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Homes for sale by state
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Before you start looking
The buying timeline

Afford it

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How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
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Closing costs, itemized
Find a buyer's agent

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3 beds New construction With a pool

5 Bedroom Homes in Middleton, WI

13 listings

5 Bedroom Homes in Middleton, WI

5 Bedroom Homes in Middleton, WI

13 Listings

5 Bedroom Homes in Middleton, WI

13 Listings

76Active

Your local team in Middleton

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

WK

Wes Kane

Thompson Kane & Company INC

NMLS #280777

$745,000

5 bd · — ba · 3,959 sqft

4862 Hickory Trail, Middleton, WI

Ryan Parkos · Coldwell Banker Real Estate Group

$1,100,000

5 bd · — ba · 4,167 sqft

6715 S Chickahauk Trail, Middleton, WI

Susan Detering · Solidarity Realty, LLC

$800,000

5 bd · — ba · 3,729 sqft

5502 Upland Trail, Middleton, WI

Stephanie Wedan · First Weber Inc

$849,900

5 bd · — ba · 2,836 sqft

4408 Blackwolf Run, Middleton, WI

Dustin Laufenberg · MHB Real Estate

$965,000

5 bd · — ba · 3,747 sqft

4525 Hooded Merganser Drive, Middleton, WI

Seth Pfaehler · The McGrady Group, LLC

$3,895,000

5 bd · — ba · 7,515 sqft

7876 Autumn Pond Trail, Middleton, WI

Todd Johnson · Bunbury & Assoc, REALTORS

$1,499,900

5 bd · — ba · 5,354 sqft

4498 Nina Lane, Middleton, WI

Aaron Weber · Compass Real Estate Wisconsin

$1,450,000

5 bd · — ba · 6,129 sqft

9715 Red Sky Drive, Middleton, WI

Ali Khan · Bunbury & Assoc, REALTORS

$849,900

5 bd · — ba · 4,128 sqft

5023 Congressional Hill, Middleton, WI

Chris Barreau · MHB Real Estate

$1,445,000

5 bd · — ba · 5,188 sqft

4516 Nina Lane, Middleton, WI

Shelly Sprinkman · Sprinkman Real Estate

$2,950,000

5 bd · — ba · 6,531 sqft

5090 Aspen Valley Court, Middleton, WI

Melissa LeGrand · @properties-elleven Christie's International

$1,150,000

5 bd · — ba · 3,413 sqft

6644 Columbus Drive, Middleton, WI

Lisa Ashley · Mahler Sotheby's International Realty

$1,500,000

5 bd · — ba · 3,543 sqft

4029 Serenbe Street, Middleton, WI

Estella Moschkau · Sprinkman Real Estate

Explore Middleton homes

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Your local team in Middleton

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

WK

Wes Kane

Thompson Kane & Company INC

NMLS #280777

Listing data & MLS disclosures

South Central Wisconsin Multiple Listing Service: The data relating to real estate for sale on this website comes in part from the Internet Data Display program of the South Central Wisconsin MLS. Real estate listings held by brokerage firms other than Realty.com are marked with the 'MLS' icon and/or include the name of the listing broker. This information, provided by seller, listing broker, and other parties, may not have been verified. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 South Central Wisconsin MLS. All Rights Reserved.
Wisconsin Real Estate Exchange (WIREX): IDX information is provided exclusively for consumers’ personal non-commercial use, may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and is deemed reliable but is not guaranteed by the MLS.

Middleton, WI community profile

Population: 22,934
Median income: $98,077
Housing units: 10,489
People per sq. mi.: 716.7
Area: 32 sq. mi.

Source: HJN community data

Middleton housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 34 sales · as of Aug 28, 2026

Homes that sold · County records, as of Aug 14, 2026

Median sale price: $630,000$454,925–$715,000 typical range
Sales: 16
Paid in cash: 25.0%

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $540,000
Homes for sale: 149
Median days on market: 18 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -4.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 2,944 sq. ft.