122

Recently Sold Middlebury, CT Homes

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  • 51 Cross Rd, 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 $647,892

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    51 Cross Rd, Middlebury, CT 06762
  • 11 Hunting Ridge 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 $826,137

    Last Listing Agent Jodi Dawley Real Estate Two

    11 Hunting Ridge Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 38 24064329, 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 Lovley Century 21 AllPoints Realty

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

    $435,000

    Sold May 20, 2026

    271 Shadduck Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,288 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Above List Price
    • $338/SF
    • 28 Days On Market

    Current Estimated Value $434,801

    Last Listing Agent Stephen Mele Houlihan Lawrence

    271 Shadduck Rd, Middlebury, CT 06762
  • 84 Munson Rd, Middlebury, CT 06762

    $675,000

    Sold Jun 08, 2026

    84 Munson Rd, Middlebury, CT 06762

    • 4 Beds
    • 5 Baths
    • 3,254 Sq Ft
    • Built 1979

    Last Sold Summary

    • 5% Below List Price
    • $207/SF
    • 59 Days On Market

    Current Estimated Value $696,659

    Last Listing Agent Adam Devine Dorrance Realty

    84 Munson Rd, Middlebury, CT 06762
  • 117 Crest Rd, Middlebury, CT 06762

    $735,000

    Sold Sep 14, 2026

    117 Crest Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,753 Sq Ft
    • Built 1959

    Last Sold Summary

    • 3% Below List Price
    • $267/SF
    • 252 Days On Market

    Current Estimated Value $779,492

    Last Listing Agent Lori Geraci BHGRE Gaetano Marra Homes

    117 Crest Rd, Middlebury, CT 06762
  • 366 Charcoal Ave, Middlebury, CT 06762

    $750,000

    Sold May 27, 2026

    366 Charcoal Ave, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,198 Sq Ft
    • Built 1998

    Last Sold Summary

    • $235/SF
    • 23 Days On Market

    Current Estimated Value $757,440

    Last Listing Agent Stephen Briotti Lamacchia Realty

    366 Charcoal Ave, Middlebury, CT 06762
  • 18 Winding Trail, 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
  • 2 Deer Run Rd, 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 $723,513

    Last Listing Agent Jodi Dawley Real Estate Two

    2 Deer Run Rd, Middlebury, CT 06762
  • 39 Independence Cir, 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 $627,529

    Last Listing Agent Arben Belica William Raveis Real Estate

    39 Independence Cir, Middlebury, CT 06762
  • 3 Pommel Ln, 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 $246,014

    Last Listing Agent Heather Dever Showcase Realty, Inc.

    3 Pommel Ln, Middlebury, CT 06762
  • 1070 Long Meadow 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
  • 1 Independence Cir, Middlebury, CT 06762

    $630,000

    Sold Jul 07, 2026

    1 Independence Cir, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,224 Sq Ft
    • Built 2005

    Last Sold Summary

    • 3% Above List Price
    • $195/SF
    • 47 Days On Market

    Current Estimated Value $622,376

    Last Listing Agent Christine Aquila Coldwell Banker Realty

    1 Independence Cir, Middlebury, CT 06762
  • 301 Steinmann Ave, Middlebury, CT 06762

    $400,000

    Sold Jul 06, 2026

    301 Steinmann Ave, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,572 Sq Ft
    • Built 1954

    Last Sold Summary

    • 7% Below List Price
    • $254/SF
    • 66 Days On Market

    Current Estimated Value $400,212

    Last Listing Agent Dawn Ciappetta Coldwell Banker Realty

    301 Steinmann Ave, Middlebury, CT 06762
  • 72 Ridgewood Dr Unit 72, Middlebury, CT 06762

    $569,900

    Sold Jul 29, 2026

    72 Ridgewood Dr Unit 72, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,428 Sq Ft
    • Built 2016

    Last Sold Summary

    • $235/SF
    • 53 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    72 Ridgewood Dr Unit 72, Middlebury, CT 06762
  • 3 Hunting Ridge Rd, Middlebury, CT 06762

    $620,000

    Sold Mar 30, 2026

    3 Hunting Ridge Rd, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,722 Sq Ft
    • Built 2023

    Last Sold Summary

    • 2% Below List Price
    • $360/SF
    • 29 Days On Market

    Current Estimated Value $620,697

    Last Listing Agent Jodi Dawley Real Estate Two

    3 Hunting Ridge Rd, Middlebury, CT 06762
  • 35 Nutmeg Rd Unit D1, Middlebury, CT 06762

    $222,500

    Sold Apr 29, 2026

    35 Nutmeg Rd Unit D1, Middlebury, CT 06762

    • 1 Bed
    • 1 Bath
    • 889 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $250/SF
    • 93 Days On Market

    Current Estimated Value $219,514

    Last Listing Agent Karen Stanco Showcase Realty, Inc.

    35 Nutmeg Rd Unit D1, Middlebury, CT 06762
  • 190 Allerton Farms Rd, 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 $454,568

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    190 Allerton Farms Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 49 24096137, Middlebury, CT 06762

    $555,423

    Sold Sep 16, 2026

    0 N Benson Rd Unit 49 24096137, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2026

    Last Sold Summary

    • 4% Above List Price
    • $285/SF
    • 1 Day On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 49 24096137, Middlebury, CT 06762
  • 314 Porter Ave, Middlebury, CT 06762

    $300,000

    Sold May 29, 2026

    314 Porter Ave, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1941

    Last Sold Summary

    • 14% Below List Price
    • $208/SF
    • 56 Days On Market

    Current Estimated Value $316,931

    Last Listing Agent Dawn Ciappetta Coldwell Banker Realty

    314 Porter Ave, Middlebury, CT 06762
  • 587 Shadduck Rd, 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 $330,529

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    587 Shadduck Rd, Middlebury, CT 06762
  • 413 Watertown Rd, Middlebury, CT 06762

    $485,000

    Sold Aug 14, 2026

    413 Watertown Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,251 Sq Ft
    • Built 1932

    Last Sold Summary

    • $215/SF
    • 17 Days On Market

    Current Estimated Value $487,214

    Last Listing Agent Emily Fitzgerald William Raveis Real Estate

    413 Watertown Rd, Middlebury, CT 06762
  • 117 Periwinkle Dr Unit 117, 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 $672,101

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    117 Periwinkle Dr Unit 117, Middlebury, CT 06762
  • 3 Winding Trail, Middlebury, CT 06762

    $559,900

    Sold Jul 16, 2026

    3 Winding Trail, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 3,179 Sq Ft
    • Built 2007

    Last Sold Summary

    • $176/SF
    • 48 Days On Market

    Current Estimated Value $558,097

    Last Listing Agent Mayra Perez Showcase Realty, Inc.

    3 Winding Trail, Middlebury, CT 06762
  • 225 Whittemore Rd, 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 $405,487

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

    225 Whittemore Rd, Middlebury, CT 06762
  • 14 Deer Run 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 $708,195

    Last Listing Agent Jodi Dawley Real Estate Two

    14 Deer Run Rd, Middlebury, CT 06762
  • 428 Breakneck Hill Rd, Middlebury, CT 06762

    $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 $590,909

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    428 Breakneck Hill Rd, Middlebury, CT 06762
  • 23 Caveson Ct Unit 23, 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 $561,602

    Last Listing Agent Arben Belica William Raveis Real Estate

    23 Caveson Ct Unit 23, Middlebury, CT 06762
  • 283 Whittemore Rd, Middlebury, CT 06762

    $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 $499,571

    Last Listing Agent Jennifer Sisco RE/MAX Heritage

    283 Whittemore Rd, Middlebury, CT 06762
  • 2 Arrowwood Ct Unit 2, Middlebury, CT 06762

    $575,000

    Sold Jul 10, 2026

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $255/SF
    • 75 Days On Market

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762
  • 818 Middlebury Rd, Middlebury, CT 06762

    $416,000

    Sold Jul 10, 2026

    818 Middlebury Rd, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 1,639 Sq Ft
    • Built 1939

    Last Sold Summary

    • 8% Above List Price
    • $254/SF
    • 44 Days On Market

    Current Estimated Value $408,647

    Last Listing Agent Brandy Hall Higgins Group Real Estate

    818 Middlebury Rd, Middlebury, CT 06762
  • 80 Anawan Ave, Middlebury, CT 06762

    $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 $512,004

    Last Listing Agent Drew Slack ERA Insite Realty Services

    80 Anawan Ave, Middlebury, CT 06762
  • /22

    $675,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,938 Sq Ft

    179 Burr Hall Rd, Middlebury, CT 06762

    This stunning ranch blends contemporary style with effortless one-level living. The open floor plan is filled with natural light, highlighted by dramatic floor-to-ceiling windows that create a bright and inviting atmosphere throughout. The beautifully updated interior features a luxurious primary suite and stylish, high-quality finishes at every turn. Designed for both everyday living and

    Lynn LaForme Regency Real Estate, LLC

    179 Burr Hall Rd, Middlebury, CT 06762
  • 541 Benson Rd, Middlebury, CT 06762

    $465,000

    Sold Jun 17, 2026

    541 Benson Rd, Middlebury, CT 06762

    • 3 Beds
    • 3 Baths
    • 1,600 Sq Ft
    • Built 1942

    Last Sold Summary

    • 11% Below List Price
    • $291/SF
    • 86 Days On Market

    Current Estimated Value $475,913

    Last Listing Agent Joseph Martino Joseph Martino Real Estate

    541 Benson Rd, Middlebury, CT 06762
  • 38 E Ridge Dr, Middlebury, CT 06762

    $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 $508,364

    Last Listing Agent Paula Basso Evjen Agency

    38 E Ridge Dr, Middlebury, CT 06762
  • 200 Northridge Dr, Middlebury, CT 06762

    $650,000

    Sold Aug 28, 2026

    200 Northridge Dr, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,360 Sq Ft
    • Built 1984

    Last Sold Summary

    • $275/SF
    • 40 Days On Market

    Current Estimated Value $659,169

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    200 Northridge Dr, Middlebury, CT 06762
  • 11 Upper Whittemore Rd, 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 $445,573

    Last Listing Agent Islam Ahmad Real Broker CT, LLC

    11 Upper Whittemore Rd, Middlebury, CT 06762
  • 622 Lakeside Blvd W, Waterbury, CT 06708

    $500,000

    Sold May 21, 2026

    622 Lakeside Blvd W, Waterbury, CT 06708

    • 3 Beds
    • 2.5 Baths
    • 2,208 Sq Ft
    • Built 1980

    Last Sold Summary

    • $226/SF
    • 4 Days On Market

    Current Estimated Value $502,966

    Last Listing Agent David Aurigemma Regency Real Estate, LLC

    622 Lakeside Blvd W, Waterbury, CT 06708
  • 45 Michael Ln, Naugatuck, CT 06770

    $520,000

    Sold Jul 16, 2026

    45 Michael Ln, Naugatuck, CT 06770

    • 4 Beds
    • 3 Baths
    • 3,168 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $164/SF
    • 12 Days On Market

    Current Estimated Value $533,078

    Last Listing Agent Andrew Walker Compass Connecticut, LLC

    45 Michael Ln, Naugatuck, CT 06770
  • 81 Amanda Ln, Naugatuck, CT 06770

    $600,000

    Sold Jun 30, 2026

    81 Amanda Ln, Naugatuck, CT 06770

    • 4 Beds
    • 4 Baths
    • 2,763 Sq Ft
    • Built 1995

    Last Sold Summary

    • $217/SF
    • 40 Days On Market

    Current Estimated Value $598,573

    Last Listing Agent Donald Fitzgerald, Jr. Showcase Realty, Inc.

    81 Amanda Ln, Naugatuck, CT 06770

Showing Results 81 - 120, Page 3 of 4

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