Recently Sold Middlebury, CT Homes

• 

  $800,000 Sold Dec 16, 2025

  1 Hampshire Ct, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,711 Sq Ft
  • Built 2008

  Last Sold Summary

  • 3% Below List Price
  • $216/SF
  • 67 Days On Market

  Current Estimated Value $809,857

  Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

  1 Hampshire Ct, Middlebury, CT 06762
• 

  $645,000 Sold Jan 27, 2026

  51 Cross Rd, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Above List Price
  • $199/SF
  • 53 Days On Market

  Current Estimated Value $626,037

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  51 Cross Rd, Middlebury, CT 06762
• 

  $820,000 Sold Dec 18, 2025

  11 Hunting Ridge Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2025

  Last Sold Summary

  • 17% Above List Price
  • $304/SF
  • 322 Days On Market

  Current Estimated Value $808,595

  Last Listing Agent Jodi Dawley Real Estate Two

  11 Hunting Ridge Rd, Middlebury, CT 06762
• 

  $511,000 Sold Oct 01, 2025

  0 N Benson Rd Unit 38 24064329, Middlebury, CT 06762

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

  Last Sold Summary

  • $262/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 38 24064329, Middlebury, CT 06762
• 

  $799,000 Sold May 02, 2025

  34 Breakneck Hill Rd, Middlebury, CT 06762

  • 5 Beds
  • 3 Baths
  • 4,551 Sq Ft
  • Built 2006

  Last Sold Summary

  • $176/SF
  • 19 Days On Market

  Current Estimated Value $848,348

  Last Listing Agent Arben Belica William Raveis Real Estate

  34 Breakneck Hill Rd, Middlebury, CT 06762
• 

  $225,000 Sold Sep 16, 2025

  288 Watertown Rd Unit Lot 3, Middlebury, CT 06762

  • Land
  • 3.07 Acres
  • $73,290 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 3, Middlebury, CT 06762
• 

  $490,000 Sold Jul 28, 2025

  115 Marney Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $291/SF
  • 86 Days On Market

  Current Estimated Value $501,505

  Last Listing Agent Allysa DeRosa Mapleridge Realty

  115 Marney Dr, Middlebury, CT 06762
• 

  $479,000 Sold May 21, 2025

  835 Whittemore Rd, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,016 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Below List Price
  • $159/SF
  • 60 Days On Market

  Current Estimated Value $514,667

  Last Listing Agent Mike Albert RE/MAX RISE

  835 Whittemore Rd, Middlebury, CT 06762
• 

  $695,000 Sold Nov 21, 2025

  18 Winding Trail, Middlebury, CT 06762

  • 3 Beds
  • 5 Baths
  • 4,051 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $172/SF
  • 36 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  18 Winding Trail, Middlebury, CT 06762
• 

  $709,900 Sold Feb 27, 2026

  2 Deer Run Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $324/SF
  • 186 Days On Market

  Current Estimated Value $710,333

  Last Listing Agent Jodi Dawley Real Estate Two

  2 Deer Run Rd, Middlebury, CT 06762
• 

  $600,000 Sold Nov 14, 2025

  39 Independence Cir, Middlebury, CT 06762

  • 4 Beds
  • 4 Baths
  • 3,382 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Below List Price
  • $177/SF
  • 110 Days On Market

  Current Estimated Value $626,759

  Last Listing Agent Arben Belica William Raveis Real Estate

  39 Independence Cir, Middlebury, CT 06762
• 

  $238,700 Sold Nov 17, 2025

  3 Pommel Ln, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,136 Sq Ft
  • Built 1996

  Last Sold Summary

  • $210/SF
  • 10 Days On Market

  Current Estimated Value $244,468

  Last Listing Agent Heather Dever Showcase Realty, Inc.

  3 Pommel Ln, Middlebury, CT 06762
• 

  $690,000 Sold Aug 01, 2025

  190 Bronson Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $242/SF
  • 54 Days On Market

  Current Estimated Value $699,623

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  190 Bronson Dr, Middlebury, CT 06762
• 

  $679,000 Sold Aug 21, 2025

  100 Fairhaven Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,988 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $227/SF
  • 28 Days On Market

  Current Estimated Value $684,683

  Last Listing Agent Tom Dorso Mapleridge Realty

  100 Fairhaven Dr, Middlebury, CT 06762
• 

  $800,000 Sold Mar 26, 2025

  23 Hunting Ridge Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2023

  Last Sold Summary

  • $296/SF
  • 350 Days On Market

  Current Estimated Value $842,345

  Last Listing Agent Jodi Dawley Real Estate Two

  23 Hunting Ridge Rd, Middlebury, CT 06762
• 

  $200,000 Sold Nov 20, 2025

  1070 Long Meadow Rd, Middlebury, CT 06762

  • Land
  • 4.56 Acres
  • $43,860 per Acre

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Alana Wall-Galvin Suburban Homes & Condos

  1070 Long Meadow Rd, Middlebury, CT 06762
• 

  $610,000 Sold Jul 09, 2025

  116 Bronson Dr, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 2,262 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $270/SF
  • 85 Days On Market

  Current Estimated Value $624,087

  Last Listing Agent Tracie Mormile Paiva Higgins Group Real Estate

  116 Bronson Dr, Middlebury, CT 06762
• 

  $370,000 Sold Jun 10, 2025

  259 White Ave, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1942

  Last Sold Summary

  • 6% Above List Price
  • $352/SF
  • 44 Days On Market

  Current Estimated Value $375,586

  Last Listing Agent Libby Tritschler William Raveis Real Estate

  259 White Ave, Middlebury, CT 06762
• 

  $670,000 Sold Jun 18, 2025

  15 Brookside Dr Unit 15, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,308 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $203/SF
  • 50 Days On Market

  Last Listing Agent Ostap Lisowitch Lisowitch Real Estate Group LLC

  15 Brookside Dr Unit 15, Middlebury, CT 06762
• 

  $640,000 Sold Apr 17, 2025

  10 Stonington Ct, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,812 Sq Ft
  • Built 2005

  Last Sold Summary

  • 8% Below List Price
  • $228/SF
  • 209 Days On Market

  Current Estimated Value $666,446

  Last Listing Agent Scott Hellriegel Berkshire Hathaway NE Prop.

  10 Stonington Ct, Middlebury, CT 06762
• 

  $591,251 Sold Aug 15, 2025

  0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,923 Sq Ft
  • Built 2025

  Last Sold Summary

  • $202/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762
• 

  $449,900 Sold Nov 19, 2025

  190 Allerton Farms Rd, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 1,744 Sq Ft
  • Built 1969

  Last Sold Summary

  • 17% Below List Price
  • $258/SF
  • 162 Days On Market

  Current Estimated Value $446,983

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  190 Allerton Farms Rd, Middlebury, CT 06762
• 

  $540,000 Sold Jul 18, 2025

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,122 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $254/SF
  • 72 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762
• 

  $310,000 Sold Feb 23, 2026

  587 Shadduck Rd, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,157 Sq Ft
  • Built 1936

  Last Sold Summary

  • 20% Below List Price
  • $268/SF
  • 155 Days On Market

  Current Estimated Value $339,732

  Last Listing Agent Dave Jones Dave Jones Realty, LLC

  587 Shadduck Rd, Middlebury, CT 06762
• 

  $730,000 Sold Jul 30, 2025

  222 Crest Rd, Middlebury, CT 06762

  • 5 Beds
  • 2.5 Baths
  • 2,442 Sq Ft
  • Built 1941

  Last Sold Summary

  • 1% Below List Price
  • $299/SF
  • 51 Days On Market

  Current Estimated Value $736,135

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  222 Crest Rd, Middlebury, CT 06762
• 

  $669,900 Sold Nov 12, 2025

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762

  • 3 Beds
  • 4 Baths
  • 3,488 Sq Ft
  • Built 2005

  Last Sold Summary

  • $192/SF
  • 60 Days On Market

  Current Estimated Value $698,401

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762
• 

  $385,000 Sold Sep 29, 2025

  225 Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 1 Bath
  • 1,630 Sq Ft
  • Built 1900

  Last Sold Summary

  • 9% Below List Price
  • $236/SF
  • 73 Days On Market

  Current Estimated Value $401,540

  Last Listing Agent Adelia Santos William Pitt Sotheby's Int'l

  225 Whittemore Rd, Middlebury, CT 06762
• 

  $485,000 Sold Aug 20, 2025

  101 Shadduck Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 2,534 Sq Ft
  • Built 1935

  Last Sold Summary

  • 4% Above List Price
  • $191/SF
  • 24 Days On Market

  Current Estimated Value $485,773

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  101 Shadduck Rd, Middlebury, CT 06762
• 

  $699,900 Sold Mar 03, 2026

  14 Deer Run Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,877 Sq Ft
  • Built 2025

  Last Sold Summary

  • $373/SF
  • 147 Days On Market

  Current Estimated Value $683,000

  Last Listing Agent Jodi Dawley Real Estate Two

  14 Deer Run Rd, Middlebury, CT 06762
• 

  $410,000 Sold Mar 28, 2025

  197 White Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft
  • Built 1928

  Last Sold Summary

  • 3% Above List Price
  • $274/SF
  • 55 Days On Market

  Current Estimated Value $427,522

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  197 White Ave, Middlebury, CT 06762
• 

  $565,000 Sold Jan 02, 2026

  23 Caveson Ct Unit 23, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,547 Sq Ft
  • Built 1996

  Last Sold Summary

  • $222/SF
  • 4 Days On Market

  Current Estimated Value $554,580

  Last Listing Agent Arben Belica William Raveis Real Estate

  23 Caveson Ct Unit 23, Middlebury, CT 06762
• 

  $385,000 Sold May 16, 2025

  66 White Ave, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 2,568 Sq Ft
  • Built 1938

  Last Sold Summary

  • 2% Above List Price
  • $150/SF
  • 139 Days On Market

  Current Estimated Value $401,545

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  66 White Ave, Middlebury, CT 06762
• 

  $625,000 Sold May 15, 2025

  129 Periwinkle Dr, Middlebury, CT 06762

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

  Last Sold Summary

  • 4% Below List Price
  • $252/SF
  • 45 Days On Market

  Current Estimated Value $631,440

  Last Listing Agent Lisa Gallagher William Raveis Real Estate

  129 Periwinkle Dr, Middlebury, CT 06762
• 

  $461,500 Sold Apr 30, 2025

  130 Christian Rd, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 1,958 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Above List Price
  • $236/SF
  • 139 Days On Market

  Current Estimated Value $487,563

  Last Listing Agent Joseph Conforti West View Properties, LLC

  130 Christian Rd, Middlebury, CT 06762
• 

  $505,000 Sold Jul 30, 2025

  1440 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $247/SF
  • 3 Days On Market

  Current Estimated Value $510,753

  Last Listing Agent Linda Mayfield RE/MAX RISE

  1440 Straits Turnpike, Middlebury, CT 06762
• 

  $461,000 Sold Feb 11, 2026

  11 Upper Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1957

  Last Sold Summary

  • $412/SF
  • 80 Days On Market

  Current Estimated Value $430,184

  Last Listing Agent Islam Ahmad Real Broker CT, LLC

  11 Upper Whittemore Rd, Middlebury, CT 06762
• 

  $515,000 Sold Jul 24, 2025

  17 Highridge Rd Unit 17, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,882 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $274/SF
  • 61 Days On Market

  Last Listing Agent Kayla O'Grady William Raveis Real Estate

  17 Highridge Rd Unit 17, Middlebury, CT 06762
• 

  $680,000 Sold Jun 11, 2025

  25 Michael Ln, Naugatuck, CT 06770

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $238/SF
  • 11 Days On Market

  Current Estimated Value $683,074

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  25 Michael Ln, Naugatuck, CT 06770
• 

  $360,000 Sold Jul 25, 2025

  173 Krodel Rd, Naugatuck, CT 06770

  • 3 Beds
  • 1 Bath
  • 1,318 Sq Ft
  • Built 1954

  Last Sold Summary

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

  Current Estimated Value $376,197

  Last Listing Agent Tanya Silva YellowBrick Real Estate LLC

  173 Krodel Rd, Naugatuck, CT 06770
• 

  $495,000 Sold Dec 22, 2025

  604 Lakeside Blvd W, Waterbury, CT 06708

  • 3 Beds
  • 3 Baths
  • 2,088 Sq Ft
  • Built 1967

  Last Sold Summary

  • $237/SF
  • 34 Days On Market

  Current Estimated Value $491,903

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  604 Lakeside Blvd W, Waterbury, CT 06708

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