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Middlebury, CT Condos for Sale

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  • 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

    $700,000

    • 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) 628-4478

    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
  • 181 Ridgewood Dr Unit 181, Middlebury, CT 06762
    181 Ridgewood Dr Unit 181, Middlebury, CT 06762
    181 Ridgewood Dr Unit 181, Middlebury, CT 06762
    /39

    $600,000

    • 3 Beds
    • 2.5 Baths
    • 2,614 Sq Ft

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    Welcome to 181 Ridgewood Drive, Middlebury - a premier Hickory Elite end-unit in the award-winning, resort-style community of Ridgewood at Middlebury. Set amidst beautifully landscaped, wooded grounds, this nearly new townhome blends modern luxury with timeless New England charm, offering a turnkey living experience in one of the region's most desirable neighborhoods. This thoughtfully upgraded

    Heather Crabtree Coldwell Banker Realty

    181 Ridgewood Dr Unit 181, 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
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    $630,000 Open Sun 12PM - 2PM

    • 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

    $559,900

    • 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 Bannon & Hebert

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
  • 29 Winding Trail Unit 29, Middlebury, CT 06762
    29 Winding Trail Unit 29, Middlebury, CT 06762
    29 Winding Trail Unit 29, Middlebury, CT 06762
    /40

    $549,900

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft

    29 Winding Trail Unit 29, Middlebury, CT 06762

    Beautiful Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath condo built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances,

    Jay Irvine Serhant Connecticut, LLC

    29 Winding Trail Unit 29, 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 Middlbury, 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
  • 0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
    /9

    $509,900 New Construction

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

    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762

    Only 4 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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
Connecticut Middlebury

Condos for Sale in Middlebury, CT

Why Live in Middlebury

Plucked from a classic New England postcard, Middlebury is a small, rural town in New Haven County in the western part of Connecticut. While big city amenities in New Haven are only a short drive away, this quaint town of 7,500 is beloved for its scenic beauty, high-ranking school system and higher education opportunities. Surrounded by lush forests, state parks, rolling hills and lakes, and with nearly 2,000 acres of conserved land. This, coupled with its education system has built Middlebury into a destination for families and outdoor enthusiasts to settle. "It's where small-town living meets urban accessibility," says Brian Shaban, local resident and Public Relations Chairman of the Middlebury Town Committee. Middlebury has maintained its tight-knit community and managed to fend off the overdeveloped urban sprawl of many of its Connecticut neighbors. "Everyone knows each other and helps each other out," Shaban says. "Almost all businesses are locally owned, and people here strive to keep it a small town. That's part of its charm, and they don't want big box stores, chains and massive developments coming in and changing that." Despite that, it's no ghost town. Within its 18.5
Learn more about living in Middlebury

Home Trends in Middlebury, CT

On average, homes in Middlebury, CT sell after 91 days on the market compared to the national average of 50 days. The median sale price for homes in Middlebury, CT over the last 12 months is $567,500, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$567,500
Median Single Family Sale Price
$557,450
Median Townhouse Sale Price
$565,000
Median 2 Bedroom Sale Price
$609,000
Average Price Per Sq Ft
$271
Number of Homes for Sale
40
Last 12 months Home Sales
110
Months of Supply
4.40
Median List Price
$599,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Middlebury, there are currently 7 condos for sale, providing a variety of options for potential buyers. With condos priced between $509,900 to $700,000, there's a range to accomodate every budget. As of June, 2025 the median home price in Middlebury is $599,900, while the average sale price is $590,507, offering insights into the local housing market. On average, condos spend 91 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.

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