114

Recently Sold Middlebury, CT Homes

Section Image
  • 8 Kimberwick Ct, Middlebury, CT 06762

    $520,000

    Sold Oct 22, 2025

    8 Kimberwick Ct, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,147 Sq Ft
    • Built 1997

    Last Sold Summary

    • 8% Below List Price
    • $242/SF
    • 78 Days On Market

    Current Estimated Value $530,108

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
  • 171 Judd Hill Rd, Middlebury, CT 06762

    $882,500

    Sold Sep 25, 2025

    171 Judd Hill Rd, Middlebury, CT 06762

    • 5 Beds
    • 4 Baths
    • 3,700 Sq Ft
    • Built 2015

    Last Sold Summary

    • 4% Below List Price
    • $239/SF
    • 49 Days On Market

    Current Estimated Value $860,966

    Last Listing Agent Donna Kennedy Compass Connecticut, LLC

    171 Judd Hill Rd, Middlebury, CT 06762
  • 6 Pommel Ln Unit 6, Middlebury, CT 06762

    $525,000

    Sold Oct 16, 2025

    6 Pommel Ln Unit 6, Middlebury, CT 06762

    • 2 Beds
    • 2.5 Baths
    • 1,917 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Above List Price
    • $274/SF
    • 52 Days On Market

    Current Estimated Value $514,410

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    6 Pommel Ln Unit 6, Middlebury, CT 06762
  • 126 Colonial Ave, Middlebury, CT 06762

    $585,000

    Sold Jan 29, 2026

    126 Colonial Ave, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 2,531 Sq Ft
    • Built 1911

    Last Sold Summary

    • 8% Below List Price
    • $231/SF
    • 152 Days On Market

    Current Estimated Value $582,383

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
  • 192 Breakneck Hill Rd, Middlebury, CT 06762

    $435,000

    Sold May 21, 2026

    192 Breakneck Hill Rd, Middlebury, CT 06762

    • 4 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $306/SF
    • 32 Days On Market

    Current Estimated Value $436,102

    Last Listing Agent Maria Pinheiro RE/MAX RISE

    192 Breakneck Hill Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

    $499,900

    Sold Sep 30, 2025

    0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

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

    Last Sold Summary

    • $256/SF
    • 0 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762
  • 0 N Benson Rd Unit 37, Middlebury, CT 06762

    $547,460

    Sold Aug 15, 2025

    0 N Benson Rd Unit 37, Middlebury, CT 06762

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

    Last Sold Summary

    • 7% Above List Price
    • $281/SF
    • 163 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 37, Middlebury, CT 06762
  • 146 Richardson Dr, Middlebury, CT 06762

    $380,000

    Sold Nov 17, 2025

    146 Richardson Dr, Middlebury, CT 06762

    • 2 Beds
    • 1.5 Baths
    • 1,499 Sq Ft
    • Built 1940

    Last Sold Summary

    • $254/SF
    • 38 Days On Market

    Current Estimated Value $376,732

    Last Listing Agent Nicholas Greene eXp Realty

    146 Richardson Dr, Middlebury, CT 06762
  • 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 $312,737

    Last Listing Agent Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, 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 $572,993

    Last Listing Agent Gina Williams Preston Gray Real Estate

    94 Upper Whittemore Rd, Middlebury, CT 06762
  • 288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

    $190,000

    Sold Apr 21, 2026

    288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

    • Land
    • 1.13 Acres
    • $168,142 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 231 Days On Market

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 5, 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 $440,135

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    69 Nick 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 $491,830

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    30 Nick 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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 $616,337

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

    1 Independence Cir, 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
  • 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
  • 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
  • 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 $509,696

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    13 Caveson Ct, 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
  • 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 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 203 Lake Shore Dr, Middlebury, CT 06762

    $365,000

    Sold Jul 01, 2025

    203 Lake Shore Dr, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $272/SF
    • 69 Days On Market

    Current Estimated Value $364,927

    Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

    203 Lake Shore Dr, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 3

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $657,098.
What is the average time to sell a house in Middlebury, CT?
The houses for sale in Middlebury, CT spend an average of 82 days on the market.
What is the number of active homes for sale in Middlebury, CT?
There are 19 active homes for sale in Middlebury, CT.
How many homes have sold over the last 12 months in Middlebury, CT?
105 homes have sold in Middlebury, CT over the last 12 months.

Home Prices in Middlebury, CT

Home Price Trends

Median Sale Price
$545,000
Median Single Family Sale Price
$545,500
Median Townhouse Sale Price
$549,936
Median 2 Bedroom Sale Price
$414,950
Median 1 Bedroom Sale Price
$222,500
Average Price Per Sq Ft
$283
Number of Homes for Sale
19
Last 12 months Home Sales
105
Months of Supply
2.20
Median List Price
$569,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-4%
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