Casselberrry/Winter Springs / Tuscawilla Homes with Lake Front Frontage

Casselberrry/Winter Springs / Tuscawilla Homes with Lake Front Frontage

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. Known for its picturesque landscapes and vibrant community, this area offers a perfect blend of suburban charm and natural beauty. With lush greenery, serene lakes, and a friendly atmosphere, it’s no wonder that many are drawn to call this remarkable place home.

One of the standout features of this region is the abundance of homes with stunning lakefront frontage. Imagine waking up each morning to the gentle lapping of water against the shore and the breathtaking views of shimmering lakes. These properties not only provide a tranquil retreat but also offer a wealth of recreational opportunities right at your doorstep. Whether you enjoy kayaking, fishing, or simply taking leisurely strolls along the water’s edge, living by the lake enhances your lifestyle in countless ways.

Winter Springs, with its charming downtown area, boasts a variety of shopping, dining, and entertainment options, making it a delightful place to spend your days. The nearby Tuscawilla community is renowned for its beautiful golf courses and parks, perfect for outdoor enthusiasts and families alike. Additionally, the region's excellent schools and family-friendly atmosphere make it an ideal location for raising children.

If you're seeking a home that combines natural beauty with community spirit, look no further than the lakefront properties in Casselberry, Winter Springs, and Tuscawilla. Here, you can experience the best of Florida living, where every day feels like a vacation. Come explore the possibilities and find your dream home in this captivating corner of Seminole County!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Lake Front Frontage

$2,299,000
32708 Zip Code
A prime redevelopment opportunity in Winter Springs. With over 3 acres of lakefront property, this site offers the rare chance to create something new — whether that’s one signature estate, two thoughtfully planned homes, or possibly three custom residences with direct water access to Little Lake Howell. Large, usable acreage in this part of Seminole County is exceptionally hard to find, making this a standout option for builders, investors, or anyone looking to craft a private multi-home compound. Important: The property is occupied. Do not enter the property or approach the home without a confirmed appointment. All access must be scheduled in advance. The existing residence, originally built in 1964 and expanded in 1994, sits quietly on the property and provides over 3,000 SF of living space. The land itself is the true centerpiece - offering mature cypress trees, west-facing sunset views, and a wide layout that lends itself naturally to future planning. Additional structures include a solid block-constructed horse barn, an oversized carport suitable for boat storage, and a private tennis court. Whether you envision a modern lakefront enclave, a multi-generational retreat, or a builder-driven redevelopment, the acreage, water access, and location combine to create a uniquely flexible canvas.

4910 E Lake Drive, Winter Springs
$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
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