Waterside Homes for Sale

Welcome to Waterside, an enchanting subdivision nestled in the heart of Lake Mary, Florida, within the picturesque Seminole County. This community is a hidden gem, perfectly blending tranquility with modern conveniences, making it an ideal place for families, retirees, and everyone in between.

Waterside boasts a stunning array of homes for sale, each designed with elegance and comfort in mind. From charming single-family residences to spacious two-story homes, there is something to suit every lifestyle and budget. The architectural styles range from contemporary to traditional, ensuring that you’ll find a home that resonates with your personal taste. Many properties feature lush landscaping, private backyards, and modern amenities, offering a perfect retreat after a long day.

Living in Waterside means enjoying the best of both worlds. The community is surrounded by serene lakes and scenic parks, providing ample opportunities for outdoor recreation such as walking, biking, and picnicking. Families will appreciate the highly-rated schools nearby, as well as the variety of shopping, dining, and entertainment options that Lake Mary has to offer.

With its prime location just a short drive from Orlando, residents can easily access the vibrant attractions of the city while returning home to the peaceful ambiance of Waterside. If you’re searching for a place that combines comfort, community, and convenience, look no further than Waterside. Explore the available homes for sale today and discover the lifestyle you’ve always dreamed of!

Newest Waterside Homes for Sale

$459,999

3 Beds ⋅ 2 Baths ⋅ O6440184 MLS

Model-like split floorplan home in Waterside! With upgraded kitchen including lots of cabinetry, granite countertops, stainless steel appliances, and breakfast bar. The master retreat features a walk-in closet, beautifully updated master bathroom with dual sinks and large garden tub. Heading out through the glass sliding doors, you’ll enter the spacious screened in patio, perfect for relaxation and gatherings, while admiring the scenic pool and private fenced backyard. With close proximity to Publix, West Oaks Mall, AMC theater, and the Orlando Health. Come check it out, and be ready to pack your bags!

2747 Cullens Court, Ocoee

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122

$799,000

4 Beds ⋅ 2 Baths ⋅ 2160490 MLS

Welcome to luxury living in the prestigious gated community of Waterside at San Pablo! Built in 2021, this immaculate home combines modern design, thoughtful upgrades, and exceptional indoor-outdoor living in one of Jacksonville's most desirable locations. Inside, you'll find a bright, open floor plan designed for both everyday living and entertaining. The chef's kitchen flows seamlessly into the spacious living area, highlighted by custom white oak built-ins at the entertainment center. A versatile flex room offers endless possibilities as a home office, dining room, playroom, fitness room, or additional living space. The split-bedroom floor plan provides privacy and functionality. The spacious primary suite is a true retreat, featuring dual vanities, a spa-like bathroom, and an oversized walk-in closet. Generously sized secondary bedrooms and abundant storage complete the home's well-designed layout. Step outside to your own private backyard oasis. The screened lanai features built-in gas hookups, making it easy to connect your outdoor grill and create the perfect setup for entertaining. Overlooking the sparkling pool, the lanai offers an ideal space to relax and enjoy Florida living year-round. Mature trees and 8- and 10-foot privacy fencing provide a peaceful, secluded backdrop rarely found in newer construction. Additional highlights include a three-car garage, ample driveway parking, and meticulous attention to detail throughout. Ideally located just minutes from the beaches, Mayo Clinic, top-rated schools, shopping, dining, and major commuter routes, this home offers the perfect balance of luxury, convenience, and the Florida lifestyle. Better than new and truly move-in ready, this is an exceptional opportunity to own one of the finest homes in Waterside at San Pablo.

13729 Hidden Oaks Lane, Jacksonville

Courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS SOUTHSIDE

Listing courtesy of KELLER WILLIAMS REALTY ATLANTIC PARTNERS SOUTHSIDE.

Listing courtesy of Emilie Bishop from KELLER WILLIAMS REALTY ATLANTIC PARTNERS SOUTHSIDE.

$3,499,900

3 Beds ⋅ 4 Baths ⋅ A4702160 MLS

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 with the confidence of a professionally managed triple-net leaseback. Leaseback terms, furnishings package, and additional details are available upon request.

800 Blue Shell Loop, I-75 East

Listing courtesy of LEE WETHERINGTON REALTY. 949-734-9200

$409,900

3 Beds ⋅ 2 Baths ⋅ O6424048 MLS

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

Listing courtesy of ALL REAL ESTATE & INVESTMENTS. 407-917-8206

$455,000

4 Beds ⋅ 3 Baths ⋅ O6392294 MLS

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

Listing courtesy of HUDSON ORLANDO, LLC. 863-381-7345

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