Siesta Key Real Estate

Siesta Key Real Estate

Welcome to Siesta Key, a stunning barrier island located in Sarasota County, Florida. Known for its pristine white sandy beaches and laid-back atmosphere, Siesta Key is a paradise for beach lovers and outdoor enthusiasts alike.

Situated on the Gulf of Mexico, Siesta Key offers visitors and residents a range of activities and attractions. The island is famous for its award-winning beaches, particularly Siesta Beach, which has been ranked as one of the best beaches in the United States. The soft, powdery sand is perfect for sunbathing, picnicking, or simply taking a leisurely stroll along the shoreline.

Beyond the beaches, Siesta Key boasts a vibrant arts and culture scene. The island is home to numerous art galleries, theaters, and live music venues, offering a diverse range of entertainment options. Visitors can explore local boutiques and shops, dine at waterfront restaurants, or enjoy a sunset cruise along the coast.

For nature enthusiasts, Siesta Key offers ample opportunities for outdoor recreation. The island is surrounded by lush mangroves and is a popular spot for kayaking, paddleboarding, and fishing. Additionally, nearby parks and nature reserves provide trails for hiking and wildlife observation.

Siesta Key is also conveniently located near the city of Sarasota, which offers even more attractions and amenities. From world-class golf courses to a vibrant downtown area with shopping and dining options, there is something for everyone in this thriving city.

Whether you are looking for a vacation destination or a place to call home, Siesta Key offers a unique blend of natural beauty, cultural experiences, and a relaxed beach lifestyle. Come and discover the magic of Siesta Key for yourself!

Newest Listings in Siesta Key

1 Beds 1 Baths Pointe On Midnight Pass SubDv. 34242 Zip Code
CLEAN. UPDATED. FULLY FURNISHED. ASTONISHING VIEWS. MOVE-IN READY! *** Discover the luxury of WATERFRONT living on Siesta Key as you step into this delightful well-maintained one-bedroom, one-bathroom renovated turn-key furnished condominium with IMPACT openings and WASHER/DRYER in the unit. Located on the SEVENTH floor at THE POINTE, a premier gated pet-friendly community on over five acres of exquisite prime waterfront real estate, this residence boasts truly mesmerizing and unrivaled views of Little Sarasota Bay, the Gulf of Mexico, and Jim Neville Nature Preserve! *** In addition to the beauty of the surroundings, the rich community amenities enhance both relaxation and activity. Boat docks. Tennis & Pickle Ball courts. Heated lap pool waterside. Spa. Sauna. Fitness rooms. Walking path. Gathering/entertainment room. Club house with full kitchen. BBQ grills. Gazebo with table and grill. Kayak/boat launch/storage. Dog walk area. Benches along water’s edge and more! *** Unit 703 is an upper-level nicely renovated unit with 946 square feet of well-designed, open-concept living areas providing the ideal space to enjoy a vibrant, active, yet tranquil lifestyle! *** The work is done! IMPACT OPENINGS. Easy to maintain tiled floors throughout. Updated kitchen and baths. 2023 HVAC. 2019/20 water heater. Fully furnished. Just bring your suitcase! *** Key FEATURES include an inviting kitchen with wood cabinetry and plenty of storage and countertop space. The open dining and living area leads to the expansive lanai overlooking the bay and nature preserve. The spacious primary bedroom with en suite updated bathroom featuring double vanities with sinks provides the perfect personal escape with amazing water and nature views and accommodates a king-size bed, includes a walk-in closet, and added storage. As mentioned, a washer and dryer are conveniently located in the utility closet off the lanai. An additional ground floor storage space will house your beach, golf, fishing gear, and extras. A deeded parking space is included. Guest parking is along the water.*** VIEWS! VIEWS! VIEWS! SPECTACULAR views greet you from every window of this fabulous unit! Marvel in the beauty of the uninhabited Jim Neville Nature Preserve and Little Sarasota Bay where you will watch the sun rise each morning and be entertained by the daily escapades of the dolphin, manatees, fish, wild and bird life, fishermen, and boaters – right from your expansive lanai outfitted with IMPACT floor to ceiling sliding glass doors! If you prefer the famous Siesta Key sun sets, sip your favorite beverage from your custom private perch in the kitchen, as you watch the glorious sun setting over the Gulf of Mexico. Sunrise, sunset, nature preserve, water views … experience it all from the convenience and privacy of your own home! #703 at The Pointe is the ideal getaway, a worthy investment allowing future rental income, and simply a spectacular place to call home! ***A STANDOUT CHOICE AMONG SIESTA KEY CONDOS! This unit’s combination of scenic views, comprehensive amenities, and a dynamic location makes it a top choice for those looking to purchase on Siesta Key. Perfectly suited for anyone seeking a serene yet engaging living environment, with easy access to beaches, dining, grocery, coffee shops, marina, free trolley, nightlife, shopping, and more.** Discover why this residence at THE POINTE could be your ideal new home or winter retreat. Contact us today! Some photos virtually staged.

9393 Midnight Pass Road Unit 703, Sarasota

2 Beds 3 Baths Point Of Rocks SubDv. 34242 Zip Code
Amazing single family in Siesta Key. Discover the allure of this enchanting vintage pool home retreat, wood fenced, nestled within strolling distance of Crescent Beach Access #13 on the renowned Siesta Key, consistently rated as the nation’s #1 beach. Rarely available in the Point of Rocks community, this property presents an exceptional opportunity single family home with a private backyard with natural landscape, a large and beautiful in-ground pool with paver patio and lots of room to entertain family and friends. This beautiful home features 2 bedrooms, 3 bathrooms, 2 lanais, living room, dining room, kitchen, one-car carport, and ample parking for both vehicles and boats. Whether utilized as a primary residence, vacation getaway, or investment with lucrative rental potential, this property provides versatility and value. Set amidst lush tropical foliage & majestic specimen palms, the expansive backyard beckons with its tranquil setting, offering space for kayaks, boats, and outdoor leisure. Inside, the charming heart-pine wood cottage exudes warmth & character, with termite-resistant features ensuring lasting quality. Step into the 1st unit and delight in the cool travertine floors, plantation shutters, and inviting open layout. The kitchen, equipped with granite countertops and wood cabinets, overlooks the lanai and pool area, seamlessly blending functionality with aesthetics. Both units offer private bedrooms and baths, ensuring comfort and privacy for residents and guests alike and a convenient laundry area by the lanai with a storage room next to it with plenty of room. Two outside showers with cold & hot water conveniently located on each side of the house. Outside, in the privacy of the lanais with travertine floors, surrounded by tropical trees, lush gardens, spectacular specimen palms, fruit trees (Key Lime, Meyer Lemon, Kaffir Lime-used in Thai cooking, Loquat Tree) and flowering plants that enhance the beautiful grounds of your backyard. Your private oasis awaits, with a sprawling pool, paver patio, and refreshing outdoor showers, perfect for entertainment and relaxation. Notably, the Point of Rocks community imposes no deed restrictions or mandatory HOA fees, fostering a sense of freedom and flexibility for homeowners. Recent upgrades... remodeled all 3 bathrooms in 2015, Lined all cast iron piping in the slab with PVC 2015, All above ground plumbing was redone between 2012-2014, Installed an irrigation in all flower beds in the back & front of the property, pool water pump & HVAC compressor in 2016, Re-screened both lanais, New flower bed in front of the living room window in 2018, Epoxy floor in the carport & in the front walkway/entrance 2019, Roof and Impact windows in 2014, Newer locks in 2024. Great boating/kayak access nearby with no fixed bridges, walking distance to Crescent Market and restaurants, or take the free Siesta Key Breeze Trolley to Siesta Key Village and a few minutes’ drive to Costco, Sprouts, Target, Publix, medical services and to culturally rich downtown Sarasota, theater, ballet, opera, museums, galleries, and more shopping. Embrace the natural beauty, savor the beachside bliss, and make every day a celebration of the vibrant culture that surrounds your perfect home in Siesta Key. Escape to your own slice of paradise, where everyday living feels like a perpetual vacation.

1132 Crescent Street, Sarasota

3 Beds 2.5 Baths Shells On Siesta Key SubDv. 34242 Zip Code
Step into the welcoming embrace of this charming Spanish-style villa, nestled just moments away from the stunning shores of Siesta Key Beach. This inviting three-bedroom, two-bathroom retreat offers the perfect blend of comfort and coastal living, with effortless access to the sun-kissed sands and gentle Gulf breezes. Recently updated with a brand-new roof and boasting a convenient elevator, this home ensures worry-free living while retaining its timeless charm. Tucked away on a serene lane off Beach Road, it provides a peaceful sanctuary within easy reach of Siesta Key Village's bustling amenities. As you step through the private gate, you'll be enchanted by the blend of classic allure and contemporary convenience. With its Spanish tile floors and elegant archways, every corner exudes a sense of coastal elegance and relaxation. Bright and airy, the interior welcomes you with abundant natural light, creating a welcoming ambiance throughout. Enjoy glimpses of the Gulf from the bedroom, offering a tranquil backdrop to your daily retreat. Step outside onto the open-air terrace and savor the laid-back Florida lifestyle as you soak in the sunshine and sea breeze.With private gated beach access just steps away, every day is an opportunity to indulge in the beauty of Siesta Key's shores. Plus, with the option for weekly rentals, this villa presents an exceptional opportunity for both homeowners and investors alike. Experience the quintessential Siesta Key lifestyle in this delightful villa – where coastal charm meets modern comfort. Explore more at

221 Tenacity Lane Unit 221, Sarasota

4 Beds 2 Baths Siesta Beach SubDv. 34242 Zip Code
Welcome to your waterfront paradise on the coveted island of Siesta Key, where coastal elegance meets unparalleled convenience. This stunning residence boasts all the features and amenities discerning buyers crave, offering a lifestyle of unparalleled elegance and convenience. As you step into this meticulously crafted home, you'll be greeted by an abundance of natural light cascading through soaring 21-foot-high ceilings in the living room, creating an inviting and airy ambiance featuring satiny, eco-friendly bamboo floors throughout. Ten-foot ceilings throughout the home further enhance the sense of space and grandeur, while oversized windows frame picturesque views of the tranquil waterfront, seamlessly blending indoor and outdoor living. The heart of the home is the expansive, contemporary island kitchen, where culinary dreams come to life amidst panoramic vistas of the waterfront. Offering stainless steel appliances and sleek cabinetry, there's plenty of room to create fabulous meals. Whether hosting a dinner party with family and friends or enjoying a quiet morning coffee on the balcony watching the sunrise, this space will inspire you. With three bedrooms and two baths, there is ample room for relaxation and retreat. An elevator servicing all three floors ensures effortless access for all. The elevated first floor, situated a full story above ground level, offers peace of mind and protection against inclement weather. The 600-square-foot, air-conditioned, ground-level bonus space (non-conforming) features dual walk-out sliding glass doors leading to the pool and waterfront, where memories are waiting to be made. Boating enthusiasts will delight in the deep-water frontage on the Grand Canal, with a new dock featuring composite decking and a 10,000-pound boat lift, providing quick and easy access to the Sarasota Bay, Intracoastal Waterway, and Gulf of Mexico. Fish from your dock, paddleboard, or kayak on the waterway to see spectacular marine life and waterfowl, promising unforgettable moments on the water. You are sure to spot manatees lazily rolling along and dolphins frolicking. A newly constructed higher seawall with turnbacks at the property line ensures added protection. Outside, the low-maintenance yard is adorned with mature palms, offering privacy and tranquility, while landscape lighting sets the scene for enchanting evenings under the stars. And with a deep well providing water for irrigation, maintaining the lush tropical landscape is a breeze. Conveniently located close to Siesta Village’s unique boutiques, restaurants, and entertainment, and nearby Siesta Beach with its famous powdery white quartz sand and the Gulf of Mexico’s azure waters. Just 15 minutes by car to vibrant downtown Sarasota. Don't miss your opportunity to experience waterfront living on Siesta Key.

4929 Oxford Drive, Sarasota

1 Beds 1 Baths Bay Oaks Estates SubDv. 34242 Zip Code
RENOVATED, MODERN AND FRESH ** LOCATED ON THE 3RD FLOOR ** ENJOY SUBSTANTIAL CASH FLOW with SHORT TERM RENTAL PROGRAM ALREADY IN PLACE, 1 WEEK RENTALS ALLOWED ** Look no further than this open and bright 1 bedroom, 1 bath condo in sought-after Bay Oaks. This unit underwent many updates just 1 year and now boasts luxury vinyl flooring, coastal paint colors throughout, modern fans, contemporary furnishings/décor, new smart TVs with top-of-the-line technologies, gorgeous stone countertops in the kitchen and stainless appliances. The AC and water heater are newer, and you will love the stackable washer/dryer (many condos on Siesta Key are not equipped with private washer/dryers). The family room provides access to a screen patio/porch with a serene setting among the cascading oaks and peek-a-boo views of the community pool. Bay Oaks is located on the intercoastal side of Siesta Key with a variety of amenities that owners and guest love including- immediate access to a heated pool, tennis courts, 2 sets of convenient elevators in Building E, walkout pier/dock into the intercoastal, an abundance of visitor parking along with a private covered parking spot. Siesta Key is world-renowned for its sugar-powdered sand, recreational amenities directly off the public beach, refreshments and soaring palms with miles of “Caribbean-esque Gulf Waters”. Watch the sunrise over the intercoastal and step across midnight pass onto the public beach for sunset… This is the life :)

6157 Midnight Pass Road Unit E23, Sarasota

3 Beds 2.5 Baths Sara Sands SubDv. 34242 Zip Code
Welcome to your private, gated garden oasis nestled on boating water in the heart of Siesta Key. This luxurious residence epitomizes the quintessential Florida lifestyle, offering unparalleled tranquility and opulence. Boasting a seamless blend of indoor-outdoor living spaces, this three-bedroom, two-and-a-half-bath residence is meticulously renovated to exude elegance and comfort. Step inside to discover a haven where every detail has been carefully curated. The open-concept design effortlessly guides you from room to room, with easy-care tile flooring enhancing the sense of spaciousness. The kitchen is a culinary enthusiast's dream, featuring granite counters, custom wood cabinets, and stainless steel appliances. Picture-perfect views of the sparkling pool and lush gardens await as you prepare meals or gather with loved ones in the adjoining eating area. Entertaining is a delight in this home, with the expansive screened pool and spa serving as the focal point of outdoor gatherings. Bask in the Florida sunshine on the paver deck or seek shade under the covered lanai area—the choice is yours. Beyond the pool lies a sprawling, meticulously landscaped tropical yard that gently slopes towards the waterfront, offering a serene backdrop for relaxation or outdoor activities. Boating enthusiasts will relish the convenience of the 7,000-pound lift, providing easy access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Whether you prefer kayaking, paddle boarding, or fishing, your waterfront haven provides endless opportunities for aquatic adventures. When it's time to unwind, retreat to the primary bedroom suite, complete with a luxurious bath for ultimate relaxation. Two additional guest bedrooms, one of which doubles as an office, offer ample space for family or visitors. Indulge in the Bali-inspired guest bath with its indoor-outdoor shower, adding a touch of tropical paradise to your daily routine. Beyond the confines of your oasis, explore the world-renowned Siesta Beach, just moments away, where powder-white sands and breathtaking sunsets await. Discover the vibrant culture of Siesta Village, with its eclectic boutiques and restaurants, or venture to downtown Sarasota for a taste of urban sophistication and cultural richness. With its unparalleled location and laid-back elegance, this home offers the perfect sanctuary to embrace the carefree beach lifestyle you've always dreamed of. Don't miss your chance to make this exquisite retreat your own - and embark on a journey to waterfront luxury living on Siesta Key.

5140 Windward Avenue, Sarasota

4 Beds 5 Baths Harmony Sub SubDv. 34242 Zip Code
Experience the epitome of Siesta Key living in this exquisitely crafted residence, perfectly located near Siesta Village and the renowned pristine beaches, with every conceivable amenity nearby. Nestled on a generous one-third-acre lot, this 2019 custom masterpiece by award-winning John Cannon Homes epitomizes luxury and sophistication. Boasting four spacious bedrooms, an office, and five baths, this home is an entertainer's dream, designed to host large gatherings with ease and elegance. Built with an unwavering commitment to quality and luxury, every detail has been thoughtfully considered to offer unparalleled comfort and convenience. Innovative technology is woven throughout the home, allowing seamless remote control from your smartphone, a cutting-edge media system for immersive sound and visual experiences, a Lutron lighting and blind system throughout the home, and a reliable backup generator, ensuring uninterrupted enjoyment. The open-concept floor plan offers soaring ceilings illuminated by natural light. The great room flows seamlessly to the dining area and the fabulous chef’s kitchen, which features sleek custom cabinetry, an expansive island with seating, and quartz counters. Top-of-the-line Thermador appliances include a six-burner natural gas range and a built-in Miele coffee system for your culinary excellence. The primary suite is a sanctuary of relaxation, welcoming its occupants after a day filled with sun and fun. Guests are pampered with their own ensuite baths and access to bespoke entertainment options, ensuring privacy and luxury for everyone. The heart of this magnificent property is the expansive outdoor lanai, featuring a stunning pool set against the backdrop of silver travertine tile, a rejuvenating spa, and a fully equipped kitchen and bar area, living room, and fireplace, promising unforgettable moments under the sun or stars. As the sun sets, the outdoor living space becomes a central gathering spot, where music, laughter, and culinary delights blend into the perfect evening. An automated irrigation system maintains lush greenery. A high-ceiling garage with a two-car lift provides ample space for your luxury vehicles, while a comprehensive camera system, impact doors, windows and garage door, and a natural gas-powered generator ensure security and peace of mind. The high-quality construction offers an added benefit with reasonable insurance rates. This home promises a life of exquisite luxury and unmatched convenience, where the car keys are forgotten. Enjoy the convenience of being just steps away from the vibrant Village and the white quartz sands and azure waters of Siesta Beach. Welcome to your paradise on Siesta Key, where every day is a testament to the beauty of island living.

4940 Peaceable Way, Sarasota

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