Middlebury, CT Homes

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  /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
• 

  $422,000 Sold Jun 18, 2025

  64 Joy Rd, Middlebury, CT 06762

  • 3 Beds
  • 1 Bath
  • 1,688 Sq Ft
  • Built 1959

  Last Sold Summary

  • 6% Above List Price
  • $250/SF
  • 58 Days On Market

  Current Estimated Value $415,895

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  64 Joy Rd, Middlebury, CT 06762
• 

  Est $357,252 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

  • 17% Above List Price
  • $218/SF
  • 62 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Susan Woodfield Showcase Realty, Inc.
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  $599,900

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

  10 Old Waterbury Rd, Middlebury, CT 06762

  4 UNITS IN MIDDLEBURY-NOT ONLY "NEXT TO IMPOSSIBLE" TO FIND, BUT UNBELIEVABLY PRICED AT $599900! THIS "ONCE IN A LIFETIME" OPPORTUNITY CAN BE YOURS! LIVE IN ONE, AND COLLECT RENT FROM THE OTHER THREE UNITS, OR, ADD THIS ONE TO YOUR INVESTMENT PORTFOLIO AND "WATCH IT GROW"! One parcel (.41 ACRE), ON "PARKLIKE" GROUNDS WITH THE ATMOSPHERE OF NATURE ON A SHORT, NO-THRU STREET, consists of a

  Judith Caputo Advantage Realty Group, Inc.

  10 Old Waterbury Rd, 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 $421,113

  Last Listing Agent Robert Marucci Better Living Realty, LLC

  93 Fenn Rd, Middlebury, CT 06762
• 

  Est $1,105,815 Not Listed For Sale

  192 Watertown Rd, Middlebury, CT 06762

  • 3 Beds
  • 5 Baths
  • 5,073 Sq Ft
  • Built 1986

  192 Watertown Rd, Middlebury, CT 06762

  Last Sold Summary

  • 16% Above List Price
  • $187/SF
  • 91 Days On Market

  Last Sold Price $950,000

  Last Listing Agent John Donato Jr Showcase Realty, Inc.
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  $629,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,722 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
• 

  $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 $443,697

  Last Listing Agent Dean Giatas Fiorelli Realty, LLC

  28 Maple Dr, Middlebury, CT 06762
• 

  Est $399,345 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

  • 21% Above List Price
  • $222/SF
  • 112 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Heather Crabtree RE/MAX RISE
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  /19

  $229,000

  • 1 Bed
  • 1 Bath
  • 889 Sq Ft

  35 Nutmeg Rd Unit D1, Middlebury, CT 06762

  Middlebury Commons, Highly desirable 55+ community conveniently located to town center and all of its amenities. Bright second floor unit has primary BR with walk-in closet plus den/office that can serve as 2nd BR. Eat-in kitchen, laundry area, LR/DR combo with french door to deck overlooking private rear yard. Move right into this beautiful unit.

  Karen Stanco Showcase Realty, Inc.

  35 Nutmeg Rd Unit D1, Middlebury, CT 06762
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  $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 $368,017

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

  203 Lake Shore Dr, Middlebury, CT 06762
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  Est $300,677 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

  • 13% Above List Price
  • $155/SF
  • 144 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Judith Caputo Advantage Realty Group, Inc.
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  /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
• 

  $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 $801,119

  Last Listing Agent Jodi Dawley Real Estate Two

  18 Hunting Ridge Rd, Middlebury, CT 06762
• 

  Est $802,726 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

  • 11% Above List Price
  • $238/SF
  • 84 Days On Market

  Last Sold Price $720,000

  Last Listing Agent Jill Taylor RE/MAX
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  /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
• 

  $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
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  Est $627,473 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

  • 3% Below List Price
  • $231/SF
  • 8 Days On Market

  Last Sold Price $650,000

  Last Listing Agent rob raad Better Living Realty, LLC
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  /40

  $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
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  $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
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  Est $466,697 Not Listed For Sale

  910 Middlebury Rd, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,716 Sq Ft
  • Built 1900

  910 Middlebury Rd, Middlebury, CT 06762

  Last Sold Summary

  • 17% Above List Price
  • $233/SF
  • 87 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes
• 

  

  /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
• 

  $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 $232,366

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  58 Chesham Dr, Middlebury, CT 06762
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  Est $447,003 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

  • 5% Above List Price
  • $230/SF
  • 177 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Frank Durante William Raveis Real Estate
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  /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
• 

  $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 $390,255

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  43 Merideth Rd, Middlebury, CT 06762
• 

  Est $1,018,625 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

  • 14% Above List Price
  • $160/SF
  • 80 Days On Market

  Last Sold Price $895,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
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  /9

  $573,584 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 Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 60, 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 $993,818

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  593 Park Road Extension, Middlebury, CT 06762
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  Est $491,093 Not Listed For Sale

  2 Northwood Dr, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1962

  2 Northwood Dr, Middlebury, CT 06762

  Last Sold Summary

  • 6% Above List Price
  • $248/SF
  • 54 Days On Market

  Last Sold Price $465,000

  Last Listing Agent Michael Magas BHGRE Gaetano Marra Homes
• 

  $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 $480,571

  Last Listing Agent Chloe White KW Legacy Partners

  679 Christian Rd, Middlebury, CT 06762
• 

  Est $465,076 Not Listed For Sale

  106 Glenwood Ave, Middlebury, CT 06762

  • 5 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1926

  106 Glenwood Ave, Middlebury, CT 06762

  Last Sold Summary

  • 6% Above List Price
  • $254/SF
  • 25 Days On Market

  Last Sold Price $438,000

  Last Listing Agent Crosby Middlemass Coldwell Banker Realty
• 

  $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 $369,304 Not Listed For Sale

  185 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft
  • Built 1953

  185 Porter Ave, Middlebury, CT 06762

  Last Sold Summary

  • 11% Above List Price
  • $272/SF
  • 33 Days On Market

  Last Sold Price $331,900

  Last Listing Agent Beth Santos Showcase Realty, Inc.
• 

  $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 $548,817

  Last Listing Agent Maria Cohen William Raveis Real Estate

  61 Stony Brook Rd, Middlebury, CT 06762
• 

  Est $475,949 Not Listed For Sale

  31 Stony Brook Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 1969

  31 Stony Brook Rd, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $220/SF
  • 54 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Deana Daponte Dave Jones Realty, LLC
• 

  $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 $654,962

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  55 Westwood Dr, Middlebury, CT 06762
• 

  Est $521,271 Not Listed For Sale

  592 Benson Rd, Middlebury, CT 06762

  • 5 Beds
  • 2 Baths
  • 2,289 Sq Ft
  • Built 1978

  592 Benson Rd, Middlebury, CT 06762

  Last Sold Summary

  • 14% Above List Price
  • $200/SF
  • 3 Days On Market

  Last Sold Price $457,000

  Last Listing Agent Linda Andrikis West View Properties, LLC
• 

  $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

  Current Estimated Value $86,593

  Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

  440 Lake Shore Dr, Middlebury, CT 06762
• 

  Est $371,079 Not Listed For Sale

  294 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,109 Sq Ft
  • Built 1949

  294 Porter Ave, Middlebury, CT 06762

  Last Sold Summary

  • 11% Above List Price
  • $302/SF
  • 4 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Michelle Pavia William Raveis Real Estate

Showing Results 121 - 160, Page 4 of 18