Sarasota/Crescent Beach/Siesta Key Homes with Playground Community Features

Sarasota/Crescent Beach/Siesta Key Homes with Playground Community Features

Welcome to the enchanting paradise of Siesta Key, a gem nestled on Florida's Gulf Coast, where the sun-drenched beaches and vibrant community spirit create an idyllic lifestyle. Known for its powdery white sands and crystal-clear waters, Siesta Key is not just a destination; it’s a way of life. The nearby Crescent Beach offers a more tranquil setting, perfect for those seeking a serene escape, while the lively atmosphere of Sarasota is just a short drive away, providing a rich tapestry of cultural experiences, dining, and entertainment.

If you’re looking for a family-friendly community, the Homes with Playground feature in this region is a delightful highlight. These homes are designed with families in mind, offering safe, engaging spaces for children to play and explore. Imagine your little ones laughing and making memories just steps from your front door, while you relax, knowing they are enjoying the outdoors in a secure environment.

In addition to playgrounds, the Siesta Key area boasts a plethora of amenities, including parks, recreational facilities, and proximity to the beach, ensuring that every day feels like a vacation. With a warm climate year-round, outdoor activities abound, from kayaking in the bay to biking along scenic trails.

Whether you’re seeking a primary residence or a vacation home, Siesta Key’s blend of natural beauty, community spirit, and family-friendly features makes it a perfect choice. Embrace the coastal lifestyle and discover the joy of living in a community that truly has it all!

Newest Sarasota/Crescent Beach/Siesta Key Homes with Playground Community Features

$549,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Experience the best of Siesta Key living in this beautifully updated 2 bedroom, 2 bath 3rd floor condo in Sunrise Cove, offered turnkey furnished and ready for you to move in and start enjoying island life immediately. Enjoy next level comfort with a brand-new 2026 A/C system and an LED whole home in duct air purifier cool, refreshing comfort and cleaner, fresher indoor air all year long. Take in stunning back bay views from your home and enjoy an unbeatable location directly across from Turtle Beach and Park, with boat, kayak, and canoe launches, a playground, and a convenient trolley stop. Sunrise Cove delivers an exceptional amenity lineup, including two community pools, a fitness center, tennis and pickleball courts, kayak and bike storage, bayside BBQ grills, and picnic areas overlooking the water. Boat slips are available for rent with water and electric hookups, and the community includes full-time onsite facility and maintenance managers for added peace of mind. Step outside to Turtles Pub & Café, Turtles Restaurant, and a nearby marina right next door. Plus, you’re moments away from world famous Siesta Key Beach, known for its powdery quartz sand, sparkling water, and unforgettable sunsets.

9011 Midnight Pass Road Unit 329, Sarasota
$15,900,000
4 Beds ⋅ 5 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code
Inspired by the timeless grandeur of Louisiana's legendary Oak Alley Plantation, this extraordinary Gulf-to-lagoon estate is one of the most architecturally distinctive residences on Siesta Key. Positioned on a rare 1.97-acre Gulf-to-bay homesite within the private gates of The Sanderling Club, this home evokes the sophistication of a Southern manor while embracing the relaxed sophistication of Florida's Gulf Coast. A sweeping palm-lined drive, stately columned façade, and symmetrical architecture create a memorable first impression, echoing the enduring beauty that inspired its design. Constructed by Christner Bros., the residence encompasses approximately 8,209 square feet under air with four bedrooms, four full baths, one half bath, elevator access, and an oversized five-car collector's garage with dedicated workshop space. Designed for both grand-scale entertaining and refined everyday living, the home showcases soaring ceilings, handcrafted millwork, marble flooring, and a dramatic curved staircase that anchors the elegant interiors. Expansive living and dining rooms flow effortlessly onto an exceptional wraparound covered terrace, creating seamless indoor-outdoor living while framing panoramic views of the Gulf of Mexico, Heron Lagoon, and the surrounding tropical landscape. The chef's kitchen is equally suited for intimate gatherings and large-scale entertaining, featuring custom cabinetry, granite countertops, Wolf and Sub-Zero appliances, double wall ovens, generous preparation areas, and direct terrace access. A richly detailed executive office with custom built-ins, an extensive butler's pantry, media room, and abundant utility spaces further enhance the home's thoughtful design. The primary suite is a private sanctuary with terrace access, generous sitting areas, and a spa-inspired bath featuring dual vanities, extensive custom cabinetry, a walk-in shower, and abundant natural light. Three additional guest suites, each with en-suite baths, provide luxurious accommodations while overlooking the estate's lush tropical grounds. The lower level offers exceptional flexibility with expansive bonus space ideal for a wellness center, fitness studio, golf simulator, game room, collector's gallery, workshop, or additional recreational living. Impact-rated windows and doors, hurricane shutters and screens, a security system, and a newer 24-kW Kohler generator contribute to the home's enduring quality and peace of mind. The estate's setting is equally remarkable. With approximately 150 feet of pristine Gulf frontage and 150 feet of frontage along tranquil Heron Lagoon, opportunities to own a true Gulf-to-lagoon property are exceedingly rare. Launch a kayak or paddleboard from the private dock, spend afternoons on the secluded beach, or experience spectacular sunsets over the Gulf from your own backyard. Residents also enjoy the exclusive amenities of The Sanderling Club, including a private beach, marina, tennis courts, clubhouse, and one of Siesta Key's most private and prestigious waterfront communities. Just beyond the gates await Siesta Key's internationally acclaimed quartz-sand beaches, the boutiques and restaurants of Siesta Village, and the arts, dining, and cultural attractions of downtown Sarasota. 8132 Sanderling Road is a legacy estate where inspired architecture, timeless elegance, and one of Florida's rarest Gulf-to-lagoon settings come together to create an offering of exceptional significance.

8132 Sanderling Road, Sarasota
$1,845,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
Positioned on nearly an acre within the prestigious, guard-gated enclave of The Sanderling Club on Siesta Key, this exceptional waterfront homesite presents a rare opportunity to create a custom coastal estate in one of Sarasota’s most coveted communities. With over 180 feet of frontage on Heron Lagoon and the Gulf across the street, expansive water views and sunsets are everywhere creating the idyllic setting for a remarkable new residence designed to embrace Sarasota’s year-round outdoor lifestyle. The generous dimensions and waterfront setting provide the flexibility to envision everything from a contemporary architectural statement to a timeless island-inspired retreat. Residents of The Sanderling Club enjoy an unmatched lifestyle defined by privacy, security, and exclusive amenities, including a private marina, deeded beach access, 24-hour guard-gated entry, tennis, pickleball, and a casual Gulf front clubhouse. Just moments away, Siesta Key Beach, consistently ranked among America’s finest beaches and currently No. 1 by TripAdvisor, is renowned for its powder-soft quartz sand, turquoise Gulf waters, and unforgettable sunsets. Nearby, Siesta Key Village offers a vibrant collection of restaurants, cafés, boutiques, live music, and island gathering spots, creating an atmosphere that is both relaxed and distinctly coastal. Combining the privacy of The Sanderling Club with convenient access to Siesta Key’s beaches, restaurants, boutiques, and coastal recreation, this exceptional homesite offers the opportunity to create a custom residence tailored to an unparalleled island lifestyle.

7723 Sanderling Road, Sarasota
$1,100,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
Tucked beneath a canopy of mature trees in the prestigious Sanderling Club, this exceptional waterfront homesite presents a rare opportunity to own in one of Siesta Key's most established and coveted Gulf-front communities. Encompassing more than half an acre, the property offers 152 feet of frontage on tranquil Heron Lagoon, creating a peaceful natural setting for kayaking, paddleboarding, canoeing, fishing and enjoying Florida's coastal wildlife from your own backyard. The Sanderling Club is Siesta Key's original guard-gated community, renowned for its privacy, natural beauty, large homesites and timeless Old Florida character. Residents enjoy exclusive access to a private Gulf-front beach, where uncrowded, spectacular sunsets become part of everyday life. A distinctive feature of the community is its resident marina, where boat slips may be rented by homeowners, providing direct access to Sarasota Bay, the Intracoastal Waterway and the Gulf of Mexico. It is an increasingly rare convenience that allows residents to enjoy an active boating lifestyle without the expense and maintenance of private dock ownership. The Sanderling Club is also entering an exciting new chapter, with thoughtfully reimagined community gathering spaces designed to create even more opportunities for neighbors and friends to connect while preserving the beauty, character and sense of place that have long defined this treasured neighborhood. Just beyond the gates, residents enjoy easy access to the world-renowned quartz sands of Siesta Beach, the boutiques and restaurants of Siesta Village and the vibrant arts and cultural attractions of downtown Sarasota, including theater, opera, ballet, galleries and museums. One of the few remaining opportunities to create a custom waterfront residence in this remarkable community, this homesite offers the setting, privacy and lifestyle that are increasingly difficult to find on Siesta Key. Offered by a motivated seller, this is an exceptional opportunity to secure your place in one of Sarasota's most treasured coastal communities.

7219 Pine Needle Road, Sarasota
$2,795,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Discover a rare opportunity to build your dream estate within The Sanderling Club - Siesta Key’s premier and exclusive Gulf-front community known for its natural beauty, serenity, and unmatched coastal lifestyle. Set on 1.13 private acres overlooking the tranquil waters of Heron Lagoon, this cleared and ready-to-build homesite offers the perfect canvas to bring your architectural vision to life in a setting defined by timeless coastal elegance, Old Florida charm, and tropical surroundings - a true slice of paradise! Offering a rare amount of privacy, the property features no neighboring home on the left-hand side, creating an exceptionally secluded and peaceful setting. This expansive lot offers endless possibilities to create a one-of-a-kind residence tailored to your lifestyle. Stretching along the peaceful shoreline of Heron Lagoon, the setting is surrounded by calm water views, lush tropical scenery, and incredible natural beauty. Enjoy kayaking, paddleboarding, canoeing, fishing, birdwatching, or simply relaxing by the water while taking in the tranquil surroundings that make this opportunity so extraordinary. The Sanderling Club combines the beauty of Siesta Key’s coastal living with the privacy and security of an exclusive gated community. Residents enjoy private Gulf-front beach access where breathtaking sunsets over the Gulf of Mexico become part of everyday life, along with new Har-Tru tennis courts, pickleball courts, playground, marina access, and 24-hour staffed security. Boat slips, when available, provide direct access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico via the recently reopened Midnight Pass - a boater’s paradise. The community’s historic clubhouse is also entering an exciting new chapter, with newly released renderings envisioning a reimagined waterfront gathering space designed to further elevate The Sanderling Club lifestyle. Near Siesta Key’s world-renowned quartz sand beaches, Siesta Village, boutique shopping, fine dining, and Downtown Sarasota’s celebrated arts and cultural scene, this is an invitation to create your dream home in one of Florida’s most sought-after coastal destinations.

7825 Sanderling Road, Sarasota
$2,350,000
4 Beds ⋅ 4 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code
Beautifully renovated 4-bedroom, 4-bath pool home tucked behind the gates of the exclusive Sanderling Club. Surrounded by a grandfathered privacy wall and lush tropical foliage, the property is just steps from your own private beach. 2023 updates include - new roof, hurricane-impact windows/sliders and plumbing. Meticulously renovated in 2025–2026 with top-of-the-line finishes throughout the entire home. Luxury vinyl plank flooring flows through the open floor plan, complemented by granite countertops and a oversized granite island with lots of storage, Samsung appliances and an open-concept layout ideal for entertaining, with abundant indoor/outdoor living space with views of the oversized sparkling pool. The primary suite is a tranquil retreat with two walk-in closets and an en-suite bath featuring a double vanity and soaking tub. A thoughtful split plan offers two additional spacious bedrooms each with en-suite baths. A fully renovated pool house/mother-in-law suite with its own full bath adds flexible living options. Located in a waterfront community, residents of the Sanderling Club have exclusive beachfront access, tennis and pickleball courts, clubhouse and 24-hour security This home blends refined luxury with coastal lifestyle and privacy.

7345 Pine Needle Road, Sarasota
$5,250,000
6 Beds ⋅ 6 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Pre-Construction Waterfront Estate | The Sanderling Club, Siesta Key. Experience the pinnacle of coastal luxury with this rare 6-bedroom, 5.5-bath waterfront estate in the exclusive Sanderling Club on Siesta Key. Set within a private, tropical oasis with direct access to the Intracoastal Waterway, this 4Bedroom/4.5 Bath home to-be-built residence by E/M Custom Homes offers refined craftsmanship, elegant coastal architecture, and a flexible multigenerational design in addition to the existing 2/1 ADU currently on the property that comes Turnkey Furnished to move in ASAP. Come live, boat, and park on property while you build your dream home. The main home to be built features 4 bedrooms and 4.5 baths, while a detached 3-car garage includes a stunning 2-bedroom, 1-bath guest suite with its own deck and water views. Plans are ready to build, or you may bring your own vision to this extraordinary property. Inside, soaring ceilings, open-concept living areas, and panoramic water views create a light-filled sanctuary. The chef’s kitchen boasts premium appliances, custom cabinetry, a large island, and quartz countertops—perfect for entertaining. Retreat to the luxurious primary suite with spa-inspired bath and private terrace overlooking the water. Outdoors, enjoy a resort-style pool and spa, lush landscaping, and private dock with boat lift—ideal for boating, paddleboarding, or sunset cocktails. Multiple covered lanais provide stunning views from every angle. Residents of The Sanderling Club enjoy gated security, tennis and pickleball courts, a historic beachfront clubhouse, and access to the pristine sands of Siesta Key Beach. Whether you seek a full-time residence, seasonal retreat, or investment opportunity, this exceptional waterfront haven offers unmatched privacy, luxury, and lifestyle. 28' Scout Center Console Boat also available for purchase. Land only with existing 3-car garage/2BR ADU also available for purchase. Reference MLS#A4660300

7233 Midnight Pass Road, Sarasota
$2,750,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
LIVE, BOAT, PARK while you build your waterfront dream home. ONLY waterfront lot on Siesta Key with Current 2/1 ADU and 3-car garage on property! Premiere boating/waterfront lot opportunity in Sanderling Neighborhood. A rare chance to own one of the most sought-after lots in Sanderling. This private, fenced, waterfront retreat is located directly across from the neighborhood’s gated entrance, nestled in a serene basin leading to the Intracoastal Waterway. Extensive upgrades allow the future owner to enjoy the property immediately or stay on-site while building a custom beach home. Current ADU on property is offered Turnkey Furnished! Direct Waterfront Access ~150 ft of frontage along a private canal connected to the Intracoastal. Shared with only 5 neighboring Sanderling homes for enhanced privacy and exclusivity. New Garage & Apartment (2024) Two-story, block construction featuring a 1,100 sq ft 2BR/1Bath apartment with full kitchen above an oversized 3-car garage—perfect for storing vehicles, kayaks, golf carts, and more. Expansive Lot ±0.6 acre (25,553 sq ft) fenced lot with over 240 ft of frontage. Adjacent to HOA-owned land for added space, privacy, and mature vegetation—lives "like" a 1+ acre compound. Dock & Boat Lift Brand-new dock with a 10,000 lb. lift, ready for Gulf Coast boating and fishing. A 28 ft Scout boat (optional) currently sits on the lift and can be offered under a separate bill of sale. Build-Ready & Custom Plans Available. Lot is fully cleared and prepped for a custom-designed coastal contemporary home (3,300 sq ft, 3BR + Den, 4.5 Bath, pool, lanai, and more). New Build House Plans available or you can work with local Sarasota architects to tailor your dream design. Living in Sanderling means more than simply owning a piece of paradise. The neighborhood offers a suite of exclusive amenities designed for relaxation, recreation, and connection. Residents enjoy exclusive access to the soon to be newly updated Sanderling Beach Club and existing tennis & pickleball Courts: Whether you are an avid player or simply enjoy a casual match with friends, well-maintained courts are available for your enjoyment. This property stands alone in its exceptional array of features and amenities.

7233 Midnight Pass Road, Sarasota
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