Middlebury, CT Homes

• 

  Est $507,531

  Not Listed For Sale

  835 Whittemore Rd, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,016 Sq Ft
  • Built 1963

  835 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 60 Days On Market
• 

  

  

  /34

  $2,195,000

  • 3 Beds
  • 2.5 Baths
  • 3,863 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  Tucked along Big Cove on Lake Quassapaug, this custom architect designed Arts & Crafts bungalow is privately set on 14.85 serene acres with a path to your own cove frontage. Thoughtfully designed with the current owner's many updates and improvements and timeless materials, the home features a living room with a stone fireplace crafted from the property, a well-appointed kitchen with Custom Point

  Peter Klemm Klemm Real Estate Inc

  397 White Deer Rock Rd, Middlebury, CT 06762
• 

  $625,000

  Sold Jun 30, 2026

  10 Pelham Way, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,251 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $278/SF
  • 36 Days On Market

  Current Estimated Value $615,707

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  10 Pelham Way, Middlebury, CT 06762
• 

  Est $599,056

  Not Listed For Sale

  61 Carriage Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 1966

  61 Carriage Dr, Middlebury, CT 06762

  Last Sold Summary

  • 39 Days On Market
• 

  

  /2

  $900,000

  New Construction Pending

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  19 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 19 Deer Run Road (aka Lot 21) is to be built. It is a 3100 sq ft colonial with 2 car attached garage with bonus room. Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office. The primary bedroom boasts walk-in closet with custom

  Jodi Dawley Real Estate Two

  19 Deer Run Rd, Middlebury, CT 06762
• 

  $565,000

  Sold Sep 25, 2025

  181 Ridgewood Dr Unit 181, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 2022

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 90 Days On Market

  Last Listing Agent Heather Crabtree RE/MAX RISE

  181 Ridgewood Dr Unit 181, Middlebury, CT 06762
• 

  Est $567,331

  Not Listed For Sale

  141 Camp Rd, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft
  • Built 1988

  141 Camp Rd, Middlebury, CT 06762

  Last Sold Summary

  • 21 Days On Market
• 

  

  /9

  $573,572

  New Construction Pending

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

  0 N Benson Rd Unit 65, 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 65, Middlebury, CT 06762
• 

  $560,000

  Sold Jun 19, 2026

  24 Highridge Rd Unit 24, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,802 Sq Ft
  • Built 2017

  Last Sold Summary

  • $311/SF
  • 58 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  24 Highridge Rd Unit 24, Middlebury, CT 06762
• 

  Est $630,279

  Not Listed For Sale

  129 Periwinkle Dr, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 2,476 Sq Ft
  • Built 2005

  129 Periwinkle Dr, Middlebury, CT 06762

  Last Sold Summary

  • 45 Days On Market
• 

  

  /9

  $533,416

  New Construction Pending

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

  0 N Benson Rd Unit 49 24096137, 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 49 24096137, Middlebury, CT 06762
• 

  $345,000

  Sold Sep 10, 2025

  119 Christian Rd, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 866 Sq Ft
  • Built 1936

  Last Sold Summary

  • 1% Below List Price
  • $398/SF
  • 11 Days On Market

  Current Estimated Value $339,929

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  119 Christian Rd, Middlebury, CT 06762
• 

  Est $391,428

  Not Listed For Sale

  43 Merideth Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Built 1957

  43 Merideth Rd, Middlebury, CT 06762

  Last Sold Summary

  • 51 Days On Market
• 

  

  /37

  $2,850,000

  • 8 Beds
  • 8 Baths
  • 9,619 Sq Ft

  775 South St Unit 777, Middlebury, CT 06762

  Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the

  Kary Apanovitch Coldwell Banker Realty

  775 South St Unit 777, Middlebury, CT 06762
• 

  $875,000

  Sold Jun 15, 2026

  245 Upper Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,990 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Above List Price
  • $293/SF
  • 0 Days On Market

  Current Estimated Value $823,496

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  245 Upper Whittemore Rd, Middlebury, CT 06762
• 

  Est $621,616

  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

  • 99 Days On Market
• 

  

  /40

  $485,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,251 Sq Ft

  413 Watertown Rd, Middlebury, CT 06762

  Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a

  Emily Fitzgerald William Raveis Real Estate

  413 Watertown Rd, Middlebury, CT 06762
• 

  $456,000

  Sold Nov 17, 2025

  18 E Ridge Dr, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,340 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Above List Price
  • $340/SF
  • 54 Days On Market

  Current Estimated Value $453,132

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  18 E Ridge Dr, Middlebury, CT 06762
• 

  Est $401,533

  Not Listed For Sale

  44 Middlebury Terrace, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,229 Sq Ft
  • Built 1937

  44 Middlebury Terrace, Middlebury, CT 06762

  Last Sold Summary

  • 33 Days On Market
• 

  

  /9

  $525,438

  New Construction Pending

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

  0 N Benson Rd Unit 45 24089121, 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 45 24089121, Middlebury, CT 06762
• 

  $530,328

  Sold Oct 30, 2025

  0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

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

  Last Sold Summary

  • 6% Above List Price
  • $272/SF
  • 163 Days On Market

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762
• 

  Est $672,303

  Not Listed For Sale

  150 Burr Hall Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,895 Sq Ft
  • Built 1979

  150 Burr Hall Rd, Middlebury, CT 06762

  Last Sold Summary

  • 186 Days On Market
• 

  

  /9

  $572,000

  New Construction Pending

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

  0 N Benson Rd Unit 56, 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 56, Middlebury, CT 06762
• 

  $409,000

  Sold Nov 25, 2025

  115 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $273/SF
  • 39 Days On Market

  Current Estimated Value $418,937

  Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

  115 Porter Ave, Middlebury, CT 06762
• 

  Est $458,118

  Not Listed For Sale

  110 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1926

  110 Yale Ave, Middlebury, CT 06762

  Last Sold Summary

  • 33 Days On Market
• 

  

  /35

  $559,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,179 Sq Ft

  3 Winding Trail, Middlebury, CT 06762

  Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors,

  Mayra Perez Showcase Realty, Inc.

  3 Winding Trail, Middlebury, CT 06762
• 

  $706,000

  Sold Jun 30, 2026

  15 Central Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,870 Sq Ft
  • Built 1941

  Last Sold Summary

  • 2% Above List Price
  • $246/SF
  • 60 Days On Market

  Current Estimated Value $687,279

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  15 Central Rd, Middlebury, CT 06762
• 

  Est $609,476

  Not Listed For Sale

  169 Sandy Hill Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,639 Sq Ft
  • Built 1995

  169 Sandy Hill Rd, Middlebury, CT 06762

  Last Sold Summary

  • 75 Days On Market
• 

  

  /9

  $548,828

  New Construction 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
• 

  $70,000

  Sold Jun 29, 2026

  0 Ferndale Ave, Middlebury, CT 06762

  • Land
  • 1.64 Acres
  • $42,683 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 54 Days On Market

  Last Listing Agent Ken Demirs Regency Real Estate, LLC

  0 Ferndale Ave, Middlebury, CT 06762
• 

  Est $565,384

  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

  • 243 Days On Market
• 

  

  /9

  $568,564

  New Construction Pending

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

  0 N Benson Rd Unit 59 24116892, 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 59 24116892, Middlebury, CT 06762
• 

  $460,000

  Sold Aug 15, 2025

  74 Joy Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Above List Price
  • $250/SF
  • 16 Days On Market

  Current Estimated Value $455,348

  Last Listing Agent Tom Dorso Mapleridge Realty

  74 Joy Rd, Middlebury, CT 06762
• 

  Est $678,823

  Not Listed For Sale

  200 Northridge Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,360 Sq Ft
  • Built 1984

  200 Northridge Dr, Middlebury, CT 06762

  Last Sold Summary

  • 152 Days On Market
• 

  

  /35

  $385,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,639 Sq Ft

  818 Middlebury Rd, Middlebury, CT 06762

  Tucked away on a beautifully secluded setting, this storybook Cape blends timeless charm with thoughtful updates throughout. The distinctive wood and stone exterior creates unforgettable curb appeal, while the inviting interior offers warmth, character, and functionality. The sun filled living room features hardwood floors, exposed beamed ceilings, and a stunning fireplace with insert, creating

  Brandy Hall Higgins Group Real Estate

  818 Middlebury Rd, Middlebury, CT 06762
• 

  $465,000

  Sold Oct 03, 2025

  1996 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,768 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $263/SF
  • 47 Days On Market

  Current Estimated Value $457,664

  Last Listing Agent Devon O'Neill Litchfield Hills Properties LLC

  1996 Straits Turnpike, Middlebury, CT 06762
• 

  Est $453,386

  Not Listed For Sale

  252 White Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,454 Sq Ft
  • Built 1937

  252 White Ave, Middlebury, CT 06762

  Last Sold Summary

  • 4 Days On Market
• 

  

  /9

  $573,584

  New Construction Pending

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

  0 N Benson Rd Unit 60, 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 Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 60, Middlebury, CT 06762
• 

  $520,000

  Sold Aug 13, 2025

  1 Stevens Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1937

  Last Sold Summary

  • 9% Below List Price
  • $231/SF
  • 70 Days On Market

  Current Estimated Value $516,312

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  1 Stevens Rd, Middlebury, CT 06762
• 

  Est $501,657

  Not Listed For Sale

  1738 Middlebury Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,225 Sq Ft
  • Built 1961

  1738 Middlebury Rd, Middlebury, CT 06762

  Last Sold Summary

  • 32 Days On Market

Showing Results 161 - 200, Page 5 of 18