3,768

Middlebury, CT Homes

Section Image
  • 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 $610,330

    Last Listing Agent Justin Bette Century 21 Bette Real Estate

    72 Carriage Dr, Middlebury, CT 06762
    • 122 Northridge Dr, Middlebury, CT 06762

      Est $1,043,991

      Not Listed For Sale

      122 Northridge Dr, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 5,582 Sq Ft
      • Built 1982
      122 Northridge Dr, Middlebury, CT 06762

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 625 Charcoal Ave, Middlebury, CT 06762
    625 Charcoal Ave, Middlebury, CT 06762
    625 Charcoal Ave, Middlebury, CT 06762
    /29

    $945,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 4,236 Sq Ft

    625 Charcoal Ave, Middlebury, CT 06762

    Rare 20+ acres with 1920's house and 3 outbuildings in Middlebury estate area near Lake Quassapaug and the Highfield Club. Very private settling up long driveway with mature landscaping. 3 bedroom main house with multiple entertainment rooms and 2 kitchens. 3 bay car barn with large storage area and loft. 2 other small outbuildings. Great opportunity for someone with vision to bring property to

    Pels Matthews W. Raveis Lifestyles Realty

    625 Charcoal Ave, 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
    • 460 Lake Shore Dr, Middlebury, CT 06762

      Est $411,749

      Not Listed For Sale

      460 Lake Shore Dr, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1981
      460 Lake Shore Dr, Middlebury, CT 06762

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Blair Patterson William Raveis Real Estate

  • 0 N Benson Rd Unit 66, Middlebury, CT 06762
    0 N Benson Rd Unit 66, Middlebury, CT 06762
    0 N Benson Rd Unit 66, Middlebury, CT 06762
    /9

    $562,350

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 66, Middlebury, CT 06762

    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 appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 66, 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 $652,025

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    55 Westwood Dr, Middlebury, CT 06762
    • 106 Glenwood Ave, Middlebury, CT 06762

      Est $391,775

      Not Listed For Sale

      106 Glenwood Ave, Middlebury, CT 06762

      • 5 Beds
      • 2 Baths
      • 1,724 Sq Ft
      • Built 1926
      106 Glenwood Ave, Middlebury, CT 06762

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Crosby Middlemass Coldwell Banker Realty

  • 0 N Benson Rd Unit 54, Middlebury, CT 06762
    0 N Benson Rd Unit 54, Middlebury, CT 06762
    0 N Benson Rd Unit 54, Middlebury, CT 06762
    /9

    $570,600

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,349 Sq Ft

    0 N Benson Rd Unit 54, Middlebury, CT 06762

    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 appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 54, 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 $86,692

    Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

    440 Lake Shore Dr, Middlebury, CT 06762
    • 185 Porter Ave, Middlebury, CT 06762

      Est $375,687

      Not Listed For Sale

      185 Porter Ave, Middlebury, CT 06762

      • 3 Beds
      • 1 Bath
      • 1,218 Sq Ft
      • Built 1953
      185 Porter Ave, Middlebury, CT 06762

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Beth Santos Showcase Realty, Inc.

  • 1140 Southford Rd, Middlebury, CT 06762
    1140 Southford Rd, Middlebury, CT 06762
    1140 Southford Rd, Middlebury, CT 06762
    /13

    $399,000

    • Land
    • 1.5 Acres
    • $266,000 per Acre

    1140 Southford Rd, Middlebury, CT 06762

    Exceptional opportunity to acquire a 1.5-acre industrial development parcel located along the highly visible Southford Road corridor in Middlebury. Situated within the IG-40 (Gateway Industrial Design District), this property is ideally suited for flex industrial, contractor headquarters, light manufacturing, or office-warehouse development. The site benefits from access to public water and

    Robert Ghent Ghent Realty Advisors

    1140 Southford Rd, Middlebury, CT 06762
  • 24 Ridgewood Dr, Middlebury, CT 06762

    $554,000

    Sold Jun 22, 2026

    24 Ridgewood Dr, Middlebury, CT 06762

    • 3 Beds
    • 3.5 Baths
    • 2,879 Sq Ft
    • Built 2008

    Last Sold Summary

    • 3% Below List Price
    • $192/SF
    • 150 Days On Market

    Current Estimated Value $575,692

    Last Listing Agent Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
    • 31 Stony Brook Rd, Middlebury, CT 06762

      Est $491,002

      Not Listed For Sale

      31 Stony Brook Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,002 Sq Ft
      • Built 1969
      31 Stony Brook Rd, Middlebury, CT 06762

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Deana Daponte Dave Jones Realty, LLC

  • 0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
    /9

    $522,128

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762

    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 appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 46 24097231, 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 $468,274

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    • 294 Porter Ave, Middlebury, CT 06762

      Est $365,460

      Not Listed For Sale

      294 Porter Ave, Middlebury, CT 06762

      • 3 Beds
      • 3 Baths
      • 1,109 Sq Ft
      • Built 1949
      294 Porter Ave, Middlebury, CT 06762

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Michelle Pavia William Raveis Real Estate

  • 80 Pine Hollow Dr, Middlebury, CT 06762
    80 Pine Hollow Dr, Middlebury, CT 06762
    80 Pine Hollow Dr, Middlebury, CT 06762
    /39

    $724,900

    Open Sat 11AM - 1PM $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,806 Sq Ft

    80 Pine Hollow Dr, Middlebury, CT 06762

    Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

    Gina Farra Keller Williams Realty

    80 Pine Hollow 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 $1,312,069

    Last Listing Agent Jennifer Jones Coldwell Banker Realty

    122 Mirey Dam Rd, Middlebury, CT 06762
    • 66 White Ave, Middlebury, CT 06762

      Est $399,340

      Not Listed For Sale

      66 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 1.5 Baths
      • 2,568 Sq Ft
      • Built 1938
      66 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 139 Days On Market

      Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  • 0 N Benson Rd Unit 57, Middlebury, CT 06762
    0 N Benson Rd Unit 57, Middlebury, CT 06762
    0 N Benson Rd Unit 57, Middlebury, CT 06762
    /9

    $561,271

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 57, Middlebury, CT 06762

    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 appointed attached

    Renee Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 57, 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 $603,655

    Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

    1 Dogwood Ct Unit 1, Middlebury, CT 06762
    • 828 Breakneck Hill Rd, Middlebury, CT 06762

      Est $519,279

      Not Listed For Sale

      828 Breakneck Hill Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,220 Sq Ft
      • Built 1951
      828 Breakneck Hill Rd, Middlebury, CT 06762

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Mary Helen Levine Mary Helen Levine Real Estate LLC

  • 3 Brookside Dr, Middlebury, CT 06762
    3 Brookside Dr, Middlebury, CT 06762
    3 Brookside Dr, Middlebury, CT 06762
    /36

    $599,900

    $60K PRICE DROP Under Contract
    • 4 Beds
    • 4 Baths
    • 4,200 Sq Ft

    3 Brookside Dr, Middlebury, CT 06762

    Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the

    Shagufta Zahid S Factor Realty Group LLC

    3 Brookside Dr, 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
    • Unlisted Address

      Est $1,062,117

      Not Listed For Sale

      Unlisted Address

      • 5 Beds
      • 5 Baths
      • 5,800 Sq Ft
      • Built 1929
      Unlisted Address

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  • 41 Somerset Dr, Middlebury, CT 06762
    41 Somerset Dr, Middlebury, CT 06762
    41 Somerset Dr, Middlebury, CT 06762
    /9

    $939,000

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,878 Sq Ft

    41 Somerset Dr, Middlebury, CT 06762

    Under Construction in One of Middlebury's Most Desirable Neighborhoods! Welcome to the Avalon Farms community-known for its beautiful homes, manicured lawns, and thoughtfully designed landscaping that create a truly picturesque setting. The Cambridge model blends classic design with today's most sought-after features, offering a bright and open floor plan perfect for modern living. The spacious

    Jonna Dibble BHGRE Gaetano Marra Homes

    41 Somerset Dr, Middlebury, CT 06762
  • 408 Breakneck Hill Rd, Middlebury, CT 06762

    $615,000

    Sold Jun 29, 2026

    408 Breakneck Hill Rd, Middlebury, CT 06762

    • 2 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • Built 1946

    Last Sold Summary

    • 2% Below List Price
    • $333/SF
    • 71 Days On Market

    Current Estimated Value $614,258

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    408 Breakneck Hill Rd, Middlebury, CT 06762
    • 61 Stony Brook Rd, Middlebury, CT 06762

      Est $567,219

      Not Listed For Sale

      61 Stony Brook Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,804 Sq Ft
      • Built 1971
      61 Stony Brook Rd, Middlebury, CT 06762

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Maria Cohen William Raveis Real Estate

  • 251 Lake Shore Dr, Middlebury, CT 06762
    251 Lake Shore Dr, Middlebury, CT 06762
    251 Lake Shore Dr, Middlebury, CT 06762
    /38

    $499,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 2,568 Sq Ft

    251 Lake Shore Dr, Middlebury, CT 06762

    Completely renovated and thoughtfully designed, this stunning 3-bedroom Cape offers modern style, quality craftsmanship, and a glimpse of lake views. The open floor plan is perfect for today's lifestyle, featuring newly refinished hardwood floors, detailed custom woodwork, wood ceilings, and a spacious living area that flows seamlessly into the beautifully updated kitchen. The kitchen is a cook's

    Christina Zainc BHGRE Gaetano Marra Homes

    251 Lake Shore Dr, 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
    • 140 Glenwood Ave, Middlebury, CT 06762

      Est $433,075

      Not Listed For Sale

      140 Glenwood Ave, Middlebury, CT 06762

      • 2 Beds
      • 2 Baths
      • 1,638 Sq Ft
      • Built 1936
      140 Glenwood Ave, Middlebury, CT 06762

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Karen Dibble-flaherty Keller Williams Realty

  • 213 Acme Dr, Middlebury, CT 06762
    213 Acme Dr, Middlebury, CT 06762
    213 Acme Dr, Middlebury, CT 06762
    /40

    $499,000

    $16K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,833 Sq Ft

    213 Acme Dr, Middlebury, CT 06762

    Welcome to this meticulously maintained and exceptional 4-bedroom, 2.5-bathroom Colonial that perfectly blends classic comfort with wonderful living space. ADDED BONUS - Solar panels that have no monthly fee and very low usage expense! Winter months around $60 month, Summer bill typically no more than $180. Annual average $1530!! Step inside to find a warm, welcoming interior defined by beautiful

    Heidi Lester KW Legacy Partners

    213 Acme Dr, Middlebury, CT 06762
  • 10 Pelham Way, Middlebury, CT 06762

    $625,000

    Sold Jun 30, 2026

    10 Pelham Way, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,251 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $278/SF
    • 36 Days On Market

    Current Estimated Value $622,240

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    10 Pelham Way, Middlebury, CT 06762
    • 49 White Ave, Middlebury, CT 06762

      Est $389,791

      Not Listed For Sale

      49 White Ave, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 1,473 Sq Ft
      • Built 1952
      49 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Sharon Martino Regency Real Estate, LLC

  • 117 Crest Rd, Middlebury, CT 06762
    117 Crest Rd, Middlebury, CT 06762
    117 Crest Rd, Middlebury, CT 06762
    /38

    $750,000

    $9K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,753 Sq Ft

    117 Crest Rd, Middlebury, CT 06762

    Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the

    Lori Geraci BHGRE Gaetano Marra Homes

    117 Crest Rd, Middlebury, CT 06762
  • 566 Benson Rd, Middlebury, CT 06762

    $520,000

    Sold Jul 29, 2026

    566 Benson Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,020 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Above List Price
    • $257/SF
    • 37 Days On Market

    Current Estimated Value $493,204

    Last Listing Agent Ruth Zeiss William Raveis Real Estate

    566 Benson Rd, Middlebury, CT 06762
    • 5 Laurel Rd, Middlebury, CT 06762

      Est $370,612

      Not Listed For Sale

      5 Laurel Rd, Middlebury, CT 06762

      • 3 Beds
      • 1 Bath
      • 1,076 Sq Ft
      • Built 1940
      5 Laurel Rd, Middlebury, CT 06762

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Jessica Boswell LPT Realty

  • 8 Deer Run Rd, Middlebury, CT 06762
    8 Deer Run Rd, Middlebury, CT 06762
    /2

    $839,900

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    8 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 8 Deer Run Road (aka Lot 16) is just beginning construction. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    8 Deer Run Rd, 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

Showing Results 121 - 160, Page 4 of 18

Connecticut New Haven County

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