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Winnetka, IL Homes for Sale with Pool

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  • /62

    $4,499,000

    • 5 Beds
    • 7 Baths
    • 6,697 Sq Ft

    528 Roslyn Rd, Kenilworth, IL 60043

    Stunning French Manor house on one of East Kenilworth's most beautiful streets. Stylish and sophisticated, this unique home is perfectly situated near the lake, train, Sears School, and New Trier High School. Luxurious landscaping envelopes the property, highlighted by a serene backyard pool. Expansive marble foyer opens to gracious living room and charming dining room. Dramatic floating

    Dayle Lively Baird & Warner

    528 Roslyn Rd, Kenilworth, IL 60043
  • /73

    $3,495,000

    • 4 Beds
    • 6 Baths
    • 4,225 Sq Ft

    42 Woodley Rd, Winnetka, IL 60093

    Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

    Peggy Lewis @properties Christie's International Real Estate

    42 Woodley Rd, Winnetka, IL 60093
  • /53

    $5,149,000

    • 6 Beds
    • 7 Baths
    • 13,000 Sq Ft

    320 Woodley Rd, Winnetka, IL 60093

    Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof,

    Susan Maman @properties Christie's International Real Estate

    320 Woodley Rd, Winnetka, IL 60093
  • /58

    $2,439,000

    • 4 Beds
    • 7 Baths
    • 4,269 Sq Ft

    1185 Hill Rd, Winnetka, IL 60093

    Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast

    Joanne Hudson Compass

    1185 Hill Rd, Winnetka, IL 60093

Home Trends in Winnetka, IL

Housing Trends

Median Sale Price
$1,902,500
Median Single Family Sale Price
$2,100,350
Median Townhouse Sale Price
$599,999
Median 2 Bedroom Sale Price
$662,500
Median 1 Bedroom Sale Price
$265,000
Average Price Per Sq Ft
$531
Number of Homes for Sale
15
Last 12 months Home Sales
192
Months of Supply
0.90
Median List Price
$1,950,000
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
15%
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