Westside Neighborhood, WI homes for sale & real estate

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NEW 10 HRS AGO

The Harlow Plan, Uk3ff5 Sun Prairie, WI 53590
The Harlow Plan, Uk3ff5 Sun Prairie, WI 53590
The Harlow Plan, Uk3ff5 Sun Prairie, WI 53590

$522,500

3 beds2 baths1,572 sq ft

The Harlow Plan, Uk3ff5 Sun Prairie, WI 53590

2 garage spots • Car-dependent

Listing provided by Zillow

OPEN SAT, 11AM TO 1PM3D WALKTHROUGH

1106 O'Keeffe Ave, Sun Prairie, WI 53590
1106 O'Keeffe Ave, Sun Prairie, WI 53590
1106 O'Keeffe Ave, Sun Prairie, WI 53590
ABOUT THIS HOME
Westside Neighborhood, WI Homes for Sale
Set in the heart of Sun Prairie?s sought-after Smith?s Crossing, this 2015-built home blends timeless curb appeal with modern function in a walkable, connected neighborhood. With its crisp colonial-style exterior and covered front porch, the property offers a polished presence on a tree-lined street. Step out back to enjoy a private patio space, just off the two-car garage with alley access. Inside, find quality finishes throughout, including hardwood-style flooring, a kitchen island and pantry, and main-floor laundry. The full basement is partially finished, offering flexible space for work or play. Located near green space, parks, and local favorites like Beans ?n Cream and Prairie Lakes

$415,000

3 beds3 baths1,812 sq ft

1106 O'Keeffe Ave, Sun Prairie, WI 53590

3,484 sq ft lot • 2 garage spots • Car-dependent

Marine Yoo • Real Broker LLC

OPEN SUN, 12PM TO 1:30PM

3101 Weybridge Dr, Sun Prairie, WI 53590
3101 Weybridge Dr, Sun Prairie, WI 53590
3101 Weybridge Dr, Sun Prairie, WI 53590
ABOUT THIS HOME
Westside Neighborhood, WI Homes for Sale
Showings Begin Thursday, 6/26. This spacious 4-bedroom, 3.5-bath home offers 2,670 sq ft of smart updates and thoughtful design. Enjoy peace of mind with a new roof, siding, and gutters, all in 2025, plus recent upgrades including a new furnace, air conditioner, and water heater. Granite countertops and a cozy gas fireplace warm the heart of the home. The primary bedroom features a generous walk-in closet and en-suite bath. A finished basement offers added flexibility. Relax on the new deck or explore a friendly neighborhood with parks, schools, shopping, and movie nights just minutes away?Costco runs included! Offers presented as received. Ideal closing 8/14 w/ 7day post closing occupancy.

$499,900

4 beds3.5 baths2,670 sq ft

3101 Weybridge Dr, Sun Prairie, WI 53590

0.23 acre lot • $6 HOA • 2 garage spots

Jo Ferraro Real Estate Team • EXP Realty, LLC

NEW CONSTRUCTION

2117 Winding Stream Way, Sun Prairie, WI 53590
2117 Winding Stream Way, Sun Prairie, WI 53590
ABOUT THIS HOME
Westside Neighborhood, WI Homes for Sale
Move-in Ready 8/28/25! This Jackson home features a smart, open layout and checks off all your boxes. 4 bedrooms, 2.5 baths with locally crafted cabinetry and painted trim and doors throughout. Gourmet kitchen w/ island and stainless appliances plus a large pantry for added storage. Owner?s Suite has a private bath, walk-in closet, and tray ceiling. 2-car garage. Retreat to your deck for some R & R. To top it off, this home offers a one-year limited warranty, backed by our own dedicated customer service team. Make this home yours!

$749,900

4 beds2.5 baths2,782 sq ft

2117 Winding Stream Way, Sun Prairie, WI 53590

0.23 acre lot • $21 HOA • 2 garage spots

Jeff Greenlee • Stark Company, REALTORS

NEW CONSTRUCTION

1157 Hickory Hills Dr, Sun Prairie, WI 53590
1157 Hickory Hills Dr, Sun Prairie, WI 53590
ABOUT THIS HOME
Westside Neighborhood, WI Homes for Sale
Move-in Ready 9/2/25! This Harlow home features a smart, open layout and checks off all your boxes. 3 bedrooms, 2 baths with locally crafted cabinetry, and painted trim and doors throughout. Gourmet kitchen w/ island and stainless appliances. Owner?s Suite has a private bath, walk-in closet, and tray ceiling. 2-car garage. Retreat to your patio for some R & R. To top it off, this home offers a one-year limited warranty, backed by our own dedicated customer service team. Make this home yours!

$519,900

3 beds2 baths1,584 sq ft

1157 Hickory Hills Dr, Sun Prairie, WI 53590

6,969 sq ft lot • $21 HOA • 2 garage spots

Jerome Goeden • Stark Company, REALTORS

Property at 2522 Water Lily Cir, Sun Prairie, WI 53590, 3 beds, 2 baths

$609,900

3 beds2 baths1,764 sq ft

2522 Water Lily Cir, Sun Prairie, WI 53590

Scott Kramer • Stark Company, REALTORS

Property at 2418 Leopold Way, Sun Prairie, WI 53590, 4 beds, 3.5 baths

$509,000

4 beds3.5 baths2,456 sq ft

2418 Leopold Way, Sun Prairie, WI 53590

Redfin Corporation

Property at 2581 Smiths Xing #103, Sun Prairie, WI 53590, 1 bed, 1 bath

$225,000

1 bed1 bath796 sq ft

2581 Smiths Xing #103, Sun Prairie, WI 53590

Josh Lamp • Berkshire Hathaway HomeServices True Realty

Property at 335 Bella Way, Sun Prairie, WI 53590, 4 beds, 3.5 baths

$915,000

4 beds3.5 baths3,867 sq ft

335 Bella Way, Sun Prairie, WI 53590

Debbie Lindquist • Keller Williams Lake Country

Property at 2319 Leopold Way, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$539,900

4 beds2.5 baths2,042 sq ft

2319 Leopold Way, Sun Prairie, WI 53590

Jessica Janssen • Design Realty LLC

Property at 387 Bella Way, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$455,000

3 beds2.5 baths1,472 sq ft

387 Bella Way, Sun Prairie, WI 53590

Renee Crothers • RE/MAX Preferred

Property at 2149 Rosenberg Ln, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$500,000

3 beds2.5 baths2,322 sq ft

2149 Rosenberg Ln, Sun Prairie, WI 53590

Kristin Shields • MHB Real Estate

Property at 2893 Hazelnut Trl, Sun Prairie, WI 53590, 4 beds, 3.5 baths

$659,900

4 beds3.5 baths3,612 sq ft

2893 Hazelnut Trl, Sun Prairie, WI 53590

Caleb Payne • Madcityhomes.Com

Property at 2560 Water Lily Cir, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$509,900

3 beds2.5 baths1,647 sq ft

2560 Water Lily Cir, Sun Prairie, WI 53590

Norman Bondoc • Stark Company, REALTORS

Property at 2524 Leopold Way, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths2,105 sq ft

2524 Leopold Way, Sun Prairie, WI 53590

Jamie Foley • Relish Realty

Property at 2998 Triumph Dr #8, Sun Prairie, WI 53590, 2 beds, 2 baths

$299,900

2 beds2 baths1,483 sq ft

2998 Triumph Dr #8, Sun Prairie, WI 53590

Frank Pohlkamp • Assist 2 Sell Homes 4 You Realty

Property at 3247 Prospect Dr, Sun Prairie, WI 53590, 3 beds, 3.5 baths

$620,000

3 beds3.5 baths2,933 sq ft

3247 Prospect Dr, Sun Prairie, WI 53590

Kristin Shields • MHB Real Estate

Property at 1133 Hickory Hills Dr, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$524,900

3 beds2.5 baths1,861 sq ft

1133 Hickory Hills Dr, Sun Prairie, WI 53590

Jeff Greenlee • Stark Company, REALTORS

Property at 3102 Hope St, Sun Prairie, WI 53590, 5 beds, 3.5 baths

$665,000

5 beds3.5 baths3,234 sq ft

3102 Hope St, Sun Prairie, WI 53590

Alejandra Torres • Lauer Realty Group, Inc.

Property at 2138 Winding Stream Way, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$444,900

3 beds2.5 baths1,827 sq ft

2138 Winding Stream Way, Sun Prairie, WI 53590

Nick Demaria • Stark Company, REALTORS

Property at 2564 Koshkonong Way, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$574,900

4 beds2.5 baths2,033 sq ft

2564 Koshkonong Way, Sun Prairie, WI 53590

Adam Crook • Stark Company, REALTORS

Property at 2534 Koshkonong Way, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$469,900

3 beds2.5 baths1,511 sq ft

2534 Koshkonong Way, Sun Prairie, WI 53590

Natalie Mecum • Stark Company, REALTORS

Property at 2543 Water Lily Cir, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$529,900

3 beds2.5 baths1,861 sq ft

2543 Water Lily Cir, Sun Prairie, WI 53590

Kyle Wachter • Stark Company, REALTORS

Property at 2535 Water Lily Cir, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$599,900

4 beds2.5 baths2,203 sq ft

2535 Water Lily Cir, Sun Prairie, WI 53590

John Ramkey • Stark Company, REALTORS

Property at 2168 Winding Stream Way, Sun Prairie, WI 53590, 3 beds, 2 baths

$499,900

3 beds2 baths1,713 sq ft

2168 Winding Stream Way, Sun Prairie, WI 53590

Scott Kramer • Stark Company, REALTORS

Property at 1125 Hickory Hills Dr, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$489,900

3 beds2.5 baths1,647 sq ft

1125 Hickory Hills Dr, Sun Prairie, WI 53590

Veronica Isham • Stark Company, REALTORS

Property at 1214 Orchid Petal Dr, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths2,057 sq ft

1214 Orchid Petal Dr, Sun Prairie, WI 53590

Todd Pierce • Stark Company, REALTORS

Property at The Hudson Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$559,600

4 beds2.5 baths2,172 sq ft

The Hudson Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Emerald Plan, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$479,000

3 beds2.5 baths1,650 sq ft

The Emerald Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Bryant I Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$594,400

4 beds2.5 baths2,406 sq ft

The Bryant I Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Margot Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$590,600

4 beds2.5 baths2,404 sq ft

The Margot Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Hoffman Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$541,400

4 beds2.5 baths2,045 sq ft

The Hoffman Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Cooper Plan, Sun Prairie, WI 53590, 3 beds, 2 baths

$537,500

3 beds2 baths1,764 sq ft

The Cooper Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Conrad Plan, Sun Prairie, WI 53590, 3 beds, 2 baths

$571,400

3 beds2 baths1,974 sq ft

The Conrad Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Everest Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$523,700

4 beds2.5 baths2,092 sq ft

The Everest Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Carmichael Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$619,500

4 beds2.5 baths2,616 sq ft

The Carmichael Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Hendrix Plan, Sun Prairie, WI 53590, 3 beds, 2 baths

$539,200

3 beds2 baths1,841 sq ft

The Hendrix Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Atwood Plan, Sun Prairie, WI 53590, 4 beds, 2.5 baths

$589,600

4 beds2.5 baths2,446 sq ft

The Atwood Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Beryl Plan, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$456,600

3 beds2.5 baths1,503 sq ft

The Beryl Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Sawyer Plan, Sun Prairie, WI 53590, 3 beds, 2.5 baths

$497,400

3 beds2.5 baths1,880 sq ft

The Sawyer Plan, Sun Prairie, WI 53590

Listing provided by Zillow

Property at The Elaine Plan, Sun Prairie, WI 53590, 3 beds, 2 baths

$483,800

3 beds2 baths1,482 sq ft

The Elaine Plan, Sun Prairie, WI 53590

Listing provided by Zillow

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Average home prices near Westside Neighborhood, WI

Cities

Neighborhoods

Liberty Square homes for sale
$297,500
Smith's Crossing homes for sale
$500,000
Central Sun Prairie homes for sale
$410,000
Eastern Sun Prairie homes for sale
$444,950
Sandburg homes for sale
$369,450
North East Madison homes for sale
$435,000
Windsor Gardens homes for sale
$1,150,000
East Side homes for sale
$414,900
Savannah Brooks homes for sale
$809,700

Westside Neighborhood, WI real estate trends

All Home Types trends in Westside Neighborhood, WI

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$427,450

-6.6% YoY | May 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

May 2025

Growth

% YoY

Westside Neighborhood, WI

$427,450

-6.6%

See more Westside Neighborhood, WI market insights

More to explore in Westside Neighborhood, WI

How to buy a house in Westside Neighborhood, WI

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