122

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 $533,273

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
  • 178 Ridgewood Dr Unit 178, Middlebury, CT 06762

    $607,000

    Sold Jul 07, 2026

    178 Ridgewood Dr Unit 178, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,414 Sq Ft
    • Built 2022

    Last Sold Summary

    • 5% Below List Price
    • $251/SF
    • 25 Days On Market

    Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

    178 Ridgewood Dr Unit 178, 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 $872,994

    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 $519,887

    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 $597,123

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
  • 36 Highridge Rd Unit 36, Middlebury, CT 06762

    $580,000

    Sold Sep 10, 2026

    36 Highridge Rd Unit 36, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,997 Sq Ft
    • Built 2018

    Last Sold Summary

    • 1% Below List Price
    • $290/SF
    • 18 Days On Market

    Last Listing Agent John Pistorino RE/MAX RISE

    36 Highridge Rd Unit 36, 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 $444,621

    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
  • 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 $387,148

    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 $321,113

    Last Listing Agent Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, 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
  • 152 Glenwood Ave, Middlebury, CT 06762

    $224,000

    Sold Jun 29, 2026

    152 Glenwood Ave, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft
    • Built 1935

    Last Sold Summary

    • 25% Below List Price
    • $206/SF
    • 152 Days On Market

    Current Estimated Value $234,950

    Last Listing Agent Don Orsini West View Properties, LLC

    152 Glenwood Ave, Middlebury, CT 06762
  • 223 Carriage Dr, Middlebury, CT 06762

    $670,000

    Sold Jun 30, 2026

    223 Carriage Dr, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 2,484 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $270/SF
    • 95 Days On Market

    Current Estimated Value $668,285

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    223 Carriage Dr, 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 $508,261

    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 $718,822

    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 $433,556

    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 $974,861

    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 $741,829

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    200 N Farm 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
  • 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 $557,790

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    2 Dogwood Ct, Middlebury, CT 06762
  • 24 Steinmann Ave, Middlebury, CT 06762

    $467,000

    Sold Aug 24, 2026

    24 Steinmann Ave, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft
    • Built 1940

    Last Sold Summary

    • 4% Above List Price
    • $339/SF
    • 4 Days On Market

    Current Estimated Value $443,426

    Last Listing Agent Michael Mastronardi Keller Williams Realty

    24 Steinmann Ave, Middlebury, CT 06762
  • 64 Watertown Rd, Middlebury, CT 06762

    $759,900

    Sold Jun 30, 2026

    64 Watertown Rd, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 4,094 Sq Ft
    • Built 1987

    Last Sold Summary

    • $186/SF
    • 73 Days On Market

    Current Estimated Value $755,091

    Last Listing Agent Olivia Bueno William Raveis Real Estate

    64 Watertown Rd, Middlebury, CT 06762
  • 555 Whittemore Rd, Middlebury, CT 06762

    $340,000

    Sold Sep 10, 2026

    555 Whittemore Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 1,855 Sq Ft
    • Built 1946

    Last Sold Summary

    • 24% Below List Price
    • $183/SF
    • 54 Days On Market

    Current Estimated Value $445,448

    Last Listing Agent Deb Smolley Dave Jones Realty, LLC

    555 Whittemore Rd, 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 $318,862

    Last Listing Agent Kary Apanovitch Coldwell Banker Realty

    82 Tucker Hill Rd, 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 $935,746

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    851 South St, Middlebury, CT 06762
  • 28 Hunting Ridge Rd, Middlebury, CT 06762

    $740,000

    Sold Sep 09, 2026

    28 Hunting Ridge Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,466 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $300/SF
    • 548 Days On Market

    Current Estimated Value $820,667

    Last Listing Agent Jodi Dawley Real Estate Two

    28 Hunting Ridge Rd, 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
  • 0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762

    $509,900

    Sold Sep 18, 2026

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2026

    Last Sold Summary

    • $261/SF
    • 0 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
  • 1252 Straits Turnpike, Middlebury, CT 06762

    $245,000

    Sold Sep 11, 2026

    1252 Straits Turnpike, Middlebury, CT 06762

    • 4 Beds
    • 1 Bath
    • 1,848 Sq Ft
    • Built 1929

    Last Sold Summary

    • 18% Below List Price
    • $133/SF
    • 62 Days On Market

    Current Estimated Value $300,131

    Last Listing Agent Gianna Alberti ALBERTI REALTY ASSOCIATES, LLC

    1252 Straits Turnpike, 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 $622,376

    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 $409,100

    Last Listing Agent Martha Quaratella Coldwell Banker Realty

    32 Yale Ave, 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 $524,846

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    13 Caveson Ct, Middlebury, CT 06762
  • 286 Mirey Dam Rd, Middlebury, CT 06762

    $900,000

    Sold Jul 09, 2026

    286 Mirey Dam Rd, Middlebury, CT 06762

    • 4 Beds
    • 3 Baths
    • 4,451 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Below List Price
    • $202/SF
    • 14 Days On Market

    Current Estimated Value $925,228

    Last Listing Agent Pam Famiglietti William Raveis Real Estate

    286 Mirey Dam 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 $360,654

    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
  • 36 Independence Cir, Middlebury, CT 06762

    $670,000

    Sold Aug 31, 2026

    36 Independence Cir, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $191/SF
    • 19 Days On Market

    Current Estimated Value $653,556

    Last Listing Agent David Hughes Century 21 AllPoints Realty

    36 Independence Cir, 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
  • 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 $809,073

    Last Listing Agent Jodi Dawley Real Estate Two

    18 Deer Run Rd, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 4

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $636,464.
What is the average time to sell a house in Middlebury, CT?
The houses for sale in Middlebury, CT spend an average of 74 days on the market.
What is the number of active homes for sale in Middlebury, CT?
There are 32 active homes for sale in Middlebury, CT.
How many homes have sold over the last 12 months in Middlebury, CT?
114 homes have sold in Middlebury, CT over the last 12 months.

Home Price Trends

Median Sale Price
$565,000
Median Single Family Sale Price
$585,000
Median Townhouse Sale Price
$565,000
Median 2 Bedroom Sale Price
$457,450
Median 1 Bedroom Sale Price
$223,700
Average Price Per Sq Ft
$279
Number of Homes for Sale
122
Last 12 months Home Sales
114
Months of Supply
3.40
Median List Price
$585,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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