Middlebury, CT Homes

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  $599,900 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,749 Sq Ft

  428 Breakneck Hill Rd, Middlebury, CT 06762

  Set on more than 4 peaceful, pastoral acres, this beautifully remodeled ranch offers the ideal blend of character, craftsmanship, and modern comfort. Lovingly restored during the owner's tenure, the home showcases thoughtful upgrades and timeless details throughout. A newly built oversized two car garage provides excellent storage and convenience. Inside, the custom kitchen-designed and crafted

  

  Mary Ann Hebert

  BHGRE Gaetano Marra Homes

  (203) 693-8994

  428 Breakneck Hill Rd, Middlebury, CT 06762
• Explore Middlebury

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  $1,800 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,604 Sq Ft
  • House for Rent

  1129 Southford Rd, Middlebury, CT 06762

  1 BR lower level apartment with all utilities included. In unit washer and dryer, private rear entrance. Freshly painted and new carpet. Conveniently located to route 84

  Doug Rose Scalzo Real Estate

  1129 Southford Rd, Middlebury, CT 06762
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  $505,000 Sold Jul 30, 2025

  1440 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $247/SF
  • 3 Days On Market

  Current Estimated Value $494,747

  Last Listing Agent Linda Mayfield RE/MAX RISE

  1440 Straits Turnpike, Middlebury, CT 06762
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  Est $679,264 Not Listed For Sale

  11 Strathmore Rd, Middlebury, CT 06762

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

  11 Strathmore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 4% Above List Price
  • $241/SF
  • 15 Days On Market

  Last Sold Price $655,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
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  $699,900

  • Land
  • 2.31 Acres
  • $302,987 per Acre

  Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762

  This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond.

  

  Mary Ann Hebert

  BHGRE Gaetano Marra Homes

  (475) 255-6254

  Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
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  $3,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • House for Rent

  346 Middlebury Rd, Middlebury, CT 06762

  Welcome home to this completely renovated and expanded cape located on almost 3/4 acre of private park-like grounds! Conveniently located in the heart of Middlebury just steps from Bristol Park and the Middlebury Greenway, you'll love the open concept modern feel with new kitchen cabinets, granite counters and stainless-steel appliances. The open concept main level provides great space to

  Tanya Uhelsky RE/MAX RISE

  346 Middlebury Rd, Middlebury, CT 06762
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  $520,000 Sold Oct 22, 2025

  8 Kimberwick Ct, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,147 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 78 Days On Market

  Current Estimated Value $532,760

  Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

  8 Kimberwick Ct, Middlebury, CT 06762
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  Est $632,018 Not Listed For Sale

  89 Tyler Crossing, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,704 Sq Ft
  • Built 1998

  89 Tyler Crossing, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $216/SF
  • 99 Days On Market

  Last Sold Price $585,000

  Last Listing Agent Matt Rose Keller Williams Realty
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  $75,000 Pending

  • Land
  • 1.64 Acres
  • $45,732 per Acre

  0 Ferndale Ave, Middlebury, CT 06762

  For Sale: Unique Development Opportunity Offering a rare opportunity to acquire a three-lot subdivision in Middlebury. This property consists of three separate parcels that must be sold together. While previously approved, buyers are responsible for verifying the current status of approvals and conducting their own due diligence. The site presents some challenges due to significant ledge, which

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 258-7617

  0 Ferndale Ave, Middlebury, CT 06762
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  $17,000 total monthly price

  • 5 Beds
  • 7 Baths
  • 6,600 Sq Ft
  • House for Rent

  372 Tucker Hill Rd, Middlebury, CT 06762

  5 bedrooms 4,3 baths cape house set on 3.5 acres.

  Naima Mazouzi Eagle Eye Realty PLLC

  372 Tucker Hill Rd, Middlebury, CT 06762
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  $620,000 Sold Mar 28, 2025

  191 Ridgewood Dr Unit 191, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $233/SF
  • 79 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  191 Ridgewood Dr Unit 191, Middlebury, CT 06762
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  Est $537,770 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

  • 8% Above List Price
  • $213/SF
  • 243 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes
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  $750,000

  • 4 Beds
  • 4 Baths
  • 3,360 Sq Ft

  200 N Farm Rd, Middlebury, CT 06762

  Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth

  Jackie Desmarais Showcase Realty, Inc.

  200 N Farm Rd, Middlebury, CT 06762
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  $480,000 Sold Apr 25, 2025

  36 Aveline Ave, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft
  • Built 1952

  Last Sold Summary

  • $269/SF
  • 44 Days On Market

  Current Estimated Value $488,913

  Last Listing Agent Wayne Watt Jr. THE CONNECTICUT AGENCY LLC

  36 Aveline Ave, Middlebury, CT 06762
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  Est $768,945 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

  • 5% Above List Price
  • $244/SF
  • 92 Days On Market

  Last Sold Price $735,000

  Last Listing Agent Allen Grealish Coldwell Banker Realty
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  $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
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  $882,500 Sold Sep 25, 2025

  171 Judd Hill Rd, Middlebury, CT 06762

  • 5 Beds
  • 4 Baths
  • 3,700 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $239/SF
  • 49 Days On Market

  Current Estimated Value $864,780

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  171 Judd Hill Rd, Middlebury, CT 06762
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  Est $391,135 Not Listed For Sale

  91 Richardson Dr, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,788 Sq Ft
  • Built 1975

  91 Richardson Dr, Middlebury, CT 06762

  Last Sold Summary

  • 4% Above List Price
  • $210/SF
  • 69 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.
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  $739,900 Open Sun 12PM - 2PM

  • 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
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  $525,000 Sold Oct 16, 2025

  6 Pommel Ln Unit 6, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 1,917 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Above List Price
  • $274/SF
  • 52 Days On Market

  Current Estimated Value $518,029

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  6 Pommel Ln Unit 6, Middlebury, CT 06762
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  Est $553,813 Not Listed For Sale

  1053 Middlebury Rd, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 2,373 Sq Ft
  • Built 1971

  1053 Middlebury Rd, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $217/SF
  • 146 Days On Market

  Last Sold Price $515,000

  Last Listing Agent Barbara Sivba Coldwell Banker Realty
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  $545,400 Pending

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

  0 N Benson Rd Unit 62, 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 62, Middlebury, CT 06762
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  $585,000 Sold Jan 29, 2026

  126 Colonial Ave, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 2,531 Sq Ft
  • Built 1911

  Last Sold Summary

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

  Current Estimated Value $591,809

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  126 Colonial Ave, Middlebury, CT 06762
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  Est $624,211 Not Listed For Sale

  428 Benson Rd, Middlebury, CT 06762

  • 5 Beds
  • 4 Baths
  • 3,106 Sq Ft
  • Built 1962

  428 Benson Rd, Middlebury, CT 06762

  Last Sold Summary

  • 10% Above List Price
  • $184/SF
  • 55 Days On Market

  Last Sold Price $570,000

  Last Listing Agent Jason Malagutti Regency Real Estate, LLC
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  $569,500 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,295 Sq Ft

  1 Arrowwood Ct Unit 1, Middlebury, CT 06762

  Special end unit townhome filled with natural sunlight and serene pond views. Built in 2019 and meticulously maintained, this home offers the feel of new construction throughout. The main level features rich hardwood floors, expanded kitchen cabinetry, and access from the kitchen to a private, expanded deck, perfect for outdoor dining or relaxing. The living room includes a gas-burning fireplace

  Christina Zainc BHGRE Gaetano Marra Homes

  1 Arrowwood Ct Unit 1, Middlebury, CT 06762
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  $710,500 Sold Jun 20, 2025

  407 Chestnut Cir Unit 78, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 2,292 Sq Ft
  • Built 2023

  Last Sold Summary

  • 8% Above List Price
  • $310/SF
  • 520 Days On Market

  Current Estimated Value $634,693

  Last Listing Agent Jodi Dawley Real Estate Two

  407 Chestnut Cir Unit 78, Middlebury, CT 06762
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  Not Listed For Sale

  15 Lakeview Dr, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 2024

  15 Lakeview Dr, Middlebury, CT 06762

  Last Sold Summary

  • $250/SF
  • 78 Days On Market

  Last Sold Price $700,000

  Last Listing Agent George Harlamon Realty Group of New England, LLC
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  $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
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  $499,900 Sold Sep 30, 2025

  0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Built 2025

  Last Sold Summary

  • $256/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762
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  Not Listed For Sale

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft
  • Built 2014

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  Last Sold Summary

  • $219/SF
  • 83 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Karen Rigopulos BHGRE Gaetano Marra Homes
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  /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
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  $342,000 Sold Mar 21, 2025

  28 Yale Ave, Middlebury, CT 06762

  • 1 Bed
  • 2 Baths
  • 1,434 Sq Ft
  • Built 1923

  Last Sold Summary

  • 2% Below List Price
  • $238/SF
  • 6 Days On Market

  Current Estimated Value $363,341

  Last Listing Agent Lysa Napoli Showcase Realty, Inc.

  28 Yale Ave, Middlebury, CT 06762
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  Not Listed For Sale

  6 Burr Hall Rd, Middlebury, CT 06762

  6 Burr Hall Rd, Middlebury, CT 06762

  Last Sold Summary

  • 41 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Nancy Langrock William Raveis Real Estate
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  $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
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  $547,460 Sold Aug 15, 2025

  0 N Benson Rd Unit 37, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Above List Price
  • $281/SF
  • 163 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 37, Middlebury, CT 06762
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  Est $1,395,004 Not Listed For Sale

  397 White Deer Rock Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,363 Sq Ft
  • Built 2008

  397 White Deer Rock Rd, Middlebury, CT 06762

  Last Sold Summary

  • 18% Below List Price
  • $506/SF
  • 50 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  $649,900 Under Contract

  • 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
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  $380,000 Sold Nov 17, 2025

  146 Richardson Dr, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,499 Sq Ft
  • Built 1940

  Last Sold Summary

  • $254/SF
  • 38 Days On Market

  Current Estimated Value $374,291

  Last Listing Agent Nicholas Greene eXp Realty

  146 Richardson Dr, Middlebury, CT 06762
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  Est $549,403 Not Listed For Sale

  436 Judd Rd, Southbury, CT 06488

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1790

  436 Judd Rd, Southbury, CT 06488

  Last Sold Summary

  • 13% Above List Price
  • $389/SF
  • 47 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.
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  $810,000 New Construction

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

  6 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) 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

  6 Deer Run Rd, Middlebury, CT 06762

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