Middleton, WI Homes for Sale (102 Real Estate Listings)

$1,150,000

3944 Caribou Road, Middleton

Every detail of this beautifully updated home has been thoughtfully curated to create a space that's both elegant and inviting. The stunning remodeled kitchen features custom cabinetry, marb...

$1,150,000

6644 Columbus Dr, Middleton

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...

Mahler Sotheby's International Realty

$1,120,000

3324 Glacier Ridge Road, Middleton

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...

$1,100,000

6715 S Chickahauk Trail, Middleton

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...

$1,050,000

6711 S Chickahauk Trail, Middleton

High atop the hills of the Conservancy View Neighborhood in Middleton, this 5 bed, 3 bath custom built contemporary craftsman will impress the most discerning homebuyer. Imagine waking up to...

$1,000,000 Lake Mendota

2809 Dewey Court, Middleton

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...

$999,900

8685 Airport Road, Middleton

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...

$965,000

4525 Hooded Merganser Drive, Middleton

Brand new, never-lived-in 2026 Parade of Homes home by Encore Builders on a premium Redtail Ridge lot with commanding sunrise views of Pheasant Branch Conservancy from all three levels! Thou...

$895,000

4912 St Annes Drive, Middleton

Stunning craftsman bungalow built by Brio in the Community of Bishops Bay. This home features incredible craftsmanship and a thoughtful layout. The main level boasts wood floors and oversize...

$849,900

5023 Congressional Hill, Middleton

Experience luxury living in Middleton's highly sought-after Bishops Bay community! This stunning 5-bed home offers exceptional space, thoughtful design, & high-end finishes throughout. Hardw...

$849,900

7226 Hubbard Avenue, Middleton

Classic 1920 Craftsman bungalow on a prime corner lot in the heart of downtown Middleton — that rarely comes to market. This 3-BR, 2.5-BA character home blends original charm with everyday l...

$849,900

4408 Blackwolf Run, Middleton

Show 8/19. Welcome home to this stunning 5 bedroom ranch-style retreat where thoughtful design meets effortless comfort! A charming front porch welcomes you into an open-concept layout boast...

$825,000

7116 Applewood Drive, Middleton

Tucked in a beautiful wooded setting in Applewood Hills, this distinctive 4-bed, 2.5-bath home blends privacy, architectural character and thoughtful high-end updates. The light-filled main ...

$800,000

4434 Misty Valley Drive, Middleton

Immaculate Middleton Ridge home on a quiet cul-de-sac in the Middleton-Cross Plains School District! This 4-bedroom, 3.5-bath home offers over 3,700 finished sq. ft. with an open floor plan,...

$800,000

1619 Elderwood Circle, Middleton

Timeless Style, Exceptional Space, Endless Possibilities! Set on a quiet cul-de-sac, this single-family house offers the space and features that make home feel special. This classic two-stor...

$800,000

5502 Upland Trail, Middleton

Welcome home to this immaculate and beautifully maintained 5-bedroom home in the desirable Northlake neighborhood, offering an impressive combination of space, style, and privacy. With no ne...

$799,900

5019 Sawgrass Terrace, Middleton

Beautiful custom home in sought-after Bishops Bay offering 4+ bedrooms, 3.5 baths, and 4,000+ sq ft of finished living space. Bright, open floor plan features engineered wood floors and floo...

$775,000

6805 Aldo Leopold Way, Middleton

Charming 4-bedroom, 3.5-bath Craftsman in sought-after Middleton Hills Neighborhood and the Middleton School District! The main level features beautiful wood floors, a spacious kitchen with ...