Pleasant Hill Homes with Pool

Welcome to Lake Winnebago, MO, where the charm of small-town living meets the allure of top-notch education! Nestled in Cass County, this picturesque community is served by the highly regarded Pleasant Hill School District. Known for its commitment to academic excellence, Pleasant Hill offers a variety of educational programs designed to inspire and nurture students from kindergarten through high school. With dedicated teachers, modern facilities, and a strong sense of community, parents can rest assured that their children are receiving an exceptional education.

Lake Winnebago is not only known for its beautiful scenery and friendly atmosphere but also for its stunning homes that come with the added luxury of private pools. Imagine spending warm summer days lounging by your own oasis, hosting barbecues, or enjoying a refreshing swim right in your backyard. These homes with pools offer a perfect blend of relaxation and entertainment, making them an ideal choice for families and individuals alike.

Living in Lake Winnebago means you’ll enjoy the best of both worlds: a serene suburban lifestyle with easy access to the vibrant amenities of nearby cities. Whether you're taking a stroll along the lake, engaging in community events, or participating in local sports, there’s always something to do. Plus, with the excellent schools in the Pleasant Hill district, you can be confident that your children are thriving academically while enjoying the benefits of a close-knit community.

Explore the charming homes with pools in Lake Winnebago today, and discover the perfect place for your family to grow and thrive!

Newest Pleasant Hill Homes with Pool

$775,000

4 Beds ⋅ 4 Baths

Welcome to your private paradise. This custom-built reverse 1.5-story estate sits on a stunning acre lot surrounded by mature trees, breathtaking views and a new 4th car garage. Inside, an expansive open floor plan invites you in with upgraded flooring throughout and sunlit, generous room sizes. The chef’s kitchen features custom cabinetry, subtle under-cabinet lighting, and a walk-in pantry thoughtfully equipped with a direct garage pass-through door. Main-level living is at its finest in the primary suite, which connects seamlessly through a custom walk-in closet to the main-floor laundry room (with an additional laundry setup in the lower level). Outdoor living here is second to none. Entertain across the full-length rear deck, relax by the fire on the covered patio with its own outdoor fireplace, or take a dip in the custom in-ground pool with diving board. Space abounds in the lower level equipped with a bar! Exceptional custom quality on an irreplaceable lot—this home is a rare find.

1504 Country Club Drive, Pleasant Hill

Listing courtesy of Ken Hoover Group of Keller Williams KC North.

$650,000

4 Beds ⋅ 2.5 Baths

Seller Motivated !! Experience the perfect balance of country living and modern comfort with this beautifully maintained1 1/2 story home situated on 9 scenic acres Ideally located just off blacktop south of 50 hwy. This beautiful home features light filled living spaces, 4 bedroom, 2 1/2 baths designed for comfortable everyday living and entertaining. Step outside and enjoy your own private outdoor retreat featuring 30x15 inground pool with new cement patio creating the perfect setup for summer gatherings, relaxing weekends, and entertaining guests. The Stocked pond adds even more charm and recreation with bass, blue gill and catfish right from your own property. Need room for hobbies, storage, equipment, or workshop? The impressive 30x60 pole barn offers endless possibilities for contractors, hobbyists, car enthusiasts, small business owners, or anyone needing extra functional space. Plus a 30x36 barn. An additional storage shed provides even more versatility. If you've been searching for a country home with acreage, pool, pond, outbuilding, and easy highway access near the Kansas City metro area, this property delivers the rare combination of rural tranquility and modern convenience. This is more than a home. It's a lifestyle opportunity with space to live , relax, entertain, and enjoy the outdoors.

38206 E 177 Street, Pleasant Hill

Listing courtesy of Cathy Pollard of RE/MAX Elite, REALTORS.

$1,100,000

4 Beds ⋅ 4.5 Baths

Here’s your chance to live and roam on 10 +/- acres just across the Jackson County line in Cass County, Missouri. This amazing home on acreage is located just 20 minutes south of Lee’s Summit along a blacktop road and only a half mile off Highway 291. Talk about a prime location! You will fall in love with the 300+ foot paved driveway access to the house that sits perfectly overlooking the property. Enjoy the sunrise and sunset views from the front porch or back deck. Most of the property consists of open pasture ground that offers a blank canvas with so many possibilities. The driveway is lined with mature oak trees and several nice shade trees, along with landscaping surrounding the house. Also, there is a gardening area complete with established fruit trees, grape vines, and a chicken coop. The 4 bedroom (plus 1 non-conforming), 4.5 bathroom house was built in 1999 and offers plenty of space for the family and entertainment. It’s a must-see! The main level features a living room with a fireplace, vaulted ceilings, an oversized eat-in kitchen, an office, and a massive master suite. The upstairs includes 3 spacious bedrooms, 2 bathrooms, and a large play area. The finished walkout basement is complete with a full kitchen, large living area, bathroom, non-conforming bedroom, safe room, washer/dryer hookups, and plenty of storage space. Don’t forget about the incredible deck off the main level with amazing views and a covered patio underneath. It gets even better with the resort-style swimming pool with a slide and waterfall. This is the perfect setup to relax or entertain! New house updates include exterior paint, carpet, refinished hardwood floors, fixtures, fans, and more. Also, the swimming pool was completely replaced 3 years ago. Surveillance system with 20 cameras. Another bonus is the 5,000 square foot insulated outbuilding complete with concrete, electricity, and water. It offers so many possibilities for storage. Perhaps even business use.

18200 E 191st Street, Pleasant Hill

Listing courtesy of Skyler Wirsig of Midwest Land Group.

$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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