3,798

Middlebury, CT Homes

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  • 10 Ridgewood Dr, Middlebury, CT 06762
    10 Ridgewood Dr, Middlebury, CT 06762
    10 Ridgewood Dr, Middlebury, CT 06762
    /38

    $539,900

    Open Sat 12PM - 2PM
    • 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
  • 111 North St, Middlebury, CT 06762
    111 North St, Middlebury, CT 06762
    111 North St, 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 $530,108

    Last Listing Agent Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
  • 700 Watertown Rd, Middlebury, CT 06762
    700 Watertown Rd, Middlebury, CT 06762
    700 Watertown Rd, Middlebury, CT 06762
    /40

    $615,000

    • 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
  • 10 Old Waterbury Rd Unit 1, Middlebury, CT 06762
    10 Old Waterbury Rd Unit 1, Middlebury, CT 06762
    10 Old Waterbury Rd Unit 1, Middlebury, CT 06762
    /8

    $1,300 Per Month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Apartment for Rent

    10 Old Waterbury Rd Unit 1, Middlebury, CT 06762

    Cozy one bedroom unit for lease. Spacious living room leads to kitchenette with ample counter space. Full bathroom w/ stand up shower. Private In-ground pool with deck. Located close to schools, shopping and highways.

    Jeffrey Corcoran Corcoran Properties, LLC

    10 Old Waterbury Rd Unit 1, 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 $860,966

    Last Listing Agent Donna Kennedy Compass Connecticut, LLC

    171 Judd Hill Rd, Middlebury, CT 06762
    • 69 Nick Rd, Middlebury, CT 06762

      Est $440,135

      Not Listed For Sale

      69 Nick Rd, Middlebury, CT 06762

      • 3 Beds
      • 2.5 Baths
      • 1,414 Sq Ft
      • Built 1950
      69 Nick Rd, Middlebury, CT 06762

      Last Sold Summary

      • 38 Days On Market

  • 90 Fenn Rd, Middlebury, CT 06762
    90 Fenn Rd, Middlebury, CT 06762
    90 Fenn Rd, Middlebury, CT 06762
    /35

    $679,900

    $20K 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
  • 443 Benson Rd, Middlebury, CT 06762
    443 Benson Rd, Middlebury, CT 06762
    443 Benson Rd, Middlebury, CT 06762
    /14

    $3,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,766 Sq Ft
    • House for Rent

    443 Benson Rd, Middlebury, CT 06762

    Come view this spacious, modern four bedroom 2 full bathroom single family home for rent! This home features a fresh looking kitchen with all white appliances and plenty of white cabinetry for all your storage needs! Enjoy the experience of living on a home set back from the street and enjoy the sights of nature looking out over the extensive yard from your very own deck! Book an appointment

    Levi Judqin Brass Moon Realty

    443 Benson 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 $514,410

    Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

    6 Pommel Ln Unit 6, Middlebury, CT 06762
  • 286 Mirey Dam Rd, Middlebury, CT 06762
    286 Mirey Dam Rd, Middlebury, CT 06762
    286 Mirey Dam Rd, Middlebury, CT 06762
    /38

    $975,000

    Pending
    • 4 Beds
    • 3 Baths
    • 4,451 Sq Ft

    286 Mirey Dam Rd, Middlebury, CT 06762

    Set in one of Middlebury's most desirable neighborhoods, this lovingly maintained 4,450 sq. ft. Colonial welcomes you with a beautiful paver driveway, manicured lawn, and timeless curb appeal. Step inside the sunny two-story foyer and feel right at home. The spacious eat-in kitchen is designed for gathering, featuring granite counters, a center island, breakfast bar, and generous dining area. For

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    286 Mirey Dam Rd, Middlebury, CT 06762
  • 1404 West St, Middlebury, CT 06762
    1404 West St, Middlebury, CT 06762
    1404 West St, Middlebury, CT 06762
    /10

    $2,300 Per Month

    • 3 Beds
    • 1 Bath
    • 845 Sq Ft
    • House for Rent

    1404 West St, Middlebury, CT 06762

    Cape Cod style home located close to town center. New kitchen has granite countertops & separate pantry for extra storage. Spacious living room. Primary bedroom includes a walk-in closet. Private deck overlooks a level back yard. Walking distance to town greenway & restaurants. A must see!

    Jeffrey Corcoran Corcoran Properties, LLC

    1404 West St, 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 $582,383

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
  • 566 Benson Rd, Middlebury, CT 06762
    566 Benson Rd, Middlebury, CT 06762
    566 Benson Rd, Middlebury, CT 06762
    /39

    $480,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,020 Sq Ft

    566 Benson Rd, Middlebury, CT 06762

    Before you enter this charming oversized cape, take a look beyond the covered deck at 2.5 parklike acres that just happen to sit adjacent to 19 acres of Middlebury Land Trust. Imagine yourself relaxing there ... and then enter the house. The kitchen was remodeled with white cabinets, matching appliances, and Corian countertops that have a drainboard scored into the top by the sink, and a metal

    Agent Photo

    Ruth Zeiss

    William Raveis Real Estate

    566 Benson Rd, Middlebury, CT 06762
  • 372 Tucker Hill Rd, Middlebury, CT 06762
    372 Tucker Hill Rd, Middlebury, CT 06762
    372 Tucker Hill 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
  • 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 $436,102

    Last Listing Agent Maria Pinheiro RE/MAX RISE

    192 Breakneck Hill Rd, Middlebury, CT 06762
  • 2 Arrowwood Ct Unit 2, Middlebury, CT 06762
    2 Arrowwood Ct Unit 2, Middlebury, CT 06762
    2 Arrowwood Ct Unit 2, Middlebury, CT 06762
    /32

    $599,900

    Pending
    • 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

    2 Arrowwood Ct Unit 2, 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
  • 70 Pine Hollow Dr, Middlebury, CT 06762
    70 Pine Hollow Dr, Middlebury, CT 06762
    70 Pine Hollow Dr, Middlebury, CT 06762
    /23

    $669,000

    • 3 Beds
    • 2.5 Baths
    • 2,734 Sq Ft

    70 Pine Hollow Dr, Middlebury, CT 06762

    Nestled on 1.22 acres of park-like grounds, this 2,734 sq ft contemporary offers the 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 doors

    Agent Photo

    Simonne Corriveau

    KW Legacy Partners

    70 Pine Hollow Dr, 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
  • Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
    /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
  • 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 $376,732

    Last Listing Agent Nicholas Greene eXp Realty

    146 Richardson Dr, Middlebury, CT 06762
  • 64 Watertown Rd, Middlebury, CT 06762
    64 Watertown Rd, Middlebury, CT 06762
    64 Watertown Rd, Middlebury, CT 06762
    /32

    $759,900

    Under Contract
    • 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
  • 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 $312,737

    Last Listing Agent Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, Middlebury, CT 06762
  • 178 Ridgewood Dr Unit 178, Middlebury, CT 06762
    178 Ridgewood Dr Unit 178, Middlebury, CT 06762
    178 Ridgewood Dr Unit 178, Middlebury, CT 06762
    /40

    $639,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,414 Sq Ft

    178 Ridgewood Dr Unit 178, Middlebury, CT 06762

    Pristine is the word for this beautiful, move-in-ready townhome built in 2022, offering modern finishes, extensive tasteful upgrades, and exceptional living space throughout. Living at Ridgewood combines low-maintenance luxury with outstanding community amenities. The main level features an open-concept layout with stylish finishes and updates, including wainscoting throughout the first floor;

    Patricia Forbes Berkshire Hathaway NE Prop.

    178 Ridgewood Dr Unit 178, 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
  • 36 Highridge Rd Unit 36, Middlebury, CT 06762
    36 Highridge Rd Unit 36, Middlebury, CT 06762
    36 Highridge Rd Unit 36, Middlebury, CT 06762
    /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 $670,097

    Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

    223 Carriage Dr, Middlebury, CT 06762
  • 20 Hunting Ridge Rd, Middlebury, CT 06762
    20 Hunting Ridge Rd, Middlebury, CT 06762
    20 Hunting Ridge Rd, Middlebury, CT 06762
    /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 $491,830

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    30 Nick Rd, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 18

Connecticut New Haven County Middlebury

Real Estate & Homes

Home Prices in Middlebury, CT

The median home sale price in Middlebury, CT is $551,968, down 2% year-over-year. Homes in Middlebury sell in 83 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$551,968
Median Single Family Sale Price
$585,000
Median Townhouse Sale Price
$549,936
Median 2 Bedroom Sale Price
$465,000
Median 1 Bedroom Sale Price
$222,500
Average Price Per Sq Ft
$282
Number of Homes for Sale
17
Last 12 months Home Sales
108
Months of Supply
1.90
Median List Price
$591,251
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-2%
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