3,777

Middlebury, CT Homes

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  • 281 Watertown Rd, Middlebury, CT 06762
    281 Watertown Rd, Middlebury, CT 06762
    281 Watertown Rd, Middlebury, CT 06762
    /24

    $499,900

    • 5 Beds
    • 2 Baths
    • 2,428 Sq Ft

    281 Watertown Rd, Middlebury, CT 06762

    Welcome to this stunning Colonial, offering over 2,400 sq. ft. of living space on a rare, level 1-acre lot in one of Middlebury's most desirable locations. The first floor features an inviting eat-in kitchen with updated cabinets, new appliances, a center island, and a cozy fireplace-perfect for gathering. You'll also find a formal dining room and spacious living room, ideal for entertaining. The

    Xin Guo Coldwell Banker Realty 2000

    281 Watertown Rd, Middlebury, CT 06762
  • 112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    $510,000 Sold Oct 22, 2025

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    • 2 Beds
    • 2.5 Baths
    • 2,593 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $197/SF
    • 186 Days On Market

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
  • 0 N Benson Rd Unit 60, Middlebury, CT 06762
    0 N Benson Rd Unit 60, Middlebury, CT 06762
    0 N Benson Rd Unit 60, Middlebury, CT 06762
    /9

    $573,584 Pending

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

    0 N Benson Rd Unit 60, 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 60, Middlebury, CT 06762
  • 74 E Ridge Dr, Middlebury, CT 06762

    $385,000 Sold Mar 10, 2025

    74 E Ridge Dr, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 1,275 Sq Ft
    • Built 1954

    Last Sold Summary

    • 9% Below List Price
    • $302/SF
    • 123 Days On Market

    Current Estimated Value $401,707

    Last Listing Agent Marian Van Egas Berkshire Hathaway NE Prop.

    74 E Ridge Dr, Middlebury, CT 06762
  • 11 Upper Whittemore Rd, Middlebury, CT 06762
    11 Upper Whittemore Rd, Middlebury, CT 06762
    11 Upper Whittemore Rd, Middlebury, CT 06762
    /36

    $459,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    11 Upper Whittemore Rd, Middlebury, CT 06762

    Discover your dream home at 11 Upper Whittemore Rd, a stunningly renovated Brick Ranch nestled on a private, dead-end street with over 1.37 acres of beautiful land. This oasis boasts an unbeatable location because it provides both seclusion and connectivity: you're just moments from the recreational fun of Lake Quassapaug and Quassy Amusement Park, and the property offers easy access to major

    Islam Ahmad Real Broker CT, LLC

    11 Upper Whittemore Rd, Middlebury, CT 06762
  • 460 Lake Shore Dr, Middlebury, CT 06762

    $415,000 Sold May 23, 2025

    460 Lake Shore Dr, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $322/SF
    • 68 Days On Market

    Current Estimated Value $418,081

    Last Listing Agent Blair Patterson William Raveis Real Estate

    460 Lake Shore Dr, Middlebury, CT 06762
  • 122 Mirey Dam Rd, Middlebury, CT 06762

    $1,375,000 Sold Sep 04, 2025

    122 Mirey Dam Rd, Middlebury, CT 06762

    • 4 Beds
    • 5 Baths
    • 6,175 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $223/SF
    • 103 Days On Market

    Current Estimated Value $1,372,483

    Last Listing Agent Jennifer Jones Coldwell Banker Realty

    122 Mirey Dam Rd, Middlebury, CT 06762
  • 81 Sandy Beach Rd, Middlebury, CT 06762

    $410,000 Sold Mar 14, 2025

    81 Sandy Beach Rd, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 972 Sq Ft
    • Built 1940

    Last Sold Summary

    • 13% Below List Price
    • $422/SF
    • 61 Days On Market

    Current Estimated Value $413,510

    Last Listing Agent Wilson Lamas Realty Group of New England, LLC

    81 Sandy Beach Rd, Middlebury, CT 06762
  • 403 Chestnut Cir Unit 76, Middlebury, CT 06762

    $702,500 Sold May 23, 2025

    403 Chestnut Cir Unit 76, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 2,292 Sq Ft
    • Built 2023

    Last Sold Summary

    • 6% Above List Price
    • $307/SF
    • 533 Days On Market

    Current Estimated Value $663,971

    Last Listing Agent Jodi Dawley Real Estate Two

    403 Chestnut Cir Unit 76, Middlebury, CT 06762
  • 138 Skyline Dr, Middlebury, CT 06762

    $590,000 Sold Jun 04, 2025

    138 Skyline Dr, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,212 Sq Ft
    • Built 1960

    Last Sold Summary

    • 15% Below List Price
    • $267/SF
    • 59 Days On Market

    Current Estimated Value $593,559

    Last Listing Agent Diana Mashni RE/MAX One

    138 Skyline Dr, Middlebury, CT 06762
  • 1 Dogwood Ct Unit 1, Middlebury, CT 06762

    $575,000 Sold Nov 06, 2025

    1 Dogwood Ct Unit 1, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 3,477 Sq Ft
    • Built 2007

    Last Sold Summary

    • 15% Below List Price
    • $165/SF
    • 216 Days On Market

    Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

    1 Dogwood Ct Unit 1, Middlebury, CT 06762
  • 0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762

    $549,936 Sold Oct 30, 2025

    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $244/SF
    • 0 Days On Market

    Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
  • 401 Chestnut Cir Unit 75, Middlebury, CT 06762

    $707,200 Sold Apr 04, 2025

    401 Chestnut Cir Unit 75, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 2,292 Sq Ft
    • Built 2023

    Last Sold Summary

    • 7% Above List Price
    • $309/SF
    • 535 Days On Market

    Current Estimated Value $673,597

    Last Listing Agent Jodi Dawley Real Estate Two

    401 Chestnut Cir Unit 75, Middlebury, CT 06762
  • 203 Tower Rd, Middlebury, CT 06762

    $555,000 Sold Jan 22, 2025

    203 Tower Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,572 Sq Ft
    • Built 2001

    Last Sold Summary

    • 4% Below List Price
    • $216/SF
    • 86 Days On Market

    Current Estimated Value $589,136

    Last Listing Agent Nancy Lydell Calcagni Real Estate

    203 Tower Rd, Middlebury, CT 06762
  • 110 Glenwood Ave, Middlebury, CT 06762

    $525,000 Sold Jun 02, 2025

    110 Glenwood Ave, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,160 Sq Ft
    • Built 2006

    Last Sold Summary

    • 5% Below List Price
    • $243/SF
    • 33 Days On Market

    Current Estimated Value $540,608

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    110 Glenwood Ave, Middlebury, CT 06762
  • 111 Periwinkle Dr Unit 111, Middlebury, CT 06762

    $585,000 Sold Mar 28, 2025

    111 Periwinkle Dr Unit 111, Middlebury, CT 06762

    • 2 Beds
    • 2.5 Baths
    • 2,476 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $236/SF
    • 131 Days On Market

    Current Estimated Value $630,882

    Last Listing Agent Marvin and Laura Beninson Keller Williams Realty

    111 Periwinkle Dr Unit 111, Middlebury, CT 06762
  • 43 Ridgewood Dr Unit 43, Middlebury, CT 06762

    $493,000 Sold Jun 06, 2025

    43 Ridgewood Dr Unit 43, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,808 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $273/SF
    • 44 Days On Market

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    43 Ridgewood Dr Unit 43, Middlebury, CT 06762
  • 181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    $565,000 Sold Sep 25, 2025

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,614 Sq Ft
    • Built 2022

    Last Sold Summary

    • 6% Below List Price
    • $216/SF
    • 90 Days On Market

    Last Listing Agent Heather Crabtree RE/MAX RISE

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762
  • 119 Christian Rd, Middlebury, CT 06762

    $345,000 Sold Sep 10, 2025

    119 Christian Rd, Middlebury, CT 06762

    • 2 Beds
    • 1.5 Baths
    • 866 Sq Ft
    • Built 1936

    Last Sold Summary

    • 1% Below List Price
    • $398/SF
    • 11 Days On Market

    Current Estimated Value $346,111

    Last Listing Agent David Aurigemma Regency Real Estate, LLC

    119 Christian Rd, Middlebury, CT 06762
  • 18 E Ridge Dr, Middlebury, CT 06762

    $456,000 Sold Nov 17, 2025

    18 E Ridge Dr, Middlebury, CT 06762

    • 3 Beds
    • 3 Baths
    • 1,340 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Above List Price
    • $340/SF
    • 54 Days On Market

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    18 E Ridge Dr, Middlebury, CT 06762
  • 0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

    $530,328 Sold Oct 30, 2025

    0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

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

    Last Sold Summary

    • 6% Above List Price
    • $272/SF
    • 163 Days On Market

    Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

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