Middlebury, CT Homes

• 

  $300,000 Sold Jan 16, 2026

  73 Yale Ave, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft
  • Built 1945

  Last Sold Summary

  • 14% Below List Price
  • $273/SF
  • 50 Days On Market

  Current Estimated Value $344,291

  Last Listing Agent Jacqueline Voegeli Manzi Real Estate

  73 Yale Ave, Middlebury, CT 06762
• 

  Est $1,754,971 Not Listed For Sale

  40 Winthrop Dr, Middlebury, CT 06762

  • 4 Beds
  • 6.5 Baths
  • 4,954 Sq Ft
  • Built 2001

  40 Winthrop Dr, Middlebury, CT 06762

  Last Sold Summary

  • $353/SF
  • 94 Days On Market

  Last Sold Price $1,750,000

  Last Listing Agent John Donato Jr Showcase Realty Tristate
• 

  

  

  /38

  $659,900

  • 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
• 

  $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 $561,483

  Last Listing Agent Gina Williams Preston Gray Real Estate

  94 Upper Whittemore Rd, Middlebury, CT 06762
• 

  Est $622,469 Not Listed For Sale

  740 Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • Built 1981

  740 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 6% Above List Price
  • $208/SF
  • 27 Days On Market

  Last Sold Price $590,000

  Last Listing Agent Adrian Cote William Raveis Real Estate
• 

  /2

  $729,990 Open House 3/15

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

  321 Artillery Rd, Middlebury, CT 06762

  Coming SOON!!! Large Colonial with charm and character is 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 you. The formal living room with complete with a alrge picture window and marble fireplace will serve as a great oplace to relax at the end of a long day. The

  Frank Durante William Raveis Real Estate

  321 Artillery 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 $684,042

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  400 Long Meadow Rd, Middlebury, CT 06762
• 

  Est $609,551 Not Listed For Sale

  108 White Ave, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1953

  108 White Ave, Middlebury, CT 06762

  Last Sold Summary

  • 16% Above List Price
  • $250/SF
  • 7 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
• 

  

  /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
• 

  $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 $437,066

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  69 Nick Rd, Middlebury, CT 06762
• 

  Est $479,641 Not Listed For Sale

  28 Jensen Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft
  • Built 1970

  28 Jensen Dr, Middlebury, CT 06762

  Last Sold Summary

  • 9% Above List Price
  • $172/SF
  • 4 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.
• 

  

  /37

  $759,000

  • 4 Beds
  • 2.5 Baths
  • 2,753 Sq Ft

  117 Crest Rd, Middlebury, CT 06762

  Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the

  Lori Geraci BHGRE Gaetano Marra Homes

  117 Crest Rd, 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 $485,610

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  30 Nick Rd, Middlebury, CT 06762
• 

  Est $553,762 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

  • 4% Above List Price
  • $182/SF
  • 61 Days On Market

  Last Sold Price $530,000

  Last Listing Agent Michael Bachmann HomeSmart Homes and Estates
• 

  /2

  $709,900 Pending

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

  2 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) 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

  2 Deer Run Rd, 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 $572,219

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762
• 

  Est $646,777 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

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

  Last Sold Price $620,000

  Last Listing Agent Colleen Burne Coldwell Banker Realty
• 

  

  /9

  $545,400 Pending

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

  0 N Benson Rd Unit 64 24077175, 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 64 24077175, 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
• 

  Est $577,929 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

  • 54% Above List Price
  • $194/SF
  • 51 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Lauren Cavallo Lauren Ashley Homes LLC
• 

  /2

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,877 Sq Ft

  14 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run Rd(aka Lot 19) 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

  14 Deer Run 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

  Current Estimated Value $701,441

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  111 Dwyer Rd, Middlebury, CT 06762
• 

  Est $959,699 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
• 

  

  /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 Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 55 24086408, 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

  Current Estimated Value $969,835

  Last Listing Agent Jetlir Kulla Coldwell Banker Realty

  82 Mirey Dam Rd, Middlebury, CT 06762
• 

  Est $782,793 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

  • 12% Above List Price
  • $187/SF
  • 34 Days On Market

  Last Sold Price $699,900

  Last Listing Agent Karen Berwick Real Estate Two
• 

  

  /6

  $200,000 Pending

  • Land
  • 1.13 Acres
  • $176,991 per Acre

  288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

  Gorgeous 1.13 acre lot in a brand new subdivision. Level and on a private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD. Shared maintenance for private driveway. Flood

  John Donato Jr Showcase Realty, Inc.

  288 Watertown Rd Unit Lot 5, 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 $494,952

  Last Listing Agent Amber Segetti RE/MAX RISE

  58 Shadduck Rd, Middlebury, CT 06762
• 

  Est $507,110 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

  • 24% Above List Price
  • $152/SF
  • 37 Days On Market

  Last Sold Price $410,000

  Last Listing Agent Karen Griffin Coldwell Banker Realty
• 

  

  /19

  $259,900

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft

  152 Glenwood Ave, Middlebury, CT 06762

  2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your

  Don Orsini West View Properties, LLC

  152 Glenwood Ave, 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 $506,593 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

  • 6% Above List Price
  • $161/SF
  • 85 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Monique Jacobs RE/MAX
• 

  

  /24

  $229,900

  • Land
  • 4.67 Acres
  • $49,229 per Acre

  75 Gleneagle Rd, Middlebury, CT 06762

  LOCATION, LOCATION, LOCATION!!! ONLY LOT FOR SALE IN THIS PRIVATE, 11 LOT SUBDIVISION OF QUALITY-BUILT HIGH END HOMES. SUBDIVISION HAS THE UNIQUE BONUSES OF PUBLIC WATER & SEWER (ALREADY EXTENDED TO LOT) AND CLOSE PROXIMITY TO LOCAL RETAIL AND HIGHWAYS. 4.67 ACRE SITE TUCKED AWAY AT THE END OF A TURN-AROUND TO THE LEFT OF THE ELABORATE GAZEEBO AND LAND TRUST PROPERTY.

  Scott Tedesco Tedesco Real Estate

  75 Gleneagle Rd, Middlebury, CT 06762
• 

  $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
• 

  Est $705,149 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

  • 4% Above List Price
  • $181/SF
  • 182 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
• 

  

  /9

  $509,900 Under Contract

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

  0 N Benson Rd Unit 47 24099635, 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 Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
• 

  $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 $600,029

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  2 Dogwood Ct, Middlebury, CT 06762
• 

  Est $520,902 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

  • 2% Above List Price
  • $168/SF
  • 186 Days On Market

  Last Sold Price $508,500

  Last Listing Agent Marian Van Egas Berkshire Hathaway Home Services
• 

  

  /9

  $519,900 Pending

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

  0 N Benson Rd Unit 53 24086541, 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 53 24086541, 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 $502,261

  Last Listing Agent Robert Vignola Coldwell Banker Realty

  713 Whittemore Rd, Middlebury, CT 06762

Showing Results 41 - 80, Page 2 of 18