3,789

Middlebury, CT Homes

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    • 1232 Straits Turnpike, Middlebury, CT 06762

      Est $320,609 Not Listed For Sale

      1232 Straits Turnpike, Middlebury, CT 06762

      • 2 Beds
      • 1.5 Baths
      • 1,708 Sq Ft
      • Built 1920
      1232 Straits Turnpike, Middlebury, CT 06762

      Last Sold Summary

      • 21% Above List Price
      • $155/SF
      • 144 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

  • /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
  • 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 $369,710

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

    203 Lake Shore Dr, Middlebury, CT 06762
    • 524 Charcoal Ave, Middlebury, CT 06762

      Est $790,522 Not Listed For Sale

      524 Charcoal Ave, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 3,030 Sq Ft
      • Built 1999
      524 Charcoal Ave, Middlebury, CT 06762

      Last Sold Summary

      • 10% Above List Price
      • $238/SF
      • 84 Days On Market

      Last Sold Price $720,000

      Last Listing Agent Jill Taylor RE/MAX

  • /9

    $522,128 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
  • 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 $798,402

    Last Listing Agent Jodi Dawley Real Estate Two

    18 Hunting Ridge Rd, Middlebury, CT 06762
    • 695 Whittemore Rd, Middlebury, CT 06762

      Est $604,252 Not Listed For Sale

      695 Whittemore Rd, Middlebury, CT 06762

      • 3 Beds
      • 4.5 Baths
      • 2,813 Sq Ft
      • Built 1978
      695 Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 7% Below List Price
      • $231/SF
      • 8 Days On Market

      Last Sold Price $650,000

      Last Listing Agent rob raad Better Living Realty, LLC

  • /37

    $825,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 3,253 Sq Ft

    122 Crest Rd, Middlebury, CT 06762

    Welcome to your own private retreat at 122 Crest Road-where timeless charm meets thoughtful modern updates. This beautifully maintained 3-bedroom, 2.5-bath Cape Cod-style home is just moments from town, the library, green, and local dining. Designed with both everyday living and entertaining in mind, the home features a custom sunken great room with a dramatic wall of windows that floods the

    Heather Dever Showcase Realty, Inc.

    122 Crest 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
    • 36 Middlebury Terrace, Middlebury, CT 06762

      Est $422,328 Not Listed For Sale

      36 Middlebury Terrace, Middlebury, CT 06762

      • 3 Beds
      • 1.5 Baths
      • 1,849 Sq Ft
      • Built 1933
      36 Middlebury Terrace, Middlebury, CT 06762

      Last Sold Summary

      • 1% Below List Price
      • $230/SF
      • 177 Days On Market

      Last Sold Price $425,000

      Last Listing Agent Frank Durante William Raveis Real Estate

  • /31

    $749,900 Under Contract

    • 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
  • 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
    • 122 Northridge Dr, Middlebury, CT 06762

      Est $963,750 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

      • 8% Above List Price
      • $160/SF
      • 80 Days On Market

      Last Sold Price $895,000

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • /40

    $574,900 Under Contract

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

    292 Park Road Extension, Middlebury, CT 06762

    Discover this classic 5-bedroom, 2-bath Colonial set on a private 1.67-acre lot in desirable Middlebury. This home features hardwood floors, a bright formal living room, and a spacious dining room that opens to a cozy three-season porch overlooking the yard. The kitchen offers brand-new stainless steel appliances and the convenient first-floor bedroom includes laundry for easy main-level living.

    Tammy Ferrauola Eagle Eye Realty PLLC

    292 Park Road Extension, 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 $232,551

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    58 Chesham Dr, Middlebury, CT 06762
    • 2 Northwood Dr, Middlebury, CT 06762

      Est $467,955 Not Listed For Sale

      2 Northwood Dr, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft
      • Built 1962
      2 Northwood Dr, Middlebury, CT 06762

      Last Sold Summary

      • 1% Above List Price
      • $248/SF
      • 54 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Michael Magas BHGRE Gaetano Marra Homes

  • /30

    $479,000 Pending

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

    18 Freedom Rd, Middlebury, CT 06762

    Welcome to this charming and beautifully maintained 3BR ranch, perfectly situated on a quiet cul-de-sac. Offering the ease of one-level living, this inviting home features an open living room and dining room layout enhanced by gleaming hardwood floors, a cozy fireplace and abundant natural light. The updated kitchen boasts a large granite center island that is ideal for cooking gathering and

    Karen Stanco Showcase Realty, Inc.

    18 Freedom 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 $390,815

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    43 Merideth Rd, Middlebury, CT 06762
    • 106 Glenwood Ave, Middlebury, CT 06762

      Est $445,358 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

      • 2% Above List Price
      • $254/SF
      • 25 Days On Market

      Last Sold Price $438,000

      Last Listing Agent Crosby Middlemass Coldwell Banker Realty

  • /40

    $450,000 Pending

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

    637 Watertown Rd, Middlebury, CT 06762

    Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home.

    Jonna Dibble BHGRE Gaetano Marra Homes

    637 Watertown 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 $960,954

    Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

    593 Park Road Extension, Middlebury, CT 06762
    • 185 Porter Ave, Middlebury, CT 06762

      Est $353,089 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

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

      Last Sold Price $331,900

      Last Listing Agent Beth Santos Showcase Realty, Inc.

  • /9

    $561,271 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
  • 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 $485,886

    Last Listing Agent Chloe White KW Legacy Partners

    679 Christian Rd, Middlebury, CT 06762
    • 31 Stony Brook Rd, Middlebury, CT 06762

      Est $462,950 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

      • 5% Above List Price
      • $220/SF
      • 54 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Deana Daponte Dave Jones Realty, LLC

  • /36

    $599,900

    • 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
  • 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
    • 592 Benson Rd, Middlebury, CT 06762

      Est $495,234 Not Listed For Sale

      592 Benson Rd, Middlebury, CT 06762

      • 5 Beds
      • 2 Baths
      • 2,289 Sq Ft
      • Built 1978
      592 Benson Rd, Middlebury, CT 06762

      Last Sold Summary

      • 8% Above List Price
      • $200/SF
      • 3 Days On Market

      Last Sold Price $457,000

      Last Listing Agent Linda Andrikis West View Properties, LLC

  • /9

    $939,000 New Construction

    • 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
  • 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 $546,934

    Last Listing Agent Maria Cohen William Raveis Real Estate

    61 Stony Brook Rd, Middlebury, CT 06762
    • 294 Porter Ave, Middlebury, CT 06762

      Est $349,221 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% Above List Price
      • $302/SF
      • 4 Days On Market

      Last Sold Price $335,000

      Last Listing Agent Michelle Pavia William Raveis Real Estate

  • 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 $647,599

    Last Listing Agent Graham Klemm Klemm Real Estate Inc

    55 Westwood Dr, Middlebury, CT 06762
    • 828 Breakneck Hill Rd, Middlebury, CT 06762

      Est $507,654 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

      • 33% Above List Price
      • $173/SF
      • 17 Days On Market

      Last Sold Price $383,000

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

  • /40

    $485,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    420 Charcoal Ave, Middlebury, CT 06762

    Not Your Typical Cape Style Home! This Beautifully Maintained 3 BD Home in Middlebury is Situated on 1.70 Acres and Exemplifies all the Love and Care Taken by its Owner! Surrounded by Lush Mature Landscaping, This Home Offers a Serenity Inspired Outdoor Living Spaces! Enjoy the Sounds of Birds while Sitting on Your Rear Patio. Or Host Dinner Parties in the Enclosed Sunroom on a Cool Summer

    Bethany Lydem Stone Crest Realty LLC

    420 Charcoal Ave, 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

    Current Estimated Value $85,545

    Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

    440 Lake Shore Dr, Middlebury, CT 06762
    • Unlisted Address

      Est $1,031,190 Not Listed For Sale

      Unlisted Address

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

      Last Sold Summary

      • 24% Below List Price
      • $234/SF
      • 54 Days On Market

      Last Sold Price $1,360,000

      Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  • /37

    $759,000

    • 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
  • 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 $476,585

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    • 140 Glenwood Ave, Middlebury, CT 06762

      Est $391,006 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

      • 17% Above List Price
      • $205/SF
      • 35 Days On Market

      Last Sold Price $335,000

      Last Listing Agent Karen Dibble-flaherty Keller Williams Realty

Showing Results 121 - 160, Page 4 of 18

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