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Middlebury, CT Condos for Sale

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  • /37

    $539,900

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft

    17 Highridge Rd Unit 17, Middlebury, CT 06762

    Welcome home to this warm and inviting 3-bedroom, 2.5-bathroom townhome, offering just under 1,900 square feet of beautifully finished living space. From the moment you step into the charming two-story foyer, you'll be greeted by an abundance of natural light and a sense of openness that continues throughout the home. The spacious, open-concept layout seamlessly connects the kitchen, dining area,

    Kayla O'Grady William Raveis Real Estate

    17 Highridge Rd Unit 17, Middlebury, CT 06762
  • /37

    $660,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    6 Brookside Dr, Middlebury, CT 06762

    Welcome to 6 Brookside Drive in Middlebury, CT-a beautifully maintained 3,745 sq ft colonial-style home in the desirable Brookside subdivision. This versatile residence offers 4 bedrooms and 4 bathrooms across three finished levels, ideal for multigenerational living. The open-concept main floor features vaulted ceilings, a gas fireplace, a gourmet eat-in kitchen with smart appliances, and a

    Nutan Pawar DreamHomes Realty LLC

    6 Brookside Dr, Middlebury, CT 06762
  • /37

    $560,000

    • 3 Beds
    • 2.5 Baths
    • 2,122 Sq Ft

    39 Ridgewood Dr Unit 39, Middlebury, CT 06762

    Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The

    Jay Irvine Serhant Connecticut, LLC

    39 Ridgewood Dr Unit 39, Middlebury, CT 06762
  • /34

    $640,000

    • 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
  • /40

    $569,900

    • 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
  • /39

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft

    180 Ridgewood Dr Unit 219, Middlebury, CT 06762

    Welcome to this luxury end-unit condo built in 2022 w/ 3-Bed, 2.5-Bath in Sought-After Ridgewood.1882 Sqft w/ 4 extension to floor plan. This beautifully designed living space, offers 1 level living that many look for. Equipped w/ cathedral ceilings and a first-floor primary bedroom suite for ultimate convenience and a very rare unit. The gourmet kitchen boasts quartz countertops, stainless steel

    Jay Irvine Serhant Connecticut, LLC

    180 Ridgewood Dr Unit 219, 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
  • /37

    $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
  • /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

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 enthusi ...

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$570,000
Median Single Family Sale Price
$569,950
Median Townhouse Sale Price
$555,000
Median 2 Bedroom Sale Price
$589,450
Average Price Per Sq Ft
$268
Number of Homes for Sale
34
Last 12 months Home Sales
111
Months of Supply
3.70
Median List Price
$599,450
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
4%
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