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Middlebury, CT Homes for Sale with Pool

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  • /32

    $599,900 Coming Soon

    • 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

    (475) 267-4261

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762
  • /40

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,658 Sq Ft

    193 Ridgewood Dr Unit 193, Middlebury, CT 06762

    This beautifully upgraded condominium at Ridgewood at Middlebury offers the perfect blend of style, comfort, and low-maintenance living. Built in 2022 and showing like new, the home features sun-filled spaces, engineered wood floors throughout, and a thoughtfully designed open layout. The main level welcomes you with a seamless flow ideal for everyday living and entertaining. At the center of the

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 255-0656

    193 Ridgewood Dr Unit 193, Middlebury, CT 06762
  • /32

    $759,900 Coming Soon

    • 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
  • /25

    $585,000

    • 4 Beds
    • 3.5 Baths
    • 2,691 Sq Ft

    66 Artillery Rd, Middlebury, CT 06762

    Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The

    Maria Taylor Klemm Real Estate Inc

    66 Artillery Rd, Middlebury, CT 06762
  • /24

    $585,000 Open Sun 12PM - 2PM

    • 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
  • /40

    $2,850,000

    • 8 Beds
    • 8 Baths
    • 9,619 Sq Ft

    775 South St Unit 777, Middlebury, CT 06762

    Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the

    Kary Apanovitch Coldwell Banker Realty

    775 South St Unit 777, Middlebury, CT 06762
  • /14

    $529,900

    • 3 Beds
    • 1.5 Baths
    • 1,811 Sq Ft

    61 Sandy Hill Rd, Middlebury, CT 06762

    Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

    Arben Belica William Raveis Real Estate

    61 Sandy Hill Rd, Middlebury, CT 06762
  • /39

    $574,000

    • 3 Beds
    • 3.5 Baths
    • 2,879 Sq Ft

    24 Ridgewood Dr, Middlebury, CT 06762

    Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • /12

    $599,900

    • 5 Beds
    • 4 Baths
    • 2,345 Sq Ft

    10 Old Waterbury Rd, Middlebury, CT 06762

    4 UNITS IN MIDDLEBURY-NOT ONLY "NEXT TO IMPOSSIBLE" TO FIND, BUT UNBELIEVABLY PRICED AT $599900! THIS "ONCE IN A LIFETIME" OPPORTUNITY CAN BE YOURS! LIVE IN ONE, AND COLLECT RENT FROM THE OTHER THREE UNITS, OR, ADD THIS ONE TO YOUR INVESTMENT PORTFOLIO AND "WATCH IT GROW"! One parcel (.41 ACRE), ON "PARKLIKE" GROUNDS WITH THE ATMOSPHERE OF NATURE ON A SHORT, NO-THRU STREET, consists of a

    Judith Caputo Advantage Realty Group, Inc.

    10 Old Waterbury Rd, Middlebury, CT 06762

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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