Pleasant Hill Homes with Boat Dock Available Amenities

Welcome to Pleasant Hill School District, a vibrant educational community nestled in the heart of Lake Winnebago, Missouri. Known for its dedication to academic excellence and student development, this district serves families in Cass County with a variety of educational opportunities. With a commitment to fostering a nurturing environment, Pleasant Hill School District offers a range of programs designed to inspire and engage students, ensuring they are well-prepared for their future endeavors.

Families residing in Lake Winnebago enjoy the unique advantage of living in a picturesque lakeside community while being part of the esteemed Pleasant Hill School District. The district boasts well-rated schools, experienced educators, and a robust curriculum that emphasizes both academic achievement and character development. Parents can rest easy knowing their children are receiving a top-notch education in a supportive and enriching environment.

In addition to its educational offerings, Lake Winnebago is a haven for water enthusiasts. Many homes in this charming area come with boat dock amenities, providing direct access to the serene waters for fishing, boating, and leisurely afternoons on the lake. Imagine waking up to stunning waterfront views and the gentle sounds of nature, all while being just a stone's throw away from quality schools.

Whether you’re drawn to the excellent educational opportunities of the Pleasant Hill School District or the allure of lakeside living, Lake Winnebago offers a unique blend of community, convenience, and charm. Discover your dream home here, where every day feels like a vacation!

Newest Pleasant Hill Homes with Boat Dock 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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