6

Middlebury, CT Condos for Sale

Section Image Section Image
  • 33 Ridgewood Dr Unit 33, Middlebury, CT 06762
    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
    /40

    $689,900

    • 3 Beds
    • 4 Baths
    • 3,432 Sq Ft

    33 Ridgewood Dr Unit 33, Middlebury, CT 06762

    Walls of windows! Spectacular, light filled end unit at an award-winning townhome community in Middlebury. Turnkey! Primary bedroom on main level with newly renovated en suite bath. Gorgeous updated kitchen with modern appliances. 2 guest bedrooms on 2nd floor with large shared Jack & Jill bath. Spacious loft for bonus space or home office. Finished lower level flex space for playroom, home

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (203) 871-0910

    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
  • 18 Winding Trail, Middlebury, CT 06762
    18 Winding Trail, Middlebury, CT 06762
    18 Winding Trail, Middlebury, CT 06762
    /40

    $725,000

    • 3 Beds
    • 5 Baths
    • 4,051 Sq Ft

    18 Winding Trail, Middlebury, CT 06762

    Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDROOM SUITES, 3.2 bath has elegance and comfort, built w/ never seen upgrades. On the most sought-after private cul-de-sac St. and the best location in the complex. Enter through a grand two-story foyer with gleaming hardwood floors, cathedral ceilings & soaring windows that fill the home with natural light.

    Jay Irvine Serhant Connecticut, LLC

    18 Winding Trail, Middlebury, CT 06762
  • 2 Dogwood Ct, Middlebury, CT 06762
    2 Dogwood Ct, Middlebury, CT 06762
    2 Dogwood Ct, Middlebury, CT 06762
    /40

    $575,000

    • 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
  • 1 Dogwood Ct Unit 1, Middlebury, CT 06762
    1 Dogwood Ct Unit 1, Middlebury, CT 06762
    1 Dogwood Ct Unit 1, Middlebury, CT 06762
    /34

    $630,000

    • 3 Beds
    • 3.5 Baths
    • 3,477 Sq Ft

    1 Dogwood Ct Unit 1, Middlebury, CT 06762

    Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features

    Joyce Drakeley Drakeley Real Estate, Inc.

    1 Dogwood Ct Unit 1, Middlebury, CT 06762
  • 112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    /40

    $534,900

    • 2 Beds
    • 2.5 Baths
    • 2,593 Sq Ft

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile

    Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
  • 1 Winding Trail Unit 1, Middlebury, CT 06762
    1 Winding Trail Unit 1, Middlebury, CT 06762
    1 Winding Trail Unit 1, Middlebury, CT 06762
    /40

    $659,000

    • 4 Beds
    • 3.5 Baths
    • 3,195 Sq Ft

    1 Winding Trail Unit 1, Middlebury, CT 06762

    Don't wait to see this turn key home in the desirable Ridgewood of Middlebury, one of the areas newest and most picturesque communities. This is a unique end unit, The Emerson Model, situated in a private, quiet cornet lot. As you enter the home, you'll view the open living room/dining room, with a gas fireplace and plenty of light. The attached kitchen includes granite countertops, large cherry

    Scott Hellriegel Berkshire Hathaway NE Prop.

    1 Winding Trail Unit 1, Middlebury, CT 06762
Connecticut New Haven County Middlebury

Condos for Sale in Middlebury, CT

Why Live in Middlebury

Middlebury, Connecticut, is a picturesque New England town located in New Haven County, known for its scenic beauty and tight-knit community. With a population of 7,500, Middlebury offers a blend of rural charm and urban accessibility, being a short drive from New Haven. The town is surrounded by lush forests, state parks, rolling hills, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor activities. Residents enjoy local attractions such as Meadowview Park, Quassapaug Lake, and the Middlebury Greenway, as well as nearby state forests like Naugatuck, Mattatuck, and Paugussett, which offer extensive trails and recreational opportunities. Middlebury's educational system is highly regarded, with Pomperaug Regional School District No. 15 and Westover School providing top-notch education. The town's largest employers include Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. Middlebury maintains a low crime rate compared to the national average, contributing to its appeal for families and retirees. The housing market features classic New England homes, historic colonials, Cape Cods, and lakeside retreats, with properties often including antique barns and garden areas. Local businesses thrive in Middlebury, with popular spots like Willie’s Wood Smoked BBQ, The Local Gourmet, Vyne Restaurant, and Pies & Pub. The town's biggest entertainment draw is Quassy Amusement Park, one of the nation's oldest amusement parks. Middlebury is well-connected via Interstates 8 and 84, State Routes 63 and 64, and is close to Tweed New Haven Airport and Windsor Locks International Airport. Despite recent development proposals, the community remains committed to preserving its small-town charm.

Learn more about living in Middlebury

Home Trends in Middlebury, CT

On average, homes in Middlebury, CT sell after 95 days on the market compared to the national average of 52 days. The median sale price for homes in Middlebury, CT over the last 12 months is $555,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$555,000
Median Single Family Sale Price
$555,000
Median Townhouse Sale Price
$556,230
Median 2 Bedroom Sale Price
$629,250
Average Price Per Sq Ft
$270
Number of Homes for Sale
25
Last 12 months Home Sales
119
Months of Supply
2.50
Median List Price
$599,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Middlebury, there are currently 6 condos for sale, providing a variety of options for potential buyers. With condos priced between $534,900 to $725,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Middlebury is $599,000, while the average sale price is $592,210, offering insights into the local housing market. On average, condos spend 95 days listed before being sold. Whether you're considering condominiums, apartments for sale, or modern condos, there are options to cater to different lifestyles. Browse the range of condos for sale in Middlebury, CT, and discover your ideal residence.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group