Waterside South Real Estate

Waterside South Real Estate

Welcome to Waterside South, an enchanting subdivision nestled in the heart of Sarasota, Florida. This picturesque community is a hidden gem that perfectly blends serene living with the vibrant lifestyle Sarasota is renowned for.

Waterside South is designed for those who appreciate the beauty of nature and the charm of suburban life. The neighborhood features stunning homes that showcase modern architecture and thoughtful designs, ensuring that each residence feels like a personal retreat. With lush landscaping and meticulously maintained common areas, residents are greeted by a warm and inviting atmosphere that exudes comfort and tranquility.

One of the standout features of Waterside South is its proximity to the breathtaking waters of Sarasota Bay. Residents can enjoy leisurely strolls along scenic pathways, engage in outdoor activities, or simply soak in the stunning sunsets that paint the sky in vibrant hues. The community is also conveniently located near a variety of parks, making it an ideal spot for families and outdoor enthusiasts alike.

In addition to its natural beauty, Waterside South offers easy access to a plethora of shopping, dining, and entertainment options. Whether you’re in the mood for a gourmet meal, a casual café, or retail therapy, everything you need is just a short drive away.

With its perfect blend of tranquility, community spirit, and convenience, Waterside South is more than just a place to live; it’s a lifestyle. Come discover the charm of this delightful subdivision and see why it’s the perfect place to call home in sunny Sarasota, Florida!

Newest Listings in Waterside South

3 Beds ⋅ 3 Baths ⋅ Waterside South SubDv. ⋅ 34240 Zip Code

Experience the perfect balance of luxury, comfort, and privacy in this beautifully designed Birchwood inventory home by Stock Luxury Homes, located in the sought-after Wild Blue at Waterside community. Thoughtfully crafted for everyday living and effortless entertaining, this home offers 3 bedrooms, 2.5 bathrooms, a dedicated Study, an elegant Dining Room, and a spacious Great Room that opens seamlessly to the outdoor living area. The expansive lanai features a pool and spa overlooking a tranquil western-facing preserve with peaceful water views, creating the ideal setting to enjoy breathtaking sunsets and exceptional privacy. A 3-car garage provides ample space for vehicles and storage. Ready for immediate occupancy. Please contact us for information on additional homes and floor plans currently under construction that are not yet listed on the MLS.

257 Blue Pearl Ct., Sarasota

4 Beds ⋅ 5 Baths ⋅ Waterside South SubDv. ⋅ 34240 Zip Code

Anchor Builders, Sarasota's premier luxury custom home builder proudly presents The Martinique III, an extraordinary furnished model home in Wild Blue at Waterside. Perfectly positioned on an expansive half-acre Lapis homesite overlooking tranquil water and nature preserve views, this remarkable modern farmhouse was thoughtfully designed by acclaimed residential designer Paul Fletcher to capture breathtaking vistas from nearly every living space. A grand arrival begins with authentic white brick architecture, soaring columns, lush tropical landscaping, and an impressive auto court leading to opposing dual oversized garages, offering a four-car garage space with exceptional convenience and curb appeal. Inside, custom-crafted double entry doors open to a stunning arched foyer where timeless architecture and refined finishes immediately create a sense of warmth, elegance, and serenity. Vaulted ceilings adorned with stained wood beams, expansive walls of glass, and an abundance of natural light define the home's open-concept living spaces while seamlessly connecting the great room, dining area, and chef's kitchen. Designed for both entertaining and everyday living, the gourmet kitchen features premium appliances, custom cabinetry, luxurious countertops, and a fully equipped pantry kitchen. Every detail has been thoughtfully designed to create the perfect setting for intimate dinners or effortless entertaining while enjoying spectacular water views. Throughout the home, wide gallery hallways, rich chevron-pattern white oak flooring, bespoke millwork, designer lighting, and architectural details showcase the exceptional craftsmanship for which Anchor Builders is known. Every finish has been selected to create an inviting atmosphere. The private owner's retreat is a sanctuary unto itself, offering a peaceful sitting area, expansive dual walk-in closets, and an exquisite spa-inspired bath designed for ultimate relaxation. Three beautifully appointed ensuite guest bedrooms provide exceptional comfort and privacy, while a private study, flexible bonus room, powder bath, spacious utility room, and climate-controlled storage complete the thoughtfully designed floor plan. Outdoor living is equally extraordinary. Expansive covered living and dining areas flow effortlessly from the interior to create the ultimate Florida lifestyle. Enjoy a resort-style pool and spa, outdoor kitchen, fireplace, fire pit, and multiple gathering spaces, all perfectly positioned to embrace the serene waterfront setting. Residents of Wild Blue at Waterside enjoy an unparalleled lifestyle with convenient access by foot, bicycle, or golf cart to the future clubhouse featuring fine and casual dining, social events, a state-of-the-art fitness center, wellness classes, personal training, a golf simulator, movie theater, and more. The community also offers the Midway Sports Center with 13 acres of recreational amenities, scenic walking and biking trails, six tennis courts, eight pickleball courts, a sports pro shop, kayak launch, playground, and two dog parks. Professionally curated by acclaimed interior designer Carrie Riley of Riley Interior Design, this residence is offered fully furnished, including all designer furnishings, televisions, artwork, accessories, and décor. Pricing reflects the furnishings and is net of the builder's leaseback. Please contact the builder's representative for complete details.

258 Crystal Waters Drive, Sarasota

2 Beds ⋅ 2 Baths ⋅ Waterside South SubDv. ⋅ 34240 Zip Code

New Incentives Available - LUXURY VILLA! - In the prime location of Shellstone at Waterside this Luxury Villa offers Tile Flooring Through Out, Quartz Countertops, Tray Ceilings, Soft-Close Cabinets, 8' Doors, Impact Glass Windows, Oversized 2- Car Garage and a Screened in Lanai. It's the perfect unit for someone looking to dip their toe into Florida living or maybe someone looking to downsize in square footage and maintenance. Shellstone at Waterside is a maintenance free and amenity rich community offering Two Amenity Sites. The community features: Pickle Ball Courts, Tennis Courts, Basketball, Playgrounds, Dog Parks, Event Lawn, Screen-in Pavilion, Pool with Spa, Fitness Center, Club House and walking trails throughout the community. There is also a Lifestyle Director, Tennis Coach and Fitness Instructor. There are furnished models open to the public everyday, but please call the sales office to tour this specific unit.

9533 Lunar Dove Drive, Sarasota

3 Beds ⋅ 4 Baths ⋅ Waterside South SubDv. ⋅ 34240 Zip Code

Newly priced as part of our QUICK MOVE IN INCENTIVE SPECIAL! Located in Wild Blue at Waterside, this Cambria IV by Stock Luxury Homes offers a balance of refined design and relaxed Florida living. Timeless architecture pairs with semi-custom finishes and an open, airy layout designed for both everyday comfort and effortless entertaining. The waterfront home features three bedrooms, three and a half baths, a spacious Great Room, an elegant Dining Room, and a private Study. Expansive sliding doors open to a generous outdoor retreat with pool and spa, creating a natural extension of the living space. A three-car garage adds everyday convenience. Showcasing our new modern elevation. Please contact us for additional inventory homes not yet listed in the MLS.

312 Blue Pearl Ct., Sarasota

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Mikel Chaffee

Mike understands that buying and selling your home is one of, if not the biggest, financial decisions you will make. He knows first-hand the unparalleled value of hard work, dedication and exemplary service. With 13 homes sold in 2025 alone, putting him in the top percentile across the nation. Mike often works with his mom, Debi Chaffee Rose, as a mother-son team. Clients love their collaborative work and combined focus. Mike has a degree in management and operations, and for a number of years held his PGA Golf Certification. This experience gives him an intimate knowledge of many diverse golf and country club communities that make up the Florida lifestyle. 13 Years licensed as a Realtor, he is ready to put his experience to work, for you in any facet. Mike spends his free time with his beautiful wife Meghan, and their 4 Kids here in the town he was raised in, Bradenton Florida. They enjoy going and exploring the sunshine state together as a family.

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