Siesta Key Real Estate

Siesta Key Real Estate

Welcome to Siesta Key, Florida—a tropical paradise nestled in Sarasota County, renowned for its pristine beaches and vibrant coastal lifestyle. This idyllic barrier island, just off the southwestern coast of Florida, is celebrated for its powdery white sands, which are composed of 99% pure quartz, making it not only beautiful but also cool to the touch even on the hottest summer days. Siesta Key Beach has consistently ranked among the top beaches in the United States, drawing visitors from around the globe to bask in its sun-kissed splendor.

Beyond its stunning shores, Siesta Key boasts a charming village atmosphere, complete with quaint boutiques, delightful eateries, and lively nightlife. Stroll along Ocean Boulevard, where you can discover unique local shops and savor fresh seafood at waterfront restaurants while enjoying breathtaking sunset views. The island's vibrant community is perfect for those seeking a laid-back lifestyle infused with a touch of excitement.

Outdoor enthusiasts will find a wealth of activities to embrace, from kayaking and paddleboarding in the clear waters of the Gulf of Mexico to exploring the lush trails of the nearby Siesta Key Village or the scenic parks that dot the island. With year-round warm weather, Siesta Key is a haven for those who love the outdoors.

Whether you’re looking to invest in a vacation home, a permanent residence, or simply seeking a serene getaway, Siesta Key offers an enchanting blend of natural beauty, community spirit, and a relaxed coastal lifestyle. Come and experience the magic of Siesta Key—where every day feels like a vacation!

Newest Listings in Siesta Key

Siesta SubDv. ⋅ 34242 Zip Code

INCREDIBLE LOCATION!....INCREDIBLE BOATING WATER!....INCREDIBLE SIZED LOT!.....Rarely Available EXPANSIVE 18,000+ square foot SAILBOAT WATERFRONT property with nearly 80' Seawall providing, for the Boating Enthusiast, easy access to Hansen Bayou, Sarasota Bay & the Gulf!.......Nestled on a Quiet Street near the North Bridge of Siesta, allowing Privacy as well as Quick and Easy Proximity to both all the Arts/Dining/Shopping of downtown Sarasota Bayfront as well just MINUTES to TOP RATED SIESTA KEY BEACH!....Nearly 80' wide x 258' Deep this rectangular parcel provides the PERFECT OPPORTUNITY to Design/Build your Custom Island Estate and ENJOY the Ideal Beach and Boating Florida Lifestyle..

3601 White Lane, Sarasota

4 Beds ⋅ 3 Baths ⋅ Ten35 Seaside SubDv. ⋅ 34242 Zip Code

Welcome to Ten35 Seaside Drive, a newer mid-rise community at the south end of world-renowned Siesta Key Beach, where turquoise Gulf waters meet pristine quartz sand. Ten35 Seaside elevates island living with luxurious residences designed to highlight the area’s natural beauty. Gulf-view residence 502 offers four bedrooms, three baths, and 2,385 square feet of thoughtfully designed living space. Floor-to-ceiling glass, an open-concept interior, and expansive terraces frame sweeping views of the sea, sand, and sky. Refined finishes include porcelain tile floors, premium cabinetry, top-of-the-line appliances, and a spacious primary suite with a spa-inspired bath. The main terrace is ideal for enjoying spectacular sunsets, while a second terrace off the en-suite guest bedroom captures beautiful sunrises. The kitchen features solid-wood cabinetry, Wolf and Sub-Zero appliances, a gas cooktop, and a wine refrigerator. Additional highlights include solid-core entry and interior doors; floor-to-ceiling, hurricane-resistant balcony doors with laminated solar-tinted glass; sound-reducing laminated windows with solar-tinted glass; a recirculating hot-water system; high-efficiency heating and air conditioning; stained tongue-and-groove cypress terrace ceilings; tiled terrace floors; and two covered parking spaces.Ten35 Seaside offers amenities that complement its beachfront setting, including a swimming pool and spa, fire pit, beach lounge chairs and umbrellas, kayaks, paddleboards, concierge-arranged water activities, fitness center, and Gulf-front barbecue area. Daily beach chairs and umbrellas are also available. Residence 502 presents a rare opportunity to own a fully operational, income-producing property on Siesta Key’s Crescent Beach, one of Florida’s most desirable vacation-rental destinations. The residence is enrolled in the community’s on-site professional rental management program, providing immediate revenue while eliminating the setup time and day-to-day demands of vacation-rental ownership. Marketing, guest services, housekeeping, and operations are managed on-site, allowing owners to earn income while reserving time for personal use. Rental terms permit one-week minimum stays during the off-season and two-week minimum stays during peak season, balancing revenue potential with property preservation. Just moments from the dining and shopping of Siesta Key’s South Village, the property consistently attracts repeat visitors, supporting strong occupancy. Whether you are expanding an investment portfolio, completing a 1031 exchange, or seeking a vacation home that can offset ownership costs, Residence 502 offers a rare combination: a Gulf-front location, professional management, and rental income from day one. A must-see opportunity.

1035 Seaside Drive Unit 502, Sarasota

Sarasota Beach SubDv. ⋅ 34242 Zip Code

Rare Double-Lot Coastal Compound Opportunity on Siesta Key — Offered Together at $1,700,000 | 14,636 Total Sq. Ft. Embrace the quintessential Florida lifestyle on prestigious Palm Island—a peaceful, golf-cart-friendly sanctuary surrounded by deep-water canals, mature tropical canopies, and magnificent luxury residences. Combining Lot A (8,619 sq. ft.) and Lot B (6,017 sq. ft.), this rare joint offering creates an expansive 14,636-square-foot multi-parcel footprint, giving you the ultimate canvas to design a high-end, weather-resilient coastal estate. Are you looking for that legacy estate with a guest house where your family and friends gather for the holidays, one that will be passed down from generation to generation? Or perhaps these two parcels give the ultimate privacy you've been looking for? Or maybe you're a builder who could leverage the efficiency and convenience of building on side-by-side lots at the same time? Imagine never again having to time your beach visits around traffic, hunt for open spots, or compromise on your day because of a full parking lot. Instead, your coastal routine begins with the simple pleasure of stepping out your front door and taking a brief, effortless stroll down quiet, canopy-shaded streets. Within minutes, your toes sink into the pristine, powder-white quartz sands of Siesta Key Beach—consistently recognized among the top-ranked beaches in the world and repeatedly named the #1 beach in the United States. Whether you want to enjoy an early morning walk, take a spontaneous afternoon dip, or walk down to the water for an impromptu sunset cocktail, one of the globe's premier coastal treasures serves as a natural extension of your own backyard, completely free from the hassle of driving. Situated in the heart of Siesta Key, this prime parcel at 5323 Calle Florida offers an unbeatable location just 0.7 miles—a pleasant 15-minute stroll—from the vibrant dining, shopping, and nightlife of Siesta Key Village. Daily convenience and effortless island living are unmatched, with Sarasota Memorial Hospital just 5.6 miles away and Downtown Sarasota only 6.5 miles from your doorstep. Endless entertainment, boutique shopping, and world-class travel are all within easy reach, including St. Armands Circle (8 miles) and Sarasota-Bradenton International Airport (11.5 miles). Boating and water enthusiasts will love the proximity to nearby nautical hubs, with full-service facilities like Safe Harbor Siesta Key just 2.5 miles south, the free county-operated Turtle Beach Public Boat Ramp 5 miles down the key, and the iconic Marina Jack in downtown Sarasota under 7 miles away, making this property an extraordinary canvas for your dream coastal home or investment.

5323 Calle Florida, Sarasota

Siesta Beach SubDv. ⋅ 34242 Zip Code

Unique opportunity to own an exceptional double-lot homesite on the Grand Canal on Siesta Key. Tucked away on a quiet cul-de-sac in one of the island’s most desirable waterfront neighborhoods, this expansive property offers 107 feet of canal frontage and seawall, creating an outstanding setting for your future Siesta Key residence. Located along a low-wake arm of the Grand Canal, the property offers quick boating access to Roberts Bay, while the calm, protected basin provides a peaceful and private setting for enjoying the very best of waterfront living. Ideally situated just minutes from world-famous Siesta Beach, the shops, dining, and energy of Siesta Key Village, and the vibrant cultural attractions of downtown Sarasota, this rare homesite combines tranquility, boating access, and exceptional convenience. Please note: The existing home on the property is permitted and scheduled for demolition in September 2026, offering a unique opportunity to create a custom waterfront residence on this exceptional double-lot homesite.

4950 Commonwealth Drive, Sarasota

2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code

Live the Siesta Key lifestyle! This beautifully maintained 2-bedroom, 2-bath condo offers the perfect combination of island living, rental potential, and resort-style amenities. Ideally situated in the desirable Gulf-side community of Peppertree, this second-floor residence is just a short stroll from the tennis and pickleball courts, heated pools, and Siesta Key’s private-access beach. From the moment you arrive, you’ll appreciate the peaceful setting and tranquil views overlooking one of Peppertree’s picturesque ponds. The condo has been thoughtfully updated with all new impact windows, renovated kitchen and bathrooms, and updated flooring, creating a comfortable and inviting beach retreat. The spacious primary bedroom easily accommodates a king-size bed and features a walk-in closet. The home is offered turnkey furnished, making it ready to enjoy immediately or continue as a seasonal rental. It has consistently generated rental income during peak season, while also providing the flexibility to enjoy it personally during the off-season. Additional features include a full-size washer and dryer, newer A/C installed in 2019, a private storage unit conveniently located just outside the back patio, and a dedicated parking space. Peppertree is truly a destination within Siesta Key, offering direct Gulf-to-Bay access, a private fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ grills throughout the community, beach chairs, car wash areas, and on-site management with a rental program. High and dry with no storm damage, this exceptional condo offers the opportunity to own your own piece of paradise on world-famous Siesta Key. Whether you’re looking for a personal beach getaway, an investment property, or the best of both, this inviting Peppertree residence is ready to welcome you home.

1130 W Peppertree Lane Unit 118, Sarasota

2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code

SUNSETS, SUNSETS, SUNSETS! Experience the Siesta Key lifestyle in this turnkey furnished 5th-floor residence located in the highly desirable Peppertree Bay community. Situated on the Bayside, this 2-bedroom, 2-bath condo offers panoramic views of Siesta Key and spectacular Florida sunsets, along with private deeded beach access just across the property. Tile flooring flows throughout the residence, while the custom kitchen features granite countertops, a tile backsplash, abundant cabinetry, and brand-new stainless steel appliances. The open-concept dining and living areas extend into the enclosed lanai, creating additional space to relax, entertain, and enjoy the beautiful views. Additional features include a newer (2024) HVAC system, a new 80 gallon hot water heater, an in-unit washer and dryer, generous storage, and convenient under-building parking. Offered turnkey furnished, this residence is ready to enjoy from day one. Peppertree Bay is a sought-after Gulf-to-Bay community offering an exceptional array of amenities, including private deeded beach access, two heated swimming pools, two clubhouses with full kitchens, tennis and pickleball courts, a fitness center, fishing pier, BBQ grills, picnic areas, and an active social calendar in season. Ideally located on Siesta Key with easy access to Siesta Key Village, enjoy nearby dining, shopping, live entertainment, and everything Sarasota offers. Whether you're searching for a full-time residence, seasonal retreat, or investment property, this condo delivers the location, amenities, and lifestyle that make Siesta Key so desirable.

1200 E Peppertree Lane Unit 505, Sarasota

2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code

Virtually Staged. Experience the world renowned beaches of Siesta Key in this rarely available first floor luxury condominium steps away from your private deeded beach access. Conveniently located to Siesta Key’s south bridge, accessing the mainland, shopping in the village and access to nearby restaurants and stores is a breeze. Take the free public transport available to Siesta Village or head to Turtle Beach. Arrive home to a tastefully decorated unit with peaceful courtyard lake views. Entertaining and sharing a meal is an event with this updated chef’s kitchen. The enclosed lanai invites you for a cup of coffee, a book or contemplation. The primary suite features wood flooring, a true retreat like en-suite bath and upscale built-ins for the closet. Have peace of mind with impact windows and a new HVAC system installed 2025. There is plenty to do without going to the beach. Two heated pools, hot tubs, pickleball, tennis, fitness, fishing dock, library, beachside restrooms and more.

6265 Midnight Pass Road Unit 102, Sarasota

2 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code

Enjoy easy island living in this beautifully maintained first-floor condominium at Bay Oaks on Siesta Key. With your assigned carport just steps from the front door, there's no need to wait for elevators, making everyday living and guest arrivals effortless. This versatile one-bedroom residence features a converted den that functions as a second bedroom, allowing the property to be successfully marketed and rented as a two-bedroom vacation rental. A favorite among returning guests, this turnkey-furnished unit offers an excellent opportunity for personal enjoyment or investment income. Inside, ceramic tile flooring flows throughout the living and dining areas, while the flexible floor plan comfortably accommodates family and visitors. Step outside to a private patio surrounded by mature trees, providing a peaceful retreat and convenient rear access to the community's resort-style amenities. Residents and guests enjoy Bay Oaks' impressive amenities, including a heated pool, tennis courts, fishing dock, social room, and outdoor grilling areas. Located directly on the free Siesta Key trolley route, you'll have easy access to world-famous Siesta Beach and the shops, dining, and entertainment of Siesta Key Village. Bay Oaks permits one-week rentals, making this a highly desirable and consistently popular rental property. Sold turnkey furnished, this island getaway is ready for immediate enjoyment or rental income from day one.

6157 Midnight Pass Road Unit G11, Sarasota

3 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code

A TRUE 3-bedroom condo residence in desirable Casarina, a premier building positioned directly on the quartz white sands of #1 Siesta Key beach and the Gulf of Mexico. Step into this beautiful spacious residence and experience the flow of this open floor plan conducive to daily living, entertaining and accommodating family and friends. Sold turnkey furnished, this residence boasts impact windows & sliders providing security and protection, large ceramic floor tile throughout perfect for beach living and rich new carpet in the primary bedroom. The updated kitchen is stunning boasting neutral cabinetry, quartz countertops, stainless Jenn-Air appliances, Fisher & Paykel double dishwasher, quartzite island & breakfast bar, instant hot water faucet & 3 spacious pantries. The primary bathroom was updated in 2026 with quartzite countertops and upgraded dual vanities. Custom wood closet organizers are featured in all the bedrooms and an electric fireplace in the living room. The A/C was replaced in 2025, tankless water heater in 2023 and new screened lanai. Casarina is a secure building which has just undergone a complete building renovation & infrastructure. It offers an onsite manager and is fully funded with a 10-year capital plan and no special assessments. Besides the powder-white sand beach, experience tropical living on 7 acres of refreshed lush Florida landscaping, large refurbished heated pool and spa, cabana with outdoor kitchen & dining area, new poolside pergola with seating, 2 grilling areas, sunset decks, gas firepit with Adirondack chairs, resurfaced & lighted tennis court, 2 pickle ball courts, basketball hoop, fitness center, and social room/library. This condo offers secure under-building garage parking with an adjacent storage closet #5. The building renovation & infrastructure within the past two years includes a new reengineered resilient roof, new electrical and fire alarm systems elevated to the 2nd floor, new raised backup generator, new secured A/C units, multiple custom flood-prevention panels/dams, new ground water pump infrastructure, relined plumbing pipes, and refurbished elevators. Minutes to Siesta Village, shopping, restaurants and the culture of downtown Sarasota! So come on down and enjoy Florida living!

5880 Midnight Pass Road Unit 307, Sarasota

6 Beds ⋅ 8 Baths ⋅ Siesta Properties Inc SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. Architectural Rendering Of What Could Be Built Are For Planning Purposes Only. An Extraordinary Gulf-Front Estate Opportunity! There are few opportunities remaining to create a legacy estate directly on the Gulf of Mexico. At 7740 Sanderling Road, nearly one acre of pristine beachfront offers an exceptional canvas for a world-class custom residence in one of Florida's most exclusive coastal communities. Positioned along the sugar-white sands of Siesta Key, this rare Gulf-front homesite presents an unparalleled opportunity to design a private waterfront retreat with sweeping panoramic views of the Gulf of Mexico, spectacular year-round sunsets, and direct access to one of the world's most celebrated beaches. With expansive frontage and generous dimensions, the property invites limitless architectural possibilities—from a contemporary coastal masterpiece to a timeless estate designed for generations to enjoy. Located within the prestigious Sanderling Club, this exceptional property enjoys the distinction of being part of Siesta Key's only private, gated Gulf-front community with 24-hour manned security. Originally envisioned by renowned Architect Paul Rudolph, Sarasota School of Architecture, Sanderling Club has long been recognized as one of Sarasota's most coveted residential enclaves, where privacy, natural beauty, and architectural excellence come together in a setting unlike any other on Florida's Gulf Coast. Residents enjoy an exclusive collection of amenities, including a private beachfront clubhouse overlooking the Gulf, tennis and pickleball courts, a marina with boating access to Sarasota Bay, scenic nature canopy roads , and beautifully maintained grounds that preserve the community's tranquil coastal character. The neighborhood's low density and commitment to preserving its natural environment have made Sanderling Club one of the region's most enduring luxury addresses. Beyond the gates, Siesta Key offers an internationally acclaimed lifestyle defined by its powder-soft quartz beaches, turquoise Gulf waters, and relaxed sophistication. From waterfront dining and boutique shopping in Siesta Key Village to boating, paddleboarding, fishing, and endless days on the water, the island offers an effortless blend of recreation and refinement. Just minutes away, downtown Sarasota provides a vibrant cultural scene that rivals much larger metropolitan destinations. Residents enjoy world-class performing arts, acclaimed restaurants, private clubs, championship golf, luxury shopping, art galleries, marinas, and exceptional healthcare. From evenings at the Sarasota Opera or the Van Wezel Performing Arts Hall to waterfront dining at Marina Jack and shopping at St. Armands Circle, Sarasota continues to rank among the nation's premier luxury lifestyle destinations. Large Gulf-front homesites of this caliber have become exceedingly rare. Combining nearly an acre of buildable beachfront, extraordinary privacy, direct Gulf frontage, and the prestige of Sanderling Club, 7740 Sanderling Road represents an opportunity to create an iconic waterfront estate in one of the most desirable addresses on Florida's Gulf Coast. This is more than a homesite—it is the foundation for a legacy.

7740 Sanderling Road, Sarasota

2 Beds ⋅ 2 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code

Embrace the Siesta Key lifestyle at Tortuga Beach Club! This spacious 2-bedroom, 2-bath residence offers 1,650 square feet of living space in an intimate 77-unit Gulf-front community on the desirable south end of Siesta Key. From relaxing days along the private beachfront to unforgettable sunsets over the Gulf of Mexico, Tortuga offers the coastal lifestyle you've been dreaming of. Step inside and discover a light and inviting split-bedroom floor plan with an enclosed lanai that extends the living space and provides the perfect spot to relax and unwind. The spacious kitchen features wood cabinetry, granite countertops, abundant storage and a convenient pass-through breakfast bar overlooking the living area. A separate dining room just off the kitchen provides additional space for entertaining family and friends. The primary suite offers generous closet space, with the washer and dryer conveniently located within the primary closet. A new A/C system adds comfort and peace of mind. Tortuga Beach Club offers an impressive array of amenities designed for enjoying the best of island living. Spend your days on the private Gulf-front beach, take a swim in the heated indoor/outdoor community pool, relax in the sauna, or gather with friends on the sun deck featuring grills and seating areas. The community clubhouse offers a kitchen, library and entertainment space, while tennis and pickleball courts are conveniently located across Midnight Pass Road. Boating enthusiasts will appreciate access to boat slips across the street on the bay, with slips currently available for annual rental by application. A community laundry facility provides additional convenience when needed. The residence also includes covered parking conveniently located near the building entrance and elevator, making loading and unloading a breeze. The location completes the package! Enjoy close proximity to Turtle Beach, where you can spend the day along the shoreline, launch a kayak or simply soak up the laid-back atmosphere of south Siesta Key. You're also near some of the island's favorite dining destinations, including Ophelia's on the Bay, Turtles Restaurant and other nearby waterfront and casual dining options. Siesta Key Village, shopping, entertainment and the world-famous quartz sands of Siesta Beach are just a drive up the island. Whether you're searching for a full-time island residence or your own Siesta Key getaway, this spacious Tortuga Beach Club condominium brings together private Gulf-front beach access, boating, resort-style amenities and an exceptional south Siesta Key location. Spend your days enjoying the water and your evenings watching spectacular Gulf sunsets this is Siesta Key living at its best!

8710 Midnight Pass Road Unit 203B, Sarasota

2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

Experience true waterfront living at Sunrise Cove with spectacular Intracoastal Waterway views, breathtaking sunrises each morning, and beautiful moonrises each evening. This TURNKEY FURNISHED 2- bedroom, 2-bath condo is located on the second floor and offers the perfect blend of comfort, convenience, and resort-style amenities. The spacious living room features sliding glass doors that open to a screened-in lanai, creating the perfect setting to relax and enjoy panoramic Intracoastal views throughout the day. The primary bedroom offers a walk-in closet and en-suite bath, while the second bedroom also features a walk-in closet and beautiful views toward the Gulf of Mexico and the beach across the street. The hall bathroom includes a walk-in shower and tile flooring. The kitchen features a convenient pass-through to the dining and living areas, making entertaining effortless. Sunrise Cove offers an impressive array of amenities, including two heated swimming pools, an Olympicsize pool with restrooms and a covered lounge area, pickleball and tennis courts, a state-of-the-art fitness center, and a game room. On-site management and 30-day minimum rentals provide flexibility and excellent income-producing potential. Turtle Beach is directly across the street, while the free Siesta Key Breeze trolley stops nearby approximately every 15 minutes, making it easy to explore Siesta Key. Two popular waterfront restaurants, Turtles on the Bay and Ophelia’s on the Bay, are conveniently located right next door. Additional features include an extra storage closet conveniently located near the elevators in the laundry room. Recent community improvements include new roofs, new docks, and newly completed carports. Whether you’re looking for a vacation getaway, income-producing property, or full-time residence, this fabulous waterfront condo offers an exceptional opportunity to enjoy the best of Siesta Key living.

8977 Midnight Pass Road Unit 219, Sarasota

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