3,768

Middlebury, CT Homes

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  • /9

    $525,438

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

    0 N Benson Rd Unit 45 24089121, 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 45 24089121, 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 $489,539

    Last Listing Agent Karen Stanco Showcase Realty, Inc.

    18 Freedom Rd, Middlebury, CT 06762
    • 169 Sandy Hill Rd, Middlebury, CT 06762

      Est $627,737

      Not Listed For Sale

      169 Sandy Hill Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,639 Sq Ft
      • Built 1995
      169 Sandy Hill Rd, Middlebury, CT 06762

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  • /9

    $572,000

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

    0 N Benson Rd Unit 56, 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 56, 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 $474,914

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    637 Watertown Rd, Middlebury, CT 06762
    • 240 Carriage Dr, Middlebury, CT 06762

      Est $572,726

      Not Listed For Sale

      240 Carriage Dr, Middlebury, CT 06762

      • 4 Beds
      • 2 Baths
      • 2,351 Sq Ft
      • Built 1964
      240 Carriage Dr, Middlebury, CT 06762

      Last Sold Summary

      • 243 Days On Market

      Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  • /9

    $548,828

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 2,462 Sq Ft

    0 N Benson Rd Unit 55 24086408, 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 55 24086408, 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
    • 94 Upper Whittemore Rd, Middlebury, CT 06762

      Est $572,759

      Not Listed For Sale

      94 Upper Whittemore Rd, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 2,024 Sq Ft
      • Built 1944
      94 Upper Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Gina Williams Preston Gray Real Estate

  • /9

    $568,564

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

    0 N Benson Rd Unit 59 24116892, 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 59 24116892, Middlebury, CT 06762
  • 38 Avalon Dr, Middlebury, CT 06762

    $815,000

    Sold Jul 29, 2026

    38 Avalon Dr, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Above List Price
    • $253/SF
    • 2 Days On Market

    Current Estimated Value $774,196

    Last Listing Agent Tracy Wilson Lamacchia Realty

    38 Avalon Dr, Middlebury, CT 06762
    • 69 Nick Rd, Middlebury, CT 06762

      Est $443,396

      Not Listed For Sale

      69 Nick Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 1,414 Sq Ft
      • Built 1950
      69 Nick Rd, Middlebury, CT 06762

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Beth Santos Showcase Realty, Inc.

  • /31

    $539,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,181 Sq Ft

    4 Kimberwick Ct, Middlebury, CT 06762

    Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both

    David Scolpino Nationwide Homes

    4 Kimberwick Ct, Middlebury, CT 06762
  • 321 Artillery Rd, Middlebury, CT 06762

    $602,500

    Sold Aug 03, 2026

    321 Artillery Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft
    • Built 1955

    Last Sold Summary

    • 17% Below List Price
    • $183/SF
    • 144 Days On Market

    Current Estimated Value $696,715

    Last Listing Agent Frank Durante William Raveis Real Estate

    321 Artillery Rd, Middlebury, CT 06762
    • 252 White Ave, Middlebury, CT 06762

      Est $442,188

      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

      • 4 Days On Market

      Last Listing Agent Tom Slekis Berkshire Hathaway NE Prop.

  • /22

    $675,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,938 Sq Ft

    179 Burr Hall Rd, Middlebury, CT 06762

    This stunning ranch blends contemporary style with effortless one-level living. The open floor plan is filled with natural light, highlighted by dramatic floor-to-ceiling windows that create a bright and inviting atmosphere throughout. The beautifully updated interior features a luxurious primary suite and stylish, high-quality finishes at every turn. Designed for both everyday living and

    Lynn LaForme Regency Real Estate, LLC

    179 Burr Hall Rd, Middlebury, CT 06762
  • 420 Charcoal Ave, Middlebury, CT 06762

    $475,000

    Sold Jul 31, 2026

    420 Charcoal Ave, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft
    • Built 1883

    Last Sold Summary

    • 2% Below List Price
    • $302/SF
    • 86 Days On Market

    Current Estimated Value $484,702

    Last Listing Agent Bethany Lydem Stone Crest Realty LLC

    420 Charcoal Ave, Middlebury, CT 06762
    • 1738 Middlebury Rd, Middlebury, CT 06762

      Est $521,676

      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

      • 32 Days On Market

      Last Listing Agent April Stirling Coldwell Banker Realty

  • /9

    $573,584

    New Construction 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
  • 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 $540,092

    Last Listing Agent Lisa Clarke Dave Jones Realty, LLC

    76 Three Mile Hill Rd, Middlebury, CT 06762
    • 615 Long Meadow Rd, Middlebury, CT 06762

      Est $446,594

      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

      • 1 Day On Market

      Last Listing Agent George Noujaim Dave Jones Realty, LLC

  • /36

    $650,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    200 Northridge Dr, Middlebury, CT 06762

    Welcome to this beautifully updated contemorary ranch offering an open floor plan, vaulted ceilings, and an inviting sense of space. Nestled among million dollar homes, this property combines comfort, style, and an exceptional location. The spacious living area features a cozy wood burning fireplace and flows seamlessly into the renovated kitchen with abundant cabinetry, a breakfast bar, a coffee

    Christina Zainc BHGRE Gaetano Marra Homes

    200 Northridge Dr, 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 $829,586

    Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

    1 Hampshire Ct, Middlebury, CT 06762
    • 22 Yale Ave, Middlebury, CT 06762

      Est $364,865

      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

      • 49 Days On Market

      Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  • 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 $648,129

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    51 Cross Rd, Middlebury, CT 06762
    • 450 Long Meadow Rd, Middlebury, CT 06762

      Est $653,245

      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

      • 107 Days On Market

      Last Listing Agent Heather Dever Showcase Realty, Inc.

  • 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 $820,266

    Last Listing Agent Jodi Dawley Real Estate Two

    11 Hunting Ridge Rd, Middlebury, CT 06762
    • 400 Long Meadow Rd, Middlebury, CT 06762

      Est $710,659

      Not Listed For Sale

      400 Long Meadow Rd, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,778 Sq Ft
      • Built 2002
      400 Long Meadow Rd, Middlebury, CT 06762

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  • 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
    • 481 Long Meadow Rd, Middlebury, CT 06762

      Est $803,428

      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

      • 92 Days On Market

      Last Listing Agent Allen Grealish Coldwell Banker Realty

  • 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
    • 15 Chatham Ct, Middlebury, CT 06762

      Est $697,973

      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

      • 3 Days On Market

      Last Listing Agent Pat Blanko William Raveis Real Estate

  • 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 $434,492

    Last Listing Agent Stephen Mele Houlihan Lawrence

    271 Shadduck Rd, Middlebury, CT 06762
    • 10 Stonington Ct, Middlebury, CT 06762

      Est $678,214

      Not Listed For Sale

      10 Stonington Ct, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,812 Sq Ft
      • Built 2005
      10 Stonington Ct, Middlebury, CT 06762

      Last Sold Summary

      • 209 Days On Market

      Last Listing Agent Scott Hellriegel Berkshire Hathaway NE Prop.

  • 84 Munson Rd, Middlebury, CT 06762

    $675,000

    Sold Jun 08, 2026

    84 Munson Rd, Middlebury, CT 06762

    • 4 Beds
    • 5 Baths
    • 3,254 Sq Ft
    • Built 1979

    Last Sold Summary

    • 5% Below List Price
    • $207/SF
    • 59 Days On Market

    Current Estimated Value $695,537

    Last Listing Agent Adam Devine Dorrance Realty

    84 Munson Rd, Middlebury, CT 06762
    • 6 Colonial Ct, Middlebury, CT 06762

      Est $685,090

      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

      • 49 Days On Market

      Last Listing Agent Norinne Byrne Calcagni Real Estate

  • 366 Charcoal Ave, Middlebury, CT 06762

    $750,000

    Sold May 27, 2026

    366 Charcoal Ave, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,198 Sq Ft
    • Built 1998

    Last Sold Summary

    • $235/SF
    • 23 Days On Market

    Current Estimated Value $750,635

    Last Listing Agent Stephen Briotti Lamacchia Realty

    366 Charcoal Ave, Middlebury, CT 06762
    • 1 Chatham Ct, Middlebury, CT 06762

      Est $665,934

      Not Listed For Sale

      1 Chatham Ct, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,950 Sq Ft
      • Built 2005
      1 Chatham Ct, Middlebury, CT 06762

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Norinne Byrne Calcagni Real Estate

  • 18 Winding Trail, Middlebury, CT 06762

    $695,000

    Sold Nov 21, 2025

    18 Winding Trail, Middlebury, CT 06762

    • 3 Beds
    • 5 Baths
    • 4,051 Sq Ft
    • Built 2014

    Last Sold Summary

    • 4% Below List Price
    • $172/SF
    • 36 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    18 Winding Trail, Middlebury, CT 06762
    • 3 Independence Cir, Middlebury, CT 06762

      Est $658,547

      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

      • 23 Days On Market

      Last Listing Agent Kristen Stolfi Berkshire Hathaway NE Prop.

Showing Results 201 - 240, Page 6 of 18

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