Middleton, WI Homes for Sale (76 Real Estate Listings)

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4743 Delmara Road, Middleton

$3,500,000

4743 Delmara Road, Middleton

4 Beds 5.5 Baths 11 Acres 9,019 SqFt Single Family MLS® # 2014199

Exceptional Hart DeNoble Builders custom-built luxury home on 10+ acres in Middleton. The main level features Brazilian cherry hardwood floors, soaring ceilings, crown molding, multiple livi...

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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
Open House
3395 White Cedar Drive, Middleton

$2,124,900

↓ $25,000

3395 White Cedar Drive, Middleton

5 Beds 4.5 Baths 1 Acres 6,182 SqFt Single Family
Sat, Feb 14th, 2026 @ 12pm - 4pm
MLS® # 2004160

Exceptional 5-bedroom new build by Victory Homes of WI! Filled with natural light, this home features soaring ceilings and walls of windows. The chef’s kitchen and spacious dining area open ...

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Active
4043 Serenbe Street, Middleton

$1,799,000

↓ $51,000

4043 Serenbe Street, Middleton

5 Beds 4.5 Baths 0 Acres 4,293 SqFt Single Family MLS® # 2010370

Enjoy low maintenance living in this contemporary home at Belle Farm, where the HOA handles yard care and snow removal. Set within Middletonâs walkable, wellness focused neighborhood, this m...

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Active
4029 Serenbe Street, Middleton

$1,749,000

↓ $50,000

4029 Serenbe Street, Middleton

5 Beds 5.5 Baths 0 Acres 4,063 SqFt Single Family MLS® # 2010369

Enjoy low maintenance living in this thoughtfully designed home at Belle Farm, where the HOA handles yard care and snow removal. Perfectly positioned on a corner lot, this 5 bedroom home off...

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Pending
7484 Summit Ridge Road, Middleton

$1,399,900

7484 Summit Ridge Road, Middleton

5 Beds 3.5 Baths 1 Acres 5,135 SqFt Single Family MLS® # 2015162

Showings begin 2/25/26....

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Active
Open House
3579 Superior Oak Drive, Middleton

$1,399,000

↓ $26,000

3579 Superior Oak Drive, Middleton

5 Beds 4.5 Baths 1 Acres 4,237 SqFt Single Family
Sat, Feb 14th, 2026 @ 12pm - 4pm
MLS® # 2005829

Beautiful New Construction Home. The 1st floor open plan, with large Great Room and Kitchen/Dinette, kitchen island, large pantry and all appliances Formal Dining room and home office. Maste...

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Active
7532 Peyton Parkway, Middleton

$1,399,000

7532 Peyton Parkway, Middleton

4 Beds 3.5 Baths 1 Acres 3,801 SqFt Single Family MLS® # 2010554

NEW CONSTRUCTION! Welcome to Evans Crossing. This house is located in an area of fine homes with strong architectural requirements and in a wooded setting abutting the Pioneer Pointe golf co...

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Active
New Open House
4539 Deering Trail, Middleton

$1,395,000

4539 Deering Trail, Middleton

4 Beds 4 Baths 1 Acres 4,467 SqFt Single Family
Sat, Feb 14th, 2026 @ 12pm - 2pm
MLS® # 2016229

Beautifully designed ranch home set in a quiet rural subdivision with surrounding woods for privacy, views and wildlife. This 4-bedroom, 4-bath home offers a first-floor primary suite, while...

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Active
3615 John Muir Drive, Middleton

$1,200,000

↓ $50,000

3615 John Muir Drive, Middleton

5 Beds 4 Baths 0 Acres 3,718 SqFt Single Family MLS® # 2010149

A nature lover's oasis, backing up to Pheasant Branch Conservancy! From the moment you step onto the grand front porch, this large custom bungalow will pull you in with its use of rich redol...

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Pending
3979 Swoboda Road, Middleton

$1,200,000

3979 Swoboda Road, Middleton

5 Beds 4.5 Baths 1 Acres 4,600 SqFt Single Family MLS® # 2015376

This elegant, sun-filled home sits on a beautiful 1.15-acre lot and has been thoughtfully refreshed with fresh interior paint, updated lighting and fixtures, and a striking modern fireplace ...

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Pending
4517 Shooting Star Avenue, Middleton

$1,200,000

4517 Shooting Star Avenue, Middleton

4 Beds 3 Baths 1 Acres 4,467 SqFt Single Family MLS® # 2016002

Beautifully sited on a private .92-acre lot in Middleton, this exceptional home built by Design Shelters backs to a serene tree line, creating a peaceful setting for outdoor living and eveni...

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Pending
7403 Elmwood Avenue, Middleton

$1,199,000

↓ $26,000

7403 Elmwood Avenue, Middleton

4 Beds 2.5 Baths 0 Acres 2,997 SqFt Single Family MLS® # 2003875

Rare opportunity to own this stunning, one of a kind 4 bedroom home just steps from all downtown Middleton has to offer. Find updates & custom remodels around every corner incl the Chefs kit...

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Pending
3784 Cardinal Point Trail, Middleton

$1,150,000

↓ $100,000

3784 Cardinal Point Trail, Middleton

5 Beds 3.5 Baths 1 Acres 3,986 SqFt Single Family MLS® # 2012922

Welcome to your dream home! This spacious and thoughtfully designed home is ready for its next chapter. The open-concept layout is ideal for both everyday living and effortless entertaining....

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Active
New Open House
3534 Swoboda Road, Middleton

$1,100,000

3534 Swoboda Road, Middleton

4 Beds 3.5 Baths 1 Acres 4,320 SqFt Single Family
Sun, Feb 15th, 2026 @ 11am - 1pm
MLS® # 2015350

Showings start 2/14**Welcome to this exceptional two-story Colonial in the prestigious Cherrywood community, set on a serene, private 1.385 acre wded homesite w/coveted southern exposure & s...

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Pending
8561 Airport Road, Middleton

$999,000

↓ $51,000

8561 Airport Road, Middleton

3 Beds 2 Baths 2 Acres 2,920 SqFt Single Family MLS® # 2010042

Experience the perfect mix of historic charm and modern updates in this beautifully maintained Colonial nestled on a picturesque wooded lot in the Town of Middleton. With over 2,900 sq ft of...

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Offer-No Show
7726 Pamela Circle, Middleton

$995,000

7726 Pamela Circle, Middleton

5 Beds 3.5 Baths 1 Acres 4,647 SqFt Single Family MLS® # 2013771

Showings to begin February 5th. Get ready for this gorgeous custom 5 BR ranch on 1.5 acres in beautiful Cherrywood Acres! Youâll feel the warmth of this home upon the spacious foyer entry, t...

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Pending
3555 John Muir Drive, Middleton

$995,000

3555 John Muir Drive, Middleton

4 Beds 3.5 Baths 0 Acres 4,194 SqFt Single Family MLS® # 2014994

Step inside and prepare to be impressed! Soaring ceilings paired with rich maple trim, doors, and floors create a perfect blend of timeless elegance and inviting warmth. The gourmet kitchen ...

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Middleton, WI Real Estate Statistics

Average Price $715K
Lowest Price $155K
Highest Price $4M
Total Listings 135
Avg. Days On Market 158
Avg. Price/SQFT $285

Property Types (active listings)


As of February 14, 2026 there are 76 active Middleton, WI real estate listings for sale with an average listing price of $816,989. The highest-priced property listing is $3,500,000, while the lowest priced property can be purchased for $444,900. Middleton, WI homes for sale have an average price of $293 per square foot, based on listings with an average of 3.6 bedrooms, 2.9 bathrooms, and 2,757 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.