,900

    $60K PRICE DROP Under Contract
    • 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
  • 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 $440,489

    Last Listing Agent Dean Giatas Fiorelli Realty, LLC

    28 Maple Dr, Middlebury, CT 06762
  • 38 Avalon Dr, Middlebury, CT 06762
    38 Avalon Dr, Middlebury, CT 06762
    38 Avalon Dr, Middlebury, CT 06762
    /38

    $779,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    38 Avalon Dr, Middlebury, CT 06762

    Welcome to Avalon Farms community, located in one of Middlebury's distinctive residential communities, known for its beautifully built, upscale homes. The home is known for its European inspired architecture, beautifully preserved, natural surroundings, at the end of a cul-de-sac, which suits any stage of life you're in. Step inside to a grand two-story foyer that sets the tone for the homes

    Tracy Wilson Lamacchia Realty

    38 Avalon Dr, Middlebury, CT 06762

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