Waterside Real Estate

Waterside Real Estate

Welcome to Waterside, a serene and picturesque subdivision nestled in the heart of Florida. This charming community offers a perfect blend of natural beauty and modern living, making it an ideal choice for families, retirees, and anyone seeking a tranquil lifestyle.

Waterside is characterized by its stunning waterfront views, lush landscaping, and a variety of meticulously designed homes that cater to diverse tastes and preferences. Whether you’re looking for a cozy single-family home or a spacious estate, you’ll find an array of options that suit your needs. The architecture reflects the quintessential Florida style, with vibrant colors and open layouts that invite the warmth of the sun indoors.

One of the standout features of Waterside is its commitment to outdoor living. Residents enjoy access to beautifully maintained parks, walking trails, and community lakes that are perfect for fishing, kayaking, or simply soaking in the natural beauty. The subdivision is also conveniently located near some of Florida’s finest beaches, where you can bask in the sun or partake in a variety of water sports.

Families will appreciate the top-rated schools in the area, as well as the community’s emphasis on safety and camaraderie. With regular neighborhood events and gatherings, it’s easy to meet your neighbors and forge lasting friendships.

In addition to its charming homes and beautiful surroundings, Waterside is just a short drive away from shopping, dining, and entertainment options, providing the perfect balance of tranquility and convenience. Discover your dream home in Waterside, where every day feels like a vacation!

Newest Listings in Waterside

17108 Harbor Oak Parkway, Winter Garden
$535,000
4 Beds ⋅ 3 Baths ⋅ Waterside SubDv. ⋅ 34787 Zip Code
Welcome to this spacious two-story home in the desirable Waterside community. The first floor features an open-concept great room, dining area, and kitchen with granite countertops, a large island, walk-in pantry, and stainless-steel appliances. The great room opens directly to a covered lanai, creating a comfortable space for relaxing or entertaining. A first-floor bedroom with a full bathroom provides flexibility for guests or family members. An interior laundry room completes the first floor. Upstairs, the spacious primary suite features a private bathroom with a separate shower and soaking tub. Two additional bedrooms share a full bathroom, and an open loft provides versatile space for a home office, playroom, or additional living area. A great opportunity to enjoy comfortable living in the Waterside community with a functional and flexible floor plan.

17108 Harbor Oak Parkway, Winter Garden
800 Blue Shell Loop, Sarasota
$3,349,900
3 Beds ⋅ 4 Baths ⋅ Waterside SubDv. ⋅ 34240 Zip Code
Award-Winning Waterfront Model Home | 18-Month Triple-Net Leaseback Opportunity Experience exceptional waterfront living in Lee Wetherington Homes' award-winning Sand Dollar model, professionally designed and impeccably furnished in the prestigious Shellstone at Waterside community of Lakewood Ranch. This professionally furnished model home is offered with a separately purchased designer furnishings package under a separate Bill of Sale. Simultaneous closing includes an exclusive 18-month triple-net leaseback to Lee Wetherington Homes, creating a rare opportunity to own one of the area's premier luxury model homes while it is professionally maintained and showcased. Throughout the lease term, Lee Wetherington Homes, as tenant, will be responsible under the terms of the lease for property taxes, non-ad valorem assessments, HOA dues, hazard and liability insurance, utilities, property maintenance, operating expenses, and the initial capital contribution and amenity fee. Buyers may elect to receive lease payments monthly throughout the lease term or apply the full lease amount as a credit at closing. Designed to celebrate Florida's signature indoor-outdoor lifestyle, the Sand Dollar offers sophisticated architecture, expansive living spaces, designer-selected finishes, and a beautifully curated interior. Walls of 12ft tall glass frame tranquil waterfront views of a 200 acre lake, while seamlessly connecting the great room, gourmet kitchen, and outdoor living areas, creating an ideal setting for both everyday living and effortless entertaining. The luxurious owner's retreat offers a private sanctuary with a spa-inspired bath, while generously appointed guest suites provide exceptional comfort and privacy. Every detail reflects the renowned craftsmanship, innovative design, and timeless elegance that have defined Lee Wetherington Homes for more than four decades. Residents of Shellstone at Waterside enjoy access to the newly completed Summit Hall amenity campus, featuring a resort-style pool, state-of-the-art fitness center, elegant clubhouse, and the 13 acre Midway sports park which offers pickle-ball, tennis, basketball, outdoor fitness, dog park and playground, all within one of Lakewood Ranch's most sought-after waterfront communities. A truly exceptional opportunity to own an award-winning luxury model home. Leaseback terms, furnishings package, and additional details are available upon request.

800 Blue Shell Loop, Sarasota
2706 Kris Xing, Ocoee
$409,900
3 Beds ⋅ 2 Baths ⋅ Waterside SubDv. ⋅ 34761 Zip Code
Welcome home to this beautifully updated 3-bedroom, 2-bath pool home nestled on a spacious corner lot in the highly desirable Waterside community of Ocoee. From the moment you step inside, you’ll appreciate the fresh, modern feel with new luxury vinyl plank flooring throughout and completely renovated bathrooms featuring stylish, contemporary finishes. The thoughtfully designed floor plan offers comfortable living spaces that flow seamlessly to your private backyard oasis, where the sparkling pool is perfect for relaxing, entertaining, or enjoying Florida’s year-round sunshine. Located in a community served by A-rated schools, this home also offers unbeatable convenience with easy access to major highways, shopping, dining, and entertainment, making commuting and everyday errands a breeze. As well as a community park and walking trails for your enjoyment! With its extensive updates, prime location, generous corner lot, and inviting pool, this move-in-ready home is the perfect blend of comfort, style, and convenience. The owner had the home re-plumbed and it comes with a 10 year Labor Warranty as well as a 25 Year parts warranty! The pool screen also had a 3 year warranty on labor! Don’t miss your opportunity to make it yours!

2706 Kris Xing, Ocoee
2890 Cullens Court, Ocoee
$450,000
4 Beds ⋅ 3 Baths ⋅ Waterside SubDv. ⋅ 34761 Zip Code
Don’t Miss This Opportunity! Beautifully Updated Home in a Rapidly Growing Area! Motivated seller that will credit $5,000 towards closing. Beautiful two-story home featuring 4 bedrooms and 2.5 bathrooms, with all bedrooms upstairs for added privacy. The remodeled kitchen (2025) includes granite countertops and all appliances, while both full bathrooms have been stylishly updated. This move-in ready home offers multiple living spaces including a dining room, cozy den, laundry room, and a versatile bonus room perfect for a home office, playroom, or flex space. Additional updates include a brand new water heater (March 2026), a roof that is only 5 years old, and a spacious 2-car garage. Enjoy the fenced backyard with a shed and plenty of room to entertain or create your own outdoor retreat. Located in the growing Ocoee area with convenient access to Orlando, SR-429, and Horizon West. Nearby future developments include the proposed Ocoee Village Center featuring new shopping, dining, grocery, and retail options, as well as the Dynasty Sports & Entertainment Complex expected to bring new entertainment, restaurants, hotels, and jobs to the area.

2890 Cullens Court, Ocoee
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