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 $513,964

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  1 Stevens Rd, Middlebury, CT 06762
• 

  Est $917,012 Not Listed For Sale

  98 Leonard Rd, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,357 Sq Ft
  • Built 1941

  98 Leonard Rd, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $253/SF
  • 293 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.
• 

  $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

  Current Estimated Value $500,923

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  182 Bayberry Terrace, Middlebury, CT 06762
• 

  Est $443,400 Not Listed For Sale

  615 Long Meadow Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • Built 1980

  615 Long Meadow Rd, Middlebury, CT 06762

  Last Sold Summary

  • 4% Above List Price
  • $375/SF
  • 1 Day On Market

  Last Sold Price $425,000

  Last Listing Agent George Noujaim Dave Jones Realty, LLC
• 

  $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
• 

  Est $370,158 Not Listed For Sale

  22 Yale Ave, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Built 1926

  22 Yale Ave, Middlebury, CT 06762

  Last Sold Summary

  • $351/SF
  • 49 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
• 

  $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 $436,379

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

  1 Yale Ave, Middlebury, CT 06762
• 

  Est $619,574 Not Listed For Sale

  450 Long Meadow Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,450 Sq Ft
  • Built 2002

  450 Long Meadow Rd, Middlebury, CT 06762

  Last Sold Summary

  • 15% Above List Price
  • $157/SF
  • 107 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
• 

  $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
• 

  Est $724,363 Not Listed For Sale

  15 Chatham Ct, Middlebury, CT 06762

  • 4 Beds
  • 4 Baths
  • 4,450 Sq Ft
  • Built 2005

  15 Chatham Ct, Middlebury, CT 06762

  Last Sold Summary

  • 1% Above List Price
  • $162/SF
  • 3 Days On Market

  Last Sold Price $720,000

  Last Listing Agent Pat Blanko William Raveis Real Estate
• 

  $895,000 Sold Feb 11, 2026

  383 Leonard Rd, Middlebury, CT 06762

  • 4 Beds
  • 4.5 Baths
  • 3,220 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $278/SF
  • 81 Days On Market

  Last Listing Agent Koco Pela William Raveis Real Estate

  383 Leonard Rd, Middlebury, CT 06762
• 

  Est $681,364 Not Listed For Sale

  6 Colonial Ct, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,950 Sq Ft
  • Built 2004

  6 Colonial Ct, Middlebury, CT 06762

  Last Sold Summary

  • 5% Above List Price
  • $220/SF
  • 49 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Norinne Byrne Calcagni Real Estate
• 

  $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 $742,526

  Last Listing Agent Jodi Dawley Real Estate Two

  17 Deer Run Rd, Middlebury, CT 06762
• 

  Est $669,799 Not Listed For Sale

  3 Independence Cir, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,882 Sq Ft
  • Built 2005

  3 Independence Cir, Middlebury, CT 06762

  Last Sold Summary

  • 14% Above List Price
  • $203/SF
  • 23 Days On Market

  Last Sold Price $585,000

  Last Listing Agent Kristen Stolfi Berkshire Hathaway Home Services
• 

  $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 $642,310

  Last Listing Agent Lawren Hubal RE/MAX Right Choice

  115 Periwinkle Dr Unit 115, Middlebury, CT 06762
• 

  Est $757,401 Not Listed For Sale

  13 Independence Cir, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,600 Sq Ft
  • Built 2005

  13 Independence Cir, Middlebury, CT 06762

  Last Sold Summary

  • 11% Above List Price
  • $190/SF
  • 79 Days On Market

  Last Sold Price $685,000

  Last Listing Agent David Hughes Century 21 AllPoints Realty
• 

  $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 $657,488

  Last Listing Agent Norinne Byrne Calcagni Real Estate

  1 Chatham Ct, Middlebury, CT 06762
• 

  Est $662,073 Not Listed For Sale

  28 Independence Cir, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,882 Sq Ft
  • Built 2005

  28 Independence Cir, Middlebury, CT 06762

  Last Sold Summary

  • 17% Above List Price
  • $196/SF
  • 65 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Dawn Cabral West View Properties, LLC
• 

  $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 $529,794

  Last Listing Agent Lisa Clarke Dave Jones Realty, LLC

  76 Three Mile Hill Rd, Middlebury, CT 06762
• 

  Est $761,980 Not Listed For Sale

  37 Independence Cir, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 4,331 Sq Ft
  • Built 2004

  37 Independence Cir, Middlebury, CT 06762

  Last Sold Summary

  • 4% Above List Price
  • $170/SF
  • 2 Days On Market

  Last Sold Price $735,000

  Last Listing Agent Adele Unger William Pitt
• 

  $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 $807,786

  Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

  1 Hampshire Ct, Middlebury, CT 06762
• 

  Est $739,897 Not Listed For Sale

  28 Brookside Dr, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,512 Sq Ft
  • Built 2005

  28 Brookside Dr, Middlebury, CT 06762

  Last Sold Summary

  • 12% Above List Price
  • $188/SF
  • 127 Days On Market

  Last Sold Price $660,000

  Last Listing Agent Heather Crabtree RE/MAX RISE
• 

  $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 $622,793

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  51 Cross Rd, Middlebury, CT 06762
• 

  Est $807,550 Not Listed For Sale

  290 Christian Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,086 Sq Ft
  • Built 2006

  290 Christian Rd, Middlebury, CT 06762

  Last Sold Summary

  • 16% Above List Price
  • $227/SF
  • 105 Days On Market

  Last Sold Price $699,000

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate
• 

  $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 $806,328

  Last Listing Agent Jodi Dawley Real Estate Two

  11 Hunting Ridge Rd, Middlebury, CT 06762
• 

  Est $823,126 Not Listed For Sale

  16 Somerset Dr, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 3,377 Sq Ft
  • Built 2006

  16 Somerset Dr, Middlebury, CT 06762

  Last Sold Summary

  • 13% Above List Price
  • $216/SF
  • 182 Days On Market

  Last Sold Price $729,000

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes
• 

  $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
• 

  Est $817,066 Not Listed For Sale

  25 Avalon Dr, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 3,494 Sq Ft
  • Built 2002

  25 Avalon Dr, Middlebury, CT 06762

  Last Sold Summary

  • 7% Above List Price
  • $219/SF
  • 27 Days On Market

  Last Sold Price $765,000

  Last Listing Agent Angela Vassar Better Living Realty, LLC
• 

  $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 $871,451

  Last Listing Agent Arben Belica William Raveis Real Estate

  34 Breakneck Hill Rd, Middlebury, CT 06762
• 

  Est $632,182 Not Listed For Sale

  107 Periwinkle Dr, Middlebury, CT 06762

  • 3 Beds
  • 4 Baths
  • 3,676 Sq Ft
  • Built 2005

  107 Periwinkle Dr, Middlebury, CT 06762

  Last Sold Summary

  • 4% Above List Price
  • $166/SF
  • 52 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes
• 

  $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
• 

  Est $641,066 Not Listed For Sale

  103 Periwinkle Dr, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 2,940 Sq Ft
  • Built 2004

  103 Periwinkle Dr, Middlebury, CT 06762

  Last Sold Summary

  • 11% Above List Price
  • $196/SF
  • 106 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Jodi Dawley Real Estate Two
• 

  $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 $493,061

  Last Listing Agent Allysa DeRosa Mapleridge Realty

  115 Marney Dr, Middlebury, CT 06762
• 

  Est $341,208 Not Listed For Sale

  406 Benson Rd, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1959

  406 Benson Rd, Middlebury, CT 06762

  Last Sold Summary

  • 22% Above List Price
  • $212/SF
  • 25 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes
• 

  $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 $506,159

  Last Listing Agent Mike Albert RE/MAX RISE

  835 Whittemore Rd, Middlebury, CT 06762
• 

  Est $434,568 Not Listed For Sale

  267 White Ave, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 2,590 Sq Ft
  • Built 1942

  267 White Ave, Middlebury, CT 06762

  Last Sold Summary

  • 24% Above List Price
  • $135/SF
  • 79 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
• 

  $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
• 

  Est $496,650 Not Listed For Sale

  159 Acme Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,231 Sq Ft
  • Built 1963

  159 Acme Dr, Middlebury, CT 06762

  Last Sold Summary

  • 18% Above List Price
  • $188/SF
  • 54 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Aldo Mancini Showcase Realty, Inc.
• 

  $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 $407,181

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  10 Yale Ave, Middlebury, CT 06762
• 

  Est $608,815 Not Listed For Sale

  85 Bronson Dr, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,938 Sq Ft
  • Built 1962

  85 Bronson Dr, Middlebury, CT 06762

  Last Sold Summary

  • 15% Above List Price
  • $272/SF
  • 2 Days On Market

  Last Sold Price $527,500

  Last Listing Agent Daniel Schiavone BHGRE Gaetano Marra Homes

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