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$1,175,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Experience elevated coastal living in this beachfront penthouse condo on Siesta Key, where direct Gulf views greet you the moment you walk through the door. Bathed in natural light, this turnkey furnished residence captures breathtaking sunsets and offers an effortless blend of luxury and comfort. The bright kitchen is thoughtfully designed with granite countertops and solid wood cabinetry, perfect for both everyday living and entertaining. The flexible guest bedroom features Murphy beds, maximizing space while maintaining style and functionality. New impact windows enhance peace of mind while framing endless views of the Gulf. Located within the highly sought-after Whispering Sands, a 25-acre resort-style community, residents enjoy more than 800 feet of private Siesta Beach with powdery white sand. Amenities include two swimming pools, two clubhouses, exercise rooms, a picnic area with tiki hut and grills, kayak and canoe storage, a tranquil lagoon, and meticulously landscaped grounds. Just moments from Siesta Village, this penthouse offers the perfect balance of privacy and proximity to world-class dining, shopping, and entertainment. Whether as a full-time residence or a luxury retreat, this exceptional penthouse delivers the ultimate Siesta Beach lifestyle.

19 Whispering Sands Drive Unit 1204, Sarasota
$963,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
REMODELED GULF FRONT CONDO. NEW HURRICAN WINDOWS ON GULFRONT ROOM ALSO EQUIPPED WITH HURRICANE SHUTTERS ON OTHER WINDOWS. NEW TEAK WOOD CEILING IN BONUS ROOM OVERLOOKING THE PRISTINE QUARTZ BEACH. STYLISH GRANITE AND ALL WOOD SHAKER CABINETS. NEW KITCHENAIDE STAINLESS APPLIANCES. ALL NEW MINKAIRE CEILING FANS, BEACHY LAMINATE FLOORS, NEW SHOWER TILING, OVERSIZED VANITIES AND SOLID WOOD BARN DOORS. ONE OF ONLY 12 TRUE BEACHFRONT UNITS IN PEPPERTREE. COMPLEX HAS GATED BEACH, BBQ GRILLS, CLUBHOUSE, FITNESS AND TENNIS COURTS. WAKE UP AND TAKE A STROLL ON THE PRESTINE QUARTS BEACH, WHAT A WAY TO START YOUR DAY FINSIH WITH A SPECTULAR SUNSET.

1013 W Peppertree Drive Unit 115, Sarasota
$775,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Experience elevated coastal living in this stunning penthouse residence at 1200 E Peppertree Drive, Unit 601. Perched atop the building, this exceptional unit offers breathtaking panoramic views of the Intracoastal Waterway and downtown skyline, creating a spectacular backdrop from sunrise to sunset. Completely renovated with impeccable attention to detail, the residence features custom built-ins, high-end finishes, and a thoughtfully designed layout that blends style and functionality. The open living spaces are bathed in natural light, maximizing the views and enhancing the penthouse feel throughout. Located in the highly desirable Peppertree Bay, a rare gulf-to-bay community with deeded beach access, residents enjoy resort-style pools on both the Gulf and Bay sides, lush tropical grounds, and exceptional amenities. Just steps from world-famous Siesta Key Beach and minutes to dining, shopping, and entertainment, this is a rare opportunity to own a move-in-ready penthouse offering luxury, views, and the ultimate island lifestyle.

1200 E Peppertree Lane Unit 601, Sarasota
$729,000
2 Beds ⋅ 2 Baths ⋅ Gulf'n Bay SubDv. ⋅ 34242 Zip Code
Welcome to your slice of Paradise on Siesta Key! This beautifully renovated 2 bedroom, 2 bath, 1 car garage end unit condo is located in the highly sought after Gulf & Bay Club Bayside, offering private, deeded beach access to the world-famous Siesta Key Beach. Best of all, the property has No Hurricane Damage, providing peace of mind for full time residents, and investors alike. Enjoy the tranquil views of the pond, tennis and Pickleball courts, and the community pool from this light filled unit. Vaulted ceilings and No Unit above enhance the sense of space and privacy. The home has been thoughtfully updated with porcelain tile throughout the living areas, and a stunning fully renovated kitchen featuring Quartz countertops(including the breakfast bar), custom wood cabinetry, and stainless steel appliances. A built in desk with cabinetry creates an ideal home office or workspace. The spacious owner’s suite includes a walk in closet and an updated en-suite bathroom with new vanity, Quartz countertops, and tiled walk in shower. Adjacent to the living room, an enclosed patio offers versatile flex space, perfect for additional seating, dining, or simply enjoying your morning coffee while soaking in the Florida sunshine. Gulf & Bay Club Bayside is a resort style community offering deeded beach access, two heated pools, tennis and Pickleball courts, outdoor grilling areas, a fitness facility, and a fishing dock on the Intercoastal Waterway. With one week minimum rentals allowed and an optional on site rental office, this condo presents an excellent investment opportunity. Furnishings available under a separate contract. Ideally located just steps from the white sands of Siesta Key Beach and short distance to Siesta Key Village’s restaurants and shopping, this is a rare opportunity to own a beautifully updated condo in one of the island’s most desirable communities.

1220 Siesta Bayside Drive Unit 1220-A, Sarasota
$1,600,000
3 Beds ⋅ 3 Baths ⋅ Point Of Rocks SubDv. ⋅ 34242 Zip Code
Escape to the ultimate Siesta Key lifestyle with this rarely available, coastal contemporary condo—offering the perfect blend of luxury, privacy, and convenience with direct access to the sugar-white sands of world-renowned Siesta Key Beach and Crescent Beach. Known for its quartz-crystal sand and turquoise waters, this top-rated beach offers stunning sunsets, gentle waves, and vibrant coastal charm, all just a short stroll from your door. Nestled in a boutique enclave of only five residences, this exclusive unit has fresh interior paint, lives like a single-family home and is one of only two in its building. this unit encompasses the entire floor and shares no walls with other units. With five private patios, a built-in outdoor grill, tall ceilings and windows, and plantation shutters throughout, the light-filled layout offers an open flow between living, dining, and kitchen spaces—accented by custom cabinetry, upscale finishes throughout. The spacious primary suite provides a private retreat, while the entire home is thoughtfully designed on one level for effortless living. A private elevator offers direct access from your oversized ground-level garage, which is nearly 1,000 square feet and accommodates three vehicles plus storage, along with a private driveway for guest parking — a rare find on the Key. This property is zoned for short-term, weekly rentals and boasts a strong rental history, making it an exceptional opportunity for both personal enjoyment and possibility to earn over $120,000 in investment income. Enjoy walkable access to beachside boutiques, island restaurants, and boat rentals, plus quick and easy access on and off the island, making it ideal for both full-time living and a low-maintenance vacation home. Shared amenities include a serene pool, private owner's clubhouse, and common area used by only five residences, ensuring a peaceful and private setting. Whether you're searching for a serene retreat or a stylish beach escape with income potential, this home offers a unique opportunity to live in the heart of Siesta Key’s coastal paradise. Furnishings optional - not included in list price.

1021 Crescent Street Unit 1, Sarasota
$900,000
1 Beds ⋅ 1 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
This fully updated spacious and open condominium located on Siesta Key boasts incredible views of the Gulf of America and Siesta Key Village. Enjoy them one of your three private balconies! An abundance of bright natural light flows throughout the unit. With its private beach access, pool area, common area, and close proximity to the Siesta Key Village, this unit offers an abundance of lifestyle.

5400 Ocean Boulevard Unit 8-04, Sarasota
$1,835,000
3 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
INCREDIBLE FULL Sunset & Gulf Views!....INCREDIBLE "Everything" UPDATES & FINISHES!....INCREDIBLE Boutique Beachside Community!....Rarely Available, You will be WOWED! by this Stunning (3) Bedroom TOP FLOOR residence with GARAGE PARKING in Sought After Casarina---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 Full Gulf and Beach Views, to be further enjoyed with Morning Coffee and Evening Cocktails on the Generously Sized Lanai*****Bright & Spacious Open Floorplan with Well-Appointed Interiors were COMPLETELY and THROUGHLY renovated, including: ALL Plumbing & Fixtures; Multi-Speed HVAC along with Ductwork; Electrical; Ceilings, Custom Millwork; Polished Porcelain Tile Throughout, Hurricane Windows/Doors; and Kitchen & Baths: Layout, Solid-Wood Cabinetry; Custom Tile Backsplashes; Countertops and CAFE Appliances*****Deeded Beach Access, perfect 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---- Ideal as Second Home/Vacation, Investment or Year-Round Residence. Island Living @ It's Finest......

5880 Midnight Pass Road Unit 910, Sarasota
$4,500,000
3 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Repriced to the market - reduced $500,000! An exquisite Gulf-front penthouse - a private third floor residence with a loft and private rooftop deck overlooking Siesta Key’s pristine sands. Immerse yourself in the ultimate coastal luxury lifestyle with this spectacular Gulf-front penthouse, in an exclusive 3-residence boutique building, where each home occupies its private floor. Just near the world-renowned powdery quartz sands of Siesta Beach, this one-of-a-kind 3-bedroom, 3.5-bath residence offers breathtaking, unobstructed panoramic views of the azure Gulf waters and vibrant sunsets from nearly every room. Designed for the beach-loving connoisseur, this exceptional home features 3 spacious bedrooms, including 2 private suites, each with spa-inspired baths and floor-to-ceiling windows showcasing endless Gulf vistas. A second-story bonus room with a half bath provides a versatile space ideal for a media room, home office or guest retreat, all while offering stunning rooftop views. From the moment you get off the private-stop elevator directly into your full-floor residence, you’re met with sweeping Gulf views framed by walls of glass, filling the interiors with natural light and seamless indoor-outdoor ambiance. The expansive open-concept living space is ideal for everyday living and entertaining. The gourmet kitchen is a chef’s dream, featuring premium appliances, sleek modern cabinetry and elegant stone countertops. Travertine and rich wood flooring add warmth and refinement throughout. The magnificent rooftop terrace offers complete privacy for sunbathing, entertaining, or unwinding while enjoying soothing sea breezes and postcard-worthy sunsets. Additional luxury amenities include a secure lobby, a rare 2-car tandem garage with private driveway and private elevator access, delivering the comfort and privacy typically found only in single-family beachfront estates. On ground level, an inviting shaded outdoor lounge and dining area with a built-in grill creates the ideal setting for alfresco meals under the stars, all just a short distance along a private shell path to the soft white sands of Siesta Beach. Beyond the beach, enjoy the vibrant energy of Siesta Village, with boutique shopping, fine dining and lively nightlife just minutes away. If you value privacy, exclusivity and full-floor living paired with direct beach access, this extraordinary penthouse presents a rare opportunity to own one of Siesta Key’s most desired Gulf-front residences.

534 Beach Road, Sarasota
$452,000
1 Beds ⋅ 1 Baths ⋅ Holiday Apts SubDv. ⋅ 34242 Zip Code
Welcome to Gulf Holiday Condominium—an exceptional opportunity to own one of just 18 units in this rarely available community. This beautifully updated second-floor, 1-bedroom, 1-bath residence places you just steps from the best of what Sarasota has to offer. Inside, you’ll find stainless steel appliances, quartz and granite countertops, and modern finishes throughout, creating a bright and inviting retreat ideal for personal enjoyment or vacation rental income. If rental income is a priority, you’ll appreciate that this area allows for one-week rentals—a rarity in the surrounding communities. Gulf Holiday Condominium boasts an unbeatable location with effortless access to the white quartz sands of Siesta Key Beach and the vibrant shops, dining, and entertainment of Siesta Key Village. Opportunities like this are truly seldom available—don’t miss your chance to own a piece of paradise and proudly tell your family and friends, “I live where you vacation!

73 Avenida Messina Unit 15, Sarasota
$690,000
3 Beds ⋅ 3 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
Huge opportunity to own a spacious 2,400 sq ft, 3 bedroom condo on Siesta Key with an aggressive, new price drop! Now being offered at $799,900 - an unbelievable $339.22 per square foot (vs recent SK sales average of $460 per square foot). This is a fabulous family investment with plenty of room to sleep 8 people (Note: a 4th bedroom could easily be added). This condo has brand new floor-to-ceiling high impact hurricane sliders that run the entire length of the condo and open to a full 95’ lanai for a nice open-air feeling. Allow your family to enjoy your new vacation home, then use the successful in-house rental program to make additional income for yourself. The best of both worlds! Gated-community amenities abound here: both private beach access and intracoastal access with use of free boat slips and kayak racks. One of the largest heated pools on the Key. Brand new pickleball and tennis courts. Tropical landscaping that includes areas for nice seating on the intracoastal, outdoor grilling and picnics, shuffleboard, cornhole, and basketball goal. Fitness center and party/event space. Wheel-chair accessible property. You can go from car to kitchen with no steps! This condo offers a very desirable split floorplan with the primary bedroom on one end and the other two bedrooms on the opposite end with 2 distinct heating/cooling systems. Also includes 2.5 baths with both a tub and shower option. Generous closets in each room, plus a large owner’s closet, beach closet and unique private, full storage closet in hallway next to condo. Whether you are searching for a spacious family getaway, a peaceful primary residence, and/or a high-performing rental, this rare offering delivers.

6415 Midnight Pass Road Unit 211, Sarasota
$815,000
2 Beds ⋅ 2 Baths ⋅ Seashell SubDv. ⋅ 34242 Zip Code
Welcome to your slice of effortless Siesta Key living at the desirable Seashell Condominiums. This inviting second-floor residence, Unit 208, offers two bedrooms and two baths wrapped in a light, coastal aesthetic that immediately sets the tone for island life. Thoughtfully laid out and easy to maintain, the space feels comfortable and welcoming, while new impact windows and sliders offer peace of mind. Seashell is a boutique community of just 48 residences, creating a relaxed, neighborly atmosphere without sacrificing amenities. Residents enjoy private beach access, a heated pool, outdoor grilling areas, and a tiki hut perfect for hosting casual gatherings or enjoying lunch in the shade. The gated property also features under-building parking and onsite rental management, making ownership simple and flexible—ideal for personal use, rental income, or both. Location is key, and Seashell delivers. Situated near Captain Curt’s Plaza—often referred to as Siesta Key’s South Village—you’re moments from popular restaurants, live music, and everyday island conveniences. With the Stickney Point Bridge directly across the street, on-and-off island access is refreshingly easy. Laid-back, well-located, and designed for easy coastal living, this is Siesta Key ownership made simple.

6500 Midnight Pass Road Unit 208, Sarasota
$850,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Located in the desirable Excelsior Beach-to-Bay community, this beautifully and completely renovated top-floor end unit condominium is a peaceful coastal-inspired home defined by soaring cathedral ceilings, natural light, and designer finishes! Enjoy the private deeded access to the powder-soft sands of world-famous Crescent Beach on Siesta Key, the azure, blue waters of the Gulf of Mexico and the lush park-like grounds with mature oaks, flowing fountains, and tranquil courtyard ponds. Walk into the heart of the home which encompasses the open living and dining room, where soaring 23 ft ceilings create an airy, open ambiance. The expanded and enclosed lanai adds approximately 200 square ft of additional ac space, framed by floor-to-ceiling windows that span 30 ft and capture peaceful garden views and fill the home with soft, natural light. The kitchen, designed for both cooking and gathering, is open to the dining room and features Divitori soft-close dovetail cabinetry, pull-out drawers, two generous pantries with pull out storage, level-four matching granite counters, under-cabinet dimmable lighting, and abundant extra cabinet storage—all illuminated by recessed LED lighting. Enter the primary suite, complete with dramatic 12 ft ceiling, spacious walk-in closet with custom Container Store built-ins, and a beautifully finished bath with granite, tile, and a large glass walk-in shower. The suite feels peaceful and secluded, with lovely natural light enhancing the room’s sense of openness. The guest bedroom offers excellent privacy and comfort with plentiful closet space, plantation shutters, and convenient access to a full bath appointed with granite counters, and a glass walk-in shower. Tile flooring flows throughout, complemented by recessed LED lighting on dimmers, plantation shutters, aviation-style ceiling fans, and updated hurricane-rated windows in all areas other than the lanai. Benefit from the unit’s flexible layout, including the potential to expand into a third bedroom and bath. The all-new furnishings package makes move-in easy and can be purchased separately. Additional conveniences include in-unit laundry, new tankless water heater (2025), and new AC (2025). Enjoyment is unmatched in this beautifully landscaped, resort-style beach-to-bay community where residents and guests alike relax beneath mature live oaks, stroll past flowering gardens and ponds, and unwind at your private beach with lounge chairs or at either of Excelsior’s 2 heated pools and spas—one on the Bayfront and one on the Gulf side. Covered grilling areas, a bayside fishing pier, shaded seating, and effortless access to both the Intracoastal and the private white-sand beach create the quintessential Siesta Key lifestyle. Spanning several pristine acres, Excelsior is a well-managed condominium with strong reserves and on-site manger and offers an exceptional array of amenities, including a newly rebuilt fitness center, renovated elevators and community room (2025), 4 pickleball courts, a tennis court, shuffleboard, a clubhouse, secure parking with 2 parking spaces (1 assigned under building, 1 unassigned carport space). Perfectly positioned between Siesta Village and South Siesta’s dining and shopping, the community blends natural beauty, convenience, and coastal sophistication, delivering a truly luxurious island retreat. This is Island living as it's meant to be!

6265 Midnight Pass Road Unit 306, Sarasota
$750,000
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Welcome to the exclusive Pompano building, a well-maintained non?55+ community set within the highly sought after Siesta Harbor.. This 2 bed 2 bath, completely remodeled end unit has a wrap around balcony that provides endless views of the ocean and the Intracoastal waterway. Custom kitchen with quartz countertops wood cabinetry with glass inserts, and 2 beautifully renovated bathrooms. Significant amount of storage. 2 month rentals, no pets, washer and dry is common and is located in the corridor right outside your front door. Association fees includes Cable, Water, Trash, Sewer, Internet, Common area taxes, Community Pool, Fitness center, Escrow Reserves Fund, Insurance, Maintenance Exterior, Maintenance Grounds, Manager, Pool Maintenance, Trash.

1325 S Portofino Drive Unit 310, Sarasota
$6,499,000
4 Beds ⋅ 5 Baths ⋅ Halcyon Siesta Key SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. Welcome to Residence #201 at Halcyon Siesta Key—a rare opportunity within one of the island’s most exclusive boutique communities. With only six Gulf-front residences, Halcyon offers the ultimate in privacy, luxury, and architectural sophistication. This exquisite coastal retreat blends modern design with relaxed seaside living. Engineered hardwood floors, soft coastal hues, and floor-to-ceiling hurricane-impact windows frame sweeping views of the turquoise Gulf waters. Step off your private elevator into a bright, open floor plan designed for effortless entertaining. The gourmet kitchen features Wolf appliances, a wine fridge, and an oversized island flowing seamlessly into the dining and living spaces. The Gulf-front primary suite is a serene escape with a spa-inspired bath boasting dual vanities, a soaking tub, and a glass-enclosed shower. Two additional guest suites—each with private en-suite baths—offer exceptional comfort, while a versatile den/office provides flexibility for work or an additional bedroom. Unwind on your private Gulf-front terrace, where sunsets and sea breezes set the tone for everyday tranquility. Enjoy direct private beach access and the exclusive front amenity cabin, complete with a fitness center, bathrooms, comfortable lounge area, and an expansive deck ideal for entertaining or relaxing after a day by the water. A private two-car garage and resort-style amenities—including a beachfront pool and fire pit—complete this one-of-a-kind coastal lifestyle!

6100 Midnight Pass Road Unit 201, Sarasota
$4,690,000
3 Beds ⋅ 3 Baths ⋅ Ten35 Seaside SubDv. ⋅ 34242 Zip Code
Experience elevated coastal living at Ten35 Seaside, where modern design meets the world-famous shores of Siesta Key. Residence 501, the largest floor plan in the building, offers over 2,600 square feet of contemporary elegance with three bedrooms, three bathrooms, and an impressive 758-square-foot wraparound balcony capturing sweeping Gulf and sunset views. Inside, the residence blends style and quality with a gourmet kitchen featuring solid-wood cabinetry, Wolf and Sub-Zero appliances, an induction cooktop, and a wine refrigerator. SONOS surround sound is thoughtfully integrated throughout the home, enhancing everyday living and entertaining. Additional high-end features include floor-to-ceiling hurricane-impact glass, solid-core doors, Lutron electric shades, sound-limiting windows, high-efficiency systems, and stained tongue-and-groove cypress ceilings on the terraces. The residence also comes with one of the building’s 11 private storage lockers—a rare and valuable convenience—along with two covered parking spaces. Ten35 Seaside enhances beachfront living with resort-style amenities including a Gulf-front pool and spa, fire pit, fitness center, BBQ grilling area, beachside loungers and umbrellas, kayaks, paddleboards, and concierge-arranged water activities. Onsite management, concierge services, and an in-house rental program provide added flexibility and peace of mind, making ownership effortless whether you're home or away. In 2025 alone, this residence generated over $250,000 in rental income—an exceptional opportunity for those seeking both luxury living and strong investment performance. Residence 501 is a refined, modern retreat where incredible views, exceptional design, and full-service convenience come together effortlessly. Discover the ultimate coastal lifestyle on Siesta Key at Ten35 Seaside.

1035 Seaside Drive Unit 501, Sarasota
$855,000
2 Beds ⋅ 2 Baths ⋅ House Of The Sun (Was Known As Haleakala) SubDv. ⋅ 34242 Zip Code
Reduced 30K! The Best Views Currently Available at House of the Sun! Rarely available 3rd-floor unit in the always desirable and impeccably managed House of the Sun on Siesta Key. Positioned far forward on the north side of the building, this residence enjoys some of the best Gulf and beach views currently on the market. From both the living room and the lanai, take in sweeping views of the Gulf and Siesta Key’s world-famous white sand beach. House of the Sun offers 100 feet of direct beachfront and an exceptional location just 500 feet south of the Stickney Point Bridge, providing quick and easy access to and from the mainland. The property is also within walking distance of a wide variety of restaurants, clubs, and everyday conveniences including gourmet food and fish markets, coffee and ice cream shops, liquor store, clothing and gift shops, salons, postal and shipping services, and beach, sport, and boat rentals. Popular local favorites such as Captain Curt’s and Daiquiri Deck are just steps away. This unit has seen significant recent updates (2023–2025) including new hurricane-impact sliding glass doors and bedroom windows, a new rooftop A/C system, fresh interior paint in common areas, and new LVT flooring throughout the living areas and bedrooms. The kitchen has been upgraded with new stainless steel appliances, and additional improvements include a new master bedroom mattress, window shades, rugs, and bedding. Additional features include an in-unit washer and dryer, owner’s closet, and under-building parking. House of the Sun has also undergone extensive common-area improvements (2024–2025), including new elevators, a new hurricane-impact roof, updated pool and tennis court, enhanced pool-area common room with new exercise equipment, new gas grill stations, refreshed outdoor seating areas, landscaping, hallway paint, carpet, lighting, and upgraded Wi-Fi throughout the building. The complex is pet-friendly for owners and is known for having one of the best-run on-site rental programs on Siesta Key, offering a three-night minimum rental policy. This unit performed well in its first year in the rental pool and offers an excellent balance of personal enjoyment and rental income potential. Sale subject to future bookings.

6518 Midnight Pass Road Unit 310, Sarasota
$700,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
A rare top floor opportunity in a quiet corner of Island Reef. Stunning views of Little Sarasota Bay and the Gulf from the always-shaded lanai or balcony where sunrises and sunsets are easily visible this time of year. Renovated from top to bottom, this is one of the few units with "Impact Glass" already installed in the lanai. This is a true turn-key opportunity allows you to move in immediately and start enjoying this little corner of paradise. Kitchen features granite countertops, and the unit includes an in-residence laundry. Furnished and complete with a carport! Island Reef is a serene waterfront community, and one of the few Gulf-to-Bay communities that offers many desirable amenities including a beach, boat docks (lifts allowed), two lit tennis courts, pickleball, two fitness rooms, kayak storage, a library, billiards, a game room, a clubhouse, two heated pools and gas grills. Pet friendly! Tropical gardens enhance the appeal of Island Reef and this wonderful community, conveniently located near two of Siesta Key's popular restaurants. A complimentary trolley provides access to Siesta beach, Siesta Village offering dining, shopping, ice cream, mini donuts, cute brunch spots, dancing, and live music every night of the week.

8779 Midnight Pass Road Unit 502H, Sarasota
$1,398,000
2 Beds ⋅ 2 Baths ⋅ Siesta Sands Resort SubDv. ⋅ 34242 Zip Code
This spacious and well-appointed direct beachfront condo, located at the southern end of Crescent Beach in one of Siesta Key's most desirable boutique resort communities, offers an exceptional coastal living experience. Unit 312, situated on the 3rd floor, features 2 bedrooms, 2 bathrooms, and two private balconies overlooking the beach, where you can enjoy sweeping Gulf views, refreshing tropical breezes, and unforgettable sunsets year-round. A private parking space, in-unit laundry, and private storage add everyday convenience. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room, and the serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you just steps from Siesta Key's South Village.

1001 Point Of Rocks Road Unit 312, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Sea Village SubDv. ⋅ 34242 Zip Code
FULL GULF & SUNSET VIEWS---You will be WOWED by this TURNKEY FURNISHED Siesta Key residence, just moments to the "baby powder" quartz white sands of TOP RATED Siesta Key Beach....This Well-Appointed, Spacious & Pet Friendly Two Bedroom/2 Bath condo has many desired UPDATES: Impact Windows/Sliders; Vinyl Plank Flooring Throughout; Custom Millwork& Plantation Shutters; HVAC & Hot Water Tank replaced 2021; In Unit Washer/Dryer; and a Large Kitchen with solid wood cabinetry; stainless appliances; wine cooler & Generous amounts of Counter Space & Storage!...You will ENJOY your morning coffee Dolphin Watching and your evening cocktails soaking in the Amazing Colors of Sunset over the Gulf...Sea Village is a boutique community that is conveniently located to the dining/shopping/nightlife of the Main Village, features (2) gulfside Pools; fishing pier; Bike Storage & additional Storage Lockers....Perfect as Investment; Vacation or Year-Round Residence.

4660 Ocean Boulevard Unit E2, Sarasota
$125,000
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 14–17), 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 606, Weeks 14-17, Sarasota
$550,000
2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
Welcome to one of the best locations on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Location is fantastic! Wait until you see the grounds! You have the best of both worlds. Your new condominium is a 2 bedroom 2 bathroom split plan with brand-new hurricane sliding doors. Inside you have abundant natural light and a spacious combo kitchen/dining room/living room setting offering a move-in-ready condition. What truly sets The Anchorage apart is its canal-front dockage with first-come, first-serve boat slips, providing direct access to Sarasota Bay and the Intracoastal Waterway. For boating enthusiasts, this is an exceptional value, $10.00 per month boat slip fee. This is crazy insane ridiculous pricing for a boat slip…offering a rare opportunity to enjoy waterfront living and boating convenience without the premium price or waitlists typically found on Siesta Key. The building is solid concrete! Buyer has one car spot #77. This is a perfect investment for rental opportunities. Weekly rentals are allowed. The building and grounds are in wonderful shape! The Anchorage has so many amenities to offer owners and renters, including an Olympic-size heated swimming pool, Fitness Center, Lighted Pickleball & Tennis Courts, Clubhouse, BBQ & Picnic Areas and Kayak Storage. If you have a boat, The Anchorage also offers free dockage along the Seawall! There is a trolly that you could take to Siesta Key Village to enjoy more shopping, entertainment and dining options. Your new condo has its own carport. The Anchorage is very conveniently located near Stickney Point Bridge to give you easy access to the mainland, including downtown Sarasota!

6415 Midnight Pass Road Unit 306, Sarasota
$475,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Siesta Key Waterfront Opportunity – Unmatched full bay views from your lanai, Gulf views from your front balcony — this 2 bed, 2 bath condo offers the best of coastal living on Siesta Key. Spacious and ready for your personal touch, this condo is ideal for those looking to renovate and build equity. The community offers two bayfront pools, pickleball and tennis courts, fitness center, kayak racks, and some of the most affordable boat docks around (first come, first served). No flooding in this complex! Reserved carport next to the elevator. Turtle Beach access just across the street. Trolley stop nearby for easy island exploring. Monthly rentals allowed 12x per year with onsite management. Whether you're searching for a relaxing island escape or an income-producing property, this is your chance to own in one of Siesta Key’s most desirable waterfront communities.

8911 Midnight Pass Road Unit 410, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Castaway Cove SubDv. ⋅ 34242 Zip Code
Welcome to your boutique waterfront condominium community, Castaway Cove at the south end of Siesta Key. This is one of only eight condominiums, an end unit with a community boat slip and dock on a saltwater canal with quick access to the Gulf. Open floor plan with two bedrooms, two baths, great room and dining room views as well as a screened rear porch overlooking the canal and the Gulf. Enjoy sunsets watching the waves crashing on the beach and the manatees and dolphins splashing in your backyard. Grab a kayak and go for a perfect paddle through the mangrove tunnels or out Midnight Pass into the Gulf. Utilize the available kayak storage. New seawall and new roof on the building. The trolley is nearby and will take you right up the road to Siesta Beach or the Village. Yes, you can have it all on Siesta Key!

9226 Midnight Pass Road Unit 4A, Sarasota
$989,000
3 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
Owner Financing Available ~ Siesta Key ~ Siesta Key Beach - Private Beach Access ~ Gulf & Bay Bayside Community ~ Three Bedrooms ~ Two Bathrooms ~ Weekly Rental Property ~ Two Pools / Sauna's ~ Tennis ~ Pickleball ~ Day Dock ~ Garage (Deeded).This bright and serene two-story unit offers a welcoming second-floor entrance and is conveniently located just a short distance from the beach, making it truly move-in ready. As a weekly rental property, it is completely turn-key and situated within the desirable Gulf & Bayside Community. The residence features updates throughout and boasts an excellent layout designed for both comfort and style. Main Level Features: Upon entering, you are greeted by a light-filled kitchen equipped with a vaulted breakfast nook, stainless steel appliances, and a breakfast bar. The kitchen seamlessly flows into the dining room, which is enhanced by a wet bar and a beverage refrigerator, perfect for entertaining. The spacious living room, with its inviting vaulted ceiling, provides an ideal setting for gatherings and relaxation. The first-floor primary bedroom includes an ensuite bathroom that also serves as the guest bathroom. From here, you have access to the screened lanai, creating a seamless indoor-outdoor living experience. Tile flooring extends throughout the main level, except for the staircase leading to the upper floor. Upper Level and Additional Spaces: Upstairs, the home features a bright, multi-use loft area, as well as two luminous guest bedrooms. Each bedroom is complemented by a private Juliet balcony, and they share a bathroom with an enclosed shower. Additional conveniences include an in-unit stackable washer and dryer and a deeded, private one-car garage. Community Amenities: Residents of this community enjoy access to a variety of amenities, including private beach access, two pools, a sauna, a day dock, barbecue grills, tennis and pickleball courts, and a clubhouse. The property is beautifully showcased in photos and a drone virtual tour, inviting you to come and experience all it has to deliver. This is a weekly rental community, the management of which is at the discretion of the owner. Use the onsite management or one of your choosing. Easy to show even during active tenant stays.

1225 Siesta Bayside Drive Unit 1225B, Sarasota
$550,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Welcome to Island Reef, a fantastic Beach to Bay Luxury Resort Complex on South Siesta Key. This rarely available first floor condo offers it's owners the ultimate in convenience with easy parking at the front door. Step out your back glassed lanai to the pool and tennis /pickleball courts, and beautiful courtyard. This 2 bedroom/2 bathroom condo is fully furnished and has been used as a vacation home and part-time rental. The open floor plan has split bedrooms, a glassed lanai, kitchen dinette, inside laundry, and a pass-through kitchen to the Living and Dining area. Recent updates include luxury vinyl plank through-out, and tile floors in the lanai. New area rugs and coastal furnishings create a comfortable, easy-care setting. There is ample storage with full-wall closets in the guest bedroom, a walk-in closet in the Master Bedroom, and a linen and entry closet and large storage room off the foyer. Amenities at Island Reef are second to none. Enjoy a swim or aerobics class in a choice of 2 heated pools. The updated clubhouse can be reserved for personal use and is the site of the many social events. Other amenities include; a game room, library, fitness room, dock, beach frontage, pickleball and tennis courts, shuffleboard, kayak and bike storage and an active social program. There is an inhouse rental program and on-site manager. If you want to head to the Siesta Key Beach, the SK Village, and beyond, you can pick up the free Trolley from the Island Reef Entrance. Walk to Turtles Restaurant or Turtle Beach Park or rent a boat from the nearby Marina. If you have always wanted to live in Paradise, here is your opportunity at a great price! This unit is SOLD AS-IS. The new dock has been completed. There is a short waiting list for those who would want to rent a dock.

8773 Midnight Pass Road Unit 102G, Sarasota
$6,925,000
4 Beds ⋅ 5 Baths ⋅ Halcyon Siesta Key SubDv. ⋅ 34242 Zip Code
A Once-in-a-Lifetime Offering! Introducing Penthouse #401 at Halcyon Siesta Key—an extraordinary coastal sanctuary where architectural brilliance meets unparalleled exclusivity. This is not just a residence; it’s a legacy. Set atop a boutique, six-unit Gulf-front building, Penthouse #401 is the first and only unit ever to be offered for sale—a true rarity as timeless and coveted as the quartz-crystal sands of Siesta Key Beach, just beyond your expansive floor-to-ceiling windows. Enter through a private elevator into your own foyer and be instantly captivated by panoramic views of the Gulf of Mexico. Encompassing 3,525 square feet, this residence was masterfully designed to blend modern sophistication with relaxed coastal luxury. At the heart of the home lies a chef’s kitchen that redefines gourmet living: top-of-the-line Wolf appliances, double ovens, dual sinks, an oversized island, built-in wine fridge, walk-in pantry, coffee bar, and bespoke cabinetry—crafted for both grand entertaining and effortless everyday living. The open-concept layout flows gracefully through dining and living spaces, enhanced by polished terrazzo flooring and Lutron-controlled lighting and shades that adjust with the touch of a button. Wake up to shimmering Gulf views in the tranquil primary suite, a true retreat offering a spa-like en-suite with radiant heated floors, dual vanities, a sculptural soaking tub, and an oversized glass-enclosed shower. Step outside to a spectacular 674 sq. ft. wraparound balcony—ideal for morning espresso, sunset cocktails, or simply soaking in Siesta Key’s year-round beauty. Three additional guest suites provide private en-suite baths and generous closet space, while a full laundry room, powder bath, and abundant storage complete the home’s thoughtful layout. A private two-car garage ensures convenience and security—an invaluable feature in this exclusive enclave. Life at Halcyon is curated for ease and elegance, with upscale amenities including on-site maintenance, a historic clubhouse, beachfront pool, grilling station, fire pit, and private beach access. Just minutes from Siesta Key Village and Sarasota’s cultural and culinary delights, this location offers the perfect blend of privacy and accessibility. Penthouse #401 is more than a luxury residence—it’s a one-of-one opportunity to own a piece of Gulf-front history on Florida’s most treasured beach.

6100 Midnight Pass Road Unit 401, Sarasota
$960,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Experience the ultimate beachfront lifestyle in this stunning turn-key 2-bedroom, 2-bath second floor condo offering a full, unobstructed Gulf view on one of the best beaches in the world. From the moment you step inside, you’re greeted by breathtaking panoramic views of shimmering turquoise waters, powder-soft crystal sand, and unforgettable sunsets that paint the sky each evening. This light-filled residence features an open, inviting layout designed to maximize the incredible coastal scenery from the main living areas. The spacious primary suite offers comfort and privacy with an en-suite bath and generous closet space. A comfortable guest bedroom and second full bath provide the perfect setup for family or visitors. Enjoy the convenience of an additional dedicated storage closet, ideal for beach gear, bicycles, or seasonal belongings. Located just steps to the community pool, fitness center, clubhouse, tennis & pickleball courts and private beach access, this premier beachfront community delivers true resort-style living. Soak in the sights and sounds of waterfront life—morning coffee with sea breezes, afternoon relaxation, and sunsets that feel close enough to touch. Whether you're seeking a full-time residence, a seasonal retreat, or an investment property, this condo offers the perfect blend of comfort, amenities, and world-class beach living. For your convenience, Peppertree offers onsite rental.

1017 W Peppertree Drive Unit 116, Sarasota
$20,000
4 Beds ⋅ 4 Baths ⋅ Siesta Key Beach Residences SubDv. ⋅ 34242 Zip Code
Fractional Ownership. Experience the ultimate in coastal luxury with this Guaranteed Gulf View Deluxe 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, a spacious guest bedroom, and a den that easily serves as a fourth sleeping room—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 511, Weeks 2-3, Sarasota
$1,199,000
3 Beds ⋅ 3 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. Huge Price Reduction!!! Fourth-floor end unit offering breathtaking views of the intracoastal waterway, featuring three spacious bedrooms and three full ensuite baths. Newly installed luxury vinyl plank flooring graces the entire unit. The expansive glassed lanai boasts recently replaced sliding doors, complete with accordion shutters on the inner doors and impact-resistant glass on the outer ones. The kitchen has been thoughtfully opened up and reconfigured for optimal enjoyment. The living and dining areas are bright and roomy. Dolphin Bay is a sought-after, gated, pet-friendly community with only 50 units, each having its own private underbuilding garage, and well-known for its vibrant atmosphere. Amenities include three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier, and kayak access. The complex is well-maintained, with a freshly updated exterior and new elevators in 2024, set amidst beautifully landscaped grounds. Just a short stroll to the world-renowned, white crystal sands of Siesta Key beach. Condo fees at Dolphin Bay are being lowered in 2026.

1240 Dolphin Bay Way Unit 401, Sarasota
$1,365,000
3 Beds ⋅ 3 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.

1260 Dolphin Bay Way Unit 404, Sarasota