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$500,000
2 Beds 2 Baths Island Reef SubDv. 34242 Zip Code
Turnkey Furnished residence at Island Reef with two bedrooms and two baths. Laundry in residence. Furnished! Carport! island Reef is a serene waterfront community, one of the few gulf to Bay Community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed), Two lit Tennis Courts, Pickleball, 2 Fitness Rooms, Kayak storage, Library, Billiards, Game room, Clubhouse, two Heated Pools, and Gas grills. PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key's popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cute brunch spots and dancing and live music every night of the week.

8773 Midnight Pass Road Unit 302G, Sarasota

$385,000
2 Beds 2 Baths Siesta Harbor SubDv. 34242 Zip Code
WATERFRONT SIESTA HARBOR!DIRECT VIEWS OF THE CANAL, walk right out to the canal from your Lanai! BEACH ACCESS ACROSS THE STREET! Turn-Key Furnished with a Canal View! Move in ready, enclosed lanai with all furniture and furnishings included! Highly Sought after remodeled Unit on the Canal in the Dolphin Building! Close to the Resort-style Heated Swimming Pool and Spa on the wide part of the canal. This Charming condo is adorned with large windows, bathing the dwelling in warm, natural light. Combining dining and living space, this turn-key furnished condo is Spacious, light and airy with a Gorgeous updated kitchen with granite countertops! Just move right in or rent until you retire! It's ready for your enjoyment! Active 55+ community, close to the pool, clubhouse, beach access, SCAT, the trolley right outside your door! Beautifully done, tile through out, great coastal feel! TURNKEY FURNISHED! This is a great community lots of activities, fitness room, saunas, outdoor spa, heated pool, on site free laundry, pier on the main intracoastal waterway to relax and fish each day, plus boat slips as available, for a reasonable fee through the Association. The location is wonderful, easy on and off the key, walk to shops, restaurants, mini-donuts! Elevate your living experience in this ready-to-move-in, fully furnished home, and enjoy all the benefits and convenience it offers. Don't miss this chance to reside in one of the best locations in Sarasota; your new home awaits!

1215 S Portofino Drive Unit 107, Sarasota

$1,749,000
2 Beds 2 Baths Crystal Sands SubDv. 34242 Zip Code
Under contract-accepting backup offers. Set on the 7th floor of Crystal Sands, this fully updated residence offers a front-row position to the Gulf, with sweeping views stretching south along Crescent Beach toward Point of Rocks. Located in the sought-after “2” stack, the building sits just steps from the sand, creating a rare level of proximity to the shoreline with water views from every room. The 2-bedroom, 2-bath split floor plan is both functional and well-balanced, offering privacy between suites while keeping the main living space open and connected. Wide-plank flooring runs throughout, leading into a light-filled living and dining area that opens seamlessly to the Gulf beyond. A 30+ foot lanai spans the width of the residence and is accessible from both bedrooms and the main living area, creating an easy indoor-outdoor flow and a natural extension of the living space for everyday use. The kitchen is finished with shaker-style cabinetry, quartz countertops, a center island with bar seating, and stainless appliances, designed to feel clean, current, and easy to live in. Both bedrooms are well-proportioned with direct lanai access and calming water views, while the bathrooms have been thoughtfully updated with refined finishes, frameless glass showers, and cohesive tilework that carries the modern coastal aesthetic throughout the home. Residents of Crystal Sands enjoy direct beach access, a Gulf-front pool, and a prime location just minutes from Siesta Key Village’s dining and shops. With its combination of view, proximity to the sand, and updated interiors, this is one of those residences that simply works the moment you walk in.

6300 Midnight Pass Road Unit 702, Sarasota

$499,000
2 Beds 2 Baths Siesta Harbor SubDv. 34242 Zip Code
WATER VIEWS FROM EVERY ROOM! WATERFRONT HEATED POOL, HOT TUB, SHUFFLEBOARD,GATHERING AREA,BOAT SLIP,BEACH ACCES- LIVE IN PARADISE EVERYDAY IN this STUNNING RENOVATED CANAL-FRONT condo designer 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering private beach access to world-famous Siesta Key Beach just across the street. Situated on the fourth floor with picturesque water views, this beautifully updated unit features gorgeous quartz countertops, gray shaker cabinetry, stainless steel appliances, and brand new ceramic tile flooring throughout. Enjoy peace of mind with the glass-enclosed lanai with sliding glass windows that provides a serene retreat year-round. The open-concept layout flows seamlessly from the modernized kitchen into a bright and welcoming living space, perfect for entertaining or relaxing. Both bathrooms have been tastefully renovated, including a fully remodeled primary and guest bath, and the entire unit was freshly painted. Additional features include a private storage closet, updated lighting, and high-speed fiber optic internet. Siesta Harbor is a vibrant 55+ waterfront community along the Intracoastal Waterway, offering a heated pool, spa, clubhouse, fitness center, shuffleboard, fishing dock, sauna, BBQ area, and boat slips for up to 30’ vessels. Whether enjoying your morning walk to the beach, walking to lunch just minutes away, catching the free trolley to Siesta Key Village, or heading over the nearby bridge to explore downtown Sarasota’s dining, shopping, and cultural scene, this location offers the ultimate in coastal convenience and lifestyle. With monthly rentals allowed 12 times a year, it’s ideal as a personal escape or investment property.

1300 N Portofino Drive Unit 406, Sarasota

$582,000
2 Beds 2 Baths Island Reef SubDv. 34242 Zip Code
This is the Gulf front opportunity buyers wait for. Positioned in the highly sought after A Building at Island Reef, this two bedroom, two bath beach condo offers direct Gulf front views that simply cannot be duplicated, and is currently the lowest priced Gulf front 2/2 property on Siesta Key. Held in the same family for over 30 years, the condo has been meticulously maintained and remains exceptionally clean and comfortable as it sits today. It presents a rare combination of immediate usability and the opportunity to thoughtfully update over time, allowing a new owner to create their own vision in one of the most desirable Gulf front locations on the island. From the moment you walk in, your eye is drawn straight through to the water. The view opens across the pool, the natural flow of the grounds, and out to the Gulf of Mexico, creating a sense of space, calm, and connection that defines true waterfront living. It is the kind of view that makes you pause and take it in. The layout offers a true split floor plan, providing privacy and comfort for both owners and guests. The main living areas are open and relaxed, with Gulf views from the dining area, living room, and primary bedroom. The kitchen is generously sized, with an eat in area and built in desk space that adds flexibility, while natural light fills the space and keeps it bright and inviting. The primary suite is spacious and set apart as its own retreat, complete with an en suite bath and room to unwind. The guest bedroom is positioned on the opposite side, offering separation and privacy. A full size laundry room adds a level of everyday convenience not always found in beach condos. Impact windows are currently being installed on the lanai, adding long term value, peace of mind, and enhancing the indoor outdoor experience that is so central to Gulf front living. Island Reef is known for its true Gulf to Bay lifestyle. Mornings begin with walks along the private beach at Turtle Beach, afternoons are spent kayaking toward Midnight Pass or relaxing by the Gulf side pool, and evenings are centered around sunsets that never repeat themselves. On the bay side, boats pass throughout the day, adding another layer of movement and life to the setting. The community offers bay access with dockage and lift capability, along with direct access to Sarasota Bay and the Gulf beyond. Two heated pools, including the beautifully positioned Gulf side pool, along with tennis, pickleball, and shuffleboard courts create an active yet balanced lifestyle. Residents enjoy a clubhouse, library, fitness rooms, and gathering spaces designed for both connection and relaxation. Additional features include kayak and bike storage, a fishing pier, on site management, and a well run on site rental program offering monthly rental opportunities, providing flexibility for owners who wish to offset expenses. Winding walkways connect the community through mature landscaping and open green space, while brick paver parking areas, covered parking, secure lobby entry, elevator access, and guest parking all add to the ease of ownership. Call today for your private showing. Gulf front opportunities in this building, at this price point, are rare and do not last. Video, 3D tour, and floor plan available.

8764 Midnight Pass Road Unit A202, Sarasota

$719,000
2 Beds 2 Baths Gulf & Bay Club Bayside SubDv. 34242 Zip Code
A first-floor 2-bedroom, 2-bath residence in Gulf and Bay Club Bayside with no unit above, offering added privacy and direct access. An optional second garage is available for purchase under a separate bill of sale. Located on Siesta Key, an eight-mile barrier island consistently recognized among the top beach destinations in the United States and globally, Siesta Beach has been ranked the #1 beach in the United States and #4 in the world by Tripadvisor’s Travelers’ Choice Awards and has also been included on Travel + Leisure’s list of the World’s 50 Best Beaches as the top-ranked beach in the U.S. This unit offers 1,280 square feet and is being sold turnkey furnished. The interior has been recently updated and includes a kitchen with new appliances. Luxury vinyl flooring runs throughout the main living areas and the lanai, with tile flooring in the bathrooms and kitchen. The layout provides functional living space suitable for full-time use, seasonal occupancy, or rental use. A full-size washer and dryer are located within the unit. The living area opens to views of a protected nature preserve. The community allows weekly rentals, providing income potential. The property was not impacted by recent hurricanes. Ownership includes one private garage, with a second garage available for purchase under a separate bill of sale. Residents have private beach access to Siesta Key’s shoreline, known for its quartz sand and calm Gulf waters, along with community amenities including two pools, tennis courts, and a gated entrance with on-site management. This property may be used as a primary residence, seasonal property, or income-producing rental.

1269 Siesta Bayside Drive Unit 1269C, Sarasota

$739,000
2 Beds 2 Baths Polynesian Gardens SubDv. 34242 Zip Code
Welcome to your New Home, minutes from the world-renowned Siesta Key Beach, consistently ranked as one of the #1 beaches in the U.S famous for its powdery white quartz sand and crystal-clear Gulf waters. This impeccably remodeled turnkey furnished home offers an exceptional opportunity to enjoy the best of coastal living within the charming Polynesian Gardens community. This, home offers a refined take on island living, featuring a new roof, new AC, and impact-rated windows and doors for style, comfort, and peace of mind. Designed with a light, coastal aesthetic, the open-concept layout is both inviting and functional. At the heart of the home, the designer kitchen showcases custom white cabinetry, brand-new stainless appliances, and a tile backsplash, complemented by a dining area seamlessly positioned adjacent to the kitchen and perfect for effortless entertaining or relaxed everyday living. The home features a spacious primary suite with a beautifully appointed ensuite bath, along with a guest bedroom and full guest bathroom, offering privacy and comfort for family and visitors. The living space extends into an enclosed, expanded lanai, creating a versatile indoor-outdoor retreat to enjoy year-round. A rare highlight is the oversized private garden, offering a lush, tropical setting with exceptional privacy, an uncommon feature that truly sets this villa apart and enhances the feeling of a private coastal escape. Residents of Polynesian Gardens enjoy a resort-style lifestyle with amenities including a community pier on the intercoastal, a heated pool, and clubhouse. Beyond the community, enjoy effortless access to the vibrant energy of Siesta Key Village, known for its beachside restaurants, bars, live music, and boutique shopping, as well as the relaxed charm of Crescent Beach village. This property also offers a proven rental history with strong year-round bookings, making it an exceptional opportunity for both personal enjoyment and income potential. Whether you’re spending the day boating along the Intracoastal, enjoying the white quartz sands of Siesta Key Beach, or unwinding in your own private garden retreat, this exceptional villa captures the essence of luxury coastal living. Perfectly positioned near Siesta Key Village and the Gulf beaches, this turnkey remodeled property presents an incredible opportunity as a primary residence, vacation getaway, or income-producing investment

1218 Moonmist Circle Unit S2, Sarasota

$655,000
2 Beds 2 Baths Jamaica Royale SubDv. 34242 Zip Code
This stunning 2-bedroom, 2-bath retreat is steps from Siesta Key’s renowned powdery white sand. Fully renovated with premium, top-to-bottom upgrades (new plumbing, electrical, HVAC, and high-end appliances), this turnkey property is rental-ready. This unit has been completely redone with quality everything and no expenses spared! Enjoy immediate income and income potential with easy access to Village dining and shopping via walking or a free trolley. Jamaica Royale is a well-maintained beachfront community known for its private deeded beach and resort-style amenities, including three pools (one beachfront), newly renovated beachside restrooms and changing facilities, and an outdoor kitchen with grills and seating. With onsite rental management, this condo provides an easy, low-maintenance investment opportunity. Whether you’re searching for a turnkey vacation rental, income-producing investment property, or coastal retreat, this Jamaica Royale condo offers location, luxury, and beach good times!

5830 Midnight Pass Road Unit 86, Sarasota

$1,250,000
2 Beds 2 Baths Sarasota Surf & Racquet SubDv. 34242 Zip Code
An exceptional opportunity to secure a Gulf-front residence in the highly sought-after Sarasota Surf & Racquet Club on Siesta Key. Positioned on the 5th floor, this two-bedroom, two-bath condominium offers sweeping, unobstructed views of the Gulf of Mexico?the kind of breathtaking backdrop that defines true beachfront living. With 1,195 square feet of interior space plus an expansive 200-square-foot lanai, the layout provides the perfect canvas to create a custom coastal retreat tailored to your personal vision. From sunrise reflections to vivid sunset skies, the panoramic water views take center stage from the main living areas and outdoor space, delivering an ever-changing coastal experience. Sarasota Surf & Racquet Club is known for its prime beachfront location and resort-style setting, offering residents access to a wide array of amenities including tennis courts, swimming pools, fitness facilities, and direct access to Siesta Key?s world-renowned white sand beach. The community?s established reputation and desirable location continue to make it a favorite for both personal enjoyment and long-term investment. Offered at a compelling value reflective of its unique opportunity, this residence presents a rare chance to sec

5924 Midnight Pass Road Unit 507, Sarasota

$1,150,000
2 Beds 2 Baths Excelsior Beach To Bay SubDv. 34242 Zip Code
RARELY AVAILABLE INCOME PRODUCING EXCELSIOR GULF FRONT UNIT This large unit has been completely updated and renovated with Impact windows and new HVAC in 2025, Upgraded kitchen and all appliances, plantation shutters, and Hunter Douglas window shades, in-unit washer/dryer, custom tile throughout, tastefully appointed with fine furnishings and all the accoutrements for the Siesta Beach lifestyle. The under-building covered parking and elevators are conveniently located the spacious gulf front patio is the perfect place to relax and enjoy the fabulous views. Excelsior is your Gulf to Bay resort residence with a Private White Sand Beach, Two Large Heated Swimming Pools, Poolside Restrooms / Hot Water Showers, Shuffleboard, Two Heated Whirlpools, Two Lighted Tennis Courts, Two Pickle Ball Courts, Fitness Center, Large Gulfside Sun Deck, Beach Loungers and Chairs, Lounges & Sunbathing Parapets' Outdoor Barbecues / Picnic Areas, Intercoastal Fishing Pier / Shaded Viewing Area, Community Room and monthly community events', Library' Walk to Shopping, Dining, Bike & Boat Rentals Located just a half mile to the S village shops, dining and marina makes this a great spot to enjoy all the best that world famous Siesta Key has to offer.

6266 Midnight Pass Road Unit 404, Sarasota

$1,135,000
2 Beds 2 Baths Peppertree Bay SubDv. 34242 Zip Code
This is the one! Rarely available beach-view residence with deeded access to the renowned shores of Siesta Key Beach. Located on the third floor, this bright and inviting unit features a versatile layout, including a pull-out sofa on the lanai with a privacy partition—perfect for creating a comfortable third sleeping area for guests. The well-designed split floor plan offers a spacious dining area, an eat-in kitchen with bar seating, two generously sized bedrooms, and two full bathrooms. Ample storage can be found throughout the home, along with the added convenience of in-unit laundry. Enjoy the ultimate coastal lifestyle with just a short stroll—approximately 70 steps—to the beach, as well as easy access to the community clubhouse, fitness center, and pool. Residents are treated to an array of resort-style amenities, including two heated swimming pools, two clubhouses ideal for entertaining, tennis courts, a fully equipped fitness center, and multiple BBQ areas. A scenic fishing pier invites you to cast a line or simply relax and watch boats and yachts glide by. Ideally located just minutes from shopping, dining, entertainment, golf courses, biking trails, boating, and the vibrant arts and culture of Sarasota. Beautifully updated in 2023 (to the studs, to include all new electric and plumbing) and offered turnkey furnished, this residence is move-in ready and perfectly suited as a primary home, vacation getaway, or income-producing investment.

1080 W Peppertree Lane Unit 305A, Sarasota

$1,950,000
2 Beds 2 Baths Gulf & Bay Club SubDv. 34242 Zip Code
A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.

5740 Midnight Pass Road Unit 403, Sarasota

$510,000
2 Beds 2 Baths Whispering Sands SubDv. 34242 Zip Code
Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed indoor-outdoor living year round. As a bonus, this is a highly desirable end unit, with a wonderful extra window in the living space that invites in abundant natural light, enhancing the open, airy feel throughout. Designed for both style and function, the beautifully REMODELED, kitchen features sleek stone countertops, soothing neutral tile backsplash, an 8’ breakfast bar with seating for 4, stainless Frigidaire and Samsung appliances, soft close cabinetry, and wonderful overhead recessed lighting. Both bathrooms have been tastefully updated with stone counters, while the primary suite offers a private ensuite bath and a walk-in closet for comfortable everyday living. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Nestled on the westernmost point of Siesta Key, Whispering Sands is a highly desirable 55+ Gulf front community offering resort style living – all ideally just moments away from the colorful boutiques, dining options, and charm of world famous Siesta Key Village. The complex offers 800’ of PRIVATE quartz sand beach on the sparkling Gulf, 2 heated pools, new beachside grills and Tiki Hut, shuffleboard, and canoe/kayak storage, The main clubhouse – just steps from this unit - is currently undergoing complete remodeling and upon completion will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Effortless island living starts here. Don’t miss this opportunity to own this move-in ready, coastal escape in an exceptional island setting!

225 Hourglass Way Unit 202, Sarasota

$564,000
2 Beds 2 Baths Island Reef SubDv. 34242 Zip Code
Escape to your own slice of coastal bliss at Island Reef, a premier Gulf-to-Bay resort-style haven tucked along the serene southern shores of Siesta Key. This inviting condo delivers the perfect blend of relaxed beach living and effortless convenience, whether you're dreaming of a sun-soaked family vacation, a peaceful getaway, or an easy-care rental retreat. Picture stepping out to pristine sands just a short, enjoyable stroll away—your deeded private beach access means soft white Gulf shores and turquoise waters are right at your fingertips, no car required. For even more adventure, the free Siesta Key trolley pulls up every 15–20 minutes directly at the community entrance, whisking you north to the world-famous powdery dunes of Siesta Beach, charming Siesta Village shops and eateries, Turtle Beach Park, or the nearby marina—making exploration fun, car-free, and breezy. From your vantage point, witness breathtaking dawns painting the sky in soft pinks and golds over the bay, and evenings that transform into pure enchantment with vibrant sunsets igniting the horizon in fiery hues. For an extra touch of wonder, step onto the lanai under the moonlight to watch the waterway come alive—silver game fish leaping playfully through shimmering, star-kissed waters that sparkle like scattered diamonds in the night. Inside, this turnkey gem welcomes you with fresh coastal charm: bright, airy spaces refreshed with new paint, stylish beach-inspired furnishings, and easy-maintenance flooring that keeps things light and carefree. The open layout flows seamlessly from a well-equipped kitchen to cozy living and dining areas, while split bedrooms offer privacy and comfort for families or guests. Enjoy morning coffee on the enclosed lanai with sweeping bay views, where gentle breezes and passing boats create that ultimate island vibe. Resort perks abound to elevate every day—lounge by not one but two heated pools, join a water aerobics session, or stay active on tennis and pickleball courts. Unwind in the fitness center, game room, library, or clubhouse (perfect for gatherings), and take advantage of shuffleboard, grilling spots, boat docks, kayak storage, and a lively social calendar. Pet-friendly touches and on-site management add extra ease. Whether you're seeking full-time paradise, seasonal escapes, or a hassle-free rental opportunity, this South Siesta Key treasure captures the essence of laid-back Florida living. Move right in, soak up the salt air, and let the trolley and nearby beach paths handle the rest—your coastal dream awaits at an unbeatable value! "Abundant storage throughout, with ample closet space, multiple built-ins, and additional built-in cabinetry"

8767 Midnight Pass Road Unit 505F, Sarasota

$1,490,000
2 Beds 2 Baths Heron Lagoon Lodge Sub SubDv. 34242 Zip Code
Rare Opportunity: Last Unrestricted Deed Waterfront Property on Midnight Pass Siesta Key’s Heron Lagoon. Discover one of the most unique waterfront opportunities left on the Turtle Beach end of Siesta Key. This last unrestricted deed property on legendary Midnight Pass sits directly on the serene Heron Lagoon side, offering unparalleled flexibility with no HOA and endless possibilities for your dream coastal retreat. The existing home is a charming 2-bedroom, 1-bathroom Old Florida bungalow (966 sq ft) that has been thoughtfully remodeled while preserving its authentic island character. Oak trees frame the property, and the one story design blends seamlessly with the natural surroundings on this oversized 0.39-acre lot (approximately 47 ft of direct lagoon frontage). Step outside to your private dock complete with shower and electricity — perfect for kayaking, paddle boarding, straight into Heron Lagoon with quick, effortless access to the Gulf of America via Midnight Pass. Enjoy breathtaking west-facing sunsets every evening as the sky paints vibrant colors over the ocean — a year-round spectacle right from your backyard. Whether you envision keeping the classic bungalow, adding a pool, expanding the home, or building new under Siesta Key’s flexible zoning, this rare unrestricted parcel delivers the ultimate blank canvas. Property Highlights: 2 beds | 1 bath | 966 sq ft living area, 0.39-acre lot with direct Heron Lagoon frontage, Private boat dock with shower & electric, No HOA — unrestricted deed, West-facing Gulf sunsets, Remodeled Old Florida charm, Prime southern Siesta Key location on one of Florida’s most coveted barrier islands, and the recently opened Midnight Pass intercoastal passage to the Gulf. Don’t miss your chance to own a true piece of Siesta Key history and lifestyle. This one-of-a-kind waterfront gem will not last.

8456 Midnight Pass Road, Sarasota

$960,000
2 Beds 2 Baths Jamaica Royale SubDv. 34242 Zip Code
Rare opportunity - Jamaica Royale, Tower 1 Enjoy breathtaking Gulf views from this beautifully positioned second-floor Gulf front condo on world-famous Siesta Key Beach. This 2-bedroom,2-bathroom residence features light-filled open living and dining space. The generous areas flow effortlessly toward the Gulf creating the perfect setting for relaxed coastal living or entertaining guests. Enjoy spectacular sunsets from the expansive balcony accessible from both the living room and primary suite. Ideally located just minutes from the island's vibrant restaurants, boutique shopping and entertainment, this Jamaica Royale beauty is a MUST SEE! Whether as a primary residence, a beach retreat or an investment opportunity this condo offers the best in Gulf front living.

5830 Midnight Pass Road Unit T22, Sarasota

$645,000
2 Beds 2 Baths Sandy Cove SubDv. 34242 Zip Code
Enjoy the best of Siesta Key living in the highly sought-after Sandy Cove III, an intimate waterfront community of just 16 residences. This beautifully maintained, turnkey-furnished 2-bedroom, 2-bath condo offers comfort, style, and an unbeatable location just moments from Siesta Key Village and the Gulf. The open-concept main living area features tile flooring throughout and a thoughtfully updated kitchen with upgraded cabinetry and countertops, perfect for entertaining. Storm-rated sliding glass doors provide peace of mind while bringing in abundant natural light. An indoor laundry area adds convenience to everyday living. The second level includes a spacious guest bedroom, full bath, and a versatile bonus room currently used as an additional sleeping space—ideal for guests or a home office.Surrounded by lush tropical landscaping, Sandy Cove III offers a true coastal retreat with amenities including a heated community pool, kayak storage, and a charming historic clubhouse. Residents enjoy access to a private fishing pier and shell beach, where you can take in breathtaking Gulf views and unforgettable sunsets.This pet-friendly community is just a short walk to Siesta Key Village, known for its vibrant dining, shopping, and entertainment. Plus, you’re only a short drive to downtown Sarasota and St. Armands Circle for world-class shopping, dining, and cultural attractions. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property checks all the boxes. Schedule your private showing today and experience the very best of Siesta Key living.

218 Pass Key Road Unit 218, Sarasota

$680,000
2 Beds 2 Baths Gulf & Bay Club SubDv. 34242 Zip Code
Under contract-accepting backup offers. Turnkey furnished and beautifully updated, this 2-bedroom, 2-bath residence in Gulf & Bay Club Bayside offers an exceptional blend of comfort, convenience, and Siesta Key lifestyle. Lightly lived in and meticulously maintained, the interior features a renovated kitchen with stainless steel appliances, solid stone countertops, breakfast bar seating, recessed lighting, custom tray ceiling detail, and an open connection to the main living area that enhances both everyday living and entertaining. Large-format tile flooring runs throughout the main living spaces, while both bathrooms have been tastefully updated with stone counters and tiled shower surrounds. The spacious primary suite offers a relaxing retreat with direct access to the screened lanai, and the guest bedroom is well appointed for overnight guests. Coastal furnishings and decor create a true move-in-ready presentation. The oversized screened lanai expands the living space and provides a peaceful setting surrounded by tropical landscaping, with the community walking path just outside leading to the Intracoastal fishing area, tennis and pickleball courts, and the second pool. Ideally positioned within the community, this residence is also just a short distance to the clubhouse, fitness center, BBQ area, and main pool. Owners and guests enjoy deeded beach access through Gulf & Bay Club across the street, placing world-famous Siesta Beach just a short stroll away — consistently ranked among the finest beaches in the nation and recognized globally for its powder-white quartz sand. The free Siesta Key Trolley connects Siesta Key Village, Siesta Beach, South Village, and Turtle Beach, making car-free island living effortlessly accessible. A private garage completes the package. Whether sought as a personal retreat, seasonal escape, or a property with income-producing potential, this updated Gulf & Bay Club Bayside residence is an outstanding opportunity on Siesta Key.

1332 Siesta Bayside Drive Unit 1332C, Sarasota

$2,250,000
2 Beds 2 Baths Horizons West SubDv. 34242 Zip Code
Virtually Staged. Experience the pinnacle of island living in this 9th-floor, west-facing penthouse offering sweeping, unobstructed Gulf and Crescent Beach views from Point of Rocks to iconic Siesta Beach, where nightly sunsets paint the sky. Perfectly positioned above Siesta Key’s crystal-white sands, this spacious residence features 2 bedrooms and 2 baths with the rare opportunity to expand to a third bedroom and bath, allowing you to customize your coastal retreat. Highlights include a full laundry room, impact-rated windows, tankless water heater, dual A/C systems, and a coveted private 2-car garage with direct lobby access—one of only four in the community. Located in the prestigious Horizons West, a gated gulf-to-bay enclave spanning more than seven lush acres, residents enjoy 300 feet of private beachfront, beach cabanas, a Gulf-front pool and spa, grilling areas, a bayside pool and clubhouse, and a private intracoastal park with day dock, kayak launch, and serene mangrove setting. With SIRS and Milestone inspections complete and new landscaping throughout, this exceptional penthouse delivers luxury, privacy, and the ultimate Siesta Key beachfront lifestyle.

6140 Midnight Pass Road Unit 904, Sarasota

$570,000
2 Beds 1 Baths La Siesta SubDv. 34242 Zip Code
This turnkey condo sits right across the street from one of the #1 beaches in America! The 2 bedroom 1 bathroom condo with open floor plan overlooking the pool and courtyard, is perfect for your new home or investment opportunity near the beach. The recent updates include, new carpet, light fixtures, furniture, lanai furniture and decor. New HVAC installed 11/2025! La Siesta has on site management with their own rental program and also uses Airbnb to capture those seasonal & weekly rentals. Amenities include: Heated salt water pool, outdoor Grills, Elevator, covered Parking, guest Parking, Shuffleboard, Clubhouse w Pool Table and Fitness Equipment & Washer/Dryer on each floor of building. Each condo comes with a Storage unit w all your essentials for the beach. The public Beach has 2 tiki bars and small store. The trolleys, frog hop & multiple other transportation opportunities run all day for a free ride to the village to enjoy your favorite restaurants, shopping and grocery store. Make your appointment today!

915 Beach Road Unit 215, Siesta Key

$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 storage - 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

$1,340,900
2 Beds 2 Baths Whispering Sands SubDv. 34242 Zip Code
Experience the ultimate beachfront lifestyle in this stunning two-bedroom, two-bathroom condo that's been completely renovated with fresh style and modern touches. With 1,464 square feet of thoughtfully designed living space, this home offers breathtaking full views of the Gulf of Mexico and pristine beach right outside your door. Step inside to discover a bright, open layout that maximizes both comfort and those incredible water views. The recent renovation means everything feels brand new, from the sleek finishes to the updated amenities throughout. Both bedrooms are generously sized, including a spacious primary bedroom that serves as your personal retreat after days spent soaking up the Florida sunshine. The location puts you in the heart of Siesta Key's most desirable area, just steps from the famous powdery white sand beach that draws visitors from around the world. When you're ready to explore, Siesta Key Village is practically at your doorstep, offering an amazing collection of restaurants, shops, and entertainment options. Whether you're craving fresh seafood, tropical drinks, or just shop, the village has something for everyone. The building features a huge community pool perfect for lazy afternoons when you want a break from the beach. For daily needs, Morton's Siesta Market is conveniently nearby, and Boyd Park offers additional outdoor recreation options.

19 Whispering Sands Drive Unit 302, Sarasota

$370,000
2 Beds 2 Baths Siesta Harbor SubDv. 34242 Zip Code
Experience the best of Siesta Key living in this 55+ waterfront community at Siesta Harbor, featuring DEEDED BEACH ACCESS, beautiful WATER VIEWS and BOATING ACCESS with available slips. This well-maintained 2-bedroom, 2-bath condo overlooks a deep-water canal along the Intracoastal Waterway, with tranquil views from the living room, primary suite, and screened lanai. Offering one of the lowest-priced condos in the community, this residence presents a fantastic INVESTMENT OPPORTUNITY—enjoy it as-is or update to your personal style over time. Siesta Harbor is known for its active lifestyle and amenities, including a heated pool, spa, clubhouse, shuffleboard, barbecue area, and fishing dock. Boating enthusiasts will appreciate the option for boat slips accommodating up to approximately 30 feet (subject to availability and nominal fees). Ideally located with easy on/off island access, plus trolley and SCAT transportation nearby, and close to dining, shopping, and all that Siesta Key has to offer—this is coastal living made simple. Just steps away, enjoy Siesta Key Beach—consistently ranked among the top beaches in the world for its powdery white quartz sand and crystal-clear Gulf waters. And at the end of your day, take the convenient and free trolley to explore the nearby Siesta Key Village, filled with charming boutiques, casual and fine dining, and lively island atmosphere that perfectly captures the spirit of coastal living.

1257 S Portofino Drive Unit 203, 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

$512,000
2 Beds 2 Baths La Siesta SubDv. 34242 Zip Code
Offered at $529,000, this 2-bedroom, 2-bath residence represents one of the most competitively priced opportunities to own directly across the street from Siesta Key Beach. Enjoy effortless access to the sugar-white sand and turquoise waters with an easy five-minute walk—no driving, no searching for parking, just the relaxed coastal lifestyle that makes this location so desirable. With one of the largest two-bedroom, two-bath floor plans in the community, this residence offers approximately 940 square feet of comfortable living space with an open-concept layout designed for easy island living. The updated kitchen showcases wood cabinetry, granite countertops, and stainless steel appliances, flowing seamlessly into the dining and living areas. Tile flooring throughout provides durability and low-maintenance living, while the split-bedroom design provides added privacy for owners and guests alike. Weekly rentals are permitted during peak season, with a minimum four-day rental period during the off-season, creating exceptional flexibility and increased income-producing potential throughout the year. On-site rental management is available for owners seeking a turnkey investment, and a comprehensive investor package, including historical rental income and operating information, is available upon request. The residence also includes a deeded covered carport along with ample guest parking. 925_Beach_Rd_107_Investor_Package 2.pdf La Siesta residents enjoy a heated swimming pool, fitness center, clubhouse, and beautifully maintained tropical grounds. Located just minutes from Siesta Key Village’s restaurants, boutique shopping, and entertainment, the community offers the perfect blend of relaxation, convenience, and investment potential. Whether you’re searching for a personal beach retreat, a seasonal residence, or a high-demand vacation rental, this property offers an exceptional opportunity to own in one of Siesta Key’s most desirable locations at a compelling price.

925 Beach Road Unit 107, Sarasota