3,789

Middlebury, CT Homes

Section Image
  • 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 $463,284

    Last Listing Agent Tom Dorso Mapleridge Realty

    74 Joy Rd, Middlebury, CT 06762
    • 200 Northridge Dr, Middlebury, CT 06762

      Est $671,790 Not Listed For Sale

      200 Northridge Dr, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,360 Sq Ft
      • Built 1984
      200 Northridge Dr, Middlebury, CT 06762

      Last Sold Summary

      • 27% Above List Price
      • $225/SF
      • 152 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Wayne Watt Jr. THE CONNECTICUT AGENCY LLC

  • 541 Benson Rd, Middlebury, CT 06762
    541 Benson Rd, Middlebury, CT 06762
    541 Benson Rd, Middlebury, CT 06762
    /20

    $525,000 Pending

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

    541 Benson Rd, Middlebury, CT 06762

    Rare Two-Home Compound in Middlebury - Ideal for Investment or Owner-Occupant! An extraordinary opportunity for investors or owner-occupants looking to offset their mortgage! This unique property at 541 Benson Road features TWO distinct, detached dwellings on a private .8-acre lot, offering a total of 3 bedrooms, 3 full baths, and 4 garage bays. Unit 1: The Main Residence (2BR/2BA) This

    Joseph Martino Joseph Martino Real Estate

    541 Benson 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 $453,094

    Last Listing Agent Devon O'Neill Litchfield Hills Properties LLC

    1996 Straits Turnpike, Middlebury, CT 06762
    • 12 Joy Rd, Middlebury, CT 06762

      Est $374,206 Not Listed For Sale

      12 Joy Rd, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 1,435 Sq Ft
      • Built 1951
      12 Joy Rd, Middlebury, CT 06762

      Last Sold Summary

      • 13% Above List Price
      • $230/SF
      • 5 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Wynne Lord Coldwell Banker Realty

  • 38 E Ridge Dr, Middlebury, CT 06762
    38 E Ridge Dr, Middlebury, CT 06762
    38 E Ridge Dr, Middlebury, CT 06762
    /31

    $509,900 Pending

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

    38 E Ridge Dr, Middlebury, CT 06762

    Highest & Best due Tuesday 3/31 @5:00 pm. Welcome to 38 E Ridge Drive - Move-In Ready & Fully Updated. This beautifully renovated home is located in one of the most sought-after areas of town. With an open floor plan and hardwood floors throughout, it offers a seamless blend of comfort and style. Inside, you'll find a large living and dining room combo. The kitchen has been thoughtfully updated

    Paula Basso Evjen Agency

    38 E Ridge Dr, 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 $516,925

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    1 Stevens Rd, Middlebury, CT 06762
    • 252 White Ave, Middlebury, CT 06762

      Est $450,976 Not Listed For Sale

      252 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 1,454 Sq Ft
      • Built 1937
      252 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 6% Above List Price
      • $292/SF
      • 4 Days On Market

      Last Sold Price $425,000

      Last Listing Agent Tom Slekis Berkshire Hathaway Home Services

  • 0 N Benson Rd Unit 60, Middlebury, CT 06762
    0 N Benson Rd Unit 60, Middlebury, CT 06762
    0 N Benson Rd Unit 60, Middlebury, CT 06762
    /9

    $573,584 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 60, Middlebury, CT 06762

    Last remaining unit! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 60, 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 $495,858

    Last Listing Agent David Aurigemma Regency Real Estate, LLC

    182 Bayberry Terrace, Middlebury, CT 06762
    • 1738 Middlebury Rd, Middlebury, CT 06762

      Est $481,689 Not Listed For Sale

      1738 Middlebury Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,225 Sq Ft
      • Built 1961
      1738 Middlebury Rd, Middlebury, CT 06762

      Last Sold Summary

      • 28% Above List Price
      • $169/SF
      • 32 Days On Market

      Last Sold Price $375,000

      Last Listing Agent April Stirling Coldwell Banker Realty

  • 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
    • 98 Leonard Rd, Middlebury, CT 06762

      Est $944,693 Not Listed For Sale

      98 Leonard Rd, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 3,357 Sq Ft
      • Built 1941
      98 Leonard Rd, Middlebury, CT 06762

      Last Sold Summary

      • 11% Above List Price
      • $253/SF
      • 293 Days On Market

      Last Sold Price $850,000

      Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  • 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 $433,492

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

    1 Yale Ave, Middlebury, CT 06762
    • 615 Long Meadow Rd, Middlebury, CT 06762

      Est $426,916 Not Listed For Sale

      615 Long Meadow Rd, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 1,132 Sq Ft
      • Built 1980
      615 Long Meadow Rd, Middlebury, CT 06762

      Last Sold Summary

      • $375/SF
      • 1 Day On Market

      Last Sold Price $425,000

      Last Listing Agent George Noujaim Dave Jones Realty, LLC

  • 7 Highridge Rd Unit 7, 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
    • 22 Yale Ave, Middlebury, CT 06762

      Est $351,129 Not Listed For Sale

      22 Yale Ave, Middlebury, CT 06762

      • 2 Beds
      • 1 Bath
      • 1,053 Sq Ft
      • Built 1926
      22 Yale Ave, Middlebury, CT 06762

      Last Sold Summary

      • 5% Below List Price
      • $351/SF
      • 49 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  • 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
    • 450 Long Meadow Rd, Middlebury, CT 06762

      Est $614,637 Not Listed For Sale

      450 Long Meadow Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 3,450 Sq Ft
      • Built 2002
      450 Long Meadow Rd, Middlebury, CT 06762

      Last Sold Summary

      • 14% Above List Price
      • $157/SF
      • 107 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 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 $744,446

    Last Listing Agent Jodi Dawley Real Estate Two

    17 Deer Run Rd, Middlebury, CT 06762
    • 481 Long Meadow Rd, Middlebury, CT 06762

      Est $752,997 Not Listed For Sale

      481 Long Meadow Rd, Middlebury, CT 06762

      • 4 Beds
      • 3 Baths
      • 3,011 Sq Ft
      • Built 2001
      481 Long Meadow Rd, Middlebury, CT 06762

      Last Sold Summary

      • 2% Above List Price
      • $244/SF
      • 92 Days On Market

      Last Sold Price $735,000

      Last Listing Agent Allen Grealish Coldwell Banker Realty

  • 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 $668,747

    Last Listing Agent Norinne Byrne Calcagni Real Estate

    1 Chatham Ct, Middlebury, CT 06762
    • 15 Chatham Ct, Middlebury, CT 06762

      Est $702,180 Not Listed For Sale

      15 Chatham Ct, Middlebury, CT 06762

      • 4 Beds
      • 4 Baths
      • 4,450 Sq Ft
      • Built 2005
      15 Chatham Ct, Middlebury, CT 06762

      Last Sold Summary

      • 2% Below List Price
      • $162/SF
      • 3 Days On Market

      Last Sold Price $720,000

      Last Listing Agent Pat Blanko William Raveis Real Estate

  • 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 $529,179

    Last Listing Agent Lisa Clarke Dave Jones Realty, LLC

    76 Three Mile Hill Rd, Middlebury, CT 06762
    • 6 Colonial Ct, Middlebury, CT 06762

      Est $664,570 Not Listed For Sale

      6 Colonial Ct, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,950 Sq Ft
      • Built 2004
      6 Colonial Ct, Middlebury, CT 06762

      Last Sold Summary

      • 2% Above List Price
      • $220/SF
      • 49 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Norinne Byrne Calcagni Real Estate

  • 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 $809,890

    Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

    1 Hampshire Ct, Middlebury, CT 06762
    • 3 Independence Cir, Middlebury, CT 06762

      Est $666,195 Not Listed For Sale

      3 Independence Cir, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,882 Sq Ft
      • Built 2005
      3 Independence Cir, Middlebury, CT 06762

      Last Sold Summary

      • 14% Above List Price
      • $203/SF
      • 23 Days On Market

      Last Sold Price $585,000

      Last Listing Agent Kristen Stolfi Berkshire Hathaway Home Services

  • 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 $635,924

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    51 Cross Rd, Middlebury, CT 06762
    • 13 Independence Cir, Middlebury, CT 06762

      Est $717,438 Not Listed For Sale

      13 Independence Cir, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 3,600 Sq Ft
      • Built 2005
      13 Independence Cir, Middlebury, CT 06762

      Last Sold Summary

      • 5% Above List Price
      • $190/SF
      • 79 Days On Market

      Last Sold Price $685,000

      Last Listing Agent David Hughes Century 21 AllPoints Realty

  • 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 $807,939

    Last Listing Agent Jodi Dawley Real Estate Two

    11 Hunting Ridge Rd, Middlebury, CT 06762
    • 28 Independence Cir, Middlebury, CT 06762

      Est $661,735 Not Listed For Sale

      28 Independence Cir, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,882 Sq Ft
      • Built 2005
      28 Independence Cir, Middlebury, CT 06762

      Last Sold Summary

      • 17% Above List Price
      • $196/SF
      • 65 Days On Market

      Last Sold Price $565,000

      Last Listing Agent Dawn Cabral West View Properties, LLC

  • 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
    • 37 Independence Cir, Middlebury, CT 06762

      Est $724,849 Not Listed For Sale

      37 Independence Cir, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 4,331 Sq Ft
      • Built 2004
      37 Independence Cir, Middlebury, CT 06762

      Last Sold Summary

      • 1% Below List Price
      • $170/SF
      • 2 Days On Market

      Last Sold Price $735,000

      Last Listing Agent Adele Unger William Pitt

  • 34 Breakneck Hill Rd, 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 $834,875

    Last Listing Agent Arben Belica William Raveis Real Estate

    34 Breakneck Hill Rd, Middlebury, CT 06762
    • 28 Brookside Dr, Middlebury, CT 06762

      Est $689,436 Not Listed For Sale

      28 Brookside Dr, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 3,512 Sq Ft
      • Built 2005
      28 Brookside Dr, Middlebury, CT 06762

      Last Sold Summary

      • 4% Above List Price
      • $188/SF
      • 127 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Heather Crabtree RE/MAX RISE

  • 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
    • 290 Christian Rd, Middlebury, CT 06762

      Est $800,748 Not Listed For Sale

      290 Christian Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 3,086 Sq Ft
      • Built 2006
      290 Christian Rd, Middlebury, CT 06762

      Last Sold Summary

      • 15% Above List Price
      • $227/SF
      • 105 Days On Market

      Last Sold Price $699,000

      Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  • 115 Marney Dr, 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 $486,448

    Last Listing Agent Allysa DeRosa Mapleridge Realty

    115 Marney Dr, Middlebury, CT 06762
    • 16 Somerset Dr, Middlebury, CT 06762

      Est $801,124 Not Listed For Sale

      16 Somerset Dr, Middlebury, CT 06762

      • 3 Beds
      • 3.5 Baths
      • 3,377 Sq Ft
      • Built 2006
      16 Somerset Dr, Middlebury, CT 06762

      Last Sold Summary

      • 10% Above List Price
      • $216/SF
      • 182 Days On Market

      Last Sold Price $729,000

      Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  • 835 Whittemore Rd, 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 $512,316

    Last Listing Agent Mike Albert RE/MAX RISE

    835 Whittemore Rd, Middlebury, CT 06762

Showing Results 201 - 240, Page 6 of 18

Connecticut New Haven County Middlebury

Real Estate & Homes

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