Middlebury, CT Homes

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  $523,920 Pending

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

  0 N Benson Rd Unit 51 24117506, 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 51 24117506, Middlebury, CT 06762
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  $649,500 Sold Jul 25, 2025

  405 Chestnut Cir Unit 77, Middlebury, CT 06762

  • 2 Beds
  • 3 Baths
  • 2,292 Sq Ft
  • Built 2025

  Last Sold Summary

  • $283/SF
  • 99 Days On Market

  Current Estimated Value $652,368

  Last Listing Agent Jodi Dawley Real Estate Two

  405 Chestnut Cir Unit 77, Middlebury, CT 06762
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  Est $357,674 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 724 Sq Ft

  7 Foster St, Middlebury, CT 06762

  7 Foster St, Middlebury, CT 06762
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  $810,000 New Construction

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

  6 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) 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

  6 Deer Run Rd, Middlebury, CT 06762
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  $225,000 Sold Sep 24, 2025

  288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

  • Land
  • 3.32 Acres
  • $67,771 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 330 Days On Market

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  288 Watertown Rd Unit Lot 4, Middlebury, CT 06762
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  Est $479,566 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,823 Sq Ft

  157 Yale Ave, Middlebury, CT 06762

  157 Yale Ave, Middlebury, CT 06762
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  $574,000

  • 3 Beds
  • 3.5 Baths
  • 2,879 Sq Ft

  24 Ridgewood Dr, Middlebury, CT 06762

  Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

  Jodi Dawley Real Estate Two

  24 Ridgewood Dr, Middlebury, CT 06762
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  $615,000 Sold Oct 30, 2025

  1 Independence Cir, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,224 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Below List Price
  • $191/SF
  • 120 Days On Market

  Last Listing Agent Carol D'Amato Regency Real Estate, LLC

  1 Independence Cir, Middlebury, CT 06762
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  Est $1,632,298 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,811 Sq Ft

  700 South St, Middlebury, CT 06762

  700 South St, Middlebury, CT 06762
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  $1,085,000

  • 3 Beds
  • 4 Baths
  • 4,138 Sq Ft

  225 Crest Rd, Middlebury, CT 06762

  Exquisite French Provincial MANOR HOUSE In the heart of Middlebury Ct. On a 3.21 acre private corner lot with mature plantings, English Boxwoods, fenced and tree lined. Pool and stone seating area. Double car oversized garage. Circular drive and designated parking for family and guests lined with stone pavers. This stately house 4,138 sq. ft. (not including basement with access to the garden),

  Wilson Lamas Realty Group of New England, LLC

  225 Crest Rd, Middlebury, CT 06762
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  $1,100,000 Sold May 19, 2025

  45 E Farms Rd, Middlebury, CT 06762

  • 4 Beds
  • 6 Baths
  • 5,054 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Below List Price
  • $218/SF
  • 48 Days On Market

  Current Estimated Value $1,122,428

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  45 E Farms Rd, Middlebury, CT 06762
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  Est $518,546 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,083 Sq Ft

  133 1/2 Steinmann Ave, Middlebury, CT 06762

  133 1/2 Steinmann Ave, Middlebury, CT 06762
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  /2

  $794,900 New Construction

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

  15 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) 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

  15 Hunting Ridge Rd, Middlebury, CT 06762
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  $585,000 Sold Feb 14, 2025

  89 Tyler Crossing, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,704 Sq Ft
  • Built 1998

  Last Sold Summary

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

  Current Estimated Value $629,620

  Last Listing Agent Matt Rose Keller Williams Realty

  89 Tyler Crossing, Middlebury, CT 06762
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  Est $288,840 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 2,528 Sq Ft

  2056 Straits Turnpike, Middlebury, CT 06762

  2056 Straits Turnpike, Middlebury, CT 06762
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  /2

  $529,900

  • 3 Beds
  • 1.5 Baths
  • 1,811 Sq Ft

  61 Sandy Hill Rd, Middlebury, CT 06762

  Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

  Arben Belica William Raveis Real Estate

  61 Sandy Hill Rd, Middlebury, CT 06762
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  $63,250 Sold Dec 05, 2025

  0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

  • Land
  • 0.76 Acre
  • $83,224 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 80 Days On Market

  Last Listing Agent Rebecca Zandvliet Coldwell Banker Realty 2000

  0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
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  Est $1,053,427 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 5,938 Sq Ft

  346 South St, Middlebury, CT 06762

  346 South St, Middlebury, CT 06762
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  $522,128 Pending

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

  0 N Benson Rd Unit 46 24097231, 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 46 24097231, Middlebury, CT 06762
• 

  $593,360 Sold Oct 10, 2025

  0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

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

  Last Sold Summary

  • 17% Above List Price
  • $304/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762
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  Est $1,226,895 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 6,318 Sq Ft

  53 White Deer Rock Rd, Middlebury, CT 06762

  53 White Deer Rock Rd, Middlebury, CT 06762
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  $599,900

  • 5 Beds
  • 2 Baths
  • 1,924 Sq Ft

  292 Park Road Extension, Middlebury, CT 06762

  Discover this classic 5-bedroom, 2-bath Colonial set on a private 1.67-acre lot in desirable Middlebury. This home features hardwood floors, a bright formal living room, and a spacious dining room that opens to a cozy three-season porch overlooking the yard. The kitchen offers brand-new stainless steel appliances and the convenient first-floor bedroom includes laundry for easy main-level living.

  Tammy Ferrauola Eagle Eye Realty PLLC

  292 Park Road Extension, Middlebury, CT 06762
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  $500,000 Sold Feb 21, 2025

  240 Carriage Dr, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 2,351 Sq Ft
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • $213/SF
  • 243 Days On Market

  Current Estimated Value $539,444

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  240 Carriage Dr, Middlebury, CT 06762
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  Est $345,564 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  36 Richardson Dr, Middlebury, CT 06762

  36 Richardson Dr, Middlebury, CT 06762
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  /40

  $524,900

  • 3 Beds
  • 3.5 Baths
  • 1,918 Sq Ft

  637 Watertown Rd, Middlebury, CT 06762

  Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home.

  Jonna Dibble BHGRE Gaetano Marra Homes

  637 Watertown Rd, Middlebury, CT 06762
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  $495,000 Sold Dec 04, 2025

  116 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $214/SF
  • 51 Days On Market

  Last Listing Agent Dave Jones Dave Jones Realty, LLC

  116 Yale Ave, Middlebury, CT 06762
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  Est $1,105,815 Not Listed For Sale

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

  192 Watertown Rd, Middlebury, CT 06762

  192 Watertown Rd, Middlebury, CT 06762
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  $561,271 Pending

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

  0 N Benson Rd Unit 57, 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 57, Middlebury, CT 06762
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  $790,000 Sold Mar 31, 2025

  396 Watertown Rd, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,935 Sq Ft
  • Built 2013

  Last Sold Summary

  • 1% Below List Price
  • $201/SF
  • 64 Days On Market

  Current Estimated Value $810,572

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  396 Watertown Rd, Middlebury, CT 06762
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  Est $384,335 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,486 Sq Ft

  70 Steinmann Ave, Middlebury, CT 06762

  70 Steinmann Ave, Middlebury, CT 06762
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  $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
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  $520,000 Sold Aug 08, 2025

  29 Winding Trail Unit 29, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $244/SF
  • 117 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  29 Winding Trail Unit 29, Middlebury, CT 06762
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  Est $813,914 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,030 Sq Ft

  524 Charcoal Ave, Middlebury, CT 06762

  524 Charcoal Ave, Middlebury, CT 06762
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  /40

  $889,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,220 Sq Ft

  383 Leonard Rd, Middlebury, CT 06762

  Welcome to your dream home...just for holidays-a beautifully designed 3220 sq ft NEW CONSTRUCTION offering warmth, space and flexibility for today's modern family. With 4 generous bedrooms and 3.5 bathrooms, this home invites you to live, laugh and grow in comfort. You have to see in person to appreciate the design of each of the bedrooms with their one full bath and double closet space. The

  Koco Pela William Raveis Real Estate

  383 Leonard Rd, Middlebury, CT 06762
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  $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 $414,636

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  64 Joy Rd, Middlebury, CT 06762
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  Est $627,473 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 2,813 Sq Ft

  695 Whittemore Rd, Middlebury, CT 06762

  695 Whittemore Rd, Middlebury, CT 06762
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  /40

  $629,900 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft

  51 Cross Rd, Middlebury, CT 06762

  Highest and Best by Wednesday, 12/10, 6pm. Welcome to this beautifully maintained Colonial nestled in the highly sought-after Curtis Farms neighborhood. Thoughtfully designed, this home blends classic charm with modern comfort. The gorgeous kitchen offers abundant cabinetry, granite countertops, and a gas cooktop overlooking the breakfast bar, which enjoys a view of the stone-faced fireplace. A

  Christina Zainc BHGRE Gaetano Marra Homes

  51 Cross Rd, Middlebury, CT 06762
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  $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 $420,985

  Last Listing Agent Robert Marucci Better Living Realty, LLC

  93 Fenn Rd, Middlebury, CT 06762
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  Est $467,581 Not Listed For Sale

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

  910 Middlebury Rd, Middlebury, CT 06762

  910 Middlebury Rd, Middlebury, CT 06762
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  /40

  $709,000

  • 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

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