Sarasota/Crescent Beach/Siesta Key Condos for Sale

Sarasota/Crescent Beach/Siesta Key Condos for Sale

Welcome to the stunning region of Sarasota, home to the beautiful Crescent Beach and the renowned Siesta Key. Located in Sarasota County, Florida, Siesta Key is a charming city known for its pristine white sandy beaches, crystal-clear waters, and vibrant community.

If you are looking to invest in a piece of paradise, condos for sale in Siesta Key offer the perfect opportunity to experience the ultimate beachfront lifestyle. True Real Estate presents a diverse range of condos for sale in this sought-after area, catering to various preferences and budgets.

Imagine waking up to the sound of waves gently crashing on the shore, enjoying breathtaking sunsets from your balcony, and having world-class amenities right at your doorstep. Whether you are looking for a cozy beachfront retreat or a luxurious condo with panoramic views, True Real Estate has the perfect property for you.

Siesta Key is not just a place to live; it's a lifestyle. With an abundance of outdoor activities, upscale dining options, boutique shopping, and a vibrant arts scene, this region offers something for everyone. Whether you are a water sports enthusiast, a nature lover, or a culture seeker, Siesta Key has it all.

Don't miss the opportunity to own a piece of paradise in Siesta Key. Contact True Real Estate today to explore the finest condos for sale in this captivating region and start living the beachfront dream you've always imagined.

Newest Sarasota/Crescent Beach/Siesta Key Condos for Sale

1350 Siesta Bayside Drive Unit 1350B, Sarasota
$899,000
3 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in nearby Building 1328 on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multigenerational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddleboarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.

1350 Siesta Bayside Drive Unit 1350B, Sarasota

1328 Siesta Bayside Drive Unit 1328C, Sarasota
$699,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized windows and glass sliders fill the home with natural light and extend the living space to the screen-protected lanai, creating an ideal spot to relax after a day at the beach. The updated kitchen features stone countertops, contemporary cabinetry, quality appliances, and generous storage. The dining and living spaces connect effortlessly, giving the residence a comfortable flow for both everyday living and seasonal enjoyment. Both bedrooms provide privacy for owners and guests, and the primary suite features a walk-in closet, en-suite bath, and direct access to the lanai. A second bedroom serves well as a guest room, home office, or multi-use space. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the second floor, a townhome layout. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year Gulf & Bay Club Bayside is known for its beautiful coastal architecture and outstanding amenities. Residents enjoy two heated swimming pools, tennis courts, pickleball, a well-equipped fitness center, grilling stations, a fishing dock on the Intracoastal Waterway, and a stylish clubhouse. The community’s deeded walking beach access—located directly across the street—places you moments from Siesta Beach’s unique shores and turquoise water, making it effortless to enjoy sunrise or sunset strolls, and spontaneous beach days. Situated in the heart of Siesta Key, the location offers quick access to the island’s best attractions. Explore nearby Siesta Village, known for its open-air restaurants, boutique shops, live music, and laid-back coastal atmosphere. Boaters will appreciate the proximity to the Intracoastal Waterway, marinas, and local rental options. For even more dining, arts, and entertainment, vibrant downtown Sarasota is just a short drive away—home to the Sarasota Opera House, Van Wezel Performing Arts Hall, Selby Gardens, the Ringling Museum, St. Armands Circle, and an ever-growing culinary scene. Whether you’re seeking a full-time residence, a seasonal getaway, or an investment opportunity with weekly rentals permitted, this Gulf & Bay Club Bayside property delivers the ideal combination of location, lifestyle, and value on Siesta Key.

1328 Siesta Bayside Drive Unit 1328C, Sarasota

9397 Midnight Pass Road Unit 506, Sarasota
$665,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
LIVE WHERE THE GULF MEETS THE BAY. Discover an extraordinary island lifestyle at The Pointe on Midnight Pass, a private, gated, waterfront community at the southernmost tip of Siesta Key, uniquely positioned at the convergence of The Gulf of America, Little Sarasota Bay, and Blind Pass Lagoon. This beautifully renovated 2-bedroom, 2-bath residence captures the rare magic of both sides of the island—wake to spectacular sunrises over Little Sarasota Bay and the Jim Neville Nature Preserve, then watch the sky transform at sunset over The Gulf. Thoughtfully updated, the residence features elegant tray ceilings and recessed lighting, solid-wood cabinetry, granite countertops, stainless-steel appliances, breakfast bar and pantry, contemporary baths with floor-to-ceiling tile, ceramic tile flooring throughout, sleek white interior doors, and sun-control shades on the lanai. A spacious lanai extends the living space outdoors, creating the perfect setting for morning coffee, sunset cocktails, or watching dolphins, manatees, seabirds and boats move through the surrounding waters. A private utility room houses the washer and dryer, while ground-level storage provides coveted space for beach, boating and golf gear. And then there is The Pointe—more than five acres of waterfront living, surrounded by water on three sides and embraced by an extensive seawall, with pathways winding throughout lush, mature tropical vegetation. Enjoy a heated pool and spa, lighted tennis and pickleball courts, fitness center, sauna, clubhouse, private island pavilion with grills, kayak and canoe storage and launches, fishing areas, boat docks, and on-site management—with a vibrant social calendar during season that brings neighbors together and makes it easy to connect, participate, or simply enjoy the island lifestyle at your own pace. The newly reopened Midnight Pass adds another extraordinary dimension, reconnecting the Gulf and Intracoastal waters and enhancing the boating, fishing and wildlife experience right outside your door. Walk or bike to Turtle Beach, enjoy nearby restaurants, or take the trolley to explore more of Siesta Key. This is not simply a condominium—it is the rare opportunity to own a front-row seat to the natural beauty, wildlife and ever-changing waters of southern Siesta Key.

9397 Midnight Pass Road Unit 506, Sarasota

4708 Ocean Boulevard Unit E4, Sarasota
$2,199,000
3 Beds ⋅ 3 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.

4708 Ocean Boulevard Unit E4, Sarasota

6144 Midnight Pass Road Unit 4N, Sarasota
$1,495,000
2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code
Welcome to effortless beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, an exceptional beachfront setting, and relaxed coastal elegance come together in one very special residence. Perfectly positioned on the second floor of one of Island House’s highly desirable direct-beachfront buildings, Unit 4 North offers truly unobstructed views of the gorgeous sandy beach and sparkling Gulf of Mexico. With no neighboring building interrupting the panorama, the scenery takes center stage from the main living areas, filling the residence with natural light and creating the unmistakable feeling of being right on the water. Step outside and the beach is just moments away. The elevated second-floor location offers an appealing combination of privacy, convenience, and added peace of mind, while a convenient access ramp makes transporting luggage, groceries, and beach gear especially easy. The residence has experienced no prior water intrusion or storm damage. Inside, the condo is beautifully maintained and move-in ready, with tile flooring throughout for easy coastal living. The updated kitchen features solid-surface and granite countertops and opens comfortably to the living and dining areas, allowing the Gulf views to remain part of the experience whether you are entertaining or simply relaxing at home. Both bathrooms have been tastefully renovated with attractive tiled showers and updated finishes. Whether envisioned as a private Siesta Key retreat, a seasonal residence, or an income-producing investment, Unit 4 North offers outstanding versatility. Island House’s desirable three-night minimum rental policy provides excellent flexibility for owners who want to enjoy the property themselves while also taking advantage of strong vacation-rental potential. Island House offers an impressive collection of resort-style amenities designed for carefree island living, including professional on-site management, beautifully refreshed tropical landscaping, a heated community pool, beach chairs and chaise lounges, shaded beach cabanas, outdoor dining areas, shuffleboard, cornhole, and a welcoming clubhouse complete with billiards, foosball, board games, and gathering spaces. And when you are ready to explore beyond the beach, Siesta Key makes it effortless. Hop aboard the free Siesta Key trolley or use one of the island’s convenient local ride services to visit Siesta Key Village for restaurants, shopping, entertainment, and nightlife. Turtle Beach, boating, fishing charters, downtown Sarasota, museums, theaters, and Sarasota’s renowned arts and cultural attractions are all within easy reach. This is more than a beach condo—it is an opportunity to own a front-row seat to the Siesta Key lifestyle, where mornings begin with Gulf views, days unfold on one of Florida’s most celebrated beaches, and spectacular sunsets become part of everyday life.

6144 Midnight Pass Road Unit 4N, Sarasota

8750 Midnight Pass Road Unit 501C, Sarasota
$699,900
2 Beds ⋅ 2 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code
WELCOME TO TORTUGA ON SIESTA KEY, A TRUE TROPICAL COASTAL PARADISE! THIS 5TH-FLOOR 2-BEDROOM, 2-BATHROOM RESIDENCE SHOWCASES A SPRAWLING OPEN-CONCEPT LAYOUT WITH 1,232 SQUARE FEET OF LIVING SPACE, SWEEPING BEACH VIEWS, AND AN OVERSIZED 34-FOOT COMBINED LIVING AND FAMILY ROOM FILLED WITH NATURAL LIGHT. SITUATED ON OVER 3 ACRES OF DIRECT GULF-FRONT GROUNDS, THIS PROPERTY PRESENTS THE ULTIMATE BLEND OF ISLAND LUXURY AND RELAXATION. FRESHLY UPDATED WITH A MODERN COASTAL PALETTE, THE INTERIOR HIGHLIGHTS WOOD-LOOK LAMINATE FLOORS, CROWN MOLDING, NEUTRAL GREY ACCENTS, AND SLEEK CEILING FANS THROUGHOUT. THE PRIMARY SUITE SERVES AS A PRIVATE RETREAT FEATURING AN EXPANSIVE CLOSET WITH CUSTOM ORGANIZERS AND AN EN-SUITE BATHROOM WITH A GLASS-ENCLOSED WALK-IN SHOWER AND PEBBLE TILE FOOTING. THE SECOND BEDROOM AND FULL BATHROOM SHOWCASE PREMIUM FINISHES PERFECT FOR FAMILY OR GUESTS. INCLUDES A DEDICATED IN-UNIT LAUNDRY ROOM PLUS HURRICANE SHUTTERS FOR TOTAL PEACE OF MIND. THE TORTUGA COMMUNITY SHOWCASES RESORT-STYLE AMENITIES: DEEDED BEACH ACCESS DIRECTLY ONTO SIESTA KEY, AN INDOOR/OUTDOOR HEATED POOL, TENNIS COURTS, A CLUBHOUSE, AN ASSIGNED COVERED GARAGE SPACE, ELEVATOR ACCESS, AND A PRIVATE ENTRANCE. THE HOA FEE COVERS CABLE TV, INTERNET, WATER, SEWER, TRASH, PEST CONTROL, BUILDING MAINTENANCE, AND STRUCTURAL INSURANCE. CURRENT THREE DOCKS AVAILABLE FOR RENT FOR $300 PER YEAR UP TO 24 FT BOAT. EMBRACE THE ULTIMATE SIESTA KEY LIFESTYLE: WALK STRAIGHT ONTO THE SAND, ENJOY WATER ACTIVITIES, OR TAKE A SHORT DRIVE OVER STICKNEY POINT BRIDGE TO DOWNTOWN SARASOTA DINING, SHOPPING, AND ENTERTAINMENT. RENTAL-FRIENDLY (1-MONTH MINIMUM LEASE).CLOSE TO OPHELIAS WATERFRONT RESTAURANT AND TURTLE BEACH BOAT RAMP. COME EXPERIENCE COASTAL LIVING AT ITS FINEST!

8750 Midnight Pass Road Unit 501C, Sarasota

625 Beach Road Unit 301, Sarasota
$865,000
2 Beds ⋅ 2 Baths ⋅ Timber Land Ranchettes SubDv. ⋅ 34242 Zip Code
This beautifully furnished turnkey, two-bedroom, two-bath condominium, will charm you with the luxury of direct access to world renown ‘’Siesta Key Beach. Embrace a rare opportunity to own at ‘Tivoli By The Sea’, the perfect combination of a desirable island location with resort-style amenities. You’ll savor vivid sunsets and panoramic views of the Gulf’s turquoise waters, all from your 26-by-6-foot private balcony. This condo is in immaculate condition, and perfect for year-round living, seasonally, or as an investment property. The modern open floor plan creates a seamless indoor-outdoor flow throughout the home. Sliders from the spacious Dining Room/Living Room area offers plenty of space for entertaining. The Primary Bedroom suite, which features a king-size bed, a vanity area and walk-in closet, also has its own set of sliders to the oversized balcony. The contemporary eat-in kitchen is bright and pristine, with thoughtful updates. The large Guest Bedroom, and nearby full Guest Bath, provides family and guests with their own quiet respite. There’s also a top-floor one bedroom Guest suite, available to owners at affordable weekly reservations for their visiting guests (see the photos). ‘Tivoli By The Sea’ offers an impressive collection of amenities including: a heated swimming pool, fitness center, recreation room, tennis/pickleball court, basketball court, putting green, and ping-pong table. You’ll be a short stroll to the sugary sands of Siesta Key Beach from your private gate. The rooftop Club Room features stunning 270-degree gulf views, and can be reserved for private parties. Each condo includes a storage unit, a covered parking space, and hurricane shutter protection. The building has benefited from numerous updates in recent years. Plumbing updates in 2014, electrical updates in 2017, replacement of catwalk railings in 2019, resurfacing of the tennis and pickleball courts in 2020, and a new roof in 2023. 'Tivoli By The Sea' boasts a strong track record for weekly & monthly rentals, all handled by the on-site company, 'Beachside Management'. Less than five minutes from Siesta Key Village, the home affords convenient access to an array of restaurants, shops and nightlife. Parasailing, paddle boarding, kayaking, boating rentals, and fishing, all provide endless opportunities to enjoy the surrounding waters. Downtown Sarasota is a simple drive with its vibrant arts and entertainment scene. Your social calendar will be filled with tons of culture to enjoy with the ‘Van Wezel Performing Arts Hall’, ‘Sarasota Opera House’, ‘Asolo Repertory Theatre’, ‘Florida Studio Theatre’ and the ‘Marie Selby Botanical Gardens’. Sarasota-Bradenton International Airport is a short drive away. This wonderful condo is vacant and easy to show!

625 Beach Road Unit 301, Sarasota

9393 Midnight Pass Road Unit 302, Sarasota
$675,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
If you seek incredible views, look no further. Surrounded by water on three sides, enjoy the panoramic vistas on the southernmost end of Siesta Key. Look from the lanai to the east at scenic Neville Preserve and Little Sarasota Bay. The west-facing front of the unit is the perfect location from which to enjoy the spectacular Siesta Key sunsets with friends and neighbors. Step inside this beautifully updated turn-key furnished 2-bedroom, 2-bathroom unit and experience coastal elegance at its finest. The open-concept kitchen features stunning cabinetry, a quartz waterfall countertop, and sleek stainless-steel appliances—ideal for entertaining or enjoying quiet mornings with a view. Crown molding and recessed lighting add a refined touch throughout the space. The master suite is a private retreat with a spacious bedroom, walk-in closet, and sliding doors leading to the lanai—offering peaceful water views to wake up to each morning. The en-suite master bathroom is a spa-like sanctuary, complete with a walk-in shower, quartz countertops, and a breathtaking tiled wall and shower. The second bathroom echoes this sophisticated design with quartz counters and beautifully tiled features. A large screened-in lanai invites you to unwind while soaking in the ever-changing hues of sunrise and sunset over the Intracoastal Waterway. Additional conveniences include an in-unit washer/dryer and an assigned covered parking space. The stack pipe replacement work for this unit has been completed and all association projects are paid for and there are no outstanding assessments. A gated community, The Pointe is beautifully landscaped and features every amenity: a heated pool and spa, lighted tennis and pickleball courts, private boat docks, kayak and paddleboard racks and launch, exercise rooms, men's and women's saunas, clubhouse, a private island with a gazebo and grills, and on-site management and maintenance. This five-plus-acre property is conveniently located just a few minutes’ walk from Turtle Beach and three restaurants. Come live at the less-traveled, more tranquil end of the Key and enjoy the walking and bike paths under tree-lined Midnight Pass Road. Boat docks are available!

9393 Midnight Pass Road Unit 302, Sarasota

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