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Explore Similar Condos Within 2 Miles of Middlebury, CT

  • /37

    $699,900

    • 3 Beds
    • 3 Baths
    • 3,280 Sq Ft

    575 Inverness Ct Unit 575, Oxford, CT 06478

    Welcome to Oxford Greens, where refined living meets resort-style amenities. This exceptional Adler model, the most sought-after for its open floor plan & true ranch-style living, is ideally set on a private cul-de-sac with wide side yards & a serene, wooded backdrop. Thoughtfully upgraded by the original owner, the home features hardwood floors, a gourmet appliance package, a 3-season porch & an

    Karen Berwick Real Estate Two

    575 Inverness Ct Unit 575, Oxford, CT 06478
  • /40

    $625,000

    • 2 Beds
    • 2 Baths
    • 2,008 Sq Ft

    523 Putting Green Ln, Oxford, CT 06478

    Well-maintained Adler with recent updates, including Generac whole house generator, hot water heater, front walk and landscaping. This home has all six rooms on the main level with an unfinished lower walk-out. Unique decking with upper and lower decks. Enjoy morning sun in the front and afternoon sun on your decks with awning. Kitchen with SS, granite, and breakfast nook. M bath with double

    Tom Assheton William Pitt Sotheby's Int'l

    523 Putting Green Ln, Oxford, CT 06478
  • /36

    $629,900

    • 2 Beds
    • 2 Baths
    • 1,777 Sq Ft

    731 Championship Dr Unit 731, Oxford, CT 06478

    Welcome to this incredible Florence model at Fairview at Oxford Greens, a premier 55+ adult community nestled along a stunning 18 hole golf course. This light filled end unit offers the perfect combination of single floor living, thoughtful updates, and wonderful views. Elegant hardwood flooring flows throughout the main living areas, accented by custom moldings that add timeless sophistication.

    Matthew Perrin West View Properties, LLC

    731 Championship Dr Unit 731, Oxford, CT 06478
  • /4

    $134,900

    • 3 Beds
    • 1.5 Baths
    • 991 Sq Ft

    50 Angel Dr Unit D, Waterbury, CT 06708

    Spacious 3 bedroom, 1.5 bath newly remodeled condo. Main bedroom with a half bath. This unit has a modern kitchen with plenty of cabinetry for storage and plenty of counter space. This bright and spacious unit features a living/dining area with updated flooring and a cozy balcony off the kitchen. Off the living room you'll find 3 generously sized bedrooms with ample closet storage and 1.5 bath.

    Toure Diggs eXp Realty

    50 Angel Dr Unit D, Waterbury, CT 06708
  • /17

    $160,000

    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798

    Waiting for your personal touch! This Town In Country lower level unit features a Living Room/Dining Room combo with Fireplace and slider leading to your own private Patio, Fully applianced Kitchen, 2 spacious Bedrooms, and Full Bath. Unit freshly painted with new carpet. Convenient to complex's in-ground pool and laundry. Minutes to Woodbury's town center with its shopping, top restaurants, &

    Ron Nettleton William Raveis Real Estate

    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
  • /40

    $584,900

    • 2 Beds
    • 2 Baths
    • 2,080 Sq Ft

    301 Fairway Dr, Oxford, CT 06478

    Welcome to this 2080 sq ft Redbridge-style ranch in the highly sought-after Oxford Greens community. This sun-filled end unit offers an extra level of privacy and is filled with natural light throughout, creating an open and inviting feel from the moment you step inside. The kitchen, living, and dining areas flow seamlessly, making the layout ideal for both everyday living and entertaining. The

    Carl Demander Coldwell Banker Realty

    301 Fairway Dr, Oxford, CT 06478
  • /11

    $225,000

    • 1 Bed
    • 1 Bath
    • 610 Sq Ft

    81 Chipman St Unit 13, Waterbury, CT 06708

    Renovated Condo with garage in the heart of town plot. New kitchen features gleaming high end granite countertops, stainless steel appliances, new cabinets, and tile backsplash. Remodeled bathroom with granite. All flooring is hardwood or tile. Move right into this gorgeous condo.

    John Donato Jr Showcase Realty, Inc.

    81 Chipman St Unit 13, Waterbury, CT 06708

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.

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$543,283
Median Single Family Sale Price
$527,450
Median Townhouse Sale Price
$548,698
Median 2 Bedroom Sale Price
$676,000
Average Price Per Sq Ft
$280
Number of Homes for Sale
25
Last 12 months Home Sales
108
Months of Supply
2.80
Median List Price
$585,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-6%
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