Middleton, WI Homes for Sale under $300,000

/13
$275,900
- Land
- 0.79 Acre
- $349,241 per Acre
Lot 31 Blue Cedar Dr, Middleton, WI 53593

This .78-acre lot in the NEW Glaciers Trail Neighborhood in the Town of Middleton offers the perfect location to build your dream home with Victory Homes of WI. With the Ice Age Trail and Town Trail running through the neighborhood, outdoor enthusiasts will love the convenient access to hiking and nature. Just a quick drive to Madison's west side, this property is close to restaurants, shopping,

Keith McNeely

First Weber Inc

(608) 830-1675

Lot 31 Blue Cedar Dr, Middleton, WI 53593
Explore Middleton
/2
$265,000
- Land
- 0.1 Acre
- $2,650,000 per Acre
Lot 29 Belle Farm, Middleton, WI 53562

Build your dream home in Belle Farm, Middleton’s new eco-wellness neighborhood designed for connection, sustainability, and a better way of living. This Nest Home lot includes a beautifully designed Brio-built home plan of approximately 2,400 sq ft, blending modern architecture with energy-efficient systems and thoughtful design. With Brio’s expert team and transparent process, you’ll have a

Beth Davis Compass Real Estate Wisconsin

Lot 29 Belle Farm, Middleton, WI 53562
/2
$229,500
- Land
- 0.07 Acre
- $3,278,571 per Acre
7532 California Love Trail, Middleton, WI 53562

Seller is offering a $20,000 geothermal credit at closing for buyers who close on or before May 31, 2026. Design your own home on Lot 28 at Belle Farm. Nest lots are close to the action of Belle Farm but tucked just enough away to experience the moment to moment beauty of nature. Everyday will feel like vacation in the nest. Enjoy easy access to downtown Middleton via Parmenter Street. Belle Farm

Estella Moschkau Sprinkman Real Estate

7532 California Love Trail, Middleton, WI 53562
/12
$200,000
- Land
- 0.23 Acre
- $869,565 per Acre
653 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

653 Windy Willow Rd, Middleton, WI 53593
/12
$200,000
- Land
- 0.26 Acre
- $769,231 per Acre
661 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

661 Windy Willow Rd, Middleton, WI 53593
/3
$246,000
- Land
- 0.08 Acre
- $3,075,000 per Acre
Lot 31 Belle Farm, Middleton, WI 53562

Build your dream home in Belle Farm, Middleton’s new eco-wellness neighborhood designed for connection, sustainability, and a better way of living. This Nest Home lot includes a beautifully designed Brio-built home plan of approximately 2,400 sq ft, blending modern architecture with energy-efficient systems and thoughtful design. With Brio’s expert team and transparent process, you’ll have a

Beth Davis Compass Real Estate Wisconsin

Lot 31 Belle Farm, Middleton, WI 53562
/12
$215,000
- Land
- 0.24 Acre
- $895,833 per Acre
642 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

642 Windy Willow Rd, Middleton, WI 53593
/12
$205,000
- Land
- 0.26 Acre
- $788,462 per Acre
627 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

627 Rustic Rise Way, Middleton, WI 53593
/12
$210,000
- Land
- 0.23 Acre
- $913,043 per Acre
645 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

645 Windy Willow Rd, Middleton, WI 53593
/12
$200,000
- Land
- 0.23 Acre
- $869,565 per Acre
637 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

637 Windy Willow Rd, Middleton, WI 53593
/27
$245,000
- 2 Beds
- 1 Bath
- 866 Sq Ft
2051 Allen Blvd Unit 101, Middleton, WI 53562

First floor end unit with no neighbor across the hall! This 2 bedroom, 1 bath condo offers a convenient west side location with easy access to Madison and Middleton. Inside, you’ll find a bright, open concept living and dining space complemented by an updated, moody kitchen that adds just the right touch of character. Enjoy low maintenance living with in-unit washer and dryer, underground

Mindi Kessenich Real Broker LLC

2051 Allen Blvd Unit 101, Middleton, WI 53562
/12
$210,000
- Land
- 0.26 Acre
- $807,692 per Acre
666 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

666 Rustic Rise Way, Middleton, WI 53593
/35
$299,000
- 2 Beds
- 2 Baths
- 1,468 Sq Ft
3108 Creekview Dr Unit 7, Middleton, WI 53562

Discover your dream home in Middleton, Wisconsin! This stunning 2nd-floor, end-unit offers the perfect blend of luxury & comfort. 2 spacious bedrooms & 2 bathrooms, you'll have plenty of room to relax & unwind. Vaulted ceilings create a spacious, airy atmosphere, while the fireplace adds a cozy touch for our chilly Wisconsin winters. Step out onto the balcony & enjoy the breathtaking views of the

Dana Nowland First Weber Inc

3108 Creekview Dr Unit 7, Middleton, WI 53562
/2
$229,500
- Land
- 0.07 Acre
- $3,278,571 per Acre
4061 Morning Poem Place, Middleton, WI 53562

Seller is offering a $20,000 geothermal credit at closing for buyers who close on or before May 31, 2026. Come build on Lot 35 at Belle Farm in the coveted Middleton-Cross Plains school district. Design a custom home or choose our floor plan consisting of 3 bed, 2.5 bath, approx. 1,800 square feet with the option to finish the basement. Nest lots are close to the action of Belle Farm but tucked

Estella Moschkau Sprinkman Real Estate

4061 Morning Poem Place, Middleton, WI 53562
/12
$205,000
- Land
- 0.26 Acre
- $788,462 per Acre
643 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

643 Rustic Rise Way, Middleton, WI 53593
/6
$229,500
- Land
- 0.08 Acre
- $2,868,750 per Acre
7541 Another Way, Middleton, WI 53562

Seller is offering a $20,000 geothermal credit at closing for buyers who close on or before May 31, 2026. Come build on Lot 24 at Belle Farm in the coveted Middleton-Cross Plains school district. Design a custom home or choose our floor plan consisting of 3 beds, 2.5 baths and 2,100 square feet with the option to finish the basement. Nest Lots are close to the action of Belle Farm but tucked just

Estella Moschkau Sprinkman Real Estate

7541 Another Way, Middleton, WI 53562
/12
$210,000
- Land
- 0.23 Acre
- $913,043 per Acre
658 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

658 Rustic Rise Way, Middleton, WI 53593
/12
$210,000
- Land
- 0.27 Acre
- $777,778 per Acre
647 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

647 Rustic Rise Way, Middleton, WI 53593
/7
$229,500
- Land
- 0.07 Acre
- $3,278,571 per Acre
7539 Another Way, Middleton, WI 53562

Seller is offering a $20,000 geothermal credit at closing for buyers who close on or before May 31, 2026. Come build on Lot 25 at Belle Farm in the coveted Middleton-Cross Plains school district. Design a custom home or choose our floor plan consisting of 3 beds, 2.5 baths and 1,600 square feet in the main house with the option to finish the ADU above the garage as a 532 square foot studio

Estella Moschkau Sprinkman Real Estate

7539 Another Way, Middleton, WI 53562
/14
$210,000
- Land
- 0.33 Acre
- $636,364 per Acre
10436 Emerald Elm Rd, Middleton, WI 53593

Welcome to Westwind! Nestled on the far west side of Madison, Westwind boasts an ideal location with convenient access to the Beltline, shopping, and dining at popular destinations like Greenway Station, Downtown Middleton, Hilldale, and Downtown Madison. Enjoy a short commute to major hospitals and Epic, along with nearby walking paths, parks, and the Pioneer Pointe pool. Our community features

Amy Lessing Compass Real Estate Wisconsin

10436 Emerald Elm Rd, Middleton, WI 53593
/28
$235,000
- 2 Beds
- 2 Baths
- 1,125 Sq Ft
5518 Century Ave Unit 4, Middleton, WI 53562

Tucked into a quiet, park-like setting near Pheasant Branch Conservancy, this updated condo feels like a true retreat from the day-to-day. The refreshed kitchen features stainless steel appliances, modern cabinetry, & updated countertops, and opens naturally into a bright living space where warm bamboo floors add character & comfort. Large windows bring in great natural light & connect the space

Scott Ellingboe RE/MAX Preferred

5518 Century Ave Unit 4, Middleton, WI 53562
/3
$229,500
- Land
- 0.07 Acre
- $3,278,571 per Acre
7528 California Love Trail, Middleton, WI 53562

Seller is offering a $20,000 geothermal credit at closing for buyers who close on or before May 31, 2026. Design your own home on Lot 27 at Belle Farm. Nest lots are close to the action of Belle Farm but tucked just enough away to experience the moment to moment beauty of nature. Everyday will feel like vacation in the nest. Enjoy easy access to downtown Middleton via Parmenter Street. Belle Farm

Estella Moschkau Sprinkman Real Estate

7528 California Love Trail, Middleton, WI 53562
/12
$210,000
- Land
- 0.23 Acre
- $913,043 per Acre
649 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

649 Windy Willow Rd, Middleton, WI 53593
/28
$219,900 Open Sun 11AM - 1PM
- 2 Beds
- 2 Baths
- 864 Sq Ft
6251 Charing Cross Ln Unit E5, Middleton, WI 53562

Showings start 2/26/2026. Light, bright, and beautifully refreshed! This 2-bedroom, 1.5-bath Middleton condo offers comfortable, efficient living in an unbeatable location. Fresh paint and brand new carpet throughout create a clean, welcoming feel from the moment you step inside. The dining area opens to a private patio - perfect for relaxing or entertaining. The primary bedroom includes its own

Andrew Willits Keller Williams Realty

6251 Charing Cross Ln Unit E5, Middleton, WI 53562
/12
$200,000
- Land
- 0.23 Acre
- $869,565 per Acre
657 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

657 Windy Willow Rd, Middleton, WI 53593
/14
$220,000
- Land
- 0.3 Acre
- $733,333 per Acre
10514 Emerald Elm Rd, Middleton, WI 53593

Welcome to Westwind! Nestled on the far west side of Madison, Westwind boasts an ideal location with convenient access to the Beltline, shopping, and dining at popular destinations like Greenway Station, Downtown Middleton, Hilldale, and Downtown Madison. Enjoy a short commute to major hospitals and Epic, along with nearby walking paths, parks, and the Pioneer Pointe pool. Our community features

Amy Lessing Compass Real Estate Wisconsin

10514 Emerald Elm Rd, Middleton, WI 53593
/6
$269,000
- Land
- 0.83 Acre
- $324,096 per Acre
Lot 29 Blue Cedar Dr, Middleton, WI 53593

This is a fantastic corner lot in the luxurious Glaciers Trail neighborhood. Located in the Town of Middleton, it provides access to the much-desired Middleton School District. This lot features the perfect location to build a stunning home while being within a short drive of local shopping, restaurants, golf courses, and other amenities of Madison’s west side. The lot features half exposure.

Alden Cleary Jason Thomas Homes LLC

Lot 29 Blue Cedar Dr, Middleton, WI 53593
/5
$240,000
- Land
- 0.08 Acre
- $3,000,000 per Acre
4063 Serenbe St, Middleton, WI 53562

Seller is offering a $20,000 geothermal credit at closing for buyers who close on or before May 31, 2026. Lot 21 at Belle Farm is designed for a Chicago Row Home floor plan offering 3 to 4 bedrooms, 3.5 baths, and approximately 3,800 square feet. Chicago Row Houses at Belle farm are elegant, three-story, standalone homes inspired by historical neighborhoods in cities like Chicago, New York and

Estella Moschkau Sprinkman Real Estate

4063 Serenbe St, Middleton, WI 53562
/12
$210,000
- Land
- 0.25 Acre
- $840,000 per Acre
641 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

641 Windy Willow Rd, Middleton, WI 53593
/12
$210,000
- Land
- 0.21 Acre
- $1,000,000 per Acre
638 Windy Willow Rd, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

638 Windy Willow Rd, Middleton, WI 53593
/12
$210,000
- Land
- 0.23 Acre
- $913,043 per Acre
662 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

662 Rustic Rise Way, Middleton, WI 53593
/12
$210,000
- Land
- 0.25 Acre
- $840,000 per Acre
646 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

646 Rustic Rise Way, Middleton, WI 53593
/12
$205,000
- Land
- 0.26 Acre
- $788,462 per Acre
639 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

639 Rustic Rise Way, Middleton, WI 53593
/12
$200,000
- Land
- 0.23 Acre
- $869,565 per Acre
640 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

640 Rustic Rise Way, Middleton, WI 53593
/12
$215,000
- Land
- 0.27 Acre
- $796,296 per Acre
651 Rustic Rise Way, Middleton, WI 53593

Discover the perfect balance of city convenience and country charm at Fox Knoll, Madison’s newest sought-after subdivision! Nestled on the quiet west side and within the Middleton-Cross Plains School District, Fox Knoll offers 74 spacious single family home lots with phase one featuring 50 homesites ranging from .21 to .36 acres. Enjoy serene living with Pope Farm Conservancy and Pioneer Park

Steve Britt Spencer Real Estate Group

651 Rustic Rise Way, Middleton, WI 53593
/2
$289,900
- Land
- 0.58 Acre
- $499,828 per Acre
Lot 18 Colonial Way, Middleton, WI 53593

One of the final remaining lots! Lot 18 is a Southern-facing .58-acre lot with a tree line on the rear of the lot. Located in Pioneer Pointe of The Town of Middleton/Middleton Cross Plains School District, you are in the epicenter of Middleton’s vastly expanding west side. Within the Pioneer Pointe community, you will enjoy superb amenities such as the brand new LINKS restaurant, pool, fitness

Alden Cleary Jason Thomas Homes LLC

Lot 18 Colonial Way, Middleton, WI 53593
/14
$200,000
- Land
- 0.25 Acre
- $800,000 per Acre
10513 Emerald Elm Rd, Middleton, WI 53593

Welcome to Westwind! Nestled on the far west side of Madison, Westwind boasts an ideal location with convenient access to the Beltline, shopping, and dining at popular destinations like Greenway Station, Downtown Middleton, Hilldale, and Downtown Madison. Enjoy a short commute to major hospitals and Epic, along with nearby walking paths, parks, and the Pioneer Pointe pool. Our community features

Amy Lessing Compass Real Estate Wisconsin

10513 Emerald Elm Rd, Middleton, WI 53593
/14
$210,000
- Land
- 0.47 Acre
- $446,809 per Acre
10603 Emerald Elm Rd, Middleton, WI 53593

Welcome to Westwind! Nestled on the far west side of Madison, Westwind boasts an ideal location with convenient access to the Beltline, shopping, and dining at popular destinations like Greenway Station, Downtown Middleton, Hilldale, and Downtown Madison. Enjoy a short commute to major hospitals and Epic, along with nearby walking paths, parks, and the Pioneer Pointe pool. Our community features

Amy Lessing Compass Real Estate Wisconsin

10603 Emerald Elm Rd, Middleton, WI 53593
/29
$232,000
- 1 Bed
- 1 Bath
- 850 Sq Ft
2803 Century Harbor Rd Unit 4, Middleton, WI 53562

This 2nd floor one bedroom condo is located in the mature Century Harbor Condominiums development with frontage on Lake Mendota in the City of Middleton. Common area includes greenspace, in-ground swimming pool, shared firepit at the shorefront, and underground parking garage. There is a shared shop/craft room and bike storage room in underground garage. One underground parking stall and separate

Susan Strang Strang Realty, LLC

2803 Century Harbor Rd Unit 4, Middleton, WI 53562

Wisconsin Dane County Middleton

Home Trends in Middleton, WI

On average, homes in Middleton, WI sell after 36 days on the market compared to the national average of 54 days. The median sale price for homes in Middleton, WI over the last 12 months is $540,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$540,000

Median Single Family Sale Price

$574,890

Median 2 Bedroom Sale Price

$315,000

Median 1 Bedroom Sale Price

$270,000

Average Price Per Sq Ft

$273

Number of Homes for Sale

Last 12 months Home Sales

260

Months of Supply

2.00

Median List Price

$525,762

Median Change From 1st List Price

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

Browse a range of homes for sale under $300,000 in Middleton, offering accessible options for prospective buyers. With 39 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Middleton, WI.

Middleton Types of Homes for Sale

Middleton Homes by Price

Middleton Real Estate Listings

More About Living in Middleton

Homes for Sale in Nearby Neighborhoods

Homes for Sale in Nearby Cities

Homes for Sale in Nearby Counties

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