Casselberrry/Winter Springs / Tuscawilla Homes with Boatable Water Water Frontage

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant community is not just a place to live; it’s a lifestyle characterized by scenic landscapes, abundant recreational opportunities, and a welcoming atmosphere.

Winter Springs, known for its beautiful parks and family-friendly environment, offers a perfect blend of suburban charm and modern conveniences. With easy access to major highways, residents enjoy a quick commute to downtown Orlando, while still relishing the tranquility of a close-knit community. The area is renowned for its top-rated schools, making it an ideal choice for families looking to settle down.

One of the most alluring features of this region is its stunning homes with boatable water frontage. Imagine waking up to serene views of sparkling lakes and rivers right outside your door! These waterfront properties not only provide a picturesque backdrop but also offer endless opportunities for outdoor activities. Whether you enjoy fishing, kayaking, or simply lounging by the water, you’ll find that life on the water is both relaxing and invigorating.

Tuscawilla, with its lush golf courses and nature trails, complements the lifestyle perfectly. Residents can enjoy leisurely strolls or bike rides through its scenic paths, all while soaking in the natural beauty that surrounds them.

In Casselberry, Winter Springs, and Tuscawilla, you’ll discover a community that celebrates both the joys of nature and the comforts of home. Explore the possibilities of waterfront living and find your perfect sanctuary in this charming corner of Florida!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Boatable Water Water Frontage

$2,299,000

3 Beds ⋅ 3 Baths ⋅ Na SubDv. ⋅ 32708 Zip Code

A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private education options. Originally built in 1964, the home was thoughtfully expanded in 1994, creating a larger, more functional layout while preserving its character. Today it offers over 3,000 SF overlooking the shimmering waters of Little Lake Howell. Enjoy west-facing sunset views framed by mature cypress trees. Host friends for tennis or pickleball right in your backyard. The sizeable horse barn was engineered for exceptional durability, built with block construction and poured concrete for maximum strength. The main home includes a 3-car garage, and the barn adds an oversized carport that can easily double as covered boat storage.

4910 E Lake Drive, Winter Springs

$3,998,000

5 Beds ⋅ 7 Baths ⋅ Lake Jessup SubDv. ⋅ 32708 Zip Code

Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its breathtaking setting, grand architecture, and resort-style amenities, the property offers a level of versatility rarely available in today's market. Inspired by the elegance of the Italian countryside, the residence makes a lasting first impression with a dramatic front waterscape, lush gardens, and timeless architectural details. Inside, guests are welcomed by a grand foyer featuring exquisite marble finishes and a spectacular custom-painted 24-karat gold dome. Designed for both entertaining and everyday luxury, the expansive living spaces showcase panoramic views of beautiful Lake Jessup, soaring ceilings, stunning chandeliers, and a grand marble fireplace. The thoughtfully designed "H" floor plan encompasses more than 8,000 square feet of air-conditioned living space, offering five spacious bedrooms and six-and-a-half bathrooms, all conveniently situated on a single level. The primary suite is a true private retreat, featuring eight sets of French doors opening directly to the pool and lakefront, a custom-designed closet that doubles as a safe room, and a spa-inspired bathroom complete with a tranquil garden retreat. The gourmet chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and an oversized walk-in butler's pantry designed to accommodate large-scale entertaining. Additional luxury amenities include a temperature-controlled wine cellar, private movie theater, dedicated nanny or guest quarters, and a six-car garage with extensive attic storage. Outside, the estate transforms into a private resort. A spectacular sports pool with multiple water features serves as the centerpiece, complemented by a summer kitchen, wet bar, outdoor fireplace, and expansive covered veranda overlooking the serene waters of Lake Jessup. Whether hosting elegant weddings, unforgettable events, corporate gatherings, or private family celebrations, the setting is simply unmatched. Combining custom craftsmanship, Tuscan and Greek-inspired design elements, commercial zoning flexibility, and an irreplaceable waterfront location, this remarkable estate offers a truly rare opportunity to own one of Central Florida's most unique properties. Schedule your private tour today to experience the endless possibilities and extraordinary lifestyle this one-of-a-kind property provides.

1112 Orange Avenue, Winter Springs

Start Your Search