Middlebury, CT Homes

• 

  $409,000 Sold Nov 25, 2025

  115 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $273/SF
  • 39 Days On Market

  Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

  115 Porter Ave, Middlebury, CT 06762
• 

  Est $928,906 Not Listed For Sale

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

  98 Leonard Rd, Middlebury, CT 06762

  98 Leonard Rd, Middlebury, CT 06762
• 

  $570,000 Sold Feb 28, 2025

  428 Benson Rd, Middlebury, CT 06762

  • 5 Beds
  • 4 Baths
  • 3,106 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Above List Price
  • $184/SF
  • 55 Days On Market

  Current Estimated Value $619,039

  Last Listing Agent Jason Malagutti Regency Real Estate, LLC

  428 Benson Rd, Middlebury, CT 06762
• 

  Est $439,513 Not Listed For Sale

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

  615 Long Meadow Rd, Middlebury, CT 06762

  615 Long Meadow Rd, Middlebury, CT 06762
• 

  $460,000 Sold Aug 15, 2025

  74 Joy Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Above List Price
  • $250/SF
  • 16 Days On Market

  Current Estimated Value $461,941

  Last Listing Agent Tom Dorso Mapleridge Realty

  74 Joy Rd, Middlebury, CT 06762
• 

  Est $360,504 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,053 Sq Ft

  22 Yale Ave, Middlebury, CT 06762

  22 Yale Ave, Middlebury, CT 06762
• 

  $465,000 Sold Oct 03, 2025

  1996 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,768 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $263/SF
  • 47 Days On Market

  Current Estimated Value $466,049

  Last Listing Agent Devon O'Neill Litchfield Hills Properties LLC

  1996 Straits Turnpike, Middlebury, CT 06762
• 

  Est $619,574 Not Listed For Sale

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

  450 Long Meadow Rd, Middlebury, CT 06762

  450 Long Meadow Rd, Middlebury, CT 06762
• 

  $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
• 

  Est $739,173 Not Listed For Sale

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

  15 Chatham Ct, Middlebury, CT 06762

  15 Chatham Ct, 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
• 

  Est $695,709 Not Listed For Sale

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

  6 Colonial Ct, Middlebury, CT 06762

  6 Colonial Ct, 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
• 

  Est $671,592 Not Listed For Sale

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

  3 Independence Cir, Middlebury, CT 06762

  3 Independence Cir, 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
• 

  Est $753,871 Not Listed For Sale

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

  13 Independence Cir, Middlebury, CT 06762

  13 Independence Cir, 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
• 

  Est $662,796 Not Listed For Sale

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

  28 Independence Cir, Middlebury, CT 06762

  28 Independence Cir, 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
• 

  Est $762,233 Not Listed For Sale

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

  37 Independence Cir, Middlebury, CT 06762

  37 Independence Cir, 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
• 

  Est $696,730 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,636 Sq Ft

  27 Independence Cir, Middlebury, CT 06762

  27 Independence Cir, 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
• 

  Est $733,751 Not Listed For Sale

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

  28 Brookside Dr, Middlebury, CT 06762

  28 Brookside Dr, 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
• 

  Est $823,919 Not Listed For Sale

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

  290 Christian Rd, Middlebury, CT 06762

  290 Christian 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
• 

  Est $845,859 Not Listed For Sale

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

  16 Somerset Dr, Middlebury, CT 06762

  16 Somerset Dr, 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
• 

  Est $809,748 Not Listed For Sale

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

  25 Avalon Dr, Middlebury, CT 06762

  25 Avalon Dr, 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
• 

  Est $639,118 Not Listed For Sale

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

  107 Periwinkle Dr, Middlebury, CT 06762

  107 Periwinkle Dr, 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
• 

  Est $645,709 Not Listed For Sale

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

  103 Periwinkle Dr, Middlebury, CT 06762

  103 Periwinkle Dr, 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
• 

  Est $334,335 Not Listed For Sale

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

  406 Benson Rd, Middlebury, CT 06762

  406 Benson Rd, 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
• 

  Est $437,452 Not Listed For Sale

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

  267 White Ave, Middlebury, CT 06762

  267 White Ave, 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
• 

  Est $498,396 Not Listed For Sale

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

  159 Acme Dr, Middlebury, CT 06762

  159 Acme Dr, Middlebury, CT 06762

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