3,768

Middlebury, CT Homes

Section Image Section Image
  • /38

    $539,900

    • 3 Beds
    • 2.5 Baths
    • 2,403 Sq Ft

    10 Ridgewood Dr, Middlebury, CT 06762

    Welcome to 10 Ridgewood Drive in Middlebury, located in the highly sought-after Ridgewood community, offering exceptional amenities including a clubhouse, swimming pool & tennis courts. This beautifully maintained townhouse is being offered for sale by its original owner and has been extensively remodeled throughout. The main level features an open-concept floor plan designed for today's

    Agent Photo

    Ken Demirs

    Regency Real Estate, LLC

    10 Ridgewood Dr, Middlebury, CT 06762
  • /32

    $3,400 Per Month

    • 4 Beds
    • 2 Baths
    • 2,245 Sq Ft
    • House for Rent

    111 North St, Middlebury, CT 06762

    A beautiful rental in Middlebury, CT history. Located near "The Green" on desired North Street, This Charming Greek Revival home has so many upgrades! Sitting on private acres, this home boasts 10 spacious rooms, 4 bedrooms,LR with fireplace, DR with Fireplace,Eat In Kitchen with an island, library/office with built ins and 2 sitting rooms. The two full baths have claw tubs and have been fully

    Agent Photo

    Bonnie Wilson

    Berkshire Hathaway NE Prop.

    111 North St, 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 $534,257

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
    • 101 Shadduck Rd, Middlebury, CT 06762

      Est $507,391

      Not Listed For Sale

      101 Shadduck Rd, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 2,534 Sq Ft
      • Built 1935
      101 Shadduck Rd, Middlebury, CT 06762

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  • /40

    $590,000

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,528 Sq Ft

    700 Watertown Rd, Middlebury, CT 06762

    This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio

    Agent Photo

    Erin Giguiere

    Regall Realty, LLC

    700 Watertown Rd, 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
  • 178 Ridgewood Dr Unit 178, Middlebury, CT 06762

    $607,000

    Sold Jul 07, 2026

    178 Ridgewood Dr Unit 178, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,414 Sq Ft
    • Built 2022

    Last Sold Summary

    • 5% Below List Price
    • $251/SF
    • 25 Days On Market

    Last Listing Agent Patricia Forbes Berkshire Hathaway NE Prop.

    178 Ridgewood Dr Unit 178, Middlebury, CT 06762
    • 190 Bronson Dr, Middlebury, CT 06762

      Est $702,077

      Not Listed For Sale

      190 Bronson Dr, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,850 Sq Ft
      • Built 1972
      190 Bronson Dr, Middlebury, CT 06762

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  • /35

    $660,000

    $40K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,162 Sq Ft

    90 Fenn Rd, Middlebury, CT 06762

    The home you have been waiting for is waiting for you at 90 Fenn Road, Middlebury. Need room for inlaws? teens? an office? You can have it right here, tucked on 1.67 acres in a desirable Middlebury location. As you enter the spacious tiled foyer and look around, a formal sunken living room greets you on one side and a formal dining room on the other. You will notice the oak flooring in both

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    90 Fenn 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 $871,374

    Last Listing Agent Donna Kennedy Compass Connecticut, LLC

    171 Judd Hill Rd, Middlebury, CT 06762
    • 74 Joy Rd, Middlebury, CT 06762

      Est $465,161

      Not Listed For Sale

      74 Joy Rd, Middlebury, CT 06762

      • 3 Beds
      • 2 Baths
      • 1,842 Sq Ft
      • Built 1966
      74 Joy Rd, Middlebury, CT 06762

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Tom Dorso Mapleridge Realty

  • /38

    $950,000

    • 5 Beds
    • 3.5 Baths
    • 4,114 Sq Ft

    552 Breakneck Hill Rd, Middlebury, CT 06762

    Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    552 Breakneck 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 $525,656

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    6 Pommel Ln Unit 6, Middlebury, CT 06762
  • /39

    $349,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft

    24 Yale Ave, Middlebury, CT 06762

    Nestled on a quiet, picturesque street in one of Middlebury's classic New England neighborhoods, this warm and inviting Cape Cod offers a rare opportunity to own a move-in ready home in this highly sought-after community, at an exceptional price point. Built in 1982, this charming home features 3 bedrooms, 2 full baths, and 1,469 square feet of comfortable living space filled with bright, sunlit

    Agent Photo

    Kenneth Viele, Jr.

    Coldwell Banker Realty

    24 Yale 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 $590,714

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
    • 0 N Benson Rd Unit 37, Middlebury, CT 06762

      Not Listed For Sale

      0 N Benson Rd Unit 37, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2025
      0 N Benson Rd Unit 37, Middlebury, CT 06762

      Last Sold Summary

      • 163 Days On Market

      Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  • /35

    $575,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2 Northwood Dr, Middlebury, CT 06762

    Tucked into Middlebury's desirable Three Mile Hill neighborhood, this beautifully maintained split-level blends everyday comfort with tasteful, modern updates throughout. A welcoming foyer opens to an expansive, light-filled living room anchored by one of the home's two floor-to-ceiling fireplaces - a warm focal point for gatherings large and small. Just off the living space, the generous eat-in

    Agent Photo

    Wayne Watt Jr.

    THE CONNECTICUT AGENCY LLC

    2 Northwood Dr, Middlebury, CT 06762
  • 192 Breakneck Hill Rd, Middlebury, CT 06762

    $435,000

    Sold May 21, 2026

    192 Breakneck Hill Rd, Middlebury, CT 06762

    • 4 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $306/SF
    • 32 Days On Market

    Current Estimated Value $445,022

    Last Listing Agent Maria Pinheiro RE/MAX RISE

    192 Breakneck Hill Rd, Middlebury, CT 06762
    • 29 Winding Trail Unit 29, Middlebury, CT 06762

      Not Listed For Sale

      29 Winding Trail Unit 29, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,130 Sq Ft
      • Built 2015
      29 Winding Trail Unit 29, Middlebury, CT 06762

      Last Sold Summary

      • 117 Days On Market

      Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  • /23

    $649,900

    $19K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,174 Sq Ft

    70 Pine Hollow Dr, Middlebury, CT 06762

    SELLER MOTIVATED! Nestled on 1.22 acres of park-like grounds, this large contemporary offers privacy & serenity you've been searching for, lovingly maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French

    Agent Photo

    Simonne Corriveau

    KW Legacy Partners

    70 Pine Hollow Dr, 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
    • 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

      • 83 Days On Market

      Last Listing Agent Karen Rigopulos West View Properties, LLC

  • /40

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 1,552 Sq Ft

    123 Northwood Dr, Middlebury, CT 06762

    Step into this beautifully maintained 3-bedroom, 2.5-bath split-level home where comfort and functionality come together. Gleaming hardwood floors extend throughout the entire home. The living room features a cozy fireplace, creating the perfect space to relax. The bright kitchen opens seamlessly into the dining room, making everyday living and entertaining a breeze. From the kitchen, step out

    Agent Photo

    Jane Spino

    Showcase Realty, Inc.

    123 Northwood Dr, 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 $382,455

    Last Listing Agent Nicholas Greene eXp Realty

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

      Est $1,746,316

      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

      • 94 Days On Market

      Last Listing Agent John Donato Jr Showcase Realty Tristate

  • /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. Lot assessments #12 - $128,940 2.31

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    Lots 12,13, 14 Mirey Dam 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 $317,303

    Last Listing Agent Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, Middlebury, CT 06762
    • 45 E Farms Rd, Middlebury, CT 06762

      Est $1,138,421

      Not Listed For Sale

      45 E Farms Rd, Middlebury, CT 06762

      • 4 Beds
      • 6 Baths
      • 5,054 Sq Ft
      • Built 2000
      45 E Farms Rd, Middlebury, CT 06762

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent John Donato Jr Showcase Realty, Inc.

  • /14

    $339,900

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft

    12 Yale Ave, Middlebury, CT 06762

    Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen

    Agent Photo

    Wayne Watt Jr.

    THE CONNECTICUT AGENCY LLC

    12 Yale Ave, Middlebury, CT 06762
  • 288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

    $190,000

    Sold Apr 21, 2026

    288 Watertown Rd Unit Lot 5, Middlebury, CT 06762

    • Land
    • 1.13 Acres
    • $168,142 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 231 Days On Market

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 5, Middlebury, CT 06762
    • 28 Jensen Dr, Middlebury, CT 06762

      Est $475,883

      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

      • 4 Days On Market

      Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  • /30

    $520,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    326 Lake Shore Dr, Middlebury, CT 06762

    Experience the beauty of waterfront living in this charming 3-bedroom, 2-bath Cape Cod-style home nestled along Long Meadow Pond. Combining timeless character with thoughtful updates, this inviting home offers the perfect balance of comfort, convenience, and year-round recreation. Inside, you'll find warm and welcoming living spaces highlighted by a cozy fireplace-perfect for relaxing on cool New

    Lauren Cavallo Lauren Ashley Homes LLC

    326 Lake Shore Dr, Middlebury, CT 06762
  • 152 Glenwood Ave, Middlebury, CT 06762

    $224,000

    Sold Jun 29, 2026

    152 Glenwood Ave, Middlebury, CT 06762

    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft
    • Built 1935

    Last Sold Summary

    • 25% Below List Price
    • $206/SF
    • 152 Days On Market

    Current Estimated Value $228,462

    Last Listing Agent Don Orsini West View Properties, LLC

    152 Glenwood Ave, Middlebury, CT 06762
    • 18 Jericho Rd, Middlebury, CT 06762

      Est $559,875

      Not Listed For Sale

      18 Jericho Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 2,908 Sq Ft
      • Built 1978
      18 Jericho Rd, Middlebury, CT 06762

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Michael Bachmann HomeSmart Homes and Estates

  • /24

    $585,000

    Pending
    • 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
  • 223 Carriage Dr, Middlebury, CT 06762

    $670,000

    Sold Jun 30, 2026

    223 Carriage Dr, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 2,484 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $270/SF
    • 95 Days On Market

    Current Estimated Value $669,139

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    223 Carriage Dr, Middlebury, CT 06762
    • 150 Carriage Dr, Middlebury, CT 06762

      Est $652,466

      Not Listed For Sale

      150 Carriage Dr, Middlebury, CT 06762

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 1963
      150 Carriage Dr, Middlebury, CT 06762

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Colleen Burne Coldwell Banker Realty

  • /29

    $774,900

    New Construction $39K PRICE INCREASE
    • 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
  • 30 Nick Rd, Middlebury, CT 06762

    $480,000

    Sold Nov 07, 2025

    30 Nick Rd, Middlebury, CT 06762

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2011

    Last Sold Summary

    • 9% Below List Price
    • $192/SF
    • 113 Days On Market

    Current Estimated Value $506,680

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    30 Nick Rd, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$562,500
Median Single Family Sale Price
$574,900
Median Townhouse Sale Price
$565,000
Median 2 Bedroom Sale Price
$432,950
Median 1 Bedroom Sale Price
$222,500
Average Price Per Sq Ft
$280
Number of Homes for Sale
24
Last 12 months Home Sales
106
Months of Supply
2.70
Median List Price
$574,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home