Middlebury, CT Homes

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  $75,000 Pending

  • Land
  • 1.64 Acres
  • $45,732 per Acre

  0 Ferndale Ave, Middlebury, CT 06762

  For Sale: Unique Development Opportunity Offering a rare opportunity to acquire a three-lot subdivision in Middlebury. This property consists of three separate parcels that must be sold together. While previously approved, buyers are responsible for verifying the current status of approvals and conducting their own due diligence. The site presents some challenges due to significant ledge, which

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 258-7617

  0 Ferndale Ave, Middlebury, CT 06762
• Explore Middlebury

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  $2,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 905 Sq Ft
  • House for Rent

  35 Nutmeg Rd Unit B3, Middlebury, CT 06762

  Sought after Middlebury Commons 55+ community 4 room end unit with a brand new heating and air conditioning system. This Middlebury one level, first floor condo is in a small 55+ community with loads of privacy. Assigned 2 parking spots directly in front of this end unit. Fully applianced kitchen. Stack washer and dryer in closet. Huge living room with an atrium door leading to a private patio.

  Stephen Briotti Weichert REALTORS Briotti Group

  35 Nutmeg Rd Unit B3, Middlebury, CT 06762
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  $505,000 Sold Jul 30, 2025

  1440 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $247/SF
  • 3 Days On Market

  Current Estimated Value $495,102

  Last Listing Agent Linda Mayfield RE/MAX RISE

  1440 Straits Turnpike, Middlebury, CT 06762
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762
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  $599,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 2,531 Sq Ft

  126 Colonial Ave, Middlebury, CT 06762

  Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 x 13 heated sunroom overlooking rolling hills and distant views. On the second level, 2 bedrooms and a beautifully

  Donna Bannon BHGRE Gaetano Marra Homes

  126 Colonial Ave, Middlebury, CT 06762
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  $17,000 total monthly price

  • 5 Beds
  • 7 Baths
  • 6,600 Sq Ft
  • House for Rent

  372 Tucker Hill Rd, Middlebury, CT 06762

  5 bedrooms 4,3 baths cape house set on 3.5 acres.

  Naima Mazouzi Eagle Eye Realty PLLC

  372 Tucker Hill Rd, Middlebury, CT 06762
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  $520,000 Sold Oct 22, 2025

  8 Kimberwick Ct, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,147 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 78 Days On Market

  Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

  8 Kimberwick Ct, Middlebury, CT 06762
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  Not Listed For Sale

  6 Burr Hall Rd, Middlebury, CT 06762

  6 Burr Hall Rd, Middlebury, CT 06762
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  $334,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft

  73 Yale Ave, Middlebury, CT 06762

  This cozy comfortable 2 bed, 2 bath ranch offers the convience of one level living, with a private back yard and plenty of parking. Located close to the business center and RT 84.

  Jacqueline Voegeli Manzi Real Estate

  73 Yale Ave, Middlebury, CT 06762
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  $620,000 Sold Mar 28, 2025

  191 Ridgewood Dr Unit 191, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $233/SF
  • 79 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  191 Ridgewood Dr Unit 191, Middlebury, CT 06762
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  Est $1,455,674 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,363 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  397 White Deer Rock Rd, Middlebury, CT 06762
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  $899,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  294 Christian Rd, Middlebury, CT 06762

  New construction designed to impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with majestic soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen and heart of the home has an expansive island, granite countertops, stainless steel appliances and white shaker style

  Ellie Gollenberg BHGRE Gaetano Marra Homes

  294 Christian Rd, Middlebury, CT 06762
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  $480,000 Sold Apr 25, 2025

  36 Aveline Ave, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft
  • Built 1952

  Last Sold Summary

  • $269/SF
  • 44 Days On Market

  Current Estimated Value $488,611

  Last Listing Agent Wayne Watt Jr. THE CONNECTICUT AGENCY LLC

  36 Aveline Ave, Middlebury, CT 06762
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  Est $558,603 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Judd Rd, Southbury, CT 06488

  436 Judd Rd, Southbury, CT 06488
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  $200,000 Pending

  • Land
  • 1.13 Acres
  • $176,991 per Acre

  288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

  Gorgeous 1.13 acre lot in a brand new subdivision. Level and on a private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD. Shared maintenance for private driveway. Flood

  John Donato Jr Showcase Realty, Inc.

  288 Watertown Rd Unit Lot 5, Middlebury, CT 06762
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  $882,500 Sold Sep 25, 2025

  171 Judd Hill Rd, Middlebury, CT 06762

  • 5 Beds
  • 4 Baths
  • 3,700 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $239/SF
  • 49 Days On Market

  Current Estimated Value $883,178

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  171 Judd Hill Rd, Middlebury, CT 06762
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  Est $1,774,540 Not Listed For Sale

  • 4 Beds
  • 6.5 Baths
  • 4,954 Sq Ft

  40 Winthrop Dr, Middlebury, CT 06762

  40 Winthrop Dr, Middlebury, CT 06762
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  $299,900

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft

  152 Glenwood Ave, Middlebury, CT 06762

  2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your

  Don Orsini West View Properties, LLC

  152 Glenwood Ave, Middlebury, CT 06762
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  $1,219,659 Sold Feb 06, 2025

  25 Somerset Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft
  • Built 2024

  Last Sold Summary

  • 39% Above List Price
  • $424/SF
  • 5 Days On Market

  Current Estimated Value $1,259,508

  Last Listing Agent Ellie Gollenberg BHGRE Gaetano Marra Homes

  25 Somerset Dr, Middlebury, CT 06762
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  Est $625,383 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  740 Whittemore Rd, Middlebury, CT 06762

  740 Whittemore Rd, Middlebury, CT 06762
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  $565,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  27 Winding Trail Unit 27, Middlebury, CT 06762

  Beautiful Luxury Portman Condo in the Sought-After Ridgewood Community! This stunning 3-bed, 2.5-bath home by Toll Brothers is perfectly situated on a private cul-de-sac in one of Ridgewood's most desirable and unique locations. Offering over 2,680 SqFt of beautifully designed living space, this residence includes a rare 4-ft bump-out for added size plus a finished walk-out basement. The main

  Jay Irvine Serhant Connecticut, LLC

  27 Winding Trail Unit 27, Middlebury, CT 06762
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  $525,000 Sold Oct 16, 2025

  6 Pommel Ln Unit 6, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 1,917 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Above List Price
  • $274/SF
  • 52 Days On Market

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  6 Pommel Ln Unit 6, Middlebury, CT 06762
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  Est $542,677 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,611 Sq Ft

  212 Breakneck Hill Rd, Middlebury, CT 06762

  212 Breakneck Hill Rd, Middlebury, CT 06762
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  $509,900 Under Contract

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

  0 N Benson Rd Unit 47 24099635, 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 47 24099635, Middlebury, CT 06762
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  $710,500 Sold Jun 20, 2025

  407 Chestnut Cir Unit 78, Middlebury, CT 06762

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

  Last Sold Summary

  • 8% Above List Price
  • $310/SF
  • 520 Days On Market

  Current Estimated Value $667,806

  Last Listing Agent Jodi Dawley Real Estate Two

  407 Chestnut Cir Unit 78, Middlebury, CT 06762
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  Est $577,321 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  108 White Ave, Middlebury, CT 06762

  108 White Ave, Middlebury, CT 06762
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  $4,100,000 Pending

  • 6 Beds
  • 4 Baths
  • 5,816 Sq Ft

  7 Sandy Beach Rd, Middlebury, CT 06762

  SUPERB LAKE PROPERTY. First time on the market, this 4,811 sf shingle-style home on 6.99 acres in Lake Quassapaug's estate area offers 195 feet of direct waterfront with a private dock and small beach. Designed by renowned architect Rick Moisan and built in 2000, the residence blends timeless design with modern comfort, enjoying complete privacy and pastoral views of permanently protected

  Beverly Mosch William Pitt Sotheby's Int'l

  7 Sandy Beach Rd, Middlebury, CT 06762
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  $499,900 Sold Sep 30, 2025

  0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

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

  Last Sold Summary

  • $256/SF
  • 0 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762
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  Est $479,121 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  28 Jensen Dr, Middlebury, CT 06762

  28 Jensen Dr, Middlebury, CT 06762
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  $530,000

  • 3 Beds
  • 3.5 Baths
  • 3,103 Sq Ft

  2 Dogwood Ct, Middlebury, CT 06762

  Beautiful 3-bedroom, 3.5-bath 3179 Sqft townhouse with a 1-car garage located on of the best best private streets in the highly sought-after Ridgewood community. The resort style complex people are raving about! This spacious home offers a flexible layout perfect for modern living. The main level features hardwood floors, a half bath, a bright living room, a dining area, and an eat-in kitchen

  Jay Irvine Serhant Connecticut, LLC

  2 Dogwood Ct, Middlebury, CT 06762
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  $342,000 Sold Mar 21, 2025

  28 Yale Ave, Middlebury, CT 06762

  • 1 Bed
  • 2 Baths
  • 1,434 Sq Ft
  • Built 1923

  Last Sold Summary

  • 2% Below List Price
  • $238/SF
  • 6 Days On Market

  Current Estimated Value $362,049

  Last Listing Agent Lysa Napoli Showcase Realty, Inc.

  28 Yale Ave, Middlebury, CT 06762
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  Est $553,205 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,908 Sq Ft

  18 Jericho Rd, Middlebury, CT 06762

  18 Jericho Rd, Middlebury, CT 06762
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  $519,900 Pending

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

  0 N Benson Rd Unit 53 24086541, 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 53 24086541, Middlebury, CT 06762
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  $547,460 Sold Aug 15, 2025

  0 N Benson Rd Unit 37, Middlebury, CT 06762

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

  Last Sold Summary

  • 7% Above List Price
  • $281/SF
  • 163 Days On Market

  Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 37, Middlebury, CT 06762
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  Est $639,334 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,492 Sq Ft

  150 Carriage Dr, Middlebury, CT 06762

  150 Carriage Dr, Middlebury, CT 06762
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  $739,999

  • 4 Beds
  • 3.5 Baths
  • 2,806 Sq Ft

  80 Pine Hollow Dr, Middlebury, CT 06762

  Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

  Gina Farra Keller Williams Realty

  80 Pine Hollow Dr, Middlebury, CT 06762
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  $380,000 Sold Nov 17, 2025

  146 Richardson Dr, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,499 Sq Ft
  • Built 1940

  Last Sold Summary

  • $254/SF
  • 38 Days On Market

  Last Listing Agent Nicholas Greene eXp Realty

  146 Richardson Dr, Middlebury, CT 06762
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  Est $573,200 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  1600 Straits Turnpike, Middlebury, CT 06762

  1600 Straits Turnpike, Middlebury, CT 06762
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  $785,000

  • 4 Beds
  • 4 Baths
  • 3,360 Sq Ft

  200 N Farm Rd, Middlebury, CT 06762

  Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth

  Jackie Desmarais Showcase Realty, Inc.

  200 N Farm Rd, Middlebury, CT 06762
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  $700,000 Sold Feb 28, 2025

  15 Lakeview Dr, Middlebury, CT 06762

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 2024

  Last Sold Summary

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

  Last Listing Agent George Harlamon Realty Group of New England, LLC

  15 Lakeview Dr, Middlebury, CT 06762

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