Middlebury, CT Homes

• 

  $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

  Last Listing Agent Dean Giatas Fiorelli Realty, LLC

  28 Maple Dr, Middlebury, CT 06762
• 

  Est $418,748 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,849 Sq Ft

  36 Middlebury Terrace, Middlebury, CT 06762

  36 Middlebury Terrace, Middlebury, CT 06762
• 

  

  /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
• 

  $365,000 Sold Jul 01, 2025

  203 Lake Shore Dr, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1965

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 69 Days On Market

  Current Estimated Value $368,072

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  203 Lake Shore Dr, Middlebury, CT 06762
• 

  Est $996,402 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,582 Sq Ft

  122 Northridge Dr, Middlebury, CT 06762

  122 Northridge Dr, Middlebury, CT 06762
• 

  

  /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
• 

  $790,000 Sold Jun 30, 2025

  18 Hunting Ridge Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $293/SF
  • 298 Days On Market

  Current Estimated Value $804,519

  Last Listing Agent Jodi Dawley Real Estate Two

  18 Hunting Ridge Rd, Middlebury, CT 06762
• 

  Est $488,766 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft

  2 Northwood Dr, Middlebury, CT 06762

  2 Northwood Dr, Middlebury, CT 06762
• 

  

  /9

  $603,780 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  0 N Benson Rd Unit 48 24129196, 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 48 24129196, Middlebury, CT 06762
• 

  $505,834 Sold Oct 17, 2025

  0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762

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

  Last Sold Summary

  • $259/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762
• 

  Est $476,540 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,724 Sq Ft

  106 Glenwood Ave, Middlebury, CT 06762

  106 Glenwood Ave, Middlebury, CT 06762
• 

  

  /9

  $522,128 Pending

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

  0 N Benson Rd Unit 66 24093726, 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 66 24093726, Middlebury, CT 06762
• 

  $630,000 Sold May 15, 2025

  7 Arrowwood Ct Unit 7, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,465 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $182/SF
  • 77 Days On Market

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  7 Arrowwood Ct Unit 7, Middlebury, CT 06762
• 

  Est $363,858 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft

  185 Porter Ave, Middlebury, CT 06762

  185 Porter Ave, Middlebury, CT 06762
• 

  

  /12

  $699,900

  • 5 Beds
  • 4 Baths
  • 2,345 Sq Ft

  10 Old Waterbury Rd, Middlebury, CT 06762

  RARE OPPORTUNITY to find 4 units in MIDDLEBURY, CT! LOCATION! LOCATION! One parcel with (.41 acre) consists of a detached, 1 bedroom single family, approximately (620 s.f.), 3 units w/1 car garage under and in-ground pool. 2 car detached garage, in addition to plenty of off street parking. Public water and sewer. Separate utilities paid by tenants. Single family has oil heat and 3 family is

  Judith Caputo Advantage Realty Group, Inc.

  10 Old Waterbury Rd, Middlebury, CT 06762
• 

  $230,000 Sold Jun 19, 2025

  58 Chesham Dr, Middlebury, CT 06762

  • Land
  • 1.89 Acres
  • $121,693 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 9 Days On Market

  Current Estimated Value $235,306

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  58 Chesham Dr, Middlebury, CT 06762
• 

  Est $468,715 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft

  31 Stony Brook Rd, Middlebury, CT 06762

  31 Stony Brook Rd, Middlebury, CT 06762
• 

  

  /9

  $533,416 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 Meuse Lovley Century 21 AllPoints Realty

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

  $735,000 Sold Feb 19, 2025

  481 Long Meadow Rd, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 3,011 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $244/SF
  • 92 Days On Market

  Current Estimated Value $768,453

  Last Listing Agent Allen Grealish Coldwell Banker Realty

  481 Long Meadow Rd, Middlebury, CT 06762
• 

  Est $543,237 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,289 Sq Ft

  592 Benson Rd, Middlebury, CT 06762

  592 Benson Rd, Middlebury, CT 06762
• 

  /2

  $274,900

  • Land
  • 3.33 Acres
  • $82,553 per Acre

  19 Deer Run Rd, Middlebury, CT 06762

  Welcome to Hunting Ridge Estates, a premier 23-lot subdivision offering the perfect blend of privacy and natural beauty. This spacious 3.33-acre rear lot provides ample space to build your dream home in a peaceful, upscale setting. With multiple lot options available, you can choose the one that best suits your vision. Whether you prefer to bring your own builder or take advantage of our

  Jodi Dawley Real Estate Two

  19 Deer Run Rd, Middlebury, CT 06762
• 

  $385,000 Sold May 05, 2025

  43 Merideth Rd, Middlebury, CT 06762

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

  Last Sold Summary

  • $244/SF
  • 51 Days On Market

  Current Estimated Value $395,502

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  43 Merideth Rd, Middlebury, CT 06762
• 

  Est $359,117 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,109 Sq Ft

  294 Porter Ave, Middlebury, CT 06762

  294 Porter Ave, Middlebury, CT 06762
• 

  

  /34

  $339,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,157 Sq Ft

  587 Shadduck Rd, Middlebury, CT 06762

  Welcome to 587 Shadduck Road, Middlebury, CT! This inviting two-bedroom, one-bathroom Cape-style home offers comfort, character, and a highly desirable location. Directly across the street, enjoy access to the Larkin State Park Trail, perfect for walking, running, or biking. Inside, the kitchen is bright and functional, featuring two windows that bring in natural light, warm wood cabinetry, and

  Dave Jones Dave Jones Realty, LLC

  587 Shadduck Rd, Middlebury, CT 06762
• 

  $950,000 Sold Jul 09, 2025

  593 Park Road Extension, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 4,496 Sq Ft
  • Built 1994

  Last Sold Summary

  • 27% Below List Price
  • $211/SF
  • 428 Days On Market

  Current Estimated Value $986,794

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  593 Park Road Extension, Middlebury, CT 06762
• 

  Est $449,933 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  828 Breakneck Hill Rd, Middlebury, CT 06762

  828 Breakneck Hill Rd, Middlebury, CT 06762
• 

  

  /9

  $525,438 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 Meuse Lovley Century 21 AllPoints Realty

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

  $454,000 Sold May 08, 2025

  679 Christian Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Above List Price
  • $196/SF
  • 47 Days On Market

  Current Estimated Value $483,167

  Last Listing Agent Chloe White KW Legacy Partners

  679 Christian Rd, Middlebury, CT 06762
• 

  Est $1,121,540 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 5,800 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  /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
• 

  $240,000 Sold Oct 14, 2025

  288 Watertown Rd Unit Lot 2, Middlebury, CT 06762

  • Land
  • 4 Acres
  • $60,000 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 330 Days On Market

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  288 Watertown Rd Unit Lot 2, Middlebury, CT 06762
• 

  Est $435,851 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,638 Sq Ft

  140 Glenwood Ave, Middlebury, CT 06762

  140 Glenwood Ave, Middlebury, CT 06762
• 

  

  /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
• 

  $515,000 Sold Jul 31, 2025

  61 Stony Brook Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft
  • Built 1971

  Last Sold Summary

  • 21% Below List Price
  • $184/SF
  • 75 Days On Market

  Current Estimated Value $549,306

  Last Listing Agent Maria Cohen William Raveis Real Estate

  61 Stony Brook Rd, Middlebury, CT 06762
• 

  Est $392,927 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,473 Sq Ft

  49 White Ave, Middlebury, CT 06762

  49 White Ave, Middlebury, CT 06762
• 

  

  /9

  $568,564 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 Meuse Lovley Century 21 AllPoints Realty

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

  $675,000 Sold Sep 24, 2025

  55 Westwood Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,570 Sq Ft
  • Built 1962

  Last Sold Summary

  • 13% Below List Price
  • $263/SF
  • 192 Days On Market

  Current Estimated Value $653,505

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  55 Westwood Dr, Middlebury, CT 06762
• 

  Est $358,704 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft

  5 Laurel Rd, Middlebury, CT 06762

  5 Laurel Rd, Middlebury, CT 06762
• 

  

  /38

  $624,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  3 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 3 Hunting Ridge Road (aka Lot 1) is now complete and ready for occupancy! It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office in addition to 3 bedrooms. The primary bedroom boasts walk-in closet

  Jodi Dawley Real Estate Two

  3 Hunting Ridge Rd, Middlebury, CT 06762
• 

  $85,000 Sold Jan 07, 2026

  440 Lake Shore Dr, Middlebury, CT 06762

  • Land
  • 0.45 Acre
  • $188,889 per Acre

  Last Sold Summary

  • 258 Days On Market

  Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

  440 Lake Shore Dr, Middlebury, CT 06762

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