Middlebury, CT Homes

• 

  $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 $700,332

  Last Listing Agent Jodi Dawley Real Estate Two

  14 Deer Run Rd, Middlebury, CT 06762
• 

  Est $449,219

  Not Listed For Sale

  111 Ravenwood Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,234 Sq Ft
  • Built 1979

  111 Ravenwood Dr, Middlebury, CT 06762

  Last Sold Summary

  • 242 Days On Market
• 

  $599,900

  Sold May 01, 2026

  428 Breakneck Hill Rd, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,749 Sq Ft
  • Built 1948

  Last Sold Summary

  • $343/SF
  • 34 Days On Market

  Current Estimated Value $590,183

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  428 Breakneck Hill Rd, Middlebury, CT 06762
• 

  Est $495,716

  Not Listed For Sale

  713 Whittemore Rd, Middlebury, CT 06762

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

  713 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 2 Days On Market
• 

  $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 $544,697

  Last Listing Agent Arben Belica William Raveis Real Estate

  23 Caveson Ct Unit 23, Middlebury, CT 06762
• 

  Est $398,597

  Not Listed For Sale

  74 E Ridge Dr, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,275 Sq Ft
  • Built 1954

  74 E Ridge Dr, Middlebury, CT 06762

  Last Sold Summary

  • 123 Days On Market
• 

  $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 $499,435

  Last Listing Agent Linda Mayfield RE/MAX RISE

  1440 Straits Turnpike, Middlebury, CT 06762
• 

  Est $369,848

  Not Listed For Sale

  259 White Ave, Middlebury, CT 06762

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

  259 White Ave, Middlebury, CT 06762

  Last Sold Summary

  • 44 Days On Market
• 

  $500,000

  Sold Jun 18, 2026

  283 Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1972

  Last Sold Summary

  • 5% Below List Price
  • $200/SF
  • 36 Days On Market

  Current Estimated Value $500,818

  Last Listing Agent Jennifer Sisco RE/MAX Heritage

  283 Whittemore Rd, Middlebury, CT 06762
• 

  Est $659,018

  Not Listed For Sale

  706 Charcoal Ave, Middlebury, CT 06762

  • 5 Beds
  • 3 Baths
  • 3,508 Sq Ft
  • Built 1957

  706 Charcoal Ave, Middlebury, CT 06762

  Last Sold Summary

  • 39 Days On Market
• 

  $510,000

  Sold Jun 26, 2026

  80 Anawan Ave, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,962 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Below List Price
  • $260/SF
  • 29 Days On Market

  Current Estimated Value $528,192

  Last Listing Agent Drew Slack ERA Insite Realty Services

  80 Anawan Ave, Middlebury, CT 06762
• 

  Est $606,310

  Not Listed For Sale

  660 Whittemore Rd, Middlebury, CT 06762

  • 6 Beds
  • 4 Baths
  • 4,426 Sq Ft
  • Built 1955

  660 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 219 Days On Market
• 

  $510,000

  Sold May 22, 2026

  38 E Ridge Dr, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1970

  Last Sold Summary

  • $287/SF
  • 5 Days On Market

  Current Estimated Value $505,294

  Last Listing Agent Paula Basso Evjen Agency

  38 E Ridge Dr, Middlebury, CT 06762
• 

  Est $693,989

  Not Listed For Sale

  570 Park Road Extension, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 3,356 Sq Ft
  • Built 1979

  570 Park Road Extension, Middlebury, CT 06762

  Last Sold Summary

  • 104 Days On Market
• 

  $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 $458,025

  Last Listing Agent Islam Ahmad Real Broker CT, LLC

  11 Upper Whittemore Rd, Middlebury, CT 06762
• 

  Est $320,641

  Not Listed For Sale

  129 Glenwood Ave, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft
  • Built 1930

  129 Glenwood Ave, Middlebury, CT 06762

  Last Sold Summary

  • 39 Days On Market
• 

  $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
• 

  Est $213,761

  Not Listed For Sale

  625 Straits Turnpike, Middlebury, CT 06762

  • 2 Beds
  • Built 1936

  625 Straits Turnpike, Middlebury, CT 06762

  Last Sold Summary

  • 167 Days On Market
• 

  Est $607,155

  Not Listed For Sale

  428 Benson Rd, Middlebury, CT 06762

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

  428 Benson Rd, Middlebury, CT 06762

  Last Sold Summary

  • 55 Days On Market
• 

  Est $485,962

  Not Listed For Sale

  36 Aveline Ave, Middlebury, CT 06762

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

  36 Aveline Ave, Middlebury, CT 06762

  Last Sold Summary

  • 44 Days On Market
• 

  Est $593,455

  Not Listed For Sale

  95 Woodland Rd, Middlebury, CT 06762

  • 5 Beds
  • 3 Baths
  • 3,608 Sq Ft
  • Built 1952

  95 Woodland Rd, Middlebury, CT 06762

  Last Sold Summary

  • 28 Days On Market
• 

  Est $499,626

  Not Listed For Sale

  47 White Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,652 Sq Ft
  • Built 1972

  47 White Ave, Middlebury, CT 06762

  Last Sold Summary

  • 52 Days On Market
• 

  Est $445,283

  Not Listed For Sale

  48 Steinmann Ave, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • Built 1930

  48 Steinmann Ave, Middlebury, CT 06762

  Last Sold Summary

  • 34 Days On Market
• 

  Est $457,278

  Not Listed For Sale

  24 Steinmann Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,378 Sq Ft
  • Built 1940

  24 Steinmann Ave, Middlebury, CT 06762

  Last Sold Summary

  • 31 Days On Market
• 

  Est $438,724

  Not Listed For Sale

  43 Christian Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft
  • Built 1900

  43 Christian Rd, Middlebury, CT 06762

  Last Sold Summary

  • 114 Days On Market
• 

  Est $504,857

  Not Listed For Sale

  679 Christian Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Built 1967

  679 Christian Rd, Middlebury, CT 06762

  Last Sold Summary

  • 47 Days On Market
• 

  Est $515,111

  Not Listed For Sale

  71 Acme Dr, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,630 Sq Ft
  • Built 1947

  71 Acme Dr, Middlebury, CT 06762

  Last Sold Summary

  • 5 Days On Market
• 

  Est $622,781

  Not Listed For Sale

  117 Bronson Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft
  • Built 1952

  117 Bronson Dr, Middlebury, CT 06762

  Last Sold Summary

  • 50 Days On Market
• 

  Est $644,836

  Not Listed For Sale

  40 Dorothy Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,768 Sq Ft
  • Built 1997

  40 Dorothy Dr, Middlebury, CT 06762

  Last Sold Summary

  • 24 Days On Market
• 

  Est $939,569

  Not Listed For Sale

  275 Burr Hall Rd, Middlebury, CT 06762

  • 4 Beds
  • 5 Baths
  • 4,704 Sq Ft
  • Built 2002

  275 Burr Hall Rd, Middlebury, CT 06762

  Last Sold Summary

  • 106 Days On Market
• 

  Est $340,459

  Not Listed For Sale

  26 Fenn Rd, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1947

  26 Fenn Rd, Middlebury, CT 06762

  Last Sold Summary

  • 3 Days On Market
• 

  Est $1,021,297

  Not Listed For Sale

  17 Beacon Hill Rd, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 4,434 Sq Ft
  • Built 1977

  17 Beacon Hill Rd, Middlebury, CT 06762

  Last Sold Summary

  • 174 Days On Market
• 

  Est $443,334

  Not Listed For Sale

  192 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1984

  192 Porter Ave, Middlebury, CT 06762

  Last Sold Summary

  • 47 Days On Market
• 

  Est $533,510

  Not Listed For Sale

  110 Glenwood Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft
  • Built 2006

  110 Glenwood Ave, Middlebury, CT 06762

  Last Sold Summary

  • 33 Days On Market
• 

  Est $920,460

  Not Listed For Sale

  249 South St, Middlebury, CT 06762

  • 6 Beds
  • 3.5 Baths
  • 5,047 Sq Ft
  • Built 1815

  249 South St, Middlebury, CT 06762

  Last Sold Summary

  • 14 Days On Market
• 

  Est $364,855

  Not Listed For Sale

  28 Yale Ave, Middlebury, CT 06762

  • 1 Bed
  • 2 Baths
  • 1,434 Sq Ft
  • Built 1923

  28 Yale Ave, Middlebury, CT 06762

  Last Sold Summary

  • 6 Days On Market
• 

  Est $607,521

  Not Listed For Sale

  25 Carriage Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft
  • Built 1966

  25 Carriage Dr, Middlebury, CT 06762

  Last Sold Summary

  • 47 Days On Market
• 

  Est $456,160

  Not Listed For Sale

  1418 Straits Turnpike, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 3,371 Sq Ft
  • Built 1957

  1418 Straits Turnpike, Middlebury, CT 06762

  Last Sold Summary

  • 49 Days On Market
• 

  Est $632,707

  Not Listed For Sale

  563 Southford Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,663 Sq Ft
  • Built 1996

  563 Southford Rd, Middlebury, CT 06762

  Last Sold Summary

  • 12 Days On Market
• 

  Est $469,542

  Not Listed For Sale

  67 Algin Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 1965

  67 Algin Dr, Middlebury, CT 06762

  Last Sold Summary

  • 80 Days On Market

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