Middleton, WI Homes for Sale under $400,000

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  /7

  $229,500

  $26K PRICE DROP

  • Land
  • 3,049 Sq Ft
  • $3,278,571 per Acre

  7539 Another Way, Middleton, WI 53562

  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 apartment. This Nest Home plan provides opportunity for flexible, multigenerational living with a primary

  Estella Moschkau Sprinkman Real Estate

  7539 Another Way, Middleton, WI 53562
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• 

  

  

  /23

  $340,000

  $30K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,260 Sq Ft

  9368 Old Sauk Rd, Middleton, WI 53562

  This move-in-ready, two-bedroom, 1.5 bath condo in the highly sought-after Blackhawk neighborhood offers a seamless blend of modern updates and Middleton convenience. Step inside to find a refreshed kitchen featuring updated appliances and polished finishes, flowing into a comfortable living space designed for easy relaxation. With a stylishly updated bathroom and contemporary touches throughout,

  Belinda Thomas Compass Real Estate Wisconsin

  9368 Old Sauk Rd, Middleton, WI 53562
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  /27

  $190,000

  • 2 Beds
  • 1 Bath
  • 820 Sq Ft

  2134 Allen Blvd Unit 2, Middleton, WI 53562

  Cozy first floor 2bd/1bth garden condo features a easy access to downtown Middleton, beautiful cottonwood filled green space, and a patio view of Lake Mendota! Complex just had all roofs replaced! Condo fee includes heat, water/sewer, and hot water! Affordable and convenient, this cute condo is waiting for you.

  David Pausch Weichert, Realtors- Lakepoint

  2134 Allen Blvd Unit 2, Middleton, WI 53562
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  /7

  $199,900

  $55K PRICE INCREASE

  • Land
  • 10,018 Sq Ft
  • $869,130 per Acre

  9924 Shining Willow St, Middleton, WI 53562

  Beautiful half exposed homesite in The Willows neighborhood on Madison's West Side with Middleton Schools. Build with Midwest Homes, builder of quality custom homes since 1969. Enjoy energy and upfront savings with a Energy Star-rated, Green-Built, value-engineered home along with high end finishes and generous allowances for selections that you'll choose with our in-house designer. We build a

  Kelly Rainiero Mode Realty Network

  9924 Shining Willow St, Middleton, WI 53562
• 

  

  

  /23

  $229,000

  • 2 Beds
  • 1.5 Baths
  • 890 Sq Ft

  6243 Charing Cross Ln Unit C3, Middleton, WI 53562

  Welcome home to this beautifully updated Middleton condo offering the perfect blend of style, comfort, and convenience! This 2-bedroom, 1.5-bath unit features fresh updates throughout, creating a bright and modern feel the moment you walk in. The spacious living and dining areas flow seamlessly to a private outdoor space--perfect for relaxing or entertaining guests. Updated flooring, fresh paint,

  Osmar Golpe Premier Point Realty LLC

  6243 Charing Cross Ln Unit C3, Middleton, WI 53562
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  /3

  $229,500

  $6K PRICE DROP

  • Land
  • 3,049 Sq Ft
  • $3,278,571 per Acre

  7528 California Love Trail, Middleton, WI 53562

  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 is a sustainable residential community in Middleton, Wisconsin focused on physical and mental wellbeing

  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
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  /5

  $193,000

  • Land
  • 5,227 Sq Ft
  • $1,608,333 per Acre

  Lot 6 Belle Farm, Middleton, WI 53562

  Embrace simple living in Belle Farm, Middleton’s new eco-wellness neighborhood designed for connection, sustainability, and a better way of life. This Cabin Home lot features a thoughtfully crafted Brio-built home plan of approximately 1,300 sq ft, offering a cozy, efficient footprint without sacrificing design or comfort. Clean lines, smart spaces, and high-quality materials create a home that

  Beth Davis Compass Real Estate Wisconsin

  Lot 6 Belle Farm, Middleton, WI 53562
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  /47

  $390,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,435 Sq Ft

  Redtail Ridge 3-Unit Townhomes Plan at Redtail Ridge - Townhomes, Middleton, WI 53562

  All the comforts of home, coupled with unparalleled convenience! Spacious townhome style means open concept living, generously sized bedrooms, and ample storage space coupled with contemporary design. Shared maintenance agreement means that youll never need to worry about snow removal or landscape careall taken care of for you! Photos and tours are of a similar duplex end-unit model.

  Encore Homes, Inc Builder

  6976 Belle Fontaine Blvd Unit 37141785, Middleton, WI 53562
• 

  

  /47

  $390,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,435 Sq Ft

  Redtail Ridge 4-Unit Townhomes Plan at Redtail Ridge - Townhomes, Middleton, WI 53562

  All the comforts of home, coupled with unparalleled convenience! Spacious townhome style means open concept living, generously sized bedrooms, and ample storage space coupled with contemporary design. Shared maintenance agreement means that youll never need to worry about snow removal or landscape careall taken care of for you! Photos and tours are of a similar duplex end-unit model.

  Encore Homes, Inc Builder

  6976 Belle Fontaine Blvd Unit 37141798, Middleton, WI 53562
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  /8

  $159,000

  $9K PRICE INCREASE

  • Land
  • 8,276 Sq Ft
  • $836,842 per Acre

  9433 Cobalt St, Middleton, WI 53562

  Rare homesite in the Middleton School District on the west side of Madison. Partial front exposure possible. Build with Midwest Homes, builder of quality custom homes since 1969. Enjoy energy and upfront savings with an Energy Star-rated, Green-Built, value-engineered home and quality finishes to be chosen alongside our in-house designer. We build a limited number of homes each year to maintain

  Kelly Rainiero Mode Realty Network

  9433 Cobalt St, Middleton, WI 53562
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  /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
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  /34

  $359,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,815 Sq Ft

  719 Cricket Ln Unit 6, Middleton, WI 53562

  Pope Farm Elementary! Welcome to this rare end-unit townhome located in Middleton school district. Tucked away in a quiet setting with no through traffic, this home offers both privacy and convenience. The open-concept main level is filled with natural light thanks to additional windows unique to end units. The living room features a cozy gas fireplace, wood floor and a private balcony. Enjoy the

  Jiangjiang Liu TRR Realty LLC

  719 Cricket Ln Unit 6, Middleton, WI 53562
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  /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
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  /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
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  /15

  $179,000

  • 2 Beds
  • 1 Bath
  • 820 Sq Ft

  2162 Allen Blvd Unit 1, Middleton, WI 53562

  Affordable, sunny Middleton condo with walkout to patio and wooded courtyard. $395 condo fee includes heat, water/hot water! Two decent size bedrooms, one car attached garage plus outside parking and separate storage area. Includes all appliances. New roof installed June of 2026. Includes trash and snow removal, common area maintenance and insurance. Fun location across from Marshall Park/Lake

  Mary Whitcomb Compass Real Estate Wisconsin

  2162 Allen Blvd Unit 1, Middleton, WI 53562
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  /3

  $275,000

  • Land
  • 3,049 Sq Ft
  • $3,928,571 per Acre

  7545 California Love Trail, Middleton, WI 53562

  Come build a Custom Home on Lot 37 at Belle Farm in the Middleton-Cross Plains School District. Custom Homes are on the edge of neighborhood and nature. This lot allows for a home up to 2,000 sq ft. Belle Farm is a new residential community in Middleton, WI focused on physical and mental wellbeing and a deep respect for the earth. Preserving open space and overlooking Graber Pond, the

  Estella Moschkau Sprinkman Real Estate

  7545 California Love Trail, Middleton, WI 53562
• 

  /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
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  /5

  $240,000

  • Land
  • 3,484 Sq Ft
  • $3,000,000 per Acre

  4063 Serenbe St, Middleton, WI 53562

  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 New Orleans. Made of brick, stone or stucco, our version includes a striking and unexpectedly deep, covered

  Estella Moschkau Sprinkman Real Estate

  4063 Serenbe St, Middleton, WI 53562
• 

  

  /40

  $354,900

  $4K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,815 Sq Ft

  719 Cricket Ln Unit 1, Middleton, WI 53562

  NEW furnace, NEW A/C, NEW Water Softener, NEW Water Heater, NEW dishwasher, NEW fridge, NEW washer & dryer! Beautifully maintained condo offering spacious living in a desirable Middleton location! Bright & inviting main level features an open-concept layout w/large living room, cozy gas fireplace & seamless flow into the dining area & updated kitchen complete w/stainless steel appliances,

  Ashley Pilarowski Century 21 Affiliated

  719 Cricket Ln Unit 1, Middleton, WI 53562
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  /10

  $399,900

  • Land
  • 40,510 Sq Ft
  • $430,000 per Acre

  Lot 17 Welcome Dr, Middleton, WI 53593

  Land this special doesn't stay available for long, and your dream home deserves the perfect setting. This nearly one-acre homesite offers the rare combination of privacy, space, and prestige, with generous separation from neighboring homes that creates a relaxing and entertaining atmosphere. Located in Middleton's Cherrywood Ridge neighborhood within the acclaimed Middleton-Cross Plains Area

  Alden Cleary Jason Thomas Homes LLC

  Lot 17 Welcome Dr, Middleton, WI 53593
• 

  

  /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
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  /15

  $175,000

  $75K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 980 Sq Ft

  7401 Century Place Unit 103B, Middleton, WI 53562

  Fresh, modern, and completely turnkey! This beautifully updated Middleton condo features renovations throughout, offering a clean, move-in ready space you'll love coming home to. includes a dedicated storage unit for added convenience. Set in a vibrant, going community close to shopping, dining, and more- this is low-maintenance living at its best. (Free off-street parking, too!)

  Megan Hoy First Weber Inc - Delafield

  7401 Century Place Unit 103B, Middleton, WI 53562
• 

  

  /5

  $193,000

  • Land
  • 5,227 Sq Ft
  • $1,608,333 per Acre

  Lot 7 Belle Farm, Middleton, WI 53562

  Embrace simple living in Belle Farm, Middleton’s new eco-wellness neighborhood designed for connection, sustainability, and a better way of life. This Cabin Home lot features a thoughtfully crafted Brio-built home plan of approximately 1,300 sq ft, offering a cozy, efficient footprint without sacrificing design or comfort. Clean lines, smart spaces, and high-quality materials create a home that

  Beth Davis Compass Real Estate Wisconsin

  Lot 7 Belle Farm, Middleton, WI 53562
• 

  

  /5

  $159,000

  • Land
  • 3,920 Sq Ft
  • $1,766,667 per Acre

  6613 Junco Dr, Middleton, WI 53562

  Build in Redtail Ridge, a thoughtfully planned Middleton neighborhood offering modern living with access to nature and everyday conveniences. This homesite is located near protected green space and close to area amenities, making it well suited for buyers seeking new construction in a highly regarded community with convenient commutes. Residents enjoy access to 30+ parks and natural areas,

  Aeryn Barry Tim O'Brien Homes LLC

  6613 Junco Dr, Middleton, WI 53562
• 

  

  /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
• 

  

  /17

  $189,000

  $21K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 873 Sq Ft

  2142 Allen Blvd Unit 4, Middleton, WI 53562

  Welcome home to your charming Middleton 2-bedroom condo! This well-maintained condo offers comfortable living with incredible convenience. Conveniently located directly across the street from Marshall Park. A bus stop right outside the building to take you directly into downtown Madison. Inside, you will find a bright and functional layout designed for everyday ease. Additional highlights include

  Jonathan Minerick Homecoin.com

  2142 Allen Blvd Unit 4, Middleton, WI 53562
• 

  

  /25

  $300,000

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  3108 Creekview Dr Unit 5, Middleton, WI 53562

  Middleton schools! This beautifully updated 2-bedroom, 2-bath condo features two recently remodeled bathrooms and a spacious, open layout. The large living room with a gas fireplace opens to a private patio, creating the perfect space to relax or entertain. The generously sized kitchen and dining room offer plenty of room for gatherings. Additional highlights include private in-unit laundry, a

  Joe Armentrout Pinnacle Real Estate Group LLC

  3108 Creekview Dr Unit 5, Middleton, WI 53562
• 

  

  /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
• 

  /2

  $369,900

  • Land
  • 25,700 Sq Ft
  • $626,949 per Acre

  Lot 36 Eden Ct, Middleton, WI 53593

  Build your dream custom home with Jason Thomas Homes on Lot 36 in Pioneer Pointe, a top golf community offering scenic views and luxury homes. This spacious lot offers a flexible building area backing to the golf course, with views of the green on hole 4 at Pioneer Pointe Golf Course, making it perfect for a thoughtfully designed home that suits your lifestyle. Live in a desirable neighborhood

  Alden Cleary Jason Thomas Homes LLC

  Lot 36 Eden Ct, 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
• 

  

  /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

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