Middleton, WI Homes for Sale (88 Real Estate Listings)

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3440 Meadow Road, Middleton

$3,750,000

↓ $249,000

3440 Meadow Road, Middleton

4 Beds 4.5 Baths 15 Acres 5,345 SqFt Single Family MLS® # 2023109

15+ breathtaking acres create one of the most impressive private estates in the Town of Middleton. Rolling countryside views, beautiful white fencing, and a true park-like setting surround t...

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Active
Lot 13 Glacier Forest Court, Middleton

$2,750,000

Lot 13 Glacier Forest Court, Middleton

4 Beds 4.5 Baths 2 Acres 5,500 SqFt Single Family MLS® # 2014299

This is an example of a luxurious home that can be built on this vacant lot. This home will be a completely custom new home in any size you want, built by Michael F. Simon Builders. Expected...

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Active
3319 Saracen Way, Middleton

$2,699,000

3319 Saracen Way, Middleton

6 Beds 5.5 Baths 2 Acres 8,070 SqFt Single Family MLS® # 2019981

Located in the Town of Middleton with low taxes, on a breathtaking, mature, wooded, and private 1.5-acre lot, this extraordinary custom residence offers the high-end finishes, craftsmanship,...

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Active
7901 Windermere Court, Middleton

$1,599,000

7901 Windermere Court, Middleton

4 Beds 4.5 Baths 2 Acres 5,460 SqFt Single Family MLS® # 2032474

Custom-built home on 1.66 acres in the Town of Middleton, tucked at the end of a quiet cul-de-sac surrounded by trees and nature. Hardwood floors flow through the main level with a generous ...

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Active
7616 Tumbledown Trail, Middleton

$1,590,000

↓ $100,000

7616 Tumbledown Trail, Middleton

5 Beds 5 Baths 1 Acres 4,674 SqFt Single Family MLS® # 2026810

Exceptional custom home offering luxurious finishes & thoughtful design throughout. The stunning great room features a floor-to-ceiling fireplace flanked by custom built-in shelving. A chef'...

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Active
3702 Pheasant Branch Road, Middleton

$1,500,000

3702 Pheasant Branch Road, Middleton

3 Beds 3 Baths 0 Acres 2,427 SqFt Single Family MLS® # 2023900

Welcome to a home where style and design converge to create a truly curated luxury living experience. Privately positioned with sweeping views of Pheasant Branch Conservancy, this residence ...

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Active
9715 Red Sky Drive, Middleton

$1,450,000

↓ $50,000

9715 Red Sky Drive, Middleton

5 Beds 4.5 Baths 0 Acres 6,129 SqFt Single Family MLS® # 2023786

Nestled in the prestigious Blackhawk neighborhood and located in the highly sought-after Middleton School District, this former Parade of Homes residence showcases timeless elegance, excepti...

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Active
Open House
4830 Breakers Rock Road, Middleton

$1,425,000

↓ $25,000

4830 Breakers Rock Road, Middleton

6 Beds 3.5 Baths 0 Acres 5,035 SqFt Single Family
Sun, Oct 11th, 2026 @ 12pm - 2pm
MLS® # 2028509

Get in before the holidays! Buy down your interest rate with a credit from the seller! Nestled in the Back Nine of the Community of Bishops Bay, this custom-built Acker home was designed for...

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Active
6833 Phil Lewis Way, Middleton

$1,399,000

↓ $26,000

6833 Phil Lewis Way, Middleton

4 Beds 4.5 Baths 0 Acres 4,656 SqFt Single Family MLS® # 2017387

RECENTLY UPDATED RED BIRCH FLOORS, NEW ROOF, DECK RAILINGS & MORE! Timeless architecture meets modern sophistication in sought-after Middleton Hills. This exceptional 4+ bedroom, 4.5 bath ho...

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Pending
7744 Pamela Circle, Middleton

$1,385,000

↓ $15,000

7744 Pamela Circle, Middleton

5 Beds 4.5 Baths 2 Acres 4,955 SqFt Single Family MLS® # 2030777

Welcome to this gorgeous home set on 1.5 acres in the highly rated Middleton School District. Offering the perfect blend of space, privacy, and thorough updates, this property has been metic...

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Offer-No Show
New
2609 Middleton Beach Road, Middleton

$1,350,000 Lake Mendota

2609 Middleton Beach Road, Middleton

2 Beds 2 Baths 0 Acres 1,920 SqFt Single Family MLS® # 2033356

Rare opportunity to enjoy lake living from an exceptional setting at the end of a quiet dead-end street with 45 feet of lake frontage and some of the area's most impressive long-water views,...

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Active
7527 Fallen Oak Drive, Middleton

$1,199,900

↓ $30,000

7527 Fallen Oak Drive, Middleton

5 Beds 4.5 Baths 2 Acres 5,430 SqFt Single Family MLS® # 2023426

Spectacular pre-inspected Modern Queen Anne-Style Victorian Home custom built by Blue Line Designs on a 2A lot in the Town of Middleton. This beautifully finished home features maple, walnut...

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Active
4057 Morning Poem Place, Middleton

$1,199,000

↓ $50,000

4057 Morning Poem Place, Middleton

4 Beds 3.5 Baths 0 Acres 2,516 SqFt Single Family MLS® # 2025953

Welcome to this thoughtfully designed home at Belle Farm offering main level living with a private primary suite & an open concept kitchen, living, & dining area. The living space is light-f...

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Active
6644 Columbus Dr, Middleton

$1,150,000

6644 Columbus Dr, Middleton

5 Beds 4 Baths 0 Acres 3,413 SqFt Single Family MLS® # 1955406

Discover timeless Mid-Century Modern ranch living in the heart of Middleton. This nearly 3,500 sqft home offers exceptional space & a premier location just one block from the conservancy. Th...

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Active
6715 S Chickahauk Trail, Middleton

$1,100,000

6715 S Chickahauk Trail, Middleton

5 Beds 4.5 Baths 0 Acres 4,167 SqFt Single Family MLS® # 2031010

Back on the market with meaningful improvements—an exceptional opportunity to make this refined, thoughtfully designed home your own. The new roof, improved gutters, and refreshed landscapin...

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Active
3324 Glacier Ridge Road, Middleton

$1,095,000

↓ $25,000

3324 Glacier Ridge Road, Middleton

4 Beds 3.5 Baths 0 Acres 3,625 SqFt Single Family MLS® # 2024465

A light-filled, Frank Lloyd Wright-inspired home in desirable Middleton Hills, recently modernized throughout. The spacious gourmet kitchen features a Viking range, newer appliances and abun...

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Pending
2809 Dewey Court, Middleton

$1,000,000 Lake Mendota

2809 Dewey Court, Middleton

3 Beds 2 Baths 0 Acres 1,704 SqFt Single Family MLS® # 2019384

Two lots create a rare opportunity along a quiet channel with direct access to Lake Mendota, inviting a range of possibilities from thoughtful renovation to a ground-up custom build. The exi...

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Active
8685 Airport Road, Middleton

$999,900

↓ $175,000

8685 Airport Road, Middleton

4 Beds 3 Baths 2 Acres 3,620 SqFt Single Family MLS® # 2026028

What sets this incredible property apart is clear before you even step inside. This contemporary home is surrounded by carefully tended prairie and woods, a thriving habitat for birds, polli...

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Middleton, WI Real Estate Statistics

Average Price $679K
Lowest Price $41.4K
Highest Price $6.9M
Total Listings 202
Avg. Days On Market 123
Avg. Price/SQFT $281

Property Types (active listings)


As of October 8, 2026 there are 88 active Middleton, WI real estate listings for sale with an average listing price of $. The highest-priced property listing is $, while the lowest priced property can be purchased for $. Middleton, WI homes for sale have an average price of $ per square foot, based on listings with an average of bedrooms, bathrooms, and square feet of living space.

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Middleton, WI Real Estate & Homes For Sale

If you're looking for a great place to live in the Midwest, look no further than Middleton, Wisconsin! This charming city is located just outside Madison, full of friendly people and beautiful amenities. There's always something to do in Middleton: enjoy the many parks and trails or take advantage of the city's great shopping and dining options. Plus, Middleton is known for its excellent schools, so you can be sure your kids will get an excellent education here.

History of Middleton, Wisconsin

Michel St. Cyr founded the first permanent settlement in what would become Wisconsin when he built a trading post on the northwest shore of Lake Mendota, just west of Madison two miles back then known as "Mendotas." Native Americans had long used this area and white settlers alike for gathering places; it was here that plats were laid out during statewide debates about where our state capital should go at some point between 1831-1834 which led them to create an imaginary 'City Of Four Lakes.'

Middleton is a picturesque village in Milwaukee County. English settlers first settled it, followed closely by German immigrants, who made this their home because of its rich soil that produced much wheat-storing capacity thanks to large quantities found within our town's boundaries! A native Vermont man suggested the name "Middle," - which refers to both smack dab middle between two larger cities ( Madison ) or just plain old state right there at your fingertips. You decide how you want live life.  

Middleton is a vibrant community that offers its residents a high quality of life. It is located in the picturesque rolling hills of southern Wisconsin, just minutes from Madison, the state capital. Middleton is home to various businesses, industries, schools, parks, and recreation facilities. Middleton is a thriving art and entertainment scene. There is something for everyone in Middleton!

Are we looking for a place to call home? Contact a local real estate agent today to learn more about Middleton, Wisconsin!

Demographics of Middleton, Wisconsin

Middleton is a city in Dane County, Wisconsin, United States. The population was 17,442 at the 2010 census. Middleton is part of the Madison Metropolitan Statistical Area. The city is located partially within the town of Middleton; depending on the definition used, a small portion of the municipality may extend into the town of Westport. Middleton was first settled in 1829 and was platted as the Village of Middleton in 1848. The village was named after Middletown, Connecticut. The City of Middleton was incorporated from the village in 1902. Central State Bank Building (now Verizon Wireless) and Thorp Building are listed on the National Register of Historic Places. A thriving community with a highly educated workforce (70% of residents have a bachelor's degree or higher), Middleton is home to about 5,800 businesses, including Epic Systems, Sigma-Aldrich, and Kerry Ingredients & Flavours. The area's economy has also been bolstered by attracting numerous biomedical technology companies to Middleton. These companies reside primarily in the 375-acre University Research Park adjacent to the University of Wisconsin–Madison campus. In 2009, Budget Travel magazine ranked Middleton number 7 on its list of "The Coolest Small Towns in America."

Things to do in Middleton, Wisconsin

There are plenty of things to do in Middleton, whether you enjoy spending time outdoors or exploring the city's vibrant cultural scene. Middleton offers plenty of green space for those who love to be outside, including the Middleton Hills Nature Preserve and Pheasant Branch Conservancy. Several golf courses and parks are also perfect for a picnic or a game of frisbee. If you're looking for something more urban, Middleton's downtown area is home to several shops and restaurants and the Capital Brewery, which offers tours and tastings. No matter your interests, you're sure to find something to do in Middleton!

Events in Middleton, Wisconsin

Middleton, Wisconsin, is home to various events throughout the year. One popular event is the annual Halloween parade, featuring floats and costumes created by local businesses and organizations. The parade is held on the Saturday before Halloween and attracts visitors from all over the state. Another popular event is the Middleton Farmer's Market, held every Saturday from May to October. The market features fresh produce, baked goods, and handcrafted items from local vendors. Visitors can also enjoy live music and entertainment. The Middleton Autumnfest is another popular event, including a parade, carnival rides, and a pumpkin-carving contest. The event is held every October and attracts visitors from all over the Midwest.

Parks in Middleton, Wisconsin

Parks are an essential part of any community. They provide green space for residents to enjoy, and they can also help improve air and water quality. Middleton, Wisconsin, is home to several parks, including Hinrichs Family Farm, Middleton Hills North, Middleton Hills South, and Middleton Station. Hinrichs Family Farm is a working farm that offers public tours and events. Middleton Hills North and South are adjacent parks that feature hiking trails, picnic areas, and playgrounds. Middleton Station is a nature preserve with miles of biking, hiking, and cross-country skiing trails. These parks offer a variety of amenities and activities for residents to enjoy year-round.

Real Estate in Middleton, Wisconsin

Middleton, Wisconsin, is a great place to buy a home. The city is about 20 minutes from Madison, the state capital. The city is home to several employers, including the University of Wisconsin-Madison and Epic Systems Corporation. Middleton also has several parks and recreational facilities. Middleton is the perfect place for you if you're looking for a small-town feel with all the amenities of a larger city.

Schools in Middleton, Wisconsin

Middleton is home to many excellent schools, both public and private. Kromrey Middle School is one of the top-rated middle schools in the state, and Clark Street Community School is a well-respected private school. Middleton High School is also an excellent choice for students looking for a challenging academic program. In addition to these excellent schools, Middleton also has some excellent elementary schools, including Sunset Ridge Elementary School and West Middleton Elementary School. With so many great school options, it's no wonder that Middleton is such a popular place to live.

Why Middleton, Wisconsin?

Middleton, Wisconsin, is a great place to live for several reasons. The city has a variety of parks and recreational facilities, as well as a thriving downtown area. Middleton is also home to several excellent schools, both public and private. In addition, the city is located just 20 minutes from Madison, the state capital. Middleton is the perfect place for you if you're looking for a small-town feel with all the amenities of a larger city.