Pleasant Hill Homes with Pool Available Amenities

Welcome to the charming community of Lake Winnebago, nestled in Cass County, Missouri, where the Pleasant Hill School District shines as a beacon of educational excellence. This vibrant district is dedicated to fostering a nurturing and stimulating environment for students, offering a wide array of programs that cater to diverse interests and learning styles. Students benefit from dedicated educators, modern facilities, and a strong emphasis on academic achievement, making Pleasant Hill a top choice for families seeking a quality education.

Living in Lake Winnebago offers more than just access to outstanding schools; it provides a serene and picturesque lifestyle. Imagine coming home to a beautiful property equipped with a refreshing pool, perfect for those hot summer days. Homes with pool amenities in this area are designed for both relaxation and entertainment, allowing you to enjoy leisurely afternoons by the water or host memorable gatherings with family and friends.

The community's tranquil surroundings and scenic views create an idyllic backdrop for your dream home. Whether you prefer a cozy retreat or a spacious family abode, Lake Winnebago has a variety of properties that cater to your needs, all while being just a stone's throw away from the excellent educational opportunities offered by the Pleasant Hill School District.

Explore the possibilities of life in Lake Winnebago, where quality education meets the comforts of home, and where homes with pool amenities invite you to create lasting memories. Your dream lifestyle awaits!

Newest Pleasant Hill Homes with Pool Available Amenities

$1,100,000

Beautiful walkout, lakefront lot ready for your dream home. Life at Lake Winnebago has the feel of always being on vacation with so many community amenities. Basketball and tennis courts, walking trails, horse stables and access to the Arrowhead Yacht Club. Additional community information can be found at www.lakewinnebago.org. All docks must be approved and permited prior to the start of dock construction.

18 Checotah Bluffs Circle, Lake Winnebago

Listing courtesy of Dave Baldwin of Platinum Realty LLC.

$4,449,000

5 Beds ⋅ 4.5 Baths

Experience refined lakefront living on the private waters of Lake Winnebago in this exceptional custom modern craftsman by Walker Custom Homes—proudly prepared for Kansas City’s 2026 Artisan Tour. Perfectly positioned on a premier lot with a gentle slope to the water’s edge, this residence blends architectural elegance with resort-style amenities. Designed for both everyday comfort and elevated entertaining, the home features 4 bedrooms plus an expansive bunk room, including two luxurious main-level suites and additional bedrooms in the walkout lower level. Thoughtfully curated spaces include a private pocket office, full prep kitchens on both levels, a stunning wine cellar, and a showpiece wet bar. The lower level is truly next-level, highlighted by an incredible theater room, dedicated workout space, and seamless access to outdoor living. Step outside to your private oasis featuring a custom pool and spa, along with multiple covered decks designed to capture breathtaking lake views. Car enthusiasts and hobbyists will appreciate the suspended slab 4-car garage, complemented by a rare 5th rear garage door—perfect for lake gear and easy backyard access. Built on a 12 ft foundation, this home offers both scale and structural distinction rarely found in lakefront construction. No detail has been overlooked—finishes are truly over-the-top, with the opportunity to personalize a few selections and make this home uniquely yours. Bulkhead and dock anchors are already in place, making it easy to complete your ideal lake lifestyle. This is a rare opportunity to own a fully customized luxury retreat in one of the area’s most sought-after communities.

14 Tomahawk Circle, Lake Winnebago

Listing courtesy of James Asher of Asher Real Estate LLC.

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