8

Middleton, WI Homes for Sale with Pool

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  • /86

    $2,995,000

    • 6 Beds
    • 5.5 Baths
    • 6,626 Sq Ft

    4937 Championship Cir, Middleton, WI 53597

    Tucked away on a quiet cul-de-sac within the gated Community of Bishops Bay, this exceptional home offers a private, resort-like setting you'll never want to leave. Surrounded by mature trees and backing to the golf course, enjoy breathtaking sunset views and year-round serenity from your own backyard retreat. Spend summer days relaxing by the pool, entertaining on the patio, or unwinding in the

    Agent Photo

    Rachel Kvasnica

    Pinnacle Real Estate Group LLC

    4937 Championship Cir, Middleton, WI 53597
  • /56

    $925,000

    • 3 Beds
    • 2.5 Baths
    • 3,456 Sq Ft

    3924 S Meadow Dr, Middleton, WI 53562

    Waunakee Schools with Middleton Convenience! Tucked away on a quiet cul-de-sac in highly sought-after Fox Bluff, this beautiful home offers privacy, space, and an unbeatable location. Surrounded by mature trees and tons of green space, the property sits on a huge lot just outside of town. Residents of the Town of Westport enjoy notably lower property taxes while benefiting from an A+ location

    Matthew Lindholm Bruner Realty & Management

    3924 S Meadow Dr, Middleton, WI 53562
  • /27

    $225,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    5548 Century Ave Unit 4, Middleton, WI 53562

    Conveniently located in Middleton’s desirable Rolling Hills Condo Association, this bright & welcoming 2-bed, 2-bath condo offers a true escape from the daily grind. Sunlight streams into the spacious open-concept living area, which opens onto a private balcony overlooking rolling green lawns, mature trees, & the community pool. The well-designed galley kitchen provides ample cabinetry, counter

    Joe Shipley MHB Real Estate

    5548 Century Ave Unit 4, Middleton, WI 53562
  • /42

    $229,900

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,107 Sq Ft

    5522 Century Ave Unit 3, Middleton, WI 53562

    This 2-bed, 2-bath condo offers the perfect quiet park-like setting nestled near the Pheasant Branch Conservancy. This Garden style unit features plank flooring, a bright open concept with a private balcony overlooking the pool and gardens. The kitchen features natural wood cabinets, dedicated dining space as well as a smaller breakfast area. The primary suite includes an updated ensuite bath,

    Kelly Bakken Restaino & Associates

    5522 Century Ave Unit 3, Middleton, WI 53562
  • /56

    $2,950,000

    • 5 Beds
    • 6 Baths
    • 6,531 Sq Ft

    5090 Aspen Valley Ct, Middleton, WI 53562

    Set on a quiet cul-de-sac in Autumn Pond, with nearly three wooded acres of Enchanted Valley countryside — this is the kind of house that's already done the hosting prep for you. The pool's in. The hot tub's heated. The fire pit's waiting. A screen porch and a four-season room with a wood-burning fireplace both open onto the trees.The kitchen is built for the cook with a full table: Wolf, double

    Melissa LeGrand @properties-elleven Christie's International

    5090 Aspen Valley Ct, Middleton, WI 53562
  • /34

    $975,000

    • 4 Beds
    • 3.5 Baths
    • 4,621 Sq Ft

    7842 Big Timber Trail, Middleton, WI 53562

    Custom home in a beautiful setting, Enchanted Valley Estates and Middleton-Cross Plains schools. Live with the convenience of a subdivision on a cul-de-sac but live in privacy of the nature. More than 4,000 sq ft provides not only personal space, whether it need be for work or play, but warm gathering areas to share life. Newly refinished floors in kitchen and entry. Formal dining room with bar.

    Steve Dinehart Heartland Business Transitions, Inc

    7842 Big Timber Trail, Middleton, WI 53562
  • /41

    $695,000

    $54K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,668 Sq Ft

    1308 Shirley St, Middleton, WI 53562

    Price drop 6/23/26. Charming raised ranch in Woodside Heights enclave, just one block from Stricker's Pond, on tree-lined, quiet, well-kept and in-demand neighborhood with downtown Middleton and schools within walking distance. In-ground pool has new liner and heater (2023), slide & stone paved decking. New carpet & paint throughout. Extensive work on landscape. Expansive Great Room has tongue &

    Jane McCormick Shore Bluff Realty

    1308 Shirley St, Middleton, WI 53562
  • /25

    $300,000

    • 2 Beds
    • 2 Baths
    • 1,414 Sq Ft

    3108 Creekview Dr Unit 5, Middleton, WI 53562

    Middleton schools! This beautifully updated 2-bedroom, 2-bath condo features two recently remodeled bathrooms and a spacious, open layout. The large living room with a gas fireplace opens to a private patio, creating the perfect space to relax or entertain. The generously sized kitchen and dining room offer plenty of room for gatherings. Additional highlights include private in-unit laundry, a

    Joe Armentrout Pinnacle Real Estate Group LLC

    3108 Creekview Dr Unit 5, Middleton, WI 53562

Home Price Trends

Median Sale Price
$510,697
Median Single Family Sale Price
$522,697
Median 2 Bedroom Sale Price
$256,700
Median 1 Bedroom Sale Price
$269,900
Average Price Per Sq Ft
$278
Number of Homes for Sale
39
Last 12 months Home Sales
180
Months of Supply
2.60
Median List Price
$525,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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