Middleton, WI Homes for Sale under $300,000

/2
$210,000
- Land
- 10,018 Sq Ft
- $913,043 per Acre
654 Rustic Rise Way, Middleton, WI 53593

Build your dream home with North Design Build in Middleton’s newest luxury neighborhood, just a short walk to the elementary school. This build-to-suit opportunity has a rare lower-level exposure & a truly personalized design process—expert guidance, hands-on support, and craftsmanship that sets the standard for modern living. Decades of experience allow North DB to move beyond the cookie-cutter

Mary Browning

Compass Real Estate Wisconsin

(608) 599-5952

654 Rustic Rise Way, Middleton, WI 53593
Explore Middleton
/2
$265,000
- Land
- 4,356 Sq Ft
- $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
/3
$229,500

$6K PRICE DROP
- Land
- 3,049 Sq Ft
- $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
/27
$235,000
- 2 Beds
- 2 Baths
- 1,080 Sq Ft
5548 Century Ave Unit 4, Middleton, WI 53562

Conveniently located in Middleton’s desirable Rolling Hills Condo Association, this bright & welcoming 2-bed, 2-bath condo offers a true escape from the daily grind. Sunlight streams into the spacious open-concept living area, which opens onto a private balcony overlooking rolling green lawns, mature trees, & the community pool. The well-designed galley kitchen provides ample cabinetry, counter

Joe Shipley MHB Real Estate

5548 Century Ave Unit 4, Middleton, WI 53562
/12
$200,000

$39K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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

$37K PRICE INCREASE
- Land
- 11,325 Sq Ft
- $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
- 3,484 Sq Ft
- $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
/25
$203,000
- 2 Beds
- 1 Bath
- 820 Sq Ft
2156 Allen Blvd Unit 1, Middleton, WI 53562

Experience the perfect blend of modern luxury and serene views in this completely renovated 2-beds, 1-bath gem in the heart of Middleton. Radiating a cozy Cape Cod vibe, this home features a stunningly updated kitchen with sleek stainless steel appliances and a fully refreshed bathroom. Uniquely situated one flight up from your private garage, the living room seamlessly walks out to a lush,

Tu Le EXP Realty, LLC

2156 Allen Blvd Unit 1, Middleton, WI 53562
/42
$249,900

Open Sun 11AM - 1PM $10K PRICE DROP
- 2 Beds
- 2 Baths
- 1,107 Sq Ft
5522 Century Ave Unit 3, Middleton, WI 53562

This 2-bed, 2-bath condo offers the perfect quiet park-like setting nestled near the Pheasant Branch Conservancy. This Garden style unit features plank flooring, a bright open concept with a private balcony overlooking the pool and gardens. The kitchen features natural wood cabinets, dedicated dining space as well as a smaller breakfast area. The primary suite includes an updated ensuite bath,

Kelly Bakken Restaino & Associates

5522 Century Ave Unit 3, Middleton, WI 53562
/12
$215,000

$54K PRICE INCREASE
- Land
- 10,454 Sq Ft
- $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
$210,000

$49K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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

$15K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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
/12
$210,000

$47K PRICE INCREASE
- Land
- 11,325 Sq Ft
- $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
/2
$229,500
- Land
- 3,049 Sq Ft
- $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

$16K PRICE INCREASE
- Land
- 11,325 Sq Ft
- $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

$26K PRICE DROP
- Land
- 3,484 Sq Ft
- $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

$49K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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

$42K PRICE INCREASE
- Land
- 11,761 Sq Ft
- $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

$26K PRICE DROP
- Land
- 3,049 Sq Ft
- $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
- 14,374 Sq Ft
- $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
/3
$229,500

$6K PRICE DROP
- Land
- 3,049 Sq Ft
- $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

$49K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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
/12
$200,000

$39K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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
- 13,068 Sq Ft
- $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
- 36,154 Sq Ft
- $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
/2
$243,000
- Land
- 4,791 Sq Ft
- $2,209,091 per Acre
4051 Serenbe St, Middleton, WI 53562

Lot 18 at Belle Farm in Middleton’s eco, health and wellness neighborhood. This lot includes a curated, elegant house plan (4 bed, 2.5 bath, 2,800–3,500 sq ft), allowing you to move forward without the friction of starting from scratch. Homes here are built for long-term performance with solar, geothermal HVAC, and high quality materials designed to reduce utility costs and increase resiliency.

Estella Moschkau Sprinkman Real Estate

4051 Serenbe St, Middleton, WI 53562
/5
$240,000
- Land
- 3,484 Sq Ft
- $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

$47K PRICE INCREASE
- Land
- 10,890 Sq Ft
- $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

$28K PRICE INCREASE
- Land
- 9,147 Sq Ft
- $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

$49K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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
$205,000

$15K PRICE INCREASE
- Land
- 11,325 Sq Ft
- $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

$13K PRICE INCREASE
- Land
- 10,018 Sq Ft
- $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

$47K PRICE INCREASE
- Land
- 11,761 Sq Ft
- $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

$15K PRICE INCREASE
- Land
- 25,264 Sq Ft
- $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
- 10,890 Sq Ft
- $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
- 20,473 Sq Ft
- $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
$222,000

$10K PRICE DROP
- 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 37 days on the market compared to the national average of 58 days. The median sale price for homes in Middleton, WI over the last 12 months is $496,500, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$496,500

Median Single Family Sale Price

$500,000

Median 2 Bedroom Sale Price

$260,450

Median 1 Bedroom Sale Price

$230,000

Average Price Per Sq Ft

$279

Number of Homes for Sale

Last 12 months Home Sales

172

Months of Supply

2.20

Median List Price

$499,500

Median Change From 1st List Price

Median Home Sale Price YoY Change

-3%

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 37 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

Dane County Homes for Sale

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