Oceanfront Homes For Sale In Siesta Key

4 Beds ⋅ 4 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code

Repriced $250,000! A rare opportunity to reimagine a Gulf-front penthouse on Siesta Key. Set in a boutique condominium community near Siesta Village, this expansive four-bedroom, four-bath residence offers over 3,900 air-conditioned square feet, full Gulf views and the kind of scale, frontage and location that are seldom available. With nearly 80 feet of linear Gulf frontage, the penthouse captures sweeping vistas of the azure Gulf waters, Big Pass, Lido Key and downtown Sarasota from nearly every room. The floor plan is exceptionally spacious, with grand living areas, high ceilings, a fireplace, two balconies, an attached two-car garage and the rare flexibility that comes with a residence of this size and presence. The two-building, 22-unit complex features a pool overlooking the Gulf, offering a relaxed setting to enjoy the waterfront lifestyle. This residence presents a unique canvas for a complete custom renovation. A new owner can transform this property into a spectacular coastal showplace, tailored to today’s luxury lifestyle. The existing floor plan includes generous entertaining spaces, a large kitchen footprint, two primary-suite areas, one with a private sauna, all ready to be reinterpreted with a fresh vision and design. Just moments from Siesta Village, with its restaurants, boutiques, boating and waterfront activities, this residence also enjoys proximity to Siesta Key’s world-famous white quartz sand beach. It is an extraordinary chance to create a one-of-a-kind Gulf-front penthouse in one of the island’s desirable locations. Beyond the island, vibrant downtown Sarasota’s cultural, shopping, dining and entertainment areas are just minutes away.

4712 Ocean Boulevard Unit W10, Sarasota

$500,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

Step into your own island retreat with this rare END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for effortless living, the OPEN CONCEPT floor plan features non-slip porcelain tile placed on the diagonal, skip trowel ceiling, and a spacious light-filled living space with an additional, sunny, west facing window. The nicely RENOVATED kitchen is a standout, offering granite countertops, colorful tile backsplash, a 9’ breakfast bar, white soft-close cabinetry, and a suite of GE, Whirlpool, Frigidaire, and LG appliances, all enhanced by overhead recessed, dimmable LED lighting. The cabinetry and granite extend into the entire length of the dining area, creating additional storage and an elegant serving space ideal for entertaining. The original interior living room sliders have been removed to seamlessly incorporate the lanai, transforming it into a sun-drenched sunroom that expands your cooled living space and invites the outdoors in. Just outside, a small brick paver patio off the sunroom offers the perfect spot for grilling, sunning, or unwinding after a day at the beach. Both bathrooms in this unit have been tastefully updated with NEW vanities, fixtures, and cabinetry. Additional highlights include a complete set of 2016 hurricane impact sunroom sliders and 2025 water heater. At Whispering Sands, every day feels like a vacation—with 800’ of PRIVATE beach, two heated pools with new travertine tile decks, clubhouse – currently undergoing a complete remodel which will include a catering kitchen and fitness rooms – beachside Tiki Hut, grills, and canoe/kayak—all just a short stroll to the vibrant shops and dining options of Siesta Key Village. Your island getaway awaits!

225 Hourglass Way Unit 106, Sarasota

$1,124,000

2 Beds ⋅ 2 Baths ⋅ Horizons West SubDv. ⋅ 34242 Zip Code

Perched on the 6th floor with sweeping, unobstructed western views of the Gulf and world famous Crescent Beach, this spectacular Siesta Key condo delivers front row sunsets and frequent dolphin sightings, stretching from Point of Rocks to north Siesta Key. Ideally positioned above the gulf front pool and spa, this partially furnished island retreat is move in ready and features a full length enclosed balcony for added living space, along with impact windows and doors for peace of mind. Located in Horizons West, a coveted gulf to bay resort community spanning over 7 lushly landscaped acres, residents enjoy 300 feet of deeded private beach with cabanas, a beachside pool and spa, grilling areas, a second pool by the clubhouse, and a private Intracoastal Waterway park with day dock perfect for kayaking, paddleboarding, fishing, or relaxing among the mangroves. Conveniently access Siesta Key Village dining, shopping, and entertainment via the free island trolley and embrace the ultimate carefree coastal lifestyle. Come see what Island Life is all about.

6140 Midnight Pass Road Unit 603, Sarasota

$609,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

Welcome to effortless coastal living in this beautifully UPDATED second floor midrise residence in the premier GULF FRONT property of Whispering Sands! Designed with an OPEN CONCEPT floor plan, this light-filled condo showcases a bright, sophisticated 2023/2024 REMODELED kitchen featuring quartz countertops, stainless Samsung appliances, an impressive 8' breakfast bar with seating for 3, soft close cabinetry, and recessed lighting—all complemented by an elegant uplit tray ceiling. A true highlight is the expansive 29' x 8' lanai stretching the full length of the residence—offering an inviting extension of the living space ideal for relaxing, dining, or working from home, complete with hurricane impact sliders for total peace of mind. Both bathrooms have been tastefully updated with granite countertops and tiled, glass-enclosed walk-in showers, while ceiling fans and crown molding add comfort and sophistication throughout the unit. Beyond the residence, Whispering Sands offers true resort-style living in a premier Gulf front setting. Spend your days lounging on your private beach, taking a refreshing swim in one of two heated pools, an invigorating workout in the gym, or enjoying the vibrant social atmosphere of the clubhouse just steps from your door. Whether it’s a peaceful morning walk along the shoreline or a sunset gathering with neighbors, every day feels like a vacation. Perfectly positioned just steps from the clubhouse—currently undergoing complete remodeling in 2026—and pool, and a short stroll along the sidewalk to your 800' of your own private beach, this residence embodies the very best of resort style living. Ideally located just around the corner from the boutiques and restaurants of Siesta Key Village, you'll enjoy the perfect balance of relaxed beachfront living and easy access to dining, entertainment and island charm. Move right in and start enjoying the easy island lifestyle you’ve been dreaming of!

199 Whispering Sands Drive Unit 204, Sarasota

$670,000

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

Perfect Beach Life on Siesta Key! Tortuga Beach has so much to offer. Private 77 unit complex has the small intimate feel with a luxury with it's many offerings. Private Beachfront, Tennis & Pickleball across the street, Clubhouse with kitchen, library and entertainment area, indoor/outdoor community pool, sauna, sun deck with grills and seating, and boat slips across the street on the bay. There are 3 slips open for rental for $300 a year. Just fill out your application. With the friendly residents you can enjoy the relaxing atmosphere with the wonderful views of the Gulf of Mexico from daytime sunbathing to sunset pleasures. Upon arrival to the condo you will find an enclosed lanai to offer more living space in the 1650 Square feet. Kitchen has plenty of space with it's wood cabinets and granite countertops with pass through breakfast bar. New AC. Split Floor plan. Primary bedroom closet contains the washer dryer but Tortuga also offers a laundry facility if you are in need. Separate dining room just off the kitchen for entertainment. Covered Parking spot very close to the entrance and elevator for easy loading and unloading.

8710 Midnight Pass Road Unit 203B, Sarasota

$595,000

2 Beds ⋅ 2 Baths ⋅ Casa Blanca Villas SubDv. ⋅ 34242 Zip Code

PRICE IMPROVEMENT! Now the lowest priced 2 bed/2 bath on the Gulf side of Midnight Pass plus the added bonus of in-unit laundry, this Siesta Key condo offers unmatched value! Casa Blanca is a charming Gulf-side community with a mix of cozy villas and a three-story beachfront building overlooking the Siesta Key’s world famous Crescent Beach. This residence features 2 bedrooms and 1.5 beautifully renovated baths, thoughtfully designed for comfort and convenience. The full bath is accessible from the hallway, while the primary bedroom enjoys its own private half bath. Inside, the turnkey space is light and inviting, with comfortable furnishings and subtle coastal touches that create a relaxed, welcoming feel. The kitchen is well-equipped for everything from a hearty breakfast to a seafood dinner after a day in the sun. Step outside to enjoy true beach living—an outdoor shower makes rinsing off sand a breeze, and the screened lanai offers the perfect spot to dine al fresco, unwind with a drink, or enjoy a casual game night with friends, family or neighbors. Casa Blanca allows short-term rentals (5–7 nights, owner’s choice), making this an attractive option for both personal use and income potential. Community amenities include a large, sparkling pool just a short stroll from your front door. Hop on the Breeze Trolley to enjoy the vibrancy of the north or south village, while a quick drive has you in the heart of Sarasota: home to refined arts, entertainment and eateries that are absolutely worth the trip off the island. Whether you’re looking for an investment opportunity, seasonal escape, or full-time island retreat, this villa offers the best of Siesta Key living—comfortable, flexible, and effortlessly enjoyable.

6154 Midnight Pass Road Unit A-05, Sarasota

$620,000

2 Beds ⋅ 1 Baths ⋅ Casa Blanca Villas SubDv. ⋅ 34242 Zip Code

Positioned along the powdery white sands of Siesta Key’s renowned Crescent Beach, this villa residence within Casa Blanca Beach Resort presents an exceptional opportunity to own in one of Sarasota’s most iconic Gulf-front communities. Casa Blanca is a unique collection of individually owned villas and apartments, each thoughtfully furnished and appointed for effortless coastal living or income-producing flexibility, with minimum rental periods of just 5–7 nights depending on ownership preference. This two-bedroom residence is fully equipped with an updated kitchen and bathroom, all cookware and linens, and the conveniences of individually controlled air conditioning, cable television, and Wi-Fi, creating a seamless turnkey experience for both owners and guests. The community enhances the Gulf-front setting with a clubhouse, pool and multiple on-site laundry facilities, all designed to support easy, resort-style living. Set directly on Crescent Beach, internationally celebrated for its fine, quartz-crystal sand and consistently ranked among the top beaches in the United States, this property captures the essence of Sarasota’s coastal appeal. Ideally situated just off Stickney Point Bridge, it offers effortless access to Sarasota’s renowned dining, shopping, and cultural attractions. With Siesta Beach just steps away, this is a rare opportunity to own in a beloved beachfront destination, whether as a personal retreat, full-time residence, or high-demand investment property.

6154 Midnight Pass Road Unit 7C, Sarasota

$399,000

1 Beds ⋅ 1 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code

Virtually Staged. Welcome to Sandy Cove III, a highly sought-after waterfront community on the pristine Gulf shores of Siesta Key. Ideally located within a short stroll to both Siesta Key Village and the beach, this beautifully renovated ground-floor condo offers the perfect blend of coastal living and convenience. This 1-bedroom, 1-bath unit has been thoughtfully updated with all-new stainless steel appliances, cabinetry, bathroom vanity and shower, water heater, and fresh interior paint. Tile flooring throughout enhances the bright, open living space, while both the kitchen and bedroom provide direct access to a screened side porch perfect for relaxing. The rear patio overlooks a tropical garden creating a peaceful setting for dining and entertaining. Sandy Cove III is a pet-friendly, boutique community of just 16 units featuring a heated pool and a tranquil, park-like waterfront setting. Residents enjoy access to a private clubhouse, fishing pier, kayak storage, and both bay and Gulf water access. Whether you're seeking a full-time residence, vacation getaway, or investment opportunity with monthly rental potential, this property delivers. Experience breathtaking sunsets and the laid-back island lifestyle that make every day feel like a vacation on Siesta Key. Schedule your private showing today.

115 Pass Key Road Unit 115, Sarasota

$679,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

INCREDIBLE VIEWS!.....INCREDIBLE LOCATION!.....INCREDIBLE COMMUNITY!....You will be Impressed by this Special & Rare Opportunity for TURNKEY FURNISHED Residence with FULL WATER VIEWS throughout all Living Areas!..... Located in the Whispering Sands Community you will be able to WALK to the adjacent Village as well as ENJOY over 800' of PRIVATE deeded "white baby powder quartz sands" Beach Access; (2) Heated Pools; clubhouse, fitness center; beachside tiki and so much more in a true "residential neighborhood" setting. Bright & Spacious Open Floor Plan; Updated Kitchen and Baths with Quartz Countertops & Backsplashes; HURRICANE IMPACT SLIDERS open into an Expansive Lanai with Multiple Living Spaces---Perfect for listening to your favorite podcast or Enjoying Majestic Sunsets with Evening Cocktails----The Ultimate in the Siesta Key Lifestyle!

101 Whispering Sands Drive Unit 105, Sarasota

$1,400,000

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

You will melt away on Crescent Beach's powder/sugary white sand and float away in the shimmering waters of the Gulf of Mexico. This residence has been beautifully renovated to provide the ultimate beach home for you to call your own. The kitchen area features a day bed and a custom wood top island. Enjoy your morning coffee or sunset drink on your private lanai. Residents enjoy the heated pool/spa with cabana and outdoor kitchen, two grilling areas, a sunset beachside deck and lighted pickle ball/tennis courts. You will appreciate the on-site management office, fitness room and large community center. Come see for yourself what Casarina offers for fine beachside living.

5880 Midnight Pass Road Unit 704, Sarasota

$1,350,000

2 Beds ⋅ 2 Baths ⋅ Sarasota Surf & Racquet SubDv. ⋅ 34242 Zip Code

Great Opportunity at Sarasota Surf & Racquet Club!! Beautifully turn-key furnished 2BR/2BA condo with a split bedroom floorplan for privacy in Tower 10 Unit 3 right on the beach with a gorgeous view of the Gulf and the beautiful quartz sand beach and shoreline. The onsite rental management team takes care of your investment. You use it when you want and enjoy the great revenue stream coming your way with a rare and great opportunity to take advantage of their 3 night rental minimum policy and managing all the reservations and taking care of the upkeep and cleaning of your unit. This is really exceptional beachfront living on Siesta Key with so many resort style amenities. You have direct access to private Crescent Beach, two heated swimming pools, rental options for tents, cabanas and umbrellas, beachside and poolside BBQ grills, four pickleball courts, three tennis courts (one hard court and two Har-Tru clay) – the only clay courts for a resort community on Siesta Key. There is a fitness center on the property and a recreation room where owners can come together for fun. The interior of this unit has been re-modeled with a lovely coastal look. Both bathrooms have been beautifully re-modeled. The primary bedroom features a king size bed, large walk-in closet and has its own private vanity area and a stunning tiled walk-in shower with a seat and gorgeous glass block. The second bedroom features two queen size beds and large walk-in closet. There is a lanai/room looking out to the beach and Gulf that is perfect for a quiet space for reading or computer work. Washer and Dryer located in laundry room just steps from the unit. This resort style property has it all! Catch the trolley or walk into the Siesta Key village for great shops and lots of great casual dining or more polished dining experiences. Coastal music flows out from the open air fun places for entertainment. Come enjoy Paradise!!!

5920 Midnight Pass Road Unit 1003, Sarasota

$75,000

3 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code

Fractional Ownership. Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Package—featuring one-sixteenth ownership of an extraordinary Siesta Key Beach residence. Your dream of owning a new, high-end home on America’s #1 beach can now be a reality, offering an effortless way to enjoy the best of beachfront living without compromise. Step into an expansive, updated designer-furnished residence that radiates elegance and comfort. The floor plan includes a primary suite, a secondary suite, and a spacious guest bedroom-all thoughtfully appointed with over $150,000 in custom furnishings. The gourmet kitchen is fully equipped with top-tier appliances from Wolf, Sub-Zero, and Fisher & Paykel, complemented by imported linens and every fine detail you’d expect in a luxury coastal retreat. As an owner, you’ll enjoy the legendary hospitality and resort-style amenities of Hyatt Vacation Club, including a full-service recreation and concierge team, assistance with local activities, valet parking, and 24-hour security. Every element has been curated to deliver a seamless blend of private ownership and world-class resort living. Own your piece of paradise—and indulge in the Siesta Key lifestyle you’ve always imagined, at a fraction of the cost of full ownership.

915 Seaside Drive Unit 504, Weeks 6-7, Sarasota

$775,000

2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code

Positioned directly on the sands of world-famous Siesta Key, this 2-bedroom, 2-bath en-suite condominium offers the perfect blend of personal getaway and income-producing investment. Fully furnished and thoughtfully configured for vacation living, this residence is already an active vacation rental with proven historical returns, making it an ideal opportunity for buyers seeking a property that can help offset ownership costs while providing their own beachfront retreat. Inside, tile flooring throughout creates an easy-care coastal interior designed for high-traffic vacation use, while the split layout with two en-suite bedrooms provides privacy and comfort for guests. A large storage closet dedicated to beach gear and recreational “toys” makes it simple to keep everything needed for effortless days on the sand. From the residence, enjoy views of the Gulf of Mexico and the convenience of direct walk-out access to Siesta Key’s powdery white beach, where beach chairs are available for guests, perfect for owners and vacation renters alike. The location places you in one of the most desirable areas of the island, within walking distance to nearby restaurants, shops, and local favorites, or simply hop on the Siesta Key trolley for easy access up and down the island. With its prime beachfront setting, turnkey furnishings, and established rental performance, this property presents a compelling opportunity to own a slice of Siesta Key that can generate income while serving as your personal coastal escape.

6312 Midnight Pass Road Unit 305S, Sarasota

$2,490,000

3 Beds ⋅ 4 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code

You will be WOWED! by this Furnished 2400+ Sq Ft of Elegant BEACHSIDE LIVING with (3) Generously Sized Bedrooms & (3.5) Baths with STUNNING FINISHES THROUGHOUT!.....RARELY AVAILABLE Corner Unit in this Special Boutique Community---a Resort-Style PET FRIENDLY "low density" plush 7 acre residential complex with over 200 feet of Powdery Quartz sand frontage along with "Old Florida" Clubhouse; Courts; Beachside Pool & Cabanas and an Onsite Manager....Upon Entrance you will be Greeted with a Grand Hallway that leads to a BRIGHT & SPACIOUS Floor Plan, reminiscent of a Single Story Home...Each Bedroom is Privately Located, each with it's own Full Baths....ENTERTAINING is "Extra Special" with Expansive Living Areas and Ideally Centrally Located Wet Bar....WELL-APPOINTED INTERIORS, including: Porcelain Tile throughout; Quartz Countertops; Hurricane Impact Windows/Sliders; "Hotel Style" Primary Suite with Seating Enclave & Sumptuous Ensuite Bath; Abundant Storage & Closet Space; In-Unit Laundry and Importantly...ease of Indoor/Outdoor Living with Multiple Sliders leading to "Wrap-Around" Balcony/Lanai--Perfect for Morning Coffees or Indulging your Favorite Cocktails while Watching Majestic Sunsets over the Gulf....*****Deeded Beach Access, convenient for long strolls collecting Seashells or just "Toes in the Sand" relaxing at Top Rated Siesta Key Beach. Dining/Shopping and Nightlife of the main village are just minutes away...GARAGE PARKING...---Ideal as Second Home/Vacation, Investment or Year-Round Residence. Island Living @ It's Finest!

5880 Midnight Pass Road Unit 511, Sarasota

$1,500,000

2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code

This Rare Beachfront, Classic Coastal Modern extensively renovated 2/2 condo has your Dream View! Unobstructed Beach View of 400’ of private beach on 7 acres. Offering total building area for unit is 1568 sq ft. Modern appointed living area is 1316sq ft with additional 252 sq ft Modern Private Lanai. High demand all year Monthly (12) rentals for Investor, 2nd Home or Primary Home. There are No assessments. Passed Structural Integrity. Strong, Fully Funded Reserves. Replaced cast iron to New “PVC” drains in entire building, New building roof, New clubhouse roof lowered insurance master policy. Stilted Building, Designated Parking underneath. Gated with 24 Hr Security. Condo has Brand New HVAC 2026 with R454B gov. required cooling & New Water Tank. Designed by Owner, Floor to Ceiling integrating a cohesive Classic Coastal Modern feel throughout. Enjoy your “private outdoor living” new screened 31’x8’ Beach Lanai (no houses/buildings in line of sight) Modern flooring, locking storage Door. Condo is insulated & extremely “Quiet” w/updated PGT impact Sliders and Windows. Solar Shades are see-through when down on sliders but front windows have see-through Solar Shades & Privacy Shades. The Front has Quiet Solid Core Impact Door. Wi-Fi Thermostat. Stunning Modern Polished Porcelain, Large Rectified 24” Tile for entire condo & closets. Modern Frosted Glass Framed Solid Wood 4 Interior Doors. Frosted Glass Framed Solid Wood Interior Bifolds for all 7 closets, continuing a clean line design with 8” Solid Wood, Mitered Baseboards throughout. Calming Lighting with all LED lighting dimmers throughout & all walk-in closets. All Closets designed w/Solid Wood Shelving & fitted w/thick satin nickel Rods and Brackets to All Studs for Heavy organization needs. Both Bathrooms have Moreno Gloss Floating Soft Close Drawer Vanities w/satin nickel Series Pfister Kenzo Waterfall Faucets/Shower Handel & 4 piece Towel bar set. Kohler Skirted “Chair-Height” Toilets for both. Main bath is Designed w/24” Italian Carrera Marble Tile, full size Bench & tall Niche. Guest bathroom Designed w/24” Ivory Glass Tile & Tall Abalone Tile Niche. With owners not being a chef/cook, kitchen is gently used in immaculate condition. ALL "SMART Wi-Fi" Stainless Appliance Suite, Largest Size features; “Double Oven” 5 burner w/Warming Drawer. Refrigerator “Showcase” Triple French Door, ice/water, Middle Flex Drawer, Bottom Freezer Double Drawer. Stainless “Triple Storm” Dishwasher. Kohler 36” Large Stainless Steel Apron Sink w/Kohler Pull down Stainless Faucet. Matching to Suite are Over Size Stainless "Wi-Fi" Front Load Washing Machine & Front Load Dryer on Stainless Pedestals in “walk-in” Laundry Room, stainless light, solid wood shelving w/nickel stainless rod/brackets designed for Heavy storage needs. Owner has variety remodeled Product in front closet. This beachfront condo has been gently lived in and all the Design Aspects/Appliances are in Immaculate Condition. Clubhouse w/ 25‘x40‘ Heated Swimming Pool, Tennis & Pickleball Courts, updated Fitness room, bathrooms, your private locked Storage Room. Private Beach gate to Boardwalk w/ picnic area, 2 grills & birdwatching benches. Pet friendly, designated large pet park w/bench. “Private ISLAND Style Living” A truly Coveted Opportunity awaits you- private, unobstructed view, full condo length beachfront lanai, 6 floor, 7 acre property & 400’ beachfront. Property is available for Same Day Showings.

420 Beach Road Unit 606, Sarasota

$995,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

Embrace the rare opportunity to own a GULF FRONT residence in the coveted Siesta Key community of Whispering Sands – where breathtaking FULL GULF views, an unbeatable location, and endless potential come together. This 2 bed/2 bath 2nd floor tower unit showcases panoramic vistas of the shimmering Gulf, on 800’ of your own PRIVATE quartz sand beach, and the nightly spectacle of vibrant symphonies of colorful sunsets from your expansive 24’ open-air balcony. Offered in largely original condition, this residence is a true blank canvas—an exceptional value in today’s buyer’s market and the perfect chance to design and remodel from top to bottom in your own personal style. Create the coastal retreat you’ve always envisioned while investing in a premier Gulf front address known for its timeless appeal and strong long-term desirability. Reputable contractor names are available to help bring your vision to life. Life in the sought after 55+ community of Whispering Sands is peaceful and resort inspired. Enjoy two heated, fenced pools with new travertine decks, beach loungers for the exclusive use of owners and their guests, beachside Tiki Hut, gas grills, shuffleboard, canoe/kayak storage, and a beautifully soon to be remodeled clubhouse and Tower Lounge—the latter of which is reserved for the exclusive use of tower residents outside community events, and conveniently located on your floor. You’re also just an elevator ride down to the sparkling Gulf side pool and powder soft sand. Ideally positioned just moments from Siesta Key Village, you can leave your car behind and stroll to charming boutiques, live music, and an array of dining options. End each day with your toes in the sand or on your private balcony, savoring the tranquil rhythm of the waves and the company of friends as the sun melts into the horizon. This is more than a condo—it’s a lifestyle, a legacy of memories in the making, and a chance to secure your own piece of world class Gulf front paradise.

19 Whispering Sands Drive Unit 204, Sarasota

$6,700,000

Siesta Rev SubDv. ⋅ 34242 Zip Code

Gorgeous waterfront property offering sweeping views from Big Pass to Bayou Louise. Rarely available, one of only 10 properties with water access on the east and west, sitting on the coveted north end of Siesta Key, this exceptional parcel features 175 feet of water frontage and spans over three quarters of an acre. A property of this caliber is a rarity—don’t miss the chance to build your legacy on Sarasota’s most exclusive shoreline. With unobstructed access to both Sarasota Bay and the Gulf, this is a premier setting for boating enthusiasts seeking effortless days of fishing, cruising, or island hopping. The panoramic water views from this prestigious North Siesta Key location are truly remarkable, capturing the natural beauty of the coastline from sunrise to sunset. Large waterfront parcels of this scale and frontage are increasingly rare, offering both privacy and the opportunity to create a legacy estate in one of Sarasota’s most desirable coastal enclaves. Whether you envision designing a custom waterfront retreat tailored to your lifestyle or securing a prime land investment for the future, this property presents exceptional flexibility. The lot is available as vacant land (MLS #A4682294) or as a residential offering (MLS #A4682295) featuring a proposed custom home designed by award winning Konstant Architecture (plans complete and available). Buyers may purchase the land independently or move forward with a luxury designed new construction project with plans and permitting already in place. Located just moments from the beach, waterfront dining, and Sarasota’s vibrant cultural and entertainment scene, this property delivers an extraordinary opportunity to create your own Siesta Key masterpiece.

3550 Bayou Louise Lane, Sarasota

$1,500,000

2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code

Best beachfront value on Siesta Key!!! This second-floor condo features two bedrooms and two bathrooms, including a primary ensuite with a king-size bed and a guest bedroom. The interior offers a spacious living area, a formal dining space, and a fully equipped kitchen with granite countertops. Residents and guests can enjoy spectacular views of the Gulf of Mexico and sunsets from the private lanai. The property has recently benefited from refreshed landscaping and updated outdoor furniture. On-site amenities include a year-round heated pool, private beach access with cabanas and lounge chairs provided. A beachfront courtyard with shuffleboard, cornhole, gas grills and shaded seating are ideal for relaxation while watching sunsets. The recreation room offers air hockey, ping pong and more. Located in Island House, well known to be the top rental income producer, this unit is not only a beautiful 2nd home or vacation destination but also a highly valuable, appreciating assest/investment property. While the 2024 and 2025 seasons were impacted by hurricanes resulting in an average rental income of $80,000 a year over the last several years, these units are capable of well over $100,000. With exceptional water views and professional on-site management, this property represents a marriage of functionality, income and beauty.

6146 Midnight Pass Road Unit 12S, Sarasota

$1,799,000

3 Beds ⋅ 2 Baths ⋅ Siesta Key Beach Residences Ii SubDv. ⋅ 34242 Zip Code

Welcome to a premier Siesta Key Beach condo that delivers the ultimate combination of luxury coastal living and high-performing rental income potential. This beautifully updated 3-bedroom, 2-bath condominium is professionally managed through an established onsite program, offering owners a seamless, turnkey experience with the ability to enjoy the home personally while also participating in a proven, income-producing rental program. Located directly on world-famous Siesta Key Beach, consistently ranked among the top beaches in Florida, the U.S., and the world, this property benefits from strong year-round demand for high-end vacation rentals. Whether you’re looking for a beachfront vacation home, a short-term rental investment, or the ideal blend of both, this residence is positioned to deliver outstanding lifestyle value and long-term upside. The current owner has successfully utilized the rental program while still enjoying substantial personal use, making this an exceptional opportunity for buyers seeking a condo with documented rental history and the flexibility to reserve premium seasonal time for themselves. Inside, the condo features a bright, open layout with spacious living areas and finishes that appeal to both owners and guests. Enjoy partial Gulf of Mexico views and Siesta Key Beach scenery from the primary suite, living room, and private lanai—capturing the coastal lifestyle today’s vacation renters are looking for. Owners and guests enjoy access to desirable resort-style amenities, including a sparkling pool, fitness center, concierge services, and professional onsite management. With unbeatable beach access, nearby attractions, and a consistent track record of rental demand, this is one of the most compelling income-producing condos on Siesta Key. Schedule your private showing today and discover the value of owning a luxury Siesta Key vacation rental property.

915 Seaside Drive Unit 412, Sarasota

$115,000

3 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code

Fractional Ownership. Experience the ultimate in coastal luxury with this Premium Winter Fractional Ownership Package, offering 2 one sixteenth ownership packages of an exceptional Siesta Key Beach residence. This is a rare opportunity to own four consecutive winter weeks (Weeks 4-7), plus 2 additional float weeks—providing extended beachfront living during the most desirable season on America’s #1 beach. For buyers searching for Siesta Key real estate, fractional ownership opportunities, or a luxury Gulf-front condo for sale, this offering stands out as truly exceptional. Step into an expansive residence that radiates comfort and coastal charm. The unit has been beautifully refreshed with more than $150,000 in designer furniture and high-end furnishings, giving the home an elevated, stylish, and welcoming atmosphere. The spacious floor plan includes a primary suite, a secondary suite, and a generous guest bedroom—making it ideal for extended stays and visiting guests. The gourmet kitchen features premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtfully curated accessories that enhance the home’s luxury coastal feel. As an owner, you’ll enjoy signature Hyatt Vacation Club amenities, including full-service beach and concierge support, assistance with local activities, continental breakfast, valet parking, and 24-hour security. Every detail is designed to deliver an effortless blend of private ownership and resort-style living on Siesta Key. Claim your piece of paradise—four uninterrupted winter weeks in a spacious Gulf-front residence—and enjoy the benefits of fractional ownership at a fraction of the cost of full ownership. If you're searching for the perfect Siesta Key beachfront property, this rare four-week package offers unmatched value, flexibility, and lifestyle.

915 Seaside Drive Unit 410, Weeks 4-7, Sarasota

Oceanfront Homes For Sale In Siesta Key FL

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