Middleton Town, WI Homes for Sale under $500,000

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  $450,000

  Open Sun 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,592 Sq Ft

  7807 Big Timber Trail, Middleton, WI 53562

  Town of Middleton country living with all the conveniences! Nestled on a partially wooded 1.13-acre lot in desirable Enchanted Valley Estates, this charming one-owner 4-bedroom, 2-bath home offers privacy, character, and endless possibilities. The great room features stunning beamed ceilings and a beautiful fireplace and hearth. French doors in the kitchen open to a deck overlooking the

  

  Kelly Stelzer

  Badger Realty Team

  7807 Big Timber Trail, Middleton, WI 53562
• Explore Middleton Town

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  $375,000

  • Land
  • 33,541 Sq Ft
  • $487,013 per Acre

  Lot 15 White Cedar Dr, Middleton, WI 53593

  Premier lot in the Town of Middleton. Glaciers Trail Subdivision. Just steps away from the Ice Age Trail and Town Trails. Adjacent to and across from greenspace. It’s time to build your dream home in one of Madison’s best suburbs. Quiet street with spectacular homes. Great far west side location and Middleton Schools. Bring your own builder.

  

  Tommy Van Ess

  First Weber Inc

  Lot 15 White Cedar Dr, Middleton, WI 53593
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  /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

  654 Rustic Rise Way, Middleton, WI 53593
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  /16

  $409,900

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  613 Tabby Turn Dr, Middleton, WI 53562

  This Astor home features a smart, open layout and checks off all your boxes. 2 bedrooms, 2 baths with locally crafted cabinetry and painted trim and doors throughout. Gourmet kitchen w/ island and stainless appliances. Owner’s Suite has a private bath, walk-in closet, and tray ceiling. 1-car garage. Retreat to your deck for some R&R. To top it off, this home offers a one-year limited warranty,

  John Ramkey Stark Company, REALTORS

  613 Tabby Turn Dr, Middleton, WI 53562
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  /15

  $409,900

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,403 Sq Ft

  6136 Tabby Turn Dr, Middleton, WI 53562

  The Crest Collection: Same heart. Smarter build. We’ve refined our most loved home plans to offer the same comfort and style with more efficient layouts and simplified construction. The result? Homes that stay true to what matters— with added value built in. For site specific home plan details, please click here. All prices, promotions and specifications are subject to change at any time without

  Veridian Homes Builder

  6136 Tabby Turn Dr, Middleton, WI 53562
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  /15

  $494,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,519 Sq Ft

  620 Tabby Turn Dr, Middleton, WI 53562

  The Crest Collection: Same heart. Smarter build. We’ve refined our most loved home plans to offer the same comfort and style with more efficient layouts and simplified construction. The result? Homes that stay true to what matters— with added value built in. For site specific home plan details, please click

  Veridian Homes Builder

  620 Tabby Turn Dr, Middleton, WI 53562
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  /15

  $432,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,667 Sq Ft

  625 Schewe Rd, Middleton, WI 53562

  The Crest Collection: Same heart. Smarter build. We’ve refined our most loved home plans to offer the same comfort and style with more efficient layouts and simplified construction. The result? Homes that stay true to what matters— with added value built in. For site specific home plan details, please click

  Veridian Homes Builder

  625 Schewe Rd, Middleton, WI 53562
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  /2

  $459,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,765 Sq Ft

  607 Tabby Turn Dr, Middleton, WI 53562

  The Crest Collection: Same heart. Smarter build. We’ve refined our most loved home plans to offer the same comfort and style with more efficient layouts and simplified construction. The result? Homes that stay true to what matters— with added value built in. For site specific home plan details, please click

  Veridian Homes Builder

  607 Tabby Turn Dr, Middleton, WI 53562
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  $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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  /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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  /15

  $489,900

  New Construction

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

  612 Tabby Turn Dr, Middleton, WI 53562

  The Crest Collection: Same heart. Smarter build. We’ve refined our most loved home plans to offer the same comfort and style with more efficient layouts and simplified construction. The result? Homes that stay true to what matters— with added value built in. For site specific home plan details, please click

  Veridian Homes Builder

  612 Tabby Turn Dr, Middleton, WI 53562
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  /15

  $499,900

  New Construction

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

  616 Tabby Turn Dr, Verona, WI 53593

  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, Verona, WI 53593
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  /16

  $432,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,667 Sq Ft

  625 Schewe Rd, Verona, WI 53593

  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

  Nick DeMaria Stark Company, REALTORS

  625 Schewe Rd, Verona, WI 53593
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  /17

  $499,900

  New Construction

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

  616 Tabby Turn Dr, Middleton, WI 53562

  The Crest Collection: Same heart. Smarter build. We’ve refined our most loved home plans to offer the same comfort and style with more efficient layouts and simplified construction. The result? Homes that stay true to what matters— with added value built in. For site specific home plan details, please click

  Veridian Homes Builder

  616 Tabby Turn Dr, Middleton, WI 53562
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  /16

  $489,900

  New Construction

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

  612 Tabby Turn Dr, Verona, WI 53593

  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, Verona, WI 53593
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  $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
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  /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
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  $205,000

  $50K PRICE INCREASE

  • Land
  • 13,068 Sq Ft
  • $683,333 per Acre

  10506 Hearth Stone, Verona, 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

  10506 Hearth Stone, Verona, WI 53593
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  /12

  $220,000

  $28K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $758,621 per Acre

  640 Clear Pond, Verona, 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 Clear Pond, Verona, WI 53593
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  /12

  $200,000

  $45K PRICE INCREASE

  • Land
  • 13,068 Sq Ft
  • $666,667 per Acre

  10502 Hearth Stone, Verona, 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

  10502 Hearth Stone, Verona, WI 53593
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  /12

  $205,000

  $50K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $706,897 per Acre

  10414 Hearth Stone Dr, Verona, 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

  10414 Hearth Stone Dr, Verona, WI 53593
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  /18

  $335,000

  • 2 Beds
  • 2.5 Baths
  • 1,529 Sq Ft

  707 Cricket Ln Unit 5, Middleton, WI 53562

  Welcome Home ! Welcome to this bright and inviting 2BR, 2.5BA condo located in the desirable Middleton School District. Enjoy an open floor plan with hardwood floors, a cozy gas fireplace, and a spacious kitchen with breakfast bar and dinette. Upstairs features two large bedrooms—each with ensuite baths and walk-in closets—plus convenient second-floor laundry. Recent updates include furnace, A/C,

  Phani Palety Real Broker LLC

  707 Cricket Ln Unit 5, Middleton, WI 53562
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  /12

  $200,000

  $45K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $689,655 per Acre

  10422 Hearth Stone, Verona, 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

  10422 Hearth Stone, Verona, WI 53593
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  $474,900

  $25K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 1,737 Sq Ft

  8866 Red Beryl Dr, Middleton, WI 53562

  Pheasant Branch trail access begins right in the neighborhood! This Hidden Oaks gem is the ultimate luxury starter home, offering a vibrant, connected neighborhood where active community living comes naturally. This home features a new roof and downspouts (2026) and a water heater (2023). The main level showcases durable, pet-friendly Adura Rigid Acacia LVP flooring (2024) and luxury carpet

  Michelle Schreier Restaino & Associates

  8866 Red Beryl Dr, Middleton, WI 53562
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  /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
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  /12

  $205,000

  $50K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $706,897 per Acre

  10418 Hearth Stone, Verona, 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

  10418 Hearth Stone, Verona, WI 53593
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  /15

  $464,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,515 Sq Ft

  9109 Rustic Pine Rd, Fitchburg, WI 53593

  Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  9109 Rustic Pine Rd, Fitchburg, WI 53593
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  /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
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  $499,000

  $40K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,402 Sq Ft

  612 Bear Claw Way, Middleton, WI 53562

  Beautifully updated Middleton condo offering more than 2,400 sq. ft. and truly worry-free living! HOA covers lawn care, snow removal, roof, driveway, and exterior maintenance. The main level features a flex room, spacious great room with gas fireplace, open kitchen with updated appliances (refrigerator 2024, microwave 2026, dishwasher & gas stove 2025), and a fully updated half bath. Upstairs

  Hemen Oza Aashram Realty, LLC.

  612 Bear Claw Way, Middleton, WI 53562
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  /6

  $349,900

  $19K PRICE DROP

  • Land
  • 12,632 Sq Ft
  • $1,206,552 per Acre

  10013 Shadow Ridge Trail, Middleton, WI 53562

  The last ready-to-build lot in Blackhawk offers incredible opportunity on Madison's growing westside. Desirable location near schools, dining, shopping, and many parks. Lower level exposure possible, with rear of lot facing south, offering ample year-round natural light. Enjoy sunset walks nearby at Pope Farm Conservancy!

  Chris Barreau MHB Real Estate

  10013 Shadow Ridge Trail, Middleton, WI 53562
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  /2

  $482,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,624 Sq Ft

  9129 Rustic Pine Rd, Fitchburg, WI 53593

  Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  9129 Rustic Pine Rd, Fitchburg, WI 53593
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  /12

  $212,000

  $39K PRICE INCREASE

  • Land
  • 9,147 Sq Ft
  • $1,009,524 per Acre

  664 Clear Pond Way, Verona, 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

  664 Clear Pond Way, Verona, WI 53593
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  /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
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  /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
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  /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
• 

  $460,600

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  The Jade Plan at Acacia Ridge, Verona, WI 53593

  ROOMS DRENCHED IN NATURAL LIGHT SET THE TONE FROM THE MOMENT YOU STEP INSIDE—bright, open, and effortlessly inviting. A kitchen as distinctive as your style blends elevated design with everyday function, ready for weeknight dinners, weekend brunches, and everything in between. It’s calm, comfortable, and designed for the kind of living that never rushes. Welcome to the Jade—a home that can

  Veridian Homes Builder

  9432 Tawny Acorn Dr Unit 36446118, Verona, WI 53593
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  /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
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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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