Middlebury, CT Homes

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  /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 Lovley Century 21 AllPoints Realty

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

  $415,000 Sold May 23, 2025

  460 Lake Shore Dr, Middlebury, CT 06762

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

  Last Sold Summary

  • 5% Below List Price
  • $322/SF
  • 68 Days On Market

  Current Estimated Value $419,097

  Last Listing Agent Blair Patterson William Raveis Real Estate

  460 Lake Shore Dr, Middlebury, CT 06762
• 

  Est $385,581 Not Listed For Sale

  49 White Ave, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,473 Sq Ft
  • Built 1952

  49 White Ave, Middlebury, CT 06762

  Last Sold Summary

  • 22% Above List Price
  • $214/SF
  • 47 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Sharon Martino Regency Real Estate, LLC
• 

  Price To Be Determined New Construction

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

  Left Garage Plan at Aberdeen Estates at Benson Woods, Middlebury, CT 06762

  Lovley Development Builder

  0 N Benson Rd Unit 39340994, Middlebury, CT 06762
• 

  $1,375,000 Sold Sep 04, 2025

  122 Mirey Dam Rd, Middlebury, CT 06762

  • 4 Beds
  • 5 Baths
  • 6,175 Sq Ft
  • Built 2001

  Last Sold Summary

  • 7% Below List Price
  • $223/SF
  • 103 Days On Market

  Current Estimated Value $1,386,797

  Last Listing Agent Jennifer Jones Coldwell Banker Realty

  122 Mirey Dam Rd, Middlebury, CT 06762
• 

  Est $350,351 Not Listed For Sale

  5 Laurel Rd, Middlebury, CT 06762

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft
  • Built 1940

  5 Laurel Rd, Middlebury, CT 06762

  Last Sold Summary

  • 52% Above List Price
  • $214/SF
  • 11 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Jessica Boswell LPT Realty
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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 Lovley Century 21 AllPoints Realty

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

  $702,500 Sold May 23, 2025

  403 Chestnut Cir Unit 76, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 2,292 Sq Ft
  • Built 2023

  Last Sold Summary

  • 6% Above List Price
  • $307/SF
  • 533 Days On Market

  Current Estimated Value $659,761

  Last Listing Agent Jodi Dawley Real Estate Two

  403 Chestnut Cir Unit 76, Middlebury, CT 06762
• 

  Est $598,990 Not Listed For Sale

  82 Northwood Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,729 Sq Ft
  • Built 1960

  82 Northwood Dr, Middlebury, CT 06762

  Last Sold Summary

  • 2% Above List Price
  • $214/SF
  • 230 Days On Market

  Last Sold Price $585,000

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
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  /12

  $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
• 

  $590,000 Sold Jun 04, 2025

  138 Skyline Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,212 Sq Ft
  • Built 1960

  Last Sold Summary

  • 15% Below List Price
  • $267/SF
  • 59 Days On Market

  Current Estimated Value $595,196

  Last Listing Agent Diana Mashni RE/MAX RISE

  138 Skyline Dr, Middlebury, CT 06762
• 

  Est $757,213 Not Listed For Sale

  122 Crest Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,253 Sq Ft
  • Built 1982

  122 Crest Rd, Middlebury, CT 06762

  Last Sold Summary

  • 6% Above List Price
  • $220/SF
  • 165 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty
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  /2

  $900,000 Under Contract

  • 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
• 

  $575,000 Sold Nov 06, 2025

  1 Dogwood Ct Unit 1, Middlebury, CT 06762

  • 3 Beds
  • 3.5 Baths
  • 3,477 Sq Ft
  • Built 2007

  Last Sold Summary

  • 15% Below List Price
  • $165/SF
  • 216 Days On Market

  Current Estimated Value $601,024

  Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

  1 Dogwood Ct Unit 1, Middlebury, CT 06762
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  Est $586,516 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

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

  Last Sold Price $577,000

  Last Listing Agent Colleen Burne Coldwell Banker Realty
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  /19

  $229,000 Under Contract

  • 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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  $549,936 Sold Oct 30, 2025

  0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,252 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $244/SF
  • 0 Days On Market

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
• 

  Est $553,757 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

  • 5% Above List Price
  • $238/SF
  • 21 Days On Market

  Last Sold Price $528,000

  Last Listing Agent Olivia Hardt Berkshire Hathaway Home Services
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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 Lovley Century 21 AllPoints Realty

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

  $525,000 Sold Jun 02, 2025

  110 Glenwood Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft
  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • $243/SF
  • 33 Days On Market

  Current Estimated Value $534,418

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  110 Glenwood Ave, Middlebury, CT 06762
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  Est $410,078 Not Listed For Sale

  121 Allerton Farms Rd, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1948

  121 Allerton Farms Rd, Middlebury, CT 06762

  Last Sold Summary

  • 12% Above List Price
  • $256/SF
  • 8 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Pam Famiglietti William Raveis Real Estate
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  /13

  $349,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  314 Porter Ave, Middlebury, CT 06762

  A classic Middlebury Cape Cod offering strong potential. This 3bedroom, 2bath home sits on a 0.34acre lot and features 1,440 sq. ft. of living space plus a 900 sq. ft. basement. With an average physical condition rating and many original features, it's a handyman's dream-perfect for those looking to update, customize, and build equity. Traditional gableroof styling, aluminum siding, and a two

  Dawn Ciappetta Coldwell Banker Realty

  314 Porter Ave, Middlebury, CT 06762
• 

  $493,000 Sold Jun 06, 2025

  43 Ridgewood Dr Unit 43, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft
  • Built 2014

  Last Sold Summary

  • 4% Below List Price
  • $273/SF
  • 44 Days On Market

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  43 Ridgewood Dr Unit 43, Middlebury, CT 06762
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  Est $611,255 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

  • 4% Above List Price
  • $216/SF
  • 99 Days On Market

  Last Sold Price $585,000

  Last Listing Agent Matt Rose Keller Williams Realty
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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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  $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
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  Est $391,582 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

  • 8% Below List Price
  • $346/SF
  • 33 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.
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  /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 Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 45 24089121, 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 $345,160

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  119 Christian Rd, Middlebury, CT 06762
• 

  Est $662,668 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

  • 3% Above List Price
  • $166/SF
  • 186 Days On Market

  Last Sold Price $645,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
• 

  

  /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 Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 59 24116892, 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 $447,131

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  18 E Ridge Dr, Middlebury, CT 06762
• 

  Est $492,995 Not Listed For Sale

  463 Watertown Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,781 Sq Ft
  • Built 1983

  463 Watertown Rd, Middlebury, CT 06762

  Last Sold Summary

  • 16% Above List Price
  • $153/SF
  • 13 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Michael Vitale Vitale Realty
• 

  /2

  $99,000

  • Land
  • 1.42 Acres
  • $69,718 per Acre

  0 Webb Rd Unit 24166057, Naugatuck, CT 06770

  Beautiful land in very desirable location, build your dream home in this lovely corner of Naugatuck.Do not miss this opportunity.

  Magda Ballaro William Raveis Real Estate

  0 Webb Rd Unit 24166057, Naugatuck, CT 06770
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  $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
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  Est $443,751 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

  • 11% Below List Price
  • $278/SF
  • 33 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
• 

  

  /20

  $525,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  541 Benson Rd, Middlebury, CT 06762

  Rare Two-Home Compound in Middlebury - Ideal for Investment or Owner-Occupant! An extraordinary opportunity for investors or owner-occupants looking to offset their mortgage! This unique property at 541 Benson Road features TWO distinct, detached dwellings on a private .8-acre lot, offering a total of 3 bedrooms, 3 full baths, and 4 garage bays. Unit 1: The Main Residence (2BR/2BA) This

  Joseph Martino Joseph Martino Real Estate

  541 Benson Rd, 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 $411,374

  Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

  115 Porter Ave, Middlebury, CT 06762
• 

  Est $586,276 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

  • 12% Above List Price
  • $199/SF
  • 75 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes
• 

  

  /31

  $509,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft

  38 E Ridge Dr, Middlebury, CT 06762

  Highest & Best due Tuesday 3/31 @5:00 pm. Welcome to 38 E Ridge Drive - Move-In Ready & Fully Updated. This beautifully renovated home is located in one of the most sought-after areas of town. With an open floor plan and hardwood floors throughout, it offers a seamless blend of comfort and style. Inside, you'll find a large living and dining room combo. The kitchen has been thoughtfully updated

  Paula Basso Evjen Agency

  38 E Ridge Dr, Middlebury, CT 06762

Showing Results 161 - 200, Page 5 of 18