Middlebury, CT Homes

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  /38

  $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
• 

  $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 $436,934

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  69 Nick Rd, Middlebury, CT 06762
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  Est $529,085 Not Listed For Sale

  18 Jericho Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,908 Sq Ft
  • Built 1978

  18 Jericho Rd, Middlebury, CT 06762

  Last Sold Summary

  • $182/SF
  • 61 Days On Market

  Last Sold Price $530,000

  Last Listing Agent Michael Bachmann HomeSmart Homes and Estates
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  /40

  $569,500 Pending

  • 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
• 

  $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

  Current Estimated Value $487,804

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  30 Nick Rd, Middlebury, CT 06762
• 

  Est $624,165 Not Listed For Sale

  150 Carriage Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,492 Sq Ft
  • Built 1963

  150 Carriage Dr, Middlebury, CT 06762

  Last Sold Summary

  • 1% Above List Price
  • $249/SF
  • 4 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Colleen Burne Coldwell Banker Realty
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  /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 Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 44 24109951, 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 $573,920

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762
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  Est $597,861 Not Listed For Sale

  1600 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,932 Sq Ft
  • Built 1950

  1600 Straits Turnpike, Middlebury, CT 06762

  Last Sold Summary

  • 59% Above List Price
  • $194/SF
  • 51 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Lauren Cavallo Lauren Ashley Homes LLC
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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
• 

  $565,000 Sold Jan 14, 2026

  27 Winding Trail Unit 27, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft
  • Built 2014

  Last Sold Summary

  • $211/SF
  • 89 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  27 Winding Trail Unit 27, Middlebury, CT 06762
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  Est $956,448 Not Listed For Sale

  410 Charcoal Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,172 Sq Ft
  • Built 2006

  410 Charcoal Ave, Middlebury, CT 06762

  Last Sold Summary

  • 16% Above List Price
  • $260/SF
  • 19 Days On Market

  Last Sold Price $825,000

  Last Listing Agent Blair Patterson William Raveis Real Estate
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  /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
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  $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

  Current Estimated Value $700,534

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  111 Dwyer Rd, Middlebury, CT 06762
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  Est $770,789 Not Listed For Sale

  261 Sandy Hill Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,750 Sq Ft
  • Built 1997

  261 Sandy Hill Rd, Middlebury, CT 06762

  Last Sold Summary

  • 10% Above List Price
  • $187/SF
  • 34 Days On Market

  Last Sold Price $699,900

  Last Listing Agent Karen Berwick Real Estate Two
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  /15

  $649,900 Pending

  • 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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  $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

  Current Estimated Value $969,884

  Last Listing Agent Jetlir Kulla Coldwell Banker Realty

  82 Mirey Dam Rd, Middlebury, CT 06762
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  Est $516,994 Not Listed For Sale

  109 Marney Dr, Middlebury, CT 06762

  • 5 Beds
  • 2.5 Baths
  • 2,696 Sq Ft
  • Built 1966

  109 Marney Dr, Middlebury, CT 06762

  Last Sold Summary

  • 26% Above List Price
  • $152/SF
  • 37 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Karen Griffin Coldwell Banker Realty
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  /31

  $749,900

  • 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
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  $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 $484,521

  Last Listing Agent Amber Segetti RE/MAX RISE

  58 Shadduck Rd, Middlebury, CT 06762
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  Est $481,030 Not Listed For Sale

  530 Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 2,973 Sq Ft
  • Built 1940

  530 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • $161/SF
  • 85 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Monique Jacobs RE/MAX
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  /14

  $729,990

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

  321 Artillery Rd, Middlebury, CT 06762

  Large Colonial with charm and character ready to call home! Offering privacy on its fabulous 4 acres with magical views and abundant sunlight. The home offers four large bedrooms with ample light that will surely please. The formal living room complete with a large picture window and marble fireplace will serve as a great place to relax at the end of a long day. The dining room is ready to host

  Frank Durante William Raveis Real Estate

  321 Artillery Rd, Middlebury, CT 06762
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  $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 $771,268

  Last Listing Agent Connie Widmann William Raveis Real Estate

  34 Avalon Dr, Middlebury, CT 06762
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  Est $667,226 Not Listed For Sale

  783 Whittemore Rd, Middlebury, CT 06762

  • 5 Beds
  • 3 Baths
  • 3,728 Sq Ft
  • Built 1953

  783 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 1% Below List Price
  • $181/SF
  • 182 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
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  /25

  $700,000

  • 3 Beds
  • 2.5 Baths
  • 2,734 Sq Ft

  70 Pine Hollow Dr, Middlebury, CT 06762

  A private hilltop retreat at the end of a quiet cul-de-sac, this stunning 8-room contemporary is set well back from the road on a picturesque knoll, offering exceptional privacy and a peaceful natural setting. Custom built and proudly maintained by its original owner, the home features soaring ceilings, expansive rooms, and walls of windows that flood the interior with natural light. The open,

  Lynn LaForme Regency Real Estate, LLC

  70 Pine Hollow Dr, Middlebury, CT 06762
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  $4,050,000 Sold Jan 15, 2026

  7 Sandy Beach Rd, Middlebury, CT 06762

  • 6 Beds
  • 4 Baths
  • 5,816 Sq Ft
  • Built 2000

  Last Sold Summary

  • 1% Below List Price
  • $696/SF
  • 35 Days On Market

  Last Listing Agent Beverly Mosch William Pitt Sotheby's Int'l

  7 Sandy Beach Rd, Middlebury, CT 06762
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  Est $578,398 Not Listed For Sale

  312 Three Mile Hill Rd, Middlebury, CT 06762

  • 5 Beds
  • 2.5 Baths
  • 3,030 Sq Ft
  • Built 1950

  312 Three Mile Hill Rd, Middlebury, CT 06762

  Last Sold Summary

  • 14% Above List Price
  • $168/SF
  • 186 Days On Market

  Last Sold Price $508,500

  Last Listing Agent Marian Van Egas Berkshire Hathaway Home Services
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  /40

  $689,000 Pending

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

  84 Munson Rd, Middlebury, CT 06762

  Experience comfort, space, and scenic surroundings at 84 Munson Road, Middlebury, CT 06762, a well-situated home set in a peaceful and desirable community. This inviting property offers a thoughtfully designed layout with generous living areas filled with natural light, creating a bright and welcoming atmosphere. The main level provides ideal flow for everyday living and entertaining, while the

  Thomas Mele Dorrance Realty

  84 Munson Rd, Middlebury, CT 06762
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  $545,000 Sold Feb 26, 2026

  2 Dogwood Ct, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 3,103 Sq Ft
  • Built 2007

  Last Sold Summary

  • 8% Below List Price
  • $176/SF
  • 202 Days On Market

  Current Estimated Value $605,053

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  2 Dogwood Ct, Middlebury, CT 06762
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  Est $811,086 Not Listed For Sale

  588 Charcoal Ave, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 4,098 Sq Ft
  • Built 1982

  588 Charcoal Ave, Middlebury, CT 06762

  Last Sold Summary

  • 13% Above List Price
  • $176/SF
  • 270 Days On Market

  Last Sold Price $720,000

  Last Listing Agent Joann Murray Weichert Corporate
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  /33

  $750,000 Pending

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

  366 Charcoal Ave, Middlebury, CT 06762

  This beautiful 9 room colonial has every attention to detail and all the features that a discriminating buyer is looking for. Set on a private 3.34 acre lot with a 10' X 16' shed in a sought-after, very commuter friendly neighborhood, this 3,198 square foot residence boasts 4 bedrooms, 2-1/2 bathrooms, a bright and airy 25' X25' main floor family room with cathedral ceilings, built-ins, a

  Stephen Briotti Lamacchia Realty

  366 Charcoal Ave, Middlebury, CT 06762
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  $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 $502,993

  Last Listing Agent Robert Vignola Coldwell Banker Realty

  713 Whittemore Rd, Middlebury, CT 06762
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  Est $527,102 Not Listed For Sale

  13 Hackamore Cir, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 1,917 Sq Ft
  • Built 1998

  13 Hackamore Cir, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $255/SF
  • 34 Days On Market

  Last Sold Price $489,000

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes
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  /9

  $548,828 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
• 

  $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

  Current Estimated Value $305,778

  Last Listing Agent Kary Apanovitch Coldwell Banker Realty

  82 Tucker Hill Rd, Middlebury, CT 06762
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  Est $503,637 Not Listed For Sale

  5 Kimberwick Ct, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 1,917 Sq Ft
  • Built 1997

  5 Kimberwick Ct, Middlebury, CT 06762

  Last Sold Summary

  • 3% Above List Price
  • $254/SF
  • 55 Days On Market

  Last Sold Price $487,400

  Last Listing Agent Jane Spino Showcase Realty, Inc.
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  /16

  $427,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,422 Sq Ft

  192 Breakneck Hill Rd, Middlebury, CT 06762

  Welcome to this Charming Well Maintained 4 bedroom ranch. 2 full baths. This inviting home features a large bright living room with picture window overlooking beautiful landscaped yard. Beautiful hardwood floors through out. Needs some updating. Finished room in lower level with walk out leading to patio. Two Car Garage. Central Air. Public Sewer. House generator stays. Well Water. Don't miss out

  Maria Pinheiro RE/MAX RISE

  192 Breakneck Hill Rd, Middlebury, CT 06762
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  $649,500 Sold Jul 25, 2025

  405 Chestnut Cir Unit 77, Middlebury, CT 06762

  • 2 Beds
  • 3 Baths
  • 2,292 Sq Ft
  • Built 2025

  Last Sold Summary

  • $283/SF
  • 99 Days On Market

  Current Estimated Value $648,808

  Last Listing Agent Jodi Dawley Real Estate Two

  405 Chestnut Cir Unit 77, Middlebury, CT 06762
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  Est $289,698 Not Listed For Sale

  3 Weymouth Way, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,136 Sq Ft
  • Built 1997

  3 Weymouth Way, Middlebury, CT 06762

  Last Sold Summary

  • 21% Above List Price
  • $210/SF
  • 22 Days On Market

  Last Sold Price $238,700

  Last Listing Agent Cheryl Grabowski Weichert Corporate
• 

  

  /25

  $585,000

  • 4 Beds
  • 3.5 Baths
  • 2,691 Sq Ft

  66 Artillery Rd, Middlebury, CT 06762

  Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The

  Maria Taylor Klemm Real Estate Inc

  66 Artillery Rd, Middlebury, CT 06762

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