3,789

Middlebury, CT Homes

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  • /28

    $699,900

    • 4 Beds
    • 3.5 Baths
    • 2,484 Sq Ft

    223 Carriage Dr, Middlebury, CT 06762

    A timeless center hall colonial set in one of Middlebury's most cherished neighborhoods. This beautifully maintained home features a custom kitchen with Subzero refrigeration, Wolf gas cooktop and double ovens, marble countertops, and built-in wine storage. Hardwood floors run throughout the main living areas, where a warm and inviting family room with a gas log fireplace sits just off the

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (475) 267-1355

    223 Carriage Dr, Middlebury, CT 06762
  • /21

    $3,850 per month

    • 3 Beds
    • 2 Baths
    • 3,079 Sq Ft
    • Apartment for Rent

    771 Watertown Rd, Middlebury, CT 06762

    Enjoy quite living in this beautiful renovated 3-bedroom, 2-bath apartment. Featuring updated appliances, cozy fireplace, and spacious layout. This home is perfect for comfort and style. One bathroom includes soaking tub, brand-new patio offers a great spot to relax outdoors. Located in a serene neighborhood, this apartment combines modern updates with peaceful surroundings.

    Amanda Engala Tier 1 Real Estate

    771 Watertown Rd, Middlebury, CT 06762
  • 8 Kimberwick Ct, Middlebury, CT 06762

    $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

    Current Estimated Value $529,294

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
    • 10 Stonington Ct, Middlebury, CT 06762

      Est $679,324 Not Listed For Sale

      10 Stonington Ct, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,812 Sq Ft
      • Built 2005
      10 Stonington Ct, Middlebury, CT 06762

      Last Sold Summary

      • 6% Above List Price
      • $228/SF
      • 209 Days On Market

      Last Sold Price $640,000

      Last Listing Agent Scott Hellriegel Berkshire Hathaway Home Services

  • /32

    $599,900

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762

    Welcome to this beautifully maintained **Portman Elite** model in the highly desirable Ridgewood of Middlebury community. This bright and inviting home offers 3 bedrooms and 2.5 baths, thoughtfully designed for modern living and low maintenance comfort. The main level features an open layout with a spacious living area, dining space, and a well-appointed kitchen ideal for everyday living and

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (475) 267-4261

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762
  • /7

    $1,050 per month

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

    10 Old Waterbury Rd Unit 3, Middlebury, CT 06762

    COZY ONE BEDROOM FOR LEASE. SPACIOUS LIVING ROOM. KITCHENETTE WITH AMPLE CABINET SPACE. FULL BATHROOM W/ STAND-UP SHOWER. PRIVATE IN-GROUND POOL WITH DECK. SET IN CLOSE PROXIMITY TO SCHOOLS, SHOPPING & HIGHWAY(S).

    Jeffrey Corcoran Corcoran Properties, LLC

    10 Old Waterbury Rd Unit 3, Middlebury, CT 06762
  • 36 Aveline Ave, Middlebury, CT 06762

    $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 $489,688

    Last Listing Agent Wayne Watt Jr. THE CONNECTICUT AGENCY LLC

    36 Aveline Ave, Middlebury, CT 06762
    • 197 White Ave, Middlebury, CT 06762

      Est $420,820 Not Listed For Sale

      197 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 1,494 Sq Ft
      • Built 1928
      197 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 3% Above List Price
      • $274/SF
      • 55 Days On Market

      Last Sold Price $410,000

      Last Listing Agent Beth Santos Showcase Realty, Inc.

  • /2

    $699,900

    • Land
    • 2.31 Acres
    • $302,987 per Acre

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762

    This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond.

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (475) 255-6254

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
  • /7

    $1,800 per month

    • 1 Bed
    • 1 Bath
    • 1,604 Sq Ft
    • House for Rent

    1129 Southford Rd, Middlebury, CT 06762

    1 BR lower level apartment with all utilities included. In unit washer and dryer, private rear entrance. Freshly painted and new carpet. Conveniently located to route 84

    Doug Rose Scalzo Real Estate

    1129 Southford Rd, Middlebury, CT 06762
  • 171 Judd Hill Rd, Middlebury, CT 06762

    $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 $850,442

    Last Listing Agent Donna Kennedy Compass Connecticut, LLC

    171 Judd Hill Rd, Middlebury, CT 06762
    • 396 Watertown Rd, Middlebury, CT 06762

      Est $798,262 Not Listed For Sale

      396 Watertown Rd, Middlebury, CT 06762

      • 4 Beds
      • 3.5 Baths
      • 3,935 Sq Ft
      • Built 2013
      396 Watertown Rd, Middlebury, CT 06762

      Last Sold Summary

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

      Last Sold Price $790,000

      Last Listing Agent Beth Santos Showcase Realty, Inc.

  • /40

    $649,900

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

    193 Ridgewood Dr Unit 193, Middlebury, CT 06762

    This beautifully upgraded condominium at Ridgewood at Middlebury offers the perfect blend of style, comfort, and low-maintenance living. Built in 2022 and showing like new, the home features sun-filled spaces, engineered wood floors throughout, and a thoughtfully designed open layout. The main level welcomes you with a seamless flow ideal for everyday living and entertaining. At the center of the

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 255-0656

    193 Ridgewood Dr Unit 193, Middlebury, CT 06762
  • /33

    $17,000 per month

    • 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
  • 6 Pommel Ln Unit 6, Middlebury, CT 06762

    $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

    Current Estimated Value $514,176

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    6 Pommel Ln Unit 6, Middlebury, CT 06762
    • 191 Ridgewood Dr Unit 191, Middlebury, CT 06762

      Not Listed For Sale

      191 Ridgewood Dr Unit 191, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,658 Sq Ft
      • Built 2022
      191 Ridgewood Dr Unit 191, Middlebury, CT 06762

      Last Sold Summary

      • $233/SF
      • 79 Days On Market

      Last Sold Price $620,000

      Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  • /4

    $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

    Agent Photo

    Ken Demirs

    Regency Real Estate, LLC

    (475) 258-7617

    0 Ferndale Ave, Middlebury, CT 06762
  • 126 Colonial Ave, Middlebury, CT 06762

    $585,000 Sold Jan 29, 2026

    126 Colonial Ave, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 2,531 Sq Ft
    • Built 1911

    Last Sold Summary

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

    Current Estimated Value $580,746

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
    • 111 Periwinkle Dr Unit 111, Middlebury, CT 06762

      Est $619,195 Not Listed For Sale

      111 Periwinkle Dr Unit 111, Middlebury, CT 06762

      • 2 Beds
      • 2.5 Baths
      • 2,476 Sq Ft
      • Built 2005
      111 Periwinkle Dr Unit 111, Middlebury, CT 06762

      Last Sold Summary

      • 6% Above List Price
      • $236/SF
      • 131 Days On Market

      Last Sold Price $585,000

      Last Listing Agent Marvin and Laura Beninson Keller Williams Realty

  • /39

    $599,900 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,749 Sq Ft

    428 Breakneck Hill Rd, Middlebury, CT 06762

    Set on more than 4 peaceful, pastoral acres, this beautifully remodeled ranch offers the ideal blend of character, craftsmanship, and modern comfort. Lovingly restored during the owner's tenure, the home showcases thoughtful upgrades and timeless details throughout. A newly built oversized two car garage provides excellent storage and convenience. Inside, the custom kitchen-designed and crafted

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (203) 693-8994

    428 Breakneck Hill Rd, Middlebury, CT 06762
  • 407 Chestnut Cir Unit 78, Middlebury, CT 06762

    $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 $673,408

    Last Listing Agent Jodi Dawley Real Estate Two

    407 Chestnut Cir Unit 78, Middlebury, CT 06762
    • 47 Ridgewood Dr Unit 47, Middlebury, CT 06762

      Not Listed For Sale

      47 Ridgewood Dr Unit 47, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,463 Sq Ft
      • Built 2014
      47 Ridgewood Dr Unit 47, Middlebury, CT 06762

      Last Sold Summary

      • $219/SF
      • 83 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Karen Rigopulos West View Properties, LLC

  • /32

    $759,900 Open Sun 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 4,094 Sq Ft

    64 Watertown Rd, Middlebury, CT 06762

    Spacious and meticulously maintained Cape offering 3 bedrooms and 3.5 baths with a flexible layout designed for today's lifestyle. The main level features a stunning home office with custom built-ins and fireplace, and a kitchen with a Wolf gas range/oven, Sub-Zero refrigerator, and center island with beverage cooler. Upstairs, you'll find generously sized bedrooms, including a spacious primary

    Olivia Bueno William Raveis Real Estate

    64 Watertown Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

    $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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762
    • 6 Burr Hall Rd, Middlebury, CT 06762

      Not Listed For Sale

      6 Burr Hall Rd, Middlebury, CT 06762

      6 Burr Hall Rd, Middlebury, CT 06762

      Last Sold Summary

      • 41 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Nancy Langrock William Raveis Real Estate

  • /24

    $585,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,997 Sq Ft

    36 Highridge Rd Unit 36, Middlebury, CT 06762

    Welcome to 36 Highridge Road, a beautifully maintained home in one of Middlebury's most desirable neighborhoods. Built in 2018 and lovingly cared for by its original and only owner, this property offers the perfect blend of modern construction, thoughtful upgrades, and low-maintenance living. Step inside to find a thoughtfully designed interior enhanced with upgraded molding, elegant cabinetry,

    John Pistorino RE/MAX RISE

    36 Highridge Rd Unit 36, Middlebury, CT 06762
  • 0 N Benson Rd Unit 37, Middlebury, CT 06762

    $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 Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 37, Middlebury, CT 06762
    • 397 White Deer Rock Rd, Middlebury, CT 06762

      Est $1,664,343 Not Listed For Sale

      397 White Deer Rock Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 3,363 Sq Ft
      • Built 2008
      397 White Deer Rock Rd, Middlebury, CT 06762

      Last Sold Summary

      • 2% Below List Price
      • $506/SF
      • 50 Days On Market

      Last Sold Price $1,700,000

      Last Listing Agent Maria Taylor Klemm Real Estate Inc

  • /29

    $735,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,877 Sq Ft

    20 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 20 Hunting Ridge Road (aka Lot 11) is to be built. 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 and a 2 car attached garage. The primary bedroom boasts walk-in

    Jodi Dawley Real Estate Two

    20 Hunting Ridge Rd, Middlebury, CT 06762
  • 146 Richardson Dr, Middlebury, CT 06762

    $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

    Current Estimated Value $374,080

    Last Listing Agent Nicholas Greene eXp Realty

    146 Richardson Dr, Middlebury, CT 06762
    • 40 Winthrop Dr, Middlebury, CT 06762

      Est $1,828,256 Not Listed For Sale

      40 Winthrop Dr, Middlebury, CT 06762

      • 4 Beds
      • 6.5 Baths
      • 4,954 Sq Ft
      • Built 2001
      40 Winthrop Dr, Middlebury, CT 06762

      Last Sold Summary

      • 4% Above List Price
      • $353/SF
      • 94 Days On Market

      Last Sold Price $1,750,000

      Last Listing Agent John Donato Jr Showcase Realty Tristate

  • /40

    $750,000 Pending

    • 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
  • 73 Yale Ave, Middlebury, CT 06762

    $300,000 Sold Jan 16, 2026

    73 Yale Ave, Middlebury, CT 06762

    • 2 Beds
    • 2 Baths
    • 1,099 Sq Ft
    • Built 1945

    Last Sold Summary

    • 14% Below List Price
    • $273/SF
    • 50 Days On Market

    Current Estimated Value $309,088

    Last Listing Agent Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, Middlebury, CT 06762
    • 740 Whittemore Rd, Middlebury, CT 06762

      Est $632,490 Not Listed For Sale

      740 Whittemore Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,830 Sq Ft
      • Built 1981
      740 Whittemore Rd, Middlebury, CT 06762

      Last Sold Summary

      • 7% Above List Price
      • $208/SF
      • 27 Days On Market

      Last Sold Price $590,000

      Last Listing Agent Adrian Cote William Raveis Real Estate

  • /40

    $950,000

    • 5 Beds
    • 2.5 Baths
    • 3,301 Sq Ft

    851 South St, Middlebury, CT 06762

    Welcome to this beautifully updated home which offers modern comfort, high-end finishes & peace of mind with several upgrades already completed! Located in Middlebury's South Street neighborhood this Colonial is 3300 sq ft on a 1.85 acre lot. Step in to a bright & inviting foyer feat. a high ceiling, a custom wood & glass front door & a stunning custom handrail leading the expansive 4 bedrooms.

    Jackie Desmarais Showcase Realty, Inc.

    851 South St, Middlebury, CT 06762
  • 94 Upper Whittemore Rd, Middlebury, CT 06762

    $555,000 Sold Jul 02, 2025

    94 Upper Whittemore Rd, Middlebury, CT 06762

    • 3 Beds
    • 2 Baths
    • 2,024 Sq Ft
    • Built 1944

    Last Sold Summary

    • 3% Above List Price
    • $274/SF
    • 47 Days On Market

    Current Estimated Value $565,353

    Last Listing Agent Gina Williams Preston Gray Real Estate

    94 Upper Whittemore Rd, Middlebury, CT 06762
    • 108 White Ave, Middlebury, CT 06762

      Est $578,466 Not Listed For Sale

      108 White Ave, Middlebury, CT 06762

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1953
      108 White Ave, Middlebury, CT 06762

      Last Sold Summary

      • 10% Above List Price
      • $250/SF
      • 7 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  • /9

    $560,753 Pending

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

    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762

    5 Units Remaining! 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 52 24100213, Middlebury, CT 06762
  • 400 Long Meadow Rd, Middlebury, CT 06762

    $675,000 Sold Jun 06, 2025

    400 Long Meadow Rd, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 2,778 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Above List Price
    • $243/SF
    • 44 Days On Market

    Current Estimated Value $681,893

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    400 Long Meadow Rd, Middlebury, CT 06762
    • 28 Jensen Dr, Middlebury, CT 06762

      Est $468,558 Not Listed For Sale

      28 Jensen Dr, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,552 Sq Ft
      • Built 1970
      28 Jensen Dr, Middlebury, CT 06762

      Last Sold Summary

      • 6% Above List Price
      • $172/SF
      • 4 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

Showing Results 1 - 40, Page 1 of 18

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$543,283
Median Single Family Sale Price
$545,500
Median Townhouse Sale Price
$549,936
Median 2 Bedroom Sale Price
$676,000
Average Price Per Sq Ft
$279
Number of Homes for Sale
23
Last 12 months Home Sales
108
Months of Supply
2.60
Median List Price
$589,750
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-7%
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