121

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 $533,237

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
  • 191 Ridgewood Dr Unit 191, Middlebury, CT 06762

    $620,000 Sold Mar 28, 2025

    191 Ridgewood Dr Unit 191, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,658 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $233/SF
    • 79 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    191 Ridgewood Dr Unit 191, Middlebury, CT 06762
  • 36 Aveline Ave, Middlebury, CT 06762

    $480,000 Sold Apr 25, 2025

    36 Aveline Ave, Middlebury, CT 06762

    • 4 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1952

    Last Sold Summary

    • $269/SF
    • 44 Days On Market

    Current Estimated Value $496,199

    Last Listing Agent Wayne Watt Jr. THE CONNECTICUT AGENCY LLC

    36 Aveline Ave, 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 $888,370

    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 $515,273

    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 $582,930

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
  • 407 Chestnut Cir Unit 78, Middlebury, CT 06762

    $710,500 Sold Jun 20, 2025

    407 Chestnut Cir Unit 78, Middlebury, CT 06762

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

    Last Sold Summary

    • 8% Above List Price
    • $310/SF
    • 520 Days On Market

    Current Estimated Value $652,530

    Last Listing Agent Jodi Dawley Real Estate Two

    407 Chestnut Cir Unit 78, 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 Meuse 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 Meuse 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 $384,621

    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 $317,510

    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 $574,582

    Last Listing Agent Gina Williams Preston Gray Real Estate

    94 Upper Whittemore Rd, Middlebury, CT 06762
  • 400 Long Meadow Rd, Middlebury, CT 06762

    $675,000 Sold Jun 06, 2025

    400 Long Meadow Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,778 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Above List Price
    • $243/SF
    • 44 Days On Market

    Current Estimated Value $695,446

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    400 Long Meadow Rd, 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 $444,419

    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 $489,330

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    30 Nick Rd, Middlebury, CT 06762
  • 180 Ridgewood Dr Unit 219, Middlebury, CT 06762

    $565,000 Sold Jun 18, 2025

    180 Ridgewood Dr Unit 219, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $300/SF
    • 71 Days On Market

    Current Estimated Value $573,239

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    180 Ridgewood Dr Unit 219, 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 $701,169

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    111 Dwyer 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 $987,513

    Last Listing Agent Jetlir Kulla Coldwell Banker Realty

    82 Mirey Dam 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 $502,864

    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 $771,268

    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 $600,029

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    2 Dogwood Ct, Middlebury, CT 06762
  • 713 Whittemore Rd, Middlebury, CT 06762

    $505,000 Sold May 23, 2025

    713 Whittemore Rd, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1916

    Last Sold Summary

    • 1% Above List Price
    • $342/SF
    • 2 Days On Market

    Current Estimated Value $512,087

    Last Listing Agent Robert Vignola Coldwell Banker Realty

    713 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 $314,599

    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 $651,956

    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 $627,839

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

    1 Independence Cir, Middlebury, CT 06762
  • 45 E Farms Rd, Middlebury, CT 06762

    $1,100,000 Sold May 19, 2025

    45 E Farms Rd, Middlebury, CT 06762

    • 4 Beds
    • 6 Baths
    • 5,054 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 48 Days On Market

    Current Estimated Value $1,129,910

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    45 E Farms 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 $393,332

    Last Listing Agent Martha Quaratella Coldwell Banker Realty

    32 Yale Ave, 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 $560,350

    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 $334,208

    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
    • 0.76 Acre
    • $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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 40 24066786, 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 $500,091

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    116 Yale Ave, Middlebury, CT 06762
  • 396 Watertown Rd, Middlebury, CT 06762

    $790,000 Sold Mar 31, 2025

    396 Watertown Rd, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,935 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $201/SF
    • 64 Days On Market

    Current Estimated Value $815,464

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, 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
  • 64 Joy Rd, Middlebury, CT 06762

    $422,000 Sold Jun 18, 2025

    64 Joy Rd, Middlebury, CT 06762

    • 3 Beds
    • 1 Bath
    • 1,688 Sq Ft
    • Built 1959

    Last Sold Summary

    • 6% Above List Price
    • $250/SF
    • 58 Days On Market

    Current Estimated Value $423,549

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    64 Joy Rd, 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 $427,407

    Last Listing Agent Robert 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 $452,695

    Last Listing Agent Dean Giatas Fiorelli Realty, LLC

    28 Maple Dr, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 4

Connecticut New Haven County Middlebury

Recently Sold Real Estate & Homes in Middlebury, CT

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $650,572.
What is the average time to sell a house in Middlebury, CT?
The houses for sale in Middlebury, CT spend an average of 89 days on the market.
What is the number of active homes for sale in Middlebury, CT?
There are 20 active homes for sale in Middlebury, CT.
How many homes have sold over the last 12 months in Middlebury, CT?
112 homes have sold in Middlebury, CT over the last 12 months.

Home Trends in Middlebury, CT

On average, homes in Middlebury, CT sell after 89 days on the market compared to the national average of 55 days. The median sale price for homes in Middlebury, CT over the last 12 months is $548,698, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$548,698
Median Single Family Sale Price
$529,900
Median Townhouse Sale Price
$544,513
Median 2 Bedroom Sale Price
$702,500
Average Price Per Sq Ft
$279
Number of Homes for Sale
20
Last 12 months Home Sales
112
Months of Supply
2.10
Median List Price
$590,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group