114

Recently Sold Middlebury, CT Homes

Section Image
  • 18 Hunting Ridge Rd, Middlebury, CT 06762

    $790,000

    Sold Jun 30, 2025

    18 Hunting Ridge Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft
    • Built 2024

    Last Sold Summary

    • 1% Below List Price
    • $293/SF
    • 298 Days On Market

    Current Estimated Value $791,645

    Last Listing Agent Jodi Dawley Real Estate Two

    18 Hunting Ridge Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762

    $505,834

    Sold Oct 17, 2025

    0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2025

    Last Sold Summary

    • $259/SF
    • 0 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762
  • 72 Carriage Dr, Middlebury, CT 06762

    $600,000

    Sold Apr 21, 2026

    72 Carriage Dr, Middlebury, CT 06762

    • 4 Beds
    • 3 Baths
    • 2,878 Sq Ft
    • Built 1966

    Last Sold Summary

    • 8% Below List Price
    • $208/SF
    • 161 Days On Market

    Current Estimated Value $611,855

    Last Listing Agent Justin Bette Century 21 Bette Real Estate

    72 Carriage Dr, Middlebury, CT 06762
  • 593 Park Road Extension, Middlebury, CT 06762

    $950,000

    Sold Jul 09, 2025

    593 Park Road Extension, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 4,496 Sq Ft
    • Built 1994

    Last Sold Summary

    • 27% Below List Price
    • $211/SF
    • 428 Days On Market

    Current Estimated Value $965,578

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    593 Park Road Extension, Middlebury, CT 06762
  • 288 Watertown Rd Unit Lot 2, Middlebury, CT 06762

    $240,000

    Sold Oct 14, 2025

    288 Watertown Rd Unit Lot 2, Middlebury, CT 06762

    • Land
    • 4 Acres
    • $60,000 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 330 Days On Market

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 2, Middlebury, CT 06762
  • 61 Stony Brook Rd, Middlebury, CT 06762

    $515,000

    Sold Jul 31, 2025

    61 Stony Brook Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,804 Sq Ft
    • Built 1971

    Last Sold Summary

    • 21% Below List Price
    • $184/SF
    • 75 Days On Market

    Current Estimated Value $566,936

    Last Listing Agent Maria Cohen William Raveis Real Estate

    61 Stony Brook Rd, Middlebury, CT 06762
  • 55 Westwood Dr, Middlebury, CT 06762

    $675,000

    Sold Sep 24, 2025

    55 Westwood Dr, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,570 Sq Ft
    • Built 1962

    Last Sold Summary

    • 13% Below List Price
    • $263/SF
    • 192 Days On Market

    Current Estimated Value $649,779

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    55 Westwood Dr, Middlebury, CT 06762
  • 440 Lake Shore Dr, Middlebury, CT 06762

    $85,000

    Sold Jan 07, 2026

    440 Lake Shore Dr, Middlebury, CT 06762

    • Land
    • 19,602 Sq Ft
    • $188,889 per Acre

    Last Sold Summary

    • 258 Days On Market

    Current Estimated Value $86,389

    Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

    440 Lake Shore Dr, Middlebury, CT 06762
  • /39

    $554,000

    $20K PRICE DROP Pending
    • 3 Beds
    • 3.5 Baths
    • 2,879 Sq Ft

    24 Ridgewood Dr, Middlebury, CT 06762

    Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • 112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    $510,000

    Sold Oct 22, 2025

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    • 2 Beds
    • 2.5 Baths
    • 2,593 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $197/SF
    • 186 Days On Market

    Current Estimated Value $475,708

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
  • 122 Mirey Dam Rd, Middlebury, CT 06762

    $1,375,000

    Sold Sep 04, 2025

    122 Mirey Dam Rd, Middlebury, CT 06762

    • 4 Beds
    • 5 Baths
    • 6,175 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $223/SF
    • 103 Days On Market

    Current Estimated Value $1,356,512

    Last Listing Agent Jennifer Jones Coldwell Banker Realty

    122 Mirey Dam Rd, Middlebury, CT 06762
  • 1 Dogwood Ct Unit 1, Middlebury, CT 06762

    $575,000

    Sold Nov 06, 2025

    1 Dogwood Ct Unit 1, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 3,477 Sq Ft
    • Built 2007

    Last Sold Summary

    • 15% Below List Price
    • $165/SF
    • 216 Days On Market

    Current Estimated Value $613,109

    Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

    1 Dogwood Ct Unit 1, Middlebury, CT 06762
  • 0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762

    $549,936

    Sold Oct 30, 2025

    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Above List Price
    • $244/SF
    • 0 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
  • 193 Ridgewood Dr Unit 193, Middlebury, CT 06762

    $620,000

    Sold May 28, 2026

    193 Ridgewood Dr Unit 193, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,658 Sq Ft
    • Built 2022

    Last Sold Summary

    • 5% Below List Price
    • $233/SF
    • 41 Days On Market

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    193 Ridgewood Dr Unit 193, Middlebury, CT 06762
  • 181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    $565,000

    Sold Sep 25, 2025

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,614 Sq Ft
    • Built 2022

    Last Sold Summary

    • 6% Below List Price
    • $216/SF
    • 90 Days On Market

    Last Listing Agent Heather Crabtree RE/MAX RISE

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762
  • 24 Highridge Rd Unit 24, Middlebury, CT 06762

    $560,000

    Sold Jun 19, 2026

    24 Highridge Rd Unit 24, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,802 Sq Ft
    • Built 2017

    Last Sold Summary

    • $311/SF
    • 58 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    24 Highridge Rd Unit 24, Middlebury, CT 06762
  • 119 Christian Rd, Middlebury, CT 06762

    $345,000

    Sold Sep 10, 2025

    119 Christian Rd, Middlebury, CT 06762

    • 2 Beds
    • 1.5 Baths
    • 866 Sq Ft
    • Built 1936

    Last Sold Summary

    • 1% Below List Price
    • $398/SF
    • 11 Days On Market

    Current Estimated Value $339,929

    Last Listing Agent David Aurigemma Regency Real Estate, LLC

    119 Christian Rd, Middlebury, CT 06762
  • 245 Upper Whittemore Rd, Middlebury, CT 06762

    $875,000

    Sold Jun 15, 2026

    245 Upper Whittemore Rd, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,990 Sq Ft
    • Built 2005

    Last Sold Summary

    • 7% Above List Price
    • $293/SF
    • 0 Days On Market

    Current Estimated Value $823,496

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    245 Upper Whittemore Rd, Middlebury, CT 06762
  • 18 E Ridge Dr, Middlebury, CT 06762

    $456,000

    Sold Nov 17, 2025

    18 E Ridge Dr, Middlebury, CT 06762

    • 3 Beds
    • 3 Baths
    • 1,340 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Above List Price
    • $340/SF
    • 54 Days On Market

    Current Estimated Value $453,132

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    18 E Ridge Dr, Middlebury, CT 06762
  • 0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

    $530,328

    Sold Oct 30, 2025

    0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Above List Price
    • $272/SF
    • 163 Days On Market

    Last Listing Agent Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762
  • 115 Porter Ave, Middlebury, CT 06762

    $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

    Current Estimated Value $418,937

    Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

    115 Porter Ave, Middlebury, CT 06762
  • 74 Joy 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 $455,348

    Last Listing Agent Tom Dorso Mapleridge Realty

    74 Joy Rd, Middlebury, CT 06762
  • 1996 Straits Turnpike, 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 $457,664

    Last Listing Agent Devon O'Neill Litchfield Hills Properties LLC

    1996 Straits Turnpike, Middlebury, CT 06762
  • 1 Stevens 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 $516,312

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    1 Stevens Rd, Middlebury, CT 06762
  • 292 Park Road Extension, Middlebury, CT 06762

    $574,900

    Sold May 04, 2026

    292 Park Road Extension, Middlebury, CT 06762

    • 5 Beds
    • 2 Baths
    • 1,924 Sq Ft
    • Built 1800

    Last Sold Summary

    • 4% Below List Price
    • $299/SF
    • 136 Days On Market

    Current Estimated Value $567,028

    Last Listing Agent Tammy Ferrauola Eagle Eye Realty PLLC

    292 Park Road Extension, Middlebury, CT 06762
  • 182 Bayberry Terrace, 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

    Current Estimated Value $498,180

    Last Listing Agent David Aurigemma Regency Real Estate, LLC

    182 Bayberry Terrace, Middlebury, CT 06762
  • 0 N Benson Rd Unit 41 24061449, 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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762
  • 1 Yale Ave, 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 $430,952

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

    1 Yale Ave, Middlebury, CT 06762
  • 18 Freedom Rd, Middlebury, CT 06762

    $495,650

    Sold May 18, 2026

    18 Freedom Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,492 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Above List Price
    • $332/SF
    • 10 Days On Market

    Current Estimated Value $475,640

    Last Listing Agent Karen Stanco Showcase Realty, Inc.

    18 Freedom Rd, Middlebury, CT 06762
  • 637 Watertown Rd, Middlebury, CT 06762

    $475,000

    Sold Apr 27, 2026

    637 Watertown Rd, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 1,918 Sq Ft
    • Built 1971

    Last Sold Summary

    • 10% Below List Price
    • $248/SF
    • 102 Days On Market

    Current Estimated Value $463,609

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    637 Watertown Rd, Middlebury, CT 06762
  • 383 Leonard Rd, Middlebury, CT 06762

    $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
  • 17 Deer Run Rd, 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 $750,112

    Last Listing Agent Jodi Dawley Real Estate Two

    17 Deer Run Rd, Middlebury, CT 06762
  • 1 Chatham Ct, 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 $661,564

    Last Listing Agent Norinne Byrne Calcagni Real Estate

    1 Chatham Ct, Middlebury, CT 06762
  • 76 Three Mile Hill Rd, 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 $529,060

    Last Listing Agent Lisa Clarke Dave Jones Realty, LLC

    76 Three Mile Hill Rd, Middlebury, CT 06762
  • 1 Hampshire Ct, 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

    Current Estimated Value $809,482

    Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

    1 Hampshire Ct, Middlebury, CT 06762
  • 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 $637,039

    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 $806,753

    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
  • 288 Watertown Rd Unit Lot 3, 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
  • 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 $433,713

    Last Listing Agent Stephen Mele Houlihan Lawrence

    271 Shadduck Rd, Middlebury, CT 06762

Showing Results 41 - 80, Page 2 of 3

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