134

Recently Sold Middlebury, CT Homes

Section Image
  • 396 Watertown Rd, Middlebury, CT 06762

    $790,000 Sold Mar 31, 2025

    396 Watertown Rd, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,935 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $201/SF
    • 64 Days On Market

    Current Estimated Value $810,572

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, Middlebury, CT 06762
  • 29 Winding Trail Unit 29, Middlebury, CT 06762

    $520,000 Sold Aug 08, 2025

    29 Winding Trail Unit 29, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $244/SF
    • 117 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    29 Winding Trail Unit 29, Middlebury, CT 06762
  • 64 Joy Rd, Middlebury, CT 06762

    $422,000 Sold Jun 18, 2025

    64 Joy Rd, Middlebury, CT 06762

    • 3 Beds
    • 1 Bath
    • 1,688 Sq Ft
    • Built 1959

    Last Sold Summary

    • 6% Above List Price
    • $250/SF
    • 58 Days On Market

    Current Estimated Value $414,636

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    64 Joy Rd, Middlebury, CT 06762
  • 93 Fenn Rd, Middlebury, CT 06762

    $420,000 Sold Oct 09, 2025

    93 Fenn Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,636 Sq Ft
    • Built 1951

    Last Sold Summary

    • 1% Below List Price
    • $257/SF
    • 62 Days On Market

    Current Estimated Value $420,985

    Last Listing Agent Robert Marucci Better Living Realty, LLC

    93 Fenn Rd, Middlebury, CT 06762
  • 28 Maple Dr, Middlebury, CT 06762

    $435,000 Sold Oct 14, 2025

    28 Maple Dr, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft
    • Built 1950

    Last Sold Summary

    • 17% Below List Price
    • $273/SF
    • 233 Days On Market

    Current Estimated Value $445,114

    Last Listing Agent Dean Giatas Fiorelli Realty, LLC

    28 Maple Dr, Middlebury, CT 06762
  • 203 Lake Shore Dr, Middlebury, CT 06762

    $365,000 Sold Jul 01, 2025

    203 Lake Shore Dr, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $272/SF
    • 69 Days On Market

    Current Estimated Value $368,072

    Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

    203 Lake Shore Dr, Middlebury, CT 06762
  • 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 $804,519

    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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762
  • 7 Arrowwood Ct Unit 7, Middlebury, CT 06762

    $630,000 Sold May 15, 2025

    7 Arrowwood Ct Unit 7, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 3,465 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Below List Price
    • $182/SF
    • 77 Days On Market

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    7 Arrowwood Ct Unit 7, Middlebury, CT 06762
  • 58 Chesham Dr, Middlebury, CT 06762

    $230,000 Sold Jun 19, 2025

    58 Chesham Dr, Middlebury, CT 06762

    • Land
    • 1.89 Acres
    • $121,693 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 9 Days On Market

    Current Estimated Value $235,306

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    58 Chesham Dr, Middlebury, CT 06762
  • 481 Long Meadow Rd, Middlebury, CT 06762

    $735,000 Sold Feb 19, 2025

    481 Long Meadow Rd, Middlebury, CT 06762

    • 4 Beds
    • 3 Baths
    • 3,011 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $244/SF
    • 92 Days On Market

    Current Estimated Value $768,453

    Last Listing Agent Allen Grealish Coldwell Banker Realty

    481 Long Meadow Rd, Middlebury, CT 06762
  • 43 Merideth Rd, Middlebury, CT 06762

    $385,000 Sold May 05, 2025

    43 Merideth Rd, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Built 1957

    Last Sold Summary

    • $244/SF
    • 51 Days On Market

    Current Estimated Value $395,502

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    43 Merideth Rd, 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 $986,794

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    593 Park Road Extension, Middlebury, CT 06762
  • 396 Watertown Rd, Middlebury, CT 06762

    $790,000 Sold Mar 31, 2025

    396 Watertown Rd, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,935 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $201/SF
    • 64 Days On Market

    Current Estimated Value $810,572

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, Middlebury, CT 06762
  • 679 Christian Rd, Middlebury, CT 06762

    $454,000 Sold May 08, 2025

    679 Christian Rd, Middlebury, CT 06762

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

    Last Sold Summary

    • 1% Above List Price
    • $196/SF
    • 47 Days On Market

    Current Estimated Value $483,167

    Last Listing Agent Chloe White KW Legacy Partners

    679 Christian Rd, 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 $549,306

    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 $653,505

    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
    • 0.45 Acre
    • $188,889 per Acre

    Last Sold Summary

    • 258 Days On Market

    Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

    440 Lake Shore 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 $489,307

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
  • 74 E Ridge Dr, Middlebury, CT 06762

    $385,000 Sold Mar 10, 2025

    74 E Ridge Dr, Middlebury, CT 06762

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

    Last Sold Summary

    • 9% Below List Price
    • $302/SF
    • 123 Days On Market

    Current Estimated Value $401,707

    Last Listing Agent Marian Van Egas Berkshire Hathaway NE Prop.

    74 E Ridge Dr, Middlebury, CT 06762
  • 460 Lake Shore Dr, Middlebury, CT 06762

    $415,000 Sold May 23, 2025

    460 Lake Shore Dr, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $322/SF
    • 68 Days On Market

    Current Estimated Value $418,081

    Last Listing Agent Blair Patterson William Raveis Real Estate

    460 Lake Shore Dr, 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 $1,372,483

    Last Listing Agent Jennifer Jones Coldwell Banker Realty

    122 Mirey Dam Rd, Middlebury, CT 06762
  • 81 Sandy Beach Rd, Middlebury, CT 06762

    $410,000 Sold Mar 14, 2025

    81 Sandy Beach Rd, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 972 Sq Ft
    • Built 1940

    Last Sold Summary

    • 13% Below List Price
    • $422/SF
    • 61 Days On Market

    Current Estimated Value $413,510

    Last Listing Agent Wilson Lamas Realty Group of New England, LLC

    81 Sandy Beach Rd, Middlebury, CT 06762
  • 403 Chestnut Cir Unit 76, Middlebury, CT 06762

    $702,500 Sold May 23, 2025

    403 Chestnut Cir Unit 76, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 2,292 Sq Ft
    • Built 2023

    Last Sold Summary

    • 6% Above List Price
    • $307/SF
    • 533 Days On Market

    Current Estimated Value $663,971

    Last Listing Agent Jodi Dawley Real Estate Two

    403 Chestnut Cir Unit 76, Middlebury, CT 06762
  • 138 Skyline Dr, Middlebury, CT 06762

    $590,000 Sold Jun 04, 2025

    138 Skyline Dr, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,212 Sq Ft
    • Built 1960

    Last Sold Summary

    • 15% Below List Price
    • $267/SF
    • 59 Days On Market

    Current Estimated Value $593,559

    Last Listing Agent Diana Mashni RE/MAX RISE

    138 Skyline Dr, 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 $590,352

    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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
  • 401 Chestnut Cir Unit 75, Middlebury, CT 06762

    $707,200 Sold Apr 04, 2025

    401 Chestnut Cir Unit 75, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 2,292 Sq Ft
    • Built 2023

    Last Sold Summary

    • 7% Above List Price
    • $309/SF
    • 535 Days On Market

    Current Estimated Value $673,597

    Last Listing Agent Jodi Dawley Real Estate Two

    401 Chestnut Cir Unit 75, Middlebury, CT 06762
  • 110 Glenwood Ave, Middlebury, CT 06762

    $525,000 Sold Jun 02, 2025

    110 Glenwood Ave, Middlebury, CT 06762

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

    Last Sold Summary

    • 5% Below List Price
    • $243/SF
    • 33 Days On Market

    Current Estimated Value $540,608

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    110 Glenwood Ave, Middlebury, CT 06762
  • 111 Periwinkle Dr Unit 111, Middlebury, CT 06762

    $585,000 Sold Mar 28, 2025

    111 Periwinkle Dr Unit 111, Middlebury, CT 06762

    • 2 Beds
    • 2.5 Baths
    • 2,476 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $236/SF
    • 131 Days On Market

    Current Estimated Value $630,882

    Last Listing Agent Marvin and Laura Beninson Keller Williams Realty

    111 Periwinkle Dr Unit 111, Middlebury, CT 06762
  • 43 Ridgewood Dr Unit 43, Middlebury, CT 06762

    $493,000 Sold Jun 06, 2025

    43 Ridgewood Dr Unit 43, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 1,808 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $273/SF
    • 44 Days On Market

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    43 Ridgewood Dr Unit 43, 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
  • 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 $346,111

    Last Listing Agent David Aurigemma Regency Real Estate, LLC

    119 Christian 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

    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 Meuse 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

    Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

    115 Porter Ave, Middlebury, CT 06762
  • 428 Benson 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
  • 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 $461,941

    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 $466,049

    Last Listing Agent Devon O'Neill Litchfield Hills Properties LLC

    1996 Straits Turnpike, Middlebury, CT 06762

Showing Results 41 - 80, Page 2 of 4

Connecticut New Haven County Middlebury

Recently Sold Real Estate & Homes in Middlebury, CT

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group