Middleton, WI Homes for Sale

$1,095,000

4741 Daybreak Court, Middleton

5 Beds 4.5 Baths 1 Acres 4,552 SqFt Single Family MLS® # 2008985

Built in 2018 and set on nearly an acre, this stunning home blends modern elegance with everyday comfort. The sun-filled main level features a gourmet kitchen with an oversized quartzite isl...

$989,000

3480 Leflore Court, Middleton

5 Beds 4 Baths 1 Acres 3,473 SqFt Single Family MLS® # 2000421

NO showings until 7/19. Fantastically located, stunning and spacious home tucked away in a private neighborhood....

$825,000

7256 Riles Road, Middleton

3 Beds 2 Baths 5 Acres 3,340 SqFt Single Family MLS® # 2003049

Private woodland retreat on 5 acres in the Middleton-Cross Plains School District. This custom brick home is surrounded by mature trees, landscaped gardens, and sweeping rural views. Inside,...

$799,900

↓ $25,000

7822 Ox Trail Way, Middleton

4 Beds 2.5 Baths 1 Acres 3,145 SqFt Single Family MLS® # 2004772

This meticulously updated home is move-in ready and feels like an escape to northern Wisconsin. This home is perfect for entertaining inside and out. Enjoy the view of the wooded, oversized...

$775,000

3596 Sabaka Trail, Middleton

3 Beds 3.5 Baths 0 Acres 3,041 SqFt Single Family MLS® # 2008299

Charming bright and open tudor on a private wooded lot in the heart of Cherrywood! This extremely well maintained home shows no wear and tear, only tasteful updates. The kitchen was fully ...

$760,000

↓ $15,000

7100 Applewood Drive, Middleton

4 Beds 2 Baths 1 Acres 3,427 SqFt Single Family MLS® # 2001336

NEW ROOF on 8/11! This is one of the special ones for sure. Applewood Hill is a hidden gem - such a convenient spot, yet tucked into a secluded, wooded, charming and quiet neighborhood. One ...

$734,900

↓ $33,100

3590 Sabaka Trail, Middleton

4 Beds 2.5 Baths 0 Acres 3,323 SqFt Single Family MLS® # 2005025

Middleton Schools! - CHERRYWOOD - In the last 8 years this property was enhanced by all new LP Smart Siding, Roof, Gutters w/ gutter guards, Full Face Exterior Stone, Landscaping....the lis...

$718,900

6636 Junco Drive, Middleton

3 Beds 2.5 Baths 0 Acres 2,157 SqFt Single Family MLS® # 2005380

Under construction; est completion 12/2/2025. Welcome to Redtail Ridge—featuring Middleton Schools! Sprawling open concept ranch near Pheasant Branch Conservancy. Cook's kitchen with quartz ...

$715,000

4138 Redtail Pass, Middleton

4 Beds 2.5 Baths 0 Acres 3,221 SqFt Single Family MLS® # 2009981

Step into this expansive 4-bedroom, 2.5-bathroom residence, offering over 3,200 square feet of thoughtfully designed living space. The heart of the home is a cozy family room featuring a wor...

$700,000

3716 Lexington Circle, Middleton

3 Beds 2.5 Baths 0 Acres 3,275 SqFt Single Family MLS® # 2007399

Rare second chance! Tucked away on a quiet cul-de-sac, this beautifully cared-for property offers plenty of space inside & out. Enjoy energy savings with the 7.67 kW solar system, which is f...

$695,000

4205 Monarch Court, Middleton

5 Beds 3.5 Baths 0 Acres 3,415 SqFt Single Family MLS® # 2010118

This Extremely well maintained and spotless clean house sitting in near half acre lot is a perfect blend of quality and comfort in the Northlake neighborhood of Middleton; 24 Yrs of ownershi...

6839 Belle Fontaine Boulevard, Middleton

$628,900

↓ $5,000

6839 Belle Fontaine Boulevard, Middleton

4 Beds 2.5 Baths 0 Acres 2,230 SqFt Single Family MLS® # 1992260

Furnished model! Welcome to Redtail Ridge—featuring Middleton Schools! Spacious carriage home plan with rear-load garage features two-story great room with gas fireplace. Cooks kitchen inclu...

$624,900

6631 Redpoll Road, Middleton

3 Beds 2.5 Baths 0 Acres 1,989 SqFt Single Family MLS® # 2009654

Energy Efficient New Construction: Tim O'Brien Homes O'Keefe plan welcomes you w/ an oversized front porch inviting you into an open living space where the bright sunny Great Room features a...

New

$605,000

1504 Camberwell Court, Middleton

4 Beds 3 Baths 0 Acres 2,318 SqFt Single Family MLS® # 2010306

Welcome to 1504 Camberwell Court! This energy-efficient Middleton home sits in a quiet cul-de-sac surrounded by mature trees and beautiful flower gardens. Across from Stricker Pond, tennis c...

$604,900

↓ $10,000

6628 Linnett Lane, Middleton

3 Beds 2.5 Baths 0 Acres 1,989 SqFt Single Family MLS® # 2005915

Located in the heart of the highly sought-after Middleton School District, this stunning 3-bedroom, 2.5-bathroom home offers the perfect blend of comfort, space & functionality. Step inside ...

$603,900

↓ $5,000

6631 Junco Drive, Middleton

4 Beds 2.5 Baths 0 Acres 2,265 SqFt Single Family MLS® # 1993747

Welcome to Redtail Ridge—featuring Middleton Schools! Cook’s kitchen with granite countertops & sink, stainless steel appliances & pantry. Large great room features gas fireplace and walkout...

$599,900

↓ $10,100

1030 Rooster Run, Middleton

3 Beds 2.5 Baths 0 Acres 2,474 SqFt Single Family MLS® # 2005670

Enjoy maintenance free living! Rare opportunity to own this beautiful 3 BR, 2 Bath condo without sharing a wall with your neighbor. Inside you'll find soaring ceilings, an abundance of windo...

$599,000

3637 Mathias Way, Middleton

3 Beds 2.5 Baths 0 Acres 2,580 SqFt Single Family MLS® # 2007529

Fall in love with this Middleton stunner- 3 beds, 2.5 baths, and a long list of thoughtful updates that make it truly move-in ready. The brand-new primary suite feels like your own retreat, ...

$1,095,000

4741 Daybreak Court, Middleton

$989,000

3480 Leflore Court, Middleton

$825,000

7256 Riles Road, Middleton

$799,900

7822 Ox Trail Way, Middleton

$775,000

3596 Sabaka Trail, Middleton

$760,000

7100 Applewood Drive, Middleton

$734,900

3590 Sabaka Trail, Middleton

$718,900

6636 Junco Drive, Middleton

$715,000

4138 Redtail Pass, Middleton

$700,000

3716 Lexington Circle, Middleton

$695,000

4205 Monarch Court, Middleton

$628,900

6839 Belle Fontaine Boulevard, Middleton

$624,900

6631 Redpoll Road, Middleton

$605,000

1504 Camberwell Court, Middleton

$604,900

6628 Linnett Lane, Middleton

$603,900

6631 Junco Drive, Middleton

$599,900

1030 Rooster Run, Middleton

$599,000

3637 Mathias Way, Middleton

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