Middleton, WI Homes for Sale under $300,000

• 

  

  

  /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
• 

  

  

  /60

  $274,900

  Open Sun 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 1,073 Sq Ft

  8510 Greenway Blvd Unit 104, Middleton, WI 53562

  Comfort, convenience and condo living come together in Middleton! This 1-bedroom, 1-bath condo welcomes you with an open floor plan that makes everyday living and entertaining feel effortless. Pull up a stool at the breakfast bar, settle in beside the gas fireplace, or enjoy a quiet moment in the sunroom. Two spaces in the heated underground parking garage offer a welcome perk through every

  Matt Kornstedt Stark Company, REALTORS

  8510 Greenway Blvd Unit 104, Middleton, WI 53562
• 

  

  

  /13

  $249,000

  • 2 Beds
  • 1 Bath
  • 866 Sq Ft

  2051 Allen Blvd Unit 201, Middleton, WI 53562

  Conveniently located near shopping, restaurants, and the bus line, this beautifully updated end-unit condo offers comfort, convenience, and investment potential. Featuring 2 bedrooms, 1 full bath, an open layout, in-unit washer and dryer, and a spacious private balcony, this home is move-in ready. Enjoy the convenience of heated underground parking with one assigned space, elevator access, and

  Donna LaBarge Badger Realty Team

  2051 Allen Blvd Unit 201, Middleton, WI 53562
• 

  

  

  /5

  $249,900

  • Land
  • 7,405 Sq Ft
  • $1,470,000 per Acre

  L235 Towhee 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

  L235 Towhee Dr, 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
• 

  

  /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
• 

  

  /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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  /3

  $229,500

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

  7532 California Love Trail, Middleton, WI 53562

  Generous closing credit! Seller offering a $75,000 closing credit which can be used toward a three year rate buy down on the lot/home package and/or credit towards the home’s solar and geothermal systems. 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

  Estella Moschkau Sprinkman Real Estate

  7532 California Love Trail, Middleton, WI 53562
• 

  

  /4

  $229,500

  • Land
  • 4,356 Sq Ft
  • $2,295,000 per Acre

  Belle Farm Lots, Middleton, WI 53562

  Generous closing credit! Seller offering a $75,000 closing credit which can be used toward a three year rate buy down on the lot/home package and/or credit towards the home’s solar and geothermal systems. Lot prices from $180-$370k. Belle Farm is a new kind of residential community in Middleton focused on physical and mental wellbeing and a deep respect for the earth. Preserving open space and

  Estella Moschkau Sprinkman Real Estate

  Belle Farm Lots, Middleton, WI 53562
• 

  

  /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
• 

  

  /10

  $189,000

  • Land
  • 8,712 Sq Ft
  • $945,000 per Acre

  9326 Wilrich St, Middleton, WI 53562

  Middleton schools with full exposure across the back for a walkout lower level. This is currently one of the last home sites available in this neighborhood! Build your own custom home on this lot with Midwest Homes, local builder of high quality custom homes since 1969. We build a limited number of homes each year to maintain our high standards for craftsmanship and attention to detail. Enjoy

  Kelly Rainiero Mode Realty Network

  9326 Wilrich St, Middleton, WI 53562
• 

  

  /5

  $224,900

  • Land
  • 6,969 Sq Ft
  • $1,405,625 per Acre

  L211 Towhee 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

  L211 Towhee Dr, Middleton, WI 53562
• 

  

  /17

  $259,900

  • 2 Beds
  • 2 Baths
  • 1,107 Sq Ft

  5538 Century Ave Unit 1, Middleton, WI 53562

  Welcome home to this beautifully renovated condo featuring spacious bedrooms and stylish updates throughout. The stunning new kitchen boasts quartz countertops, modern finishes, and flows seamlessly into the living space featuring durable luxury vinyl plank flooring throughout. Both bathrooms have been updated with modern tile, creating a clean and timeless feel. Step outside and enjoy the

  Peyton Henry Berkshire Hathaway HomeServices True Realty

  5538 Century Ave Unit 1, Middleton, WI 53562
• 

  

  /5

  $204,900

  • Land
  • 8,712 Sq Ft
  • $1,024,500 per Acre

  L244 Hooded Merganser 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

  L244 Hooded Merganser Dr, Middleton, WI 53562
• 

  

  /5

  $174,900

  • Land
  • 4,791 Sq Ft
  • $1,590,000 per Acre

  L265 Thrasher St, 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

  L265 Thrasher St, Middleton, WI 53562
• 

  

  /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

  $269,900

  • Land
  • 36,154 Sq Ft
  • $325,181 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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  /16

  $159,000

  $20K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /13

  $160,000

  Open Sat 3:30PM - 5PM

  • 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!)

  Annabel Torres First Weber, Inc

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

  /2

  $243,000

  • Land
  • 4,791 Sq Ft
  • $2,209,091 per Acre

  4051 Serenbe St, Middleton, WI 53562

  Generous closing credit! Seller offering a $75,000 closing credit which can be used toward a three year rate buy down on the lot/home package and/or credit towards the home’s solar and geothermal systems. Lot 18 at Belle Farm includes an 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. Belle Farm is an Eco, Health

  Estella Moschkau Sprinkman Real Estate

  4051 Serenbe St, 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

  $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
• 

  

  /30

  $250,000

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft

  2809 Century Harbor (#3) Rd, Middleton, WI 53562

  OPEN SAT AUG 15TH 11:00-1:00! LAKE MENDOTA FRONTAGE! MODERN UPDATES! GARAGE! EXCELLENT MIDDLETON LOCATION! $250,000! Yes! This condo project has prime frontage on the Lake & possibilities for a boat slip! Rare opportunity! Perfect for those who want a second home on the lake or a year-round perfect location on the bus line w/ quick access to UW & Madison hospitals! Walk in & be greeted by a

  Peggy Acker-Farber RE/MAX Preferred

  2809 Century Harbor (#3) Rd, Middleton, WI 53562
• 

  

  /5

  $219,900

  • Land
  • 8,276 Sq Ft
  • $1,157,368 per Acre

  L253 Thrasher St, 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

  L253 Thrasher St, Middleton, WI 53562
• 

  

  /60

  $205,000

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  6235 Charing Cross Ln Unit A1, Middleton, WI 53562

  Don't miss this move-in-ready 1-bedroom, 1-bath condo offering comfortable, low-maintenance living. Enjoy the quiet outdoors on your patio. Surrounded by beautiful shared green space—perfect for relaxing or enjoying the outdoors. Additional features include 1 underground parking spot, a private storage area, and a convenient on-site laundry. Located just minutes from downtown Middleton, Greenway

  Kevin Navarro LPT Realty

  6235 Charing Cross Ln Unit A1, Middleton, WI 53562
• 

  

  /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
• 

  

  /5

  $174,900

  • Land
  • 4,356 Sq Ft
  • $1,749,000 per Acre

  L267 Thrasher St, 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

  L267 Thrasher St, Middleton, WI 53562
• 

  

  /5

  $224,900

  • Land
  • 6,969 Sq Ft
  • $1,405,625 per Acre

  L208 Hooded Merganser 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

  L208 Hooded Merganser Dr, Middleton, WI 53562

Showing Results 41 - 75, Page 2 of 2