Middlebury, CT Homes

• 

  

  

  /40

  $729,900

  $35K PRICE DROP Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,302 Sq Ft

  168 N Farm Rd, Middlebury, CT 06762

  Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath Colonial is beautifully situated on 2.34 private acres offering the perfect blend of classic charm and comfortable living. A generous entry foyer welcomes you into a thoughtfully designed home featuring a formal living room with fireplace, elegant formal dining room and a spacious eat-in kitchen complete

  Karen Stanco Showcase Realty, Inc.

  168 N Farm Rd, Middlebury, CT 06762
• 

  $390,000

  Sold Jan 14, 2026

  32 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,861 Sq Ft
  • Built 1925

  Last Sold Summary

  • $210/SF
  • 54 Days On Market

  Current Estimated Value $394,191

  Last Listing Agent Martha Quaratella Coldwell Banker Realty

  32 Yale Ave, Middlebury, CT 06762
• 

  Est $517,022

  Not Listed For Sale

  133 1/2 Steinmann Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,083 Sq Ft
  • Built 1941

  133 1/2 Steinmann Ave, Middlebury, CT 06762

  Last Sold Summary

  • 69 Days On Market
• 

  

  

  /28

  $721,000

  New Construction 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
• 

  $465,000

  Sold Jun 17, 2026

  541 Benson Rd, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1942

  Last Sold Summary

  • 11% Below List Price
  • $291/SF
  • 25 Days On Market

  Current Estimated Value $518,914

  Last Listing Agent Joseph Martino Joseph Martino Real Estate

  541 Benson Rd, Middlebury, CT 06762
• 

  Est $263,376

  Not Listed For Sale

  2056 Straits Turnpike, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 2,528 Sq Ft
  • Built 1953

  2056 Straits Turnpike, Middlebury, CT 06762

  Last Sold Summary

  • 10 Days On Market
• 

  

  /9

  $523,920

  New Construction Pending

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

  0 N Benson Rd Unit 51 24117506, 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 51 24117506, Middlebury, CT 06762
• 

  $569,500

  Sold Jun 12, 2026

  1 Arrowwood Ct Unit 1, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,295 Sq Ft
  • Built 2019

  Last Sold Summary

  • $248/SF
  • 36 Days On Market

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  1 Arrowwood Ct Unit 1, Middlebury, CT 06762
• 

  Est $1,009,567

  Not Listed For Sale

  346 South St, Middlebury, CT 06762

  • 6 Beds
  • 7 Baths
  • 5,938 Sq Ft
  • Built 1958

  346 South St, Middlebury, CT 06762

  Last Sold Summary

  • 38 Days On Market
• 

  /2

  $849,900

  New Construction $40K PRICE INCREASE

  • 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
• 

  $530,000

  Sold Mar 24, 2026

  13 Caveson Ct, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 2,011 Sq Ft
  • Built 1996

  Last Sold Summary

  • $264/SF
  • 129 Days On Market

  Current Estimated Value $517,387

  Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

  13 Caveson Ct, Middlebury, CT 06762
• 

  Est $657,856

  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

  • 15 Days On Market
• 

  

  /38

  $834,900

  New Construction $75K PRICE INCREASE

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

  15 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) 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

  15 Hunting Ridge Rd, Middlebury, CT 06762
• 

  $360,000

  Sold Jan 30, 2026

  348 Kelly Rd, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1934

  Last Sold Summary

  • 7% Above List Price
  • $469/SF
  • 24 Days On Market

  Current Estimated Value $348,913

  Last Listing Agent Stephanie Oliver Dave Jones Realty, LLC

  348 Kelly Rd, Middlebury, CT 06762
• 

  Est $339,725

  Not Listed For Sale

  36 Richardson Dr, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft
  • Built 1920

  36 Richardson Dr, Middlebury, CT 06762

  Last Sold Summary

  • 62 Days On Market
• 

  

  /39

  $879,900

  • 3 Beds
  • 3.5 Baths
  • 3,494 Sq Ft

  25 Avalon Dr, Middlebury, CT 06762

  Located in one of Middlebury's most desirable and beautifully maintained subdivisions Avalon Farms with streetlights and Belgian block lined streets, this impressive 3 bedroom, 3 full and 1 half bath Colonial offers 3,494 square feet of refined and flexible living. Set on a premium, fully usable flat lot surrounded by mature pines for year round privacy, the home features Hardie Plank siding and

  Connie Widmann William Raveis Real Estate

  25 Avalon Dr, Middlebury, CT 06762
• 

  $63,250

  Sold Dec 05, 2025

  0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

  • Land
  • 33,105 Sq Ft
  • $83,224 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 80 Days On Market

  Last Listing Agent Rebecca Zandvliet Coldwell Banker Realty 2000

  0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
• 

  Est $503,355

  Not Listed For Sale

  130 Christian Rd, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 1,958 Sq Ft
  • Built 1940

  130 Christian Rd, Middlebury, CT 06762

  Last Sold Summary

  • 139 Days On Market
• 

  

  /9

  $562,350

  New Construction Pending

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

  0 N Benson Rd Unit 66, 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 66, Middlebury, CT 06762
• 

  $593,360

  Sold Oct 10, 2025

  0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

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

  Last Sold Summary

  • 17% Above List Price
  • $304/SF
  • 0 Days On Market

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762
• 

  Est $397,853

  Not Listed For Sale

  70 Steinmann Ave, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 1,486 Sq Ft
  • Built 1971

  70 Steinmann Ave, Middlebury, CT 06762

  Last Sold Summary

  • 112 Days On Market
• 

  

  /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
• 

  $810,000

  Sold May 08, 2026

  18 Deer Run Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $370/SF
  • 29 Days On Market

  Current Estimated Value $763,333

  Last Listing Agent Jodi Dawley Real Estate Two

  18 Deer Run Rd, Middlebury, CT 06762
• 

  Est $291,782

  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

  • 144 Days On Market
• 

  

  /9

  $522,128

  New Construction 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
• 

  $495,000

  Sold Dec 04, 2025

  116 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $214/SF
  • 51 Days On Market

  Current Estimated Value $493,590

  Last Listing Agent Dave Jones Dave Jones Realty, LLC

  116 Yale Ave, Middlebury, CT 06762
• 

  Est $762,107

  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

  • 84 Days On Market
• 

  

  /37

  $825,000

  Under Contract

  • 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
• 

  $625,000

  Sold Apr 10, 2026

  16 Winding Trail, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,646 Sq Ft
  • Built 2014

  Last Sold Summary

  • $236/SF
  • 29 Days On Market

  Last Listing Agent Georgieanna Fisher Home Selling Team

  16 Winding Trail, Middlebury, CT 06762
• 

  Est $692,620

  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

  • 8 Days On Market
• 

  

  /31

  $749,900

  Pending

  • 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
• 

  $520,000

  Sold Aug 08, 2025

  29 Winding Trail Unit 29, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $244/SF
  • 117 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  29 Winding Trail Unit 29, Middlebury, CT 06762
• 

  Est $429,625

  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

  • 177 Days On Market
• 

  

  /9

  $561,271

  New Construction 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
• 

  $420,000

  Sold Oct 09, 2025

  93 Fenn Rd, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,636 Sq Ft
  • Built 1951

  Last Sold Summary

  • 1% Below List Price
  • $257/SF
  • 62 Days On Market

  Current Estimated Value $417,727

  Last Listing Agent Rob Marucci Better Living Realty, LLC

  93 Fenn Rd, Middlebury, CT 06762
• 

  Est $1,000,807

  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

  • 80 Days On Market
• 

  

  /36

  $599,900

  $60K PRICE DROP Under Contract

  • 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
• 

  $435,000

  Sold Oct 14, 2025

  28 Maple Dr, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 1,596 Sq Ft
  • Built 1950

  Last Sold Summary

  • 17% Below List Price
  • $273/SF
  • 233 Days On Market

  Current Estimated Value $440,489

  Last Listing Agent Dean Giatas Fiorelli Realty, LLC

  28 Maple Dr, Middlebury, CT 06762
• 

  Est $417,700

  Not Listed For Sale

  460 Lake Shore Dr, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1981

  460 Lake Shore Dr, Middlebury, CT 06762

  Last Sold Summary

  • 68 Days On Market
• 

  

  /38

  $779,000

  Pending

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

  38 Avalon Dr, Middlebury, CT 06762

  Welcome to Avalon Farms community, located in one of Middlebury's distinctive residential communities, known for its beautifully built, upscale homes. The home is known for its European inspired architecture, beautifully preserved, natural surroundings, at the end of a cul-de-sac, which suits any stage of life you're in. Step inside to a grand two-story foyer that sets the tone for the homes

  Tracy Wilson Lamacchia Realty

  38 Avalon Dr, Middlebury, CT 06762

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