Recently Sold Middlebury, CT Homes

• 

  $520,000 Sold Aug 13, 2025

  1 Stevens Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1937

  Last Sold Summary

  • 9% Below List Price
  • $231/SF
  • 70 Days On Market

  Current Estimated Value $517,027

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  1 Stevens Rd, Middlebury, CT 06762
• 

  $495,000 Sold Dec 22, 2025

  182 Bayberry Terrace, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 2,302 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 34 Days On Market

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  182 Bayberry Terrace, Middlebury, CT 06762
• 

  $541,566 Sold Oct 06, 2025

  0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,206 Sq Ft
  • Built 2025

  Last Sold Summary

  • $245/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762
• 

  $425,000 Sold Jul 25, 2025

  1 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 1935

  Last Sold Summary

  • 12% Below List Price
  • $238/SF
  • 40 Days On Market

  Current Estimated Value $435,839

  Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l

  1 Yale Ave, Middlebury, CT 06762
• 

  $595,000 Sold Jun 04, 2025

  7 Highridge Rd Unit 7, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2017

  Last Sold Summary

  • 1% Above List Price
  • $229/SF
  • 93 Days On Market

  Last Listing Agent Tracy Ropa-Lucifora William Raveis Real Estate

  7 Highridge Rd Unit 7, Middlebury, CT 06762
• 

  $740,000 Sold Aug 06, 2025

  17 Deer Run Rd, Middlebury, CT 06762

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

  Last Sold Summary

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

  Current Estimated Value $747,788

  Last Listing Agent Jodi Dawley Real Estate Two

  17 Deer Run Rd, Middlebury, CT 06762
• 

  $620,000 Sold Mar 21, 2025

  115 Periwinkle Dr Unit 115, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 3,276 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Below List Price
  • $189/SF
  • 108 Days On Market

  Current Estimated Value $648,216

  Last Listing Agent Lawren Hubal RE/MAX Right Choice

  115 Periwinkle Dr Unit 115, Middlebury, CT 06762
• 

  $620,000 Sold Jul 30, 2025

  1 Chatham Ct, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,950 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Below List Price
  • $210/SF
  • 45 Days On Market

  Current Estimated Value $667,008

  Last Listing Agent Norinne Byrne Calcagni Real Estate

  1 Chatham Ct, Middlebury, CT 06762
• 

  $536,000 Sold Aug 28, 2025

  76 Three Mile Hill Rd, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 2,088 Sq Ft
  • Built 1954

  Last Sold Summary

  • 15% Below List Price
  • $257/SF
  • 104 Days On Market

  Current Estimated Value $531,975

  Last Listing Agent Lisa Clarke Dave Jones Realty, LLC

  76 Three Mile Hill Rd, Middlebury, CT 06762
• 

  $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

  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

  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

  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 $845,808

  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 $494,676

  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 $509,121

  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
• 

  $390,000 Sold Mar 10, 2025

  10 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft
  • Built 1925

  Last Sold Summary

  • 1% Above List Price
  • $238/SF
  • 40 Days On Market

  Current Estimated Value $407,400

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  10 Yale Ave, 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

  Last Listing Agent Arben Belica William Raveis Real Estate

  39 Independence Cir, Middlebury, CT 06762
• 

  $375,000 Sold Feb 21, 2025

  91 Richardson Dr, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,788 Sq Ft
  • Built 1975

  Last Sold Summary

  • 6% Below List Price
  • $210/SF
  • 69 Days On Market

  Current Estimated Value $385,857

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  91 Richardson Dr, 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

  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 $690,628

  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 $680,623

  Last Listing Agent Tom Dorso Mapleridge Realty

  100 Fairhaven Dr, Middlebury, CT 06762
• 

  $375,000 Sold Feb 13, 2025

  1738 Middlebury Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,225 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Below List Price
  • $169/SF
  • 32 Days On Market

  Current Estimated Value $455,832

  Last Listing Agent April Stirling Coldwell Banker Realty

  1738 Middlebury Rd, Middlebury, CT 06762
• 

  $515,000 Sold Feb 21, 2025

  1053 Middlebury Rd, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 2,373 Sq Ft
  • Built 1971

  Last Sold Summary

  • 6% Below List Price
  • $217/SF
  • 146 Days On Market

  Current Estimated Value $544,318

  Last Listing Agent Barbara Sivba Coldwell Banker Realty

  1053 Middlebury Rd, 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 $832,621

  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 $611,045

  Last Listing Agent Tracie Mormile Paiva Higgins Group Real Estate

  116 Bronson Dr, Middlebury, CT 06762
• 

  $830,000 Sold Mar 07, 2025

  340 Burr Hall Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,197 Sq Ft
  • Built 2012

  Last Sold Summary

  • $260/SF
  • 45 Days On Market

  Current Estimated Value $874,441

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  340 Burr Hall Rd, 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 $372,260

  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
• 

  $710,000 Sold Mar 07, 2025

  409 Chestnut Cir Unit 79, Middlebury, CT 06762

  • 2 Beds
  • 3 Baths
  • 2,292 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $310/SF
  • 17 Days On Market

  Current Estimated Value $703,228

  Last Listing Agent Jodi Dawley Real Estate Two

  409 Chestnut Cir Unit 79, 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 $673,971

  Last Listing Agent Scott Hellriegel Berkshire Hathaway NE Prop.

  10 Stonington Ct, 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
• 

  $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

  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
• 

  $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 $728,250

  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

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762

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