Middlebury, CT Homes

• 

  Est $968,008 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,172 Sq Ft

  410 Charcoal Ave, Middlebury, CT 06762

  410 Charcoal Ave, Middlebury, CT 06762
• 

  

  

  /9

  $560,753 Pending

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

  0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762

  5 Units Remaining! 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 Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
• 

  $555,000 Sold Jul 02, 2025

  94 Upper Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 1944

  Last Sold Summary

  • 3% Above List Price
  • $274/SF
  • 47 Days On Market

  Current Estimated Value $560,990

  Last Listing Agent Gina Williams Preston Gray Real Estate

  94 Upper Whittemore Rd, Middlebury, CT 06762
• 

  Est $773,340 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,750 Sq Ft

  261 Sandy Hill Rd, Middlebury, CT 06762

  261 Sandy Hill Rd, Middlebury, CT 06762
• 

  

  /2

  $739,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,466 Sq Ft

  28 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ sq ft 4 bedroom colonial. Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

  Jodi Dawley Real Estate Two

  28 Hunting Ridge Rd, Middlebury, CT 06762
• 

  $675,000 Sold Jun 06, 2025

  400 Long Meadow Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,778 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Above List Price
  • $243/SF
  • 44 Days On Market

  Current Estimated Value $686,721

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  400 Long Meadow Rd, Middlebury, CT 06762
• 

  Est $512,639 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  109 Marney Dr, Middlebury, CT 06762

  109 Marney Dr, Middlebury, CT 06762
• 

  

  /9

  $509,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  0 N Benson Rd Unit 50 24118969, 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 Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
• 

  $440,000 Sold Jun 24, 2025

  69 Nick Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,414 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Above List Price
  • $311/SF
  • 38 Days On Market

  Current Estimated Value $438,415

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  69 Nick Rd, Middlebury, CT 06762
• 

  Est $504,266 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,973 Sq Ft

  530 Whittemore Rd, Middlebury, CT 06762

  530 Whittemore Rd, Middlebury, CT 06762
• 

  

  /18

  $389,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,861 Sq Ft

  32 Yale Ave, Middlebury, CT 06762

  The best value in Middlebury! Welcome to 32 Yale Avenue, a home with inviting curb appeal in a desirable neighborhood just steps from the scenic Greenway Trails. This spacious property combines architectural interest with modern amenities. Inside, you'll find generous living and dining rooms with hardwood floors throughout and a cozy fireplace for added charm. A versatile first floor bedroom is

  Martha Quaratella Coldwell Banker Realty

  32 Yale Ave, Middlebury, CT 06762
• 

  $480,000 Sold Nov 07, 2025

  30 Nick Rd, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 2,496 Sq Ft
  • Built 2011

  Last Sold Summary

  • 9% Below List Price
  • $192/SF
  • 113 Days On Market

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  30 Nick Rd, Middlebury, CT 06762
• 

  Est $698,178 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,728 Sq Ft

  783 Whittemore Rd, Middlebury, CT 06762

  783 Whittemore Rd, Middlebury, CT 06762
• 

  

  /40

  $530,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 2,011 Sq Ft

  13 Caveson Ct, Middlebury, CT 06762

  Welcome to this beautifully updated Osborn 2 model located in the highly desirable Steeplechase community, offering the convenience of natural gas, public water, and public sewer. This versatile home features two spacious primary suites-one on the main level and one upstairs-each with its own en-suite bath, providing flexible living arrangements. The main level boasts an open-concept layout with

  Kate Willoughby Gina Jacobs Real Estate

  13 Caveson Ct, Middlebury, CT 06762
• 

  $565,000 Sold Jun 18, 2025

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,882 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $300/SF
  • 71 Days On Market

  Current Estimated Value $577,084

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762
• 

  Est $522,240 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,030 Sq Ft

  312 Three Mile Hill Rd, Middlebury, CT 06762

  312 Three Mile Hill Rd, Middlebury, CT 06762
• 

  

  /24

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,660 Sq Ft

  541 Benson Rd, Middlebury, CT 06762

  MAIN HOUSE (2BR/2BA): Features an open-concept layout w/ gleaming hardwood floors. The updated kitchen is a chef's delight, boasting granite countertops, stainless steel appliances, a gas stove & pantry. The main level includes a bedroom & a NEW spa-like full bath w/ a custom tiled walk-in shower & separate soaking tub. Upstairs is a private primary suite retreat, wrapped in warm pine woodwork,

  Joseph Martino Joseph Martino Real Estate

  541 Benson Rd, Middlebury, CT 06762
• 

  $710,000 Sold Dec 18, 2025

  111 Dwyer Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,212 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $221/SF
  • 162 Days On Market

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  111 Dwyer Rd, Middlebury, CT 06762
• 

  Est $854,582 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,098 Sq Ft

  588 Charcoal Ave, Middlebury, CT 06762

  588 Charcoal Ave, Middlebury, CT 06762
• 

  

  /29

  $335,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  348 Kelly Rd, Middlebury, CT 06762

  Charming Cape Cod home ideally located just a minute from Memorial Middle School and close to everything Middlebury has to offer. This home features hardwood floors throughout, creating a warm and timeless feel from the moment you step inside. The eat in kitchen offers a comfortable space for everyday meals, while the 12x12 deck overlooks a nice yard--perfect for outdoor dining in summer and

  Stephanie Oliver Dave Jones Realty, LLC

  348 Kelly Rd, Middlebury, CT 06762
• 

  $975,000 Sold Nov 17, 2025

  82 Mirey Dam Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,471 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Above List Price
  • $281/SF
  • 4 Days On Market

  Last Listing Agent Jetlir Kulla Coldwell Banker Realty

  82 Mirey Dam Rd, Middlebury, CT 06762
• 

  Est $544,870 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,917 Sq Ft

  13 Hackamore Cir, Middlebury, CT 06762

  13 Hackamore Cir, Middlebury, CT 06762
• 

  

  /9

  $555,888 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,252 Sq Ft

  0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762

  Only 3 Units Remaining! 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 Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
• 

  $499,900 Sold Aug 26, 2025

  58 Shadduck Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,360 Sq Ft
  • Built 1934

  Last Sold Summary

  • 23% Below List Price
  • $212/SF
  • 150 Days On Market

  Current Estimated Value $489,358

  Last Listing Agent Amber Segetti RE/MAX RISE

  58 Shadduck Rd, Middlebury, CT 06762
• 

  Est $532,401 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,917 Sq Ft

  5 Kimberwick Ct, Middlebury, CT 06762

  5 Kimberwick Ct, Middlebury, CT 06762
• 

  /2

  $799,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  18 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 18 Deer Run Road (aka Lot 20) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

  Jodi Dawley Real Estate Two

  18 Deer Run Rd, Middlebury, CT 06762
• 

  $750,000 Sold Jul 23, 2025

  34 Avalon Dr, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 3,374 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $222/SF
  • 62 Days On Market

  Current Estimated Value $766,618

  Last Listing Agent Connie Widmann William Raveis Real Estate

  34 Avalon Dr, Middlebury, CT 06762
• 

  Est $332,063 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,136 Sq Ft

  3 Weymouth Way, Middlebury, CT 06762

  3 Weymouth Way, Middlebury, CT 06762
• 

  

  /7

  $925,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  22 Somerset Dr, Middlebury, CT 06762

  TO BE BUILT. One of the most desirable neighborhoods in Middlebury! The Avalon Farms community is comprised of lovely homes, manicured lawns, and beautiful gardens resulting in a unique aesthetic. The Cambridge model showcases a classic design combined with today's "must haves" that will meet all your expectations of an open floor plan. The great room with a cathedral ceiling, fireplace, and

  Ellie Gollenberg BHGRE Gaetano Marra Homes

  22 Somerset Dr, Middlebury, CT 06762
• 

  $655,000 Sold Feb 14, 2025

  11 Strathmore Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft
  • Built 1984

  Last Sold Summary

  • 5% Above List Price
  • $241/SF
  • 15 Days On Market

  Current Estimated Value $679,264

  Last Listing Agent Heather Dever Showcase Realty, Inc.

  11 Strathmore Rd, Middlebury, CT 06762
• 

  Est $564,463 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,461 Sq Ft

  5 Pommel Ln, Middlebury, CT 06762

  5 Pommel Ln, Middlebury, CT 06762
• 

  

  /5

  $1,600,000

  • Land
  • 29 Acres
  • $55,172 per Acre

  0 White Birch Unit 24141986, Middlebury, CT 06762

  Attention Builders, Developers, and Investors: fully approved 10 LOT Subdivision for sale in the charming town of Middlebury, CT (29 Acres total) With comprehensive approvals in place including Planning & Zoning, Wetlands, and Health Department clearances, you can get straight to work developing your vision. Each lot is designed to feature a private well and connection to public sewer. Middlebury

  Donna Kennedy Compass Connecticut, LLC

  0 White Birch Unit 24141986, Middlebury, CT 06762
• 

  $505,000 Sold May 23, 2025

  713 Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft
  • Built 1916

  Last Sold Summary

  • 1% Above List Price
  • $342/SF
  • 2 Days On Market

  Current Estimated Value $499,482

  Last Listing Agent Robert Vignola Coldwell Banker Realty

  713 Whittemore Rd, Middlebury, CT 06762
• 

  Est $575,083 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  9 Caveson Ct, Middlebury, CT 06762

  9 Caveson Ct, Middlebury, CT 06762
• 

  

  /28

  $721,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  3 Pine Ridge Unit 23, Middlebury, CT 06762

  Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

  Robert Michaud Michaud Real Estate

  3 Pine Ridge Unit 23, Middlebury, CT 06762
• 

  $304,150 Sold Oct 24, 2025

  82 Tucker Hill Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 941 Sq Ft
  • Built 1936

  Last Sold Summary

  • 5% Below List Price
  • $323/SF
  • 24 Days On Market

  Last Listing Agent Kary Apanovitch Coldwell Banker Realty

  82 Tucker Hill Rd, Middlebury, CT 06762
• 

  Est $560,839 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  17 Caveson Ct, Middlebury, CT 06762

  17 Caveson Ct, Middlebury, CT 06762
• 

  

  /15

  $649,900

  • 4 Beds
  • 3 Baths
  • 2,878 Sq Ft

  72 Carriage Dr, Middlebury, CT 06762

  A grand Cape Cod-style home, nestled in a wonderful and convenient neighborhood. The interior has been freshly painted, and the main level features primarily hardwood flooring. Just off the foyer, you'll find a sunken living room that welcomes you. The spacious eat-in kitchen has been remodeled and opens to the formal dining room, making it perfect for entertaining. Adjacent to the kitchen is a

  Justin Bette Century 21 Bette Real Estate

  72 Carriage Dr, Middlebury, CT 06762
• 

  $600,000 Sold Mar 13, 2025

  6 Ridgewood Dr, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,071 Sq Ft
  • Built 2007

  Last Sold Summary

  • $195/SF
  • 71 Days On Market

  Current Estimated Value $626,345

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  6 Ridgewood Dr, Middlebury, CT 06762
• 

  Est $384,079 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,244 Sq Ft

  130 White Ave, Middlebury, CT 06762

  130 White Ave, Middlebury, CT 06762

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