Middleton, WI Homes for Sale under $500,000

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  /38

  $458,500

  New Construction $5K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,130 Sq Ft

  6842 Belle Fontaine Blvd, Middleton, WI 53562

  Under construction; estimated completion 8/27/26. Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance

  Encore Homes, Inc Builder

  6842 Belle Fontaine Blvd, Middleton, WI 53562
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  /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
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  /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
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  /53

  $390,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  3550 Valley Ridge Rd, Middleton, WI 53562

  Welcome to Orchid Heights Townhomes! Located close to beautiful Lake Mendota, walking trails and the scenic of Pheasant Branch Conservancy. Enjoy low-maintenance living with lawn care and snow removal included, a community pool and picnic area. This beautifully updated townhome features a completely renovated kitchen, updated bathrooms, updated flooring and new carpet on the upper level. The

  Jeannie LaMarre Keller Williams Inspire

  3550 Valley Ridge Rd, Middleton, WI 53562
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  /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
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  /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
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  /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
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  /15

  $499,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,528 Sq Ft

  616 Tabby Turn Dr, Middleton, WI 53562

  This Jade home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable luxury

  Veronica Isham Stark Company, REALTORS

  616 Tabby Turn Dr, Middleton, WI 53562
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  /30

  $250,000

  Open Sat 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft

  2809 Century Harbor 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 Rd, Middleton, WI 53562
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  /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
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  /35

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 2,280 Sq Ft

  7340 Century Place, Middleton, WI 53562

  THE WORDS YOU WISH TO HEAR IN REAL ESTATE ARE- LOCATION, LOCATION, AND LOCATION. LOCATED JUST BLOCKS AWAY FROM NORTHSIDE ELEMENTARY SCHOOL AND KROMREY MIDDLE SCHOOL, MAKE THIS A SPECIAL HOME. RAISED RANCH, 3 BEDROOMS, 2.5 BATHS, 1720 SF, SCREEN PORCH, GAS FP, 2 CAR GARAGE, AND A .285 ACRE LOT. THE ESTATE IS DOING SOME UPDATES AND REPAIRS TO THE HOME: FRESHLY PAINTED MASTER BEDROOM AND SECOND

  Mike Adler Restaino & Associates

  7340 Century Place, Middleton, WI 53562
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  /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
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  /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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  /16

  $489,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft

  612 Tabby Turn Dr, Middleton, WI 53562

  This Chelsea home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge® cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler®, Moen®, and Shaw®. Durable

  Scott Kramer Stark Company, REALTORS

  612 Tabby Turn Dr, Middleton, WI 53562
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  /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
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  /40

  $444,500

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,130 Sq Ft

  6882 Belle Fontaine Blvd, Middleton, WI 53562

  Move-in ready! Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with unimpeded views of 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement with rec room and full bath INCLUDED. Garage enters at basement level. Shared

  Encore Homes, Inc Builder

  6882 Belle Fontaine Blvd, Middleton, WI 53562
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  /2

  $495,000

  • Land
  • 28,314 Sq Ft
  • $761,538 per Acre

  5933 Sunday Dr, Westport, WI 53597

  LOT 321: This homesite is now available in the second phase of The Prairie Estates Neighborhood in The Community of Bishops Bay. The lot backs to Hole 9 on the Bishops Bay Country Club Golf Course. At 0.65 acres, the lot offers many home design options. This section of The Prairie Estates Neighborhood is a gated area in The Community of Bishops Bay. Choose from one of our exceptional builders to

  Janie Krohmer T. Wall Enterprises Mgt, LLC

  5933 Sunday Dr, Westport, WI 53597
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  /18

  $475,000

  • Land
  • 39,639 Sq Ft
  • $521,978 per Acre

  L 327 Sunday Dr, Westport, WI 53597

  LOT 327: This homesite is now available in The Community of Bishops Bay. This lot is in the gated section in The Prairie Estates Neighborhood on Sunday Drive and is adjacent to the 14 acre Jacobsen Park. The back of the lot has exceptional views of the countryside north to Waunakee. Extensive walking paths throughout the community that connect to the North Mendota Wildlife Prairie Unit and The

  Janie Krohmer T. Wall Enterprises Mgt, LLC

  L 327 Sunday Dr, Westport, WI 53597

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