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6480 Midnight Pass Road Unit 211, Sarasota
$1,200,000
2 Beds ⋅ 2 Baths ⋅ Siesta Breakers SubDv. ⋅ 34242 Zip Code
Rare, exquisitely curated beachfront condo on Siesta Key. This lightly used - meticulously cared for - end unit home has never been rented, although the community allows much desired weekly rentals generating healthy investment income. Located on Crescent Beach, known for its tranquil beach vibe, enjoy 300 feet of prime location deeded beach access with quartz-crystal, powder-soft fine white sand that remains cool even on the hottest days. This two-bedroom, two-bath condo has been renovated and designed with an upscale and sophisticated feel within a light and airy beach home. All furnishings, accessories, dishes and linens included in this TURNKEY FURNISHED condo. The open floorplan is perfect for entertaining family and friends. The resort feel primary bedroom includes a large walk-in closet and oversized bathroom. The second bedroom has been redesigned to comfortably sleep 4 with ample storage. The living room, primary bedroom and balcony all feature stunning views of the beach, gulf and Siesta’s spectacular sunsets. This condo is in Siesta Breakers, a gated complex within easy walking distance of dining, shopping, and a full-service marina with boat rentals. Play a game of tennis or pickleball on the two community courts. Leave your car at home and walk or take the free Trolley to nearby Siesta Key Village. This ideal location features easy access on and off the Key allowing more time to enjoy your coastal waterfront living. Welcome home to Siesta Key.

6480 Midnight Pass Road Unit 211, Sarasota

7247 Turnstone Road, Sarasota
$1,190,000
Sanderling Club SubDv. ⋅ 34242 Zip Code
Welcome to an extraordinary opportunity within the Sanderling Club, one of Siesta Key’s most prestigious and renowned gated communities. Nestled along the coveted Gulf of Mexico coastline, this enclave is celebrated for its unrivaled privacy, beautiful natural old Florida lanes, and rare beach-to-bay access giving a lifestyle few communities can offer.This nearly one-acre homesite is truly one of the best opportunities in Sarasota to build an unbelievable estate in a world-class neighborhood. Opportunities of this caliber on Siesta Key are exceptionally rare, making this property a remarkable find for those seeking to create a legacy home. Adding to its value, the property also conveys with 1/9th ownership of a separate lot across the lagoon, providing even more unique benefits and future possibilities. Life in the Sanderling Club is as rich as it is relaxing. Residents enjoy exclusive access to a private, sugar-sand beach offering some of the most breathtaking sunset views on Siesta Key, along with a bayfront marina providing direct sailboat access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. The community fosters year-round activities and social events, all while preserving the timeless charm of an Old Florida setting. Enhancing this lifestyle, residents can look forward to a brand-new private clubhouse currently being designed, future beachside cabanas, and the enjoyment of tennis courts, making the Sanderling Club one of the most desirable and dynamic communities on the island. Beyond the gates, you’re just minutes from the world-famous quartz sands of Siesta Beach, the charm of the South Siesta Village, the boutiques and dining of the north Siesta Village, and a short drive to downtown Sarasota’s vibrant arts and cultural scene, featuring award-winning restaurants, theaters, ballet, opera, galleries, and museums. Whether envisioning a modern coastal retreat or a timeless island estate, this homesite offers the perfect canvas in a community where natural beauty, exclusivity, and lifestyle converge.

7247 Turnstone Road, Sarasota

421 Island Circle, Sarasota
$1,180,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Ideally located on Palm Island in the heart of Siesta Key, this elevated block-construction home offers the ultimate blend of style and resilience. Situated on nearly a quarter-acre, this 2-bedroom, 2-bathroom residence includes a generously-sized office currently utilized as a 3rd bedroom. Elevated over 10 feet, the home features a metal roof (2019), hurricane impact windows (2019), newer HVAC (2022) and new exterior paint (2026). The interior shines with fresh paint, designer lighting, and a custom statement banquette. An updated kitchen with marble countertops is open to the ample living and dining space, perfect for entertaining. The oversized owner’s suite boasts a walk-in closet and an ensuite bath with dual sinks, and double doors opening to the deck and pool area. Outside, enjoy the newly installed heated pool and paver deck overlooking a tranquil saltwater pond, which provides additional privacy. Just blocks from the world-famous Siesta Key Beach and less than a mile from the Village, this is island living at its finest.

421 Island Circle, Sarasota

19 Whispering Sands Drive Unit 1204, Sarasota
$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

3721 Flamingo Avenue, Sarasota
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Restore a piece of architectural history or build your dream home on this prime waterfront lot on Bay Island, the gateway to Siesta Key and one of the island’s exclusive communities. Designed by renowned architect Ben Baldwin, a leading figure in the Mid-Century Modern movement, this residence offers timeless design and exceptional potential. The existing 3,321-square-foot concrete block home features 14 glass sliders, skylights and serene views of bamboo, palms and the lagoon. Baldwin’s vision of light, scale and nature is intact—awaiting restoration after flood remediation. The property includes an 11,458=-square-foot corner lot with lush landscaping, a tranquil lagoon/canal with easy bay access, and a detached space once used as a professional darkroom—ideal for conversion to a guest suite. Featured in the February 2024 issue of Key Life Magazine. In the City of Sarasota limits, an excellent investment with seven-day minimum rental period. Minutes to Siesta Key Beach, Siesta Village and Sarasota’s mainland. This is the lowest-priced waterfront home in Bay Island, offering a rare opportunity to own and restore a Sarasota architectural treasure.

3721 Flamingo Avenue, Sarasota

521 Cummings Street, Sarasota
$1,160,000
3 Beds ⋅ 3 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Tucked away on a quiet cul-de-sac on north Siesta Key, this Key West-inspired canal-front retreat captures the ease of casual island living with boating water, inviting outdoor spaces and easy access to Siesta Village, the famous white quartz sands of Siesta Beach and the azure waters of the Gulf. Set along 95 feet of private canal frontage just off the Grand Canal, the property offers a dock, a covered 5,000-pound boat lift and direct access to the Intracoastal Waterway, creating an ideal setting for those who want to enjoy the water from their own backyard. Designed for effortless indoor-outdoor living, the home features an expansive elevated deck and contemporary cable railings overlooking the canal and surrounding natural scenery, a heated pool with a cascading stone waterfall, a covered bar area and a fenced, low-maintenance yard surrounded by tropical landscaping. Whether hosting friends, relaxing after a day on the boat or enjoying the island breeze, the outdoor areas offer a private, versatile setting for everyday enjoyment. Inside, vaulted ceilings, a neutral palette and an open-concept layout create a light, comfortable atmosphere. The kitchen is positioned at the heart of the home and features granite countertops, stainless steel appliances, dual sinks, a center island with a JennAir cooktop and a breakfast bar that connects easily to the main living and dining areas. A wood-burning fireplace adds warmth and character to the gathering space. The primary suite offers a peaceful retreat with sliding glass doors opening to a screened lanai, along with an en-suite bath featuring dual vanities, a walk-in shower and a charming window seat. Two additional bedrooms are thoughtfully positioned in their own wing with a full bath and convenient laundry room nearby. Additional features include impact glass on most openings, hurricane-rated doors, metal roof, Nichiha siding, Trex decking, cable railings, two garages and a full pool bath, bonus room and storage area on the ground level. Positioned at one of the highest elevations on the street, the home offers added peace of mind in storm season. Just a short distance from Siesta Key’s renowned beaches, vibrant Village dining, boutiques and nightlife, this move-in-ready waterfront home offers exceptional flexibility as a full-time residence, seasonal getaway or investment opportunity in one of Sarasota’s most beloved island communities. Close to the Out-of-Door Academy’s lower school and only 15 minutes by car to vibrant downtown Sarasota’s restaurants, shopping and entertainment.

521 Cummings Street, Sarasota

1141 Sun N Sea Drive, Sarasota
$1,160,000
4 Beds ⋅ 2 Baths ⋅ Sarasota By The Sea SubDv. ⋅ 34242 Zip Code
Exceptional Investment Opportunity Awaits! Just a two-minute stroll from the stunning white sands of Siesta Key Beach, Sun & Sea Island Hideaways presents a rare chance to own a fully remodeled, high-income-producing duplex in an ideal island setting. With zoning for short-term rentals, this incredible retreat offers remarkable flexibility: live in one unit while renting the other, or maximize your earnings by leasing both units to vacationers year-round. The property is fully furnished and has future bookings in place, ensuring immediate income potential. Nestled in the sought-after south end of Siesta Key, the property exudes tropical allure with interiors featuring updated terrazzo floors, chic furnishings, and modern upgrades, including new appliances, a new roof, and new AC units for both residences. Each 2-bedroom, 1-bathroom unit is thoughtfully designed for comfort, featuring bright, open living spaces that embody the essence of island living. A shared indoor laundry area adds convenience, while an outdoor shower provides the perfect way to conclude a beach day. The expansive, fully fenced backyard is a private oasis, with lush, low-maintenance landscaping, synthetic turf, and a sizable composite deck perfect for sunset gatherings, outdoor dining, or relaxation. A nearby community pool is accessible to owners and guests, and four designated parking spaces offer added convenience for owners and visitors. With a proven track record of strong rentals and high demand from vacationers, Sun & Sea Island Hideaways is more than just a home—it’s an investment in the ultimate island lifestyle. Whether you're seeking a profitable rental property or a private sanctuary with income potential, this Siesta Key treasure is ready to fulfill your island dreams.

1141 Sun N Sea Drive, Sarasota

19 Whispering Sands Drive Unit 1105, Sarasota
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Sleek. Contemporary. Timeless elegance—with breathtaking views. Welcome to Whispering Sands, Unit #1105. This exquisite residence showcases thoughtfully curated finishes throughout, blending refined design with effortless coastal living. Crown molding, recessed lighting, and ceiling fans are just a few of the elegant details that set the tone. Offered turn-key and beautifully furnished with pieces from Bernhardt, Crate & Barrel, and more, this home is truly move-in ready. The cook’s kitchen is nothing short of divine and designed for entertaining. Stunning Cambria® quartz countertops are complemented by an impressive 8-foot waterfall breakfast bar. Abundant graceful cabinetry features soft-close doors and drawers throughout. The premium BOSCH stainless-steel appliance suite includes a refrigerator, range, dishwasher, built-in drawer microwave, and a 32-bottle wine refrigerator. Wide-plank tile flooring flows seamlessly throughout the home, creating an expansive, cohesive, and airy feel. The dining and living areas are ideal for everything from an intimate weeknight dinner and movie to larger gatherings with family and friends. Floor-to-ceiling impact glass sliders in both the living room and primary bedroom frame stunning views of the beach and the Gulf—and those unforgettable sunsets. Hunter Douglas motorized, light-filtering shades allow you to tailor the ambiance to suit your mood. The primary suite rivals a luxury hotel, offering sweeping Gulf views right from the bed. The spa-inspired bath is beautifully appointed with dual sinks, a vanity, abundant storage, a rainfall shower with built-in bench, and striking tile work—your own private sanctuary. The guest bedroom provides a welcoming retreat for visitors, conveniently located near a private guest bath. This gracious home delivers beauty, sophistication, and timeless design—just steps from a private beach, swimming pools, clubhouse, Tower Lounge, and the charm of Siesta Village.

19 Whispering Sands Drive Unit 1105, Sarasota

4915 Primrose Path, Sarasota
$1,150,000
Siesta Beach SubDv. ⋅ 34242 Zip Code
Fantastic lot to build your dream house on ~ .32 of an ACRE and on a great canal-front lot (100x154x81). CONSTRUCTION FINACING AVAILABLE FOR QUALIFIED BUYER! This home has had significant storm damage and is now being sold as a tear down!! Situated in one of Sarasota’s premier canal locations, this property is located a quick bike ride to the beautiful sands of Siesta Key beach. Siesta Key Village is known for its endless shopping and dining venues, and just a bridge away from the mainland and all that Sarasota has to offer. With no HOA or CDD, and a large waterfront lot, this home is the perfect vacation or year round destination. Don’t miss this opportunity to own a piece of paradise. This home is being sold "as-is" and will require a cash transaction.

4915 Primrose Path, Sarasota

4915 Primrose Path, Sarasota
$1,150,000
6 Beds ⋅ 5 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Fantastic lot to build your dream house on ~ .32 of an ACRE and on a great canal-front lot (100x154x81). CONSTRUCTION FINACING AVAILABLE FOR QUALIFIED BUYER! This home has had significant storm damage and is now being sold as a tear down!! Situated in one of Sarasota’s premier canal locations, this property is located a quick bike ride to the beautiful sands of Siesta Key beach. Siesta Key Village is known for its endless shopping and dining venues, and just a bridge away from the mainland and all that Sarasota has to offer. With no HOA or CDD, and a large waterfront lot, this home is the perfect vacation or year round destination. Don’t miss this opportunity to own a piece of paradise. This home is being sold "as-is" and will require a cash transaction.

4915 Primrose Path, Sarasota

5740 Midnight Pass Road Unit 104F, Sarasota
$1,125,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Incredible Gulf-front first-floor residence (10’ elevation) within the amenity-rich 32-acre campus of the Gulf & Bay community on Siesta Key. This 2-bedroom, 2-bath furnished condominium is ideally positioned in the highly desirable F Building and offers direct walk-out access to the beach with unobstructed views of 800 feet of private shoreline and the expansive Gulf of Mexico. Just steps from the sand, this exceptional location delivers the ultimate Gulf & Bay lifestyle—blending convenience, privacy, and breathtaking coastal scenery. This unit did not flood during recent storms. The remodeled kitchen features abundant cabinetry, a beverage cooler, and a comfortable eat-in area with a built-in desk. The primary suite captures beautiful Gulf views and includes a walk-in closet plus an additional wall closet. The en-suite bath has been tastefully remodeled with a frameless travertine shower, dual vanities, and a dedicated makeup area. The spacious guest bedroom offers two full Murphy beds, providing flexible sleeping accommodations. Additional highlights include a new A/C system (2025), 20" x 20" tile throughout the main living areas, and smooth ceilings—no popcorn. Gulf & Bay is truly one of the best resort complexes on Siesta key featuring: 2 clubhouses, 3 heated pools, pickleball courts, tennis courts (1 HarTru), well equipped fitness center, hot tub, multiple grill areas all leading out to World Famous, gorgeous Siesta Key Beach!

5740 Midnight Pass Road Unit 104F, Sarasota

5916 Midnight Pass Road Unit W102, Sarasota
$1,125,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Surf & Racquet SubDv. ⋅ 34242 Zip Code
If tennis and pickleball courts, beachfront living, and exceptional rental potential are at the top of your list, welcome to Surf & Racquet Club on Siesta Key—where resort-style amenities and timeless island appeal come together seamlessly. This sought-after ground-floor residence in Building W (5916) offers effortless access, direct proximity to the beach, and a lifestyle that balances relaxation with activity. The interior has been thoughtfully renovated with a clean, sophisticated coastal aesthetic. The kitchen is a standout, featuring crisp white cabinetry, elegant quartzite countertops, stainless steel appliances, double ovens, recessed lighting, and bar seating ideal for casual entertaining or morning coffee before a walk on the sand. Both bathrooms have been updated to complement the home’s refined yet relaxed design. Warm hardwood floors provide a rich foundation in the living area, paired with fresh neutral tones and curated furnishings with woven textures—rattan and bamboo elements that nod to island living while maintaining an elevated feel. The primary suite offers a versatile vanity area, perfect for getting ready for an exciting night in Siesta Key’s vibrant village or preparing for another sun-filled day. The enclosed lanai, framed by expansive windows, overlooks the lush 13-acre grounds of Surf & Racquet with tranquil views toward the pool and palm-lined pathways leading to Siesta Key’s world-renowned beach. Your ownership grants access to 2 heated swimming pools, fitness center, a BBQ pavilion, and a recreation hall as well as an active tennis calendar where owners come together for fitness, fellowship and fun. Whether you’re seeking a polished beachfront retreat or a high-performing investment in one of the island’s most iconic communities, this residence delivers comfort, style, and the unmistakable allure of Siesta Key living.

5916 Midnight Pass Road Unit W102, Sarasota

6342 Midnight Pass Road Unit 423, Sarasota
$1,125,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ph 1 & 2 SubDv. ⋅ 34242 Zip Code
Experience effortless beachfront living from this turnkey-furnished, second-floor condominium with elevator access and sweeping views of the turquoise waters of the Gulf of Mexico and the newly updated pool area. Enjoy morning coffee to the sound of the surf and spectacular sunsets with uninterrupted shoreline views. BEST OF ALL - THIS UNIT SUSTAINED NO HURRICANE DAMAGE! Located at Midnight Cove, a highly sought-after gulf-to-bay community on Crescent Beach, this spacious 2-bedroom, 2-bath residence offers a welcoming coastal-style foyer and an open, updated kitchen with solid surface counters, closet pantry and a breakfast bar with seating for four. The living and dining areas open to a screened lanai featuring chaise lounges, a dining table, and bar counter—perfect for relaxed indoor-outdoor living. The primary suite includes a large walk-in closet and an updated ensuite bath with new cabinetry, countertops, fixtures, and a glass-enclosed shower. A separate in-unit laundry room provides added storage, while the guest bedroom and second bath comfortably accommodate family and friends. Designed for low-maintenance living, Midnight Cove offers resort-style amenities including two pools, private beach access, tennis courts, boat dockage, fitness room, barbecue areas, and gated entry. An onsite, professionally managed rental office makes ownership effortless, with many repeat guests and strong rental demand. Ideally located just minutes from Siesta Key Village’s shops and dining, and within easy reach of Sarasota-Bradenton International Airport and Tampa International Airport, this property is perfect as a primary residence, vacation home, or income-producing investment. Extensive rental history available. Ideal for a 1031 exchange.

6342 Midnight Pass Road Unit 423, Sarasota

5244 Winding Way, Sarasota
$1,125,000
4 Beds ⋅ 4 Baths ⋅ Twin Oak Pond SubDv. ⋅ 34242 Zip Code
Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here

5244 Winding Way, Sarasota

5790 Midnight Pass Road Unit 406, Sarasota
$1,120,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Experience quintessential Siesta Key living at 5790 Midnight Pass Rd, Unit 406, a beautifully updated 2-bedroom, 2-bath residence with sweeping Gulf views and an unbeatable location just minutes from the sugar-white sands and the energy of Siesta Village. Inside, a thoughtfully designed layout offers a spacious living and dining area that flows to the Gulf-facing side of the home, where impact windows frame breathtaking water vistas and add peace of mind. The remodeled kitchen pairs modern finishes with everyday functionality, while both bedrooms have been tastefully refreshed for a clean, coastal feel - ideal for relaxed island living. Set within the renowned Gulf & Bay Club, residents enjoy a true resort lifestyle with three heated pools (including a lap pool), private beach access with beach chairs, shaded tiki huts, and grilling areas perfect for sunset dinners. The amenity lineup is exceptional: 8 tennis courts (including Har-Tru surfaces), pickleball, basketball, and shuffleboard, plus a fully equipped fitness center with cardio, free weights, and a yoga space. Unwind after the beach in the hot tub spa or one of six dry saunas. Two expansive clubhouses add to the community's lively social atmosphere with billiards, gathering rooms, and seasonal events, tournaments, and group outings. Beyond the gates, you'll love the convenience of the free island trolley and easy access to Siesta Key's boutiques, dining, live music, and nightlife. And when you're ready for a change of pace, Downtown Sarasota is just a short drive away - offering acclaimed arts, theatre, cultural attractions, and waterfront dining. Secure and gated, Gulf & Bay Club is one of the most desirable Gulf-front communities on Siesta Key, making Unit 406 a standout opportunity for full-time residents, seasonal owners, or investors seeking exceptional amenities in an iconic beachfront setting.

5790 Midnight Pass Road Unit 406, Sarasota

6281 Midnight Pass Road Unit 6281, Sarasota
$1,115,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Investment opportunity with strong rental potential—this Siesta Key waterfront villa offers two-week minimum rentals, private deeded beach access, and an oversized private 2-car garage, an exceptionally rare combination. Located in Excelsior Beach to Bay, this updated 2-bedroom, 2-bath residence is set directly on the Intracoastal Waterway and elevated above its garage, capturing panoramic bay views from nearly every room. The fully furnished, light-filled home features an open floor plan, floor-to-ceiling hurricane-impact glass doors, tile flooring throughout, a remodeled kitchen with white cabinetry and stainless appliances, and a dry bar for easy entertaining. The primary suite enjoys sweeping water views. Recent updates include a new HVAC system (2024). Store your kayak right under the building for easy access to launching your boat. This community offers convenient access to the south bridge, placing Sarasota's dining, shopping, cultural venues, and medical services just minutes away. This Villa offers the best of coastal living. This pet-friendly, resort-style community offers pools, tennis and pickleball courts, a fitness center, fishing pier, and private deeded access to Siesta Key Beach. Ideally located near the South Bridge with quick access to Sarasota dining, shopping, and culture—making it equally well suited as a luxury vacation rental, seasonal income property, or personal waterfront retreat.

6281 Midnight Pass Road Unit 6281, Sarasota

5830 Midnight Pass Road Unit 705, Sarasota
$1,113,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale Tower Ii SubDv. ⋅ 34242 Zip Code
Welcome to your beachfront oasis! VIDEO WALK THROUGH AVAILABLE UPON REQUEST. Discover your perfect getaway in this beautifully refreshed 7th-floor condo, offering stunning balcony views of the Gulf of Mexico. With 1,285 square feet of living space, this fully furnished property features 2 bedrooms and 2 full bathrooms—all you need to bring is your bathing suit and toothbrush! The light-filled great room seamlessly connects the kitchen, living area, and dining space, making it ideal for relaxation and entertaining. Recent upgrades include new HVAC (3/2026), elegant touches like solid surface countertops, a stylish backsplash, and pendant lighting in the kitchen, along with a freshly painted interior and new lighted ceiling fans, The primary bathroom boasts a new solid surface vanity, a backlit mirror, a glass shower door, and designer tiled flooring, just to name a few. After a day at the beach, take a refreshing dip in the pool or unwind on your spacious balcony while watching the sunset. With an onsite management team, your beach retreat promises to be both profitable and hassle-free. This condo has a robust rental history, making it a fantastic investment opportunity for vacation rentals. Residents and guests of Jamaica Royal benefit from deeded assigned parking and access to private beach chairs. Located in a prime area, you can easily explore local restaurants and enjoy live music, all just a trolley or bike ride away. Don’t miss your chance to own this incredible piece of paradise!

5830 Midnight Pass Road Unit 705, Sarasota

6300 Midnight Pass Road Unit 403, Sarasota
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
Experience the best of beachfront living at Crystal Sands on Siesta Key! Located on the 4th floor, this spacious 2-bedroom, 2-bath condominium offers direct, unobstructed views of the beach and sparkling Gulf of Mexico—providing a spectacular backdrop for sunsets and relaxed coastal living. This residence presents an exciting opportunity to create your own Siesta Key retreat. A true blank canvas, the interior is ready for the next owner to bring their vision to life and personalize the space to reflect their own style and taste. Whether you are looking for a full-time residence, vacation getaway, or investment property, the possibilities are exceptional. Crystal Sands is a desirable Gulf-front community situated directly on beautiful Crescent Beach. With a two-week minimum rental policy for tower residences, owners can enjoy added flexibility for seasonal and vacation rentals while still maintaining the feel of an established residential community.

6300 Midnight Pass Road Unit 403, Sarasota

5569 Shadow Lawn Drive, Sarasota
$1,100,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
NEW SOD AND LANDSCAPING JUST INSTALLED, and a brand-new irrigation system was installed as well to keep everything to paradise standards! Welcome to the heart of world-renowned Siesta Key, where coastal living meets modern luxury. This fully renovated, solidly constructed home offers exceptional quality and thoughtful upgrades throughout, including PGT hurricane-impact windows, multiple triple-panel sliding impact glass doors, and a 2019 tile roof. Step inside through beautifully etched, Florida-themed French doors into an open-concept floor plan filled with natural light streaming from the screened lanai. The spacious living and dining areas seamlessly connect to a chef-inspired kitchen, complete with an induction range, griddle, and premium finishes—perfect for entertaining. The home features wood-grain luxury vinyl flooring throughout and tastefully updated bathrooms. The private primary suite is situated on one side of the home and includes an attached office, offering a quiet retreat. Just beyond, you’ll find a generously sized laundry room with a brand-new stackable washer and dryer. The opposite side of the home hosts additional bedrooms and a guest bathroom, providing comfort and privacy for family or visitors. Outdoors, enjoy your own private oasis with a saltwater pool and a brand-new, state-of-the-art pump system. Located in the highly desirable Siesta Isles community, this property is ideally positioned for strong rental potential, offering opportunities for annual, monthly, or seasonal income. Enjoy the convenience of being just a 10-minute walk or 5-minute bike ride to Siesta Key Beach—without the need to access main roads. Move-in ready and perfectly situated, this exceptional home offers the ultimate in coastal living. Schedule your private showing today.

5569 Shadow Lawn Drive, Sarasota

20 Whispering Sands Drive Unit 1201, Sarasota
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!

20 Whispering Sands Drive Unit 1201, Sarasota

5760 Midnight Pass Road Unit 307D, Sarasota
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Welcome to Gulf & Bay Club, the premier condominium community on Siesta Key Beach. This fully remodeled third-floor unit is offered mostly furnished and showcases high-end finishes, including solid wood cabinetry, quartz countertops, stainless steel appliances, recessed lighting, and wood-look tile flooring throughout. Enjoy stunning views of the freshwater lake, fountains, island lagoon, swimming pools, sandy beach, and the Gulf of America from your private lanai. The kitchen features white soft-close cabinets and a built-in desk, while the spacious primary suite offers lanai access and an en-suite bath with dual sinks and a walk-in shower. The second bedroom includes a generous closet and would comfortably fit two queen beds. A private laundry room with a full-size washer and dryer adds convenience. Gulf & Bay Club spans 32 acres with 800 feet of private beach and offers unmatched amenities including three heated pools, indoor spa, dry saunas, tennis, pickleball, racquetball, basketball, shuffleboard, billiards, a commercial-grade fitness center, BBQ and picnic areas, electric car charging stations, a car wash area, two clubhouses, a rentable guest suite, and 24-hour gated security. Wi-Fi is available throughout the property. Located adjacent to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor for its powdery white quartz sand, this property offers a rare opportunity to enjoy resort-style living in one of Florida’s most coveted coastal communities.

5760 Midnight Pass Road Unit 307D, Sarasota

5453 Avenida Del Mare, Sarasota
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Exceptional opportunity on TWO buildable lots just 15 houses from Siesta Key Beach and a leisurely stroll from the village. The existing midcentury durable concrete block 3br/2ba home features pecky cypress siding and beamed ceilings. There is an additional free standing guest cottage. The home was impacted by last years storms, but has been stripped to the studs and is waiting for someone to put their finishing touches on it. Tremendous potential awaits. Restore and renew the existing structure or tear down and build your own tropical dream home. Investors may want to take advantage of the 2 lot configuration to develop TWO stunning residences. Plans and competitive pricing for new construction are available. Whether you delight in renovating this iconic midcentury gem, start fresh with a custom built masterpiece, or take advantage of the terrific investment opportunity of TWO buildable lots, this is a terrific opportunity to realize your dream in this desirable coastal paradise.

5453 Avenida Del Mare, Sarasota

5400 Ocean Boulevard Unit 6-4, Sarasota
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
Virtually Staged. Virtually Staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets convenience. Prepare to be captivated by panoramic vistas from your three spacious private balconies. Enjoy unobstructed views of pristine white sand beaches, sparkling aqua Gulf waters, downtown Sarasota's skyline, and even Longboat Key on clear days. Watch the twinkling lights of Siesta Key Village create an unforgettable backdrop as the sun sets—easily among the best views on Siesta Key. Enter through an inviting foyer with elegant tiled flooring leading into a beautifully updated kitchen featuring granite countertops & modern cabinetry. The spacious living area showcases dual sliding glass doors framing stunning Gulf views. The generous dining area provides ample space for entertaining. The primary bedroom features a private Gulf-view balcony with two full-size beds and an elegant ensuite bath with updated tile, modern cabinetry, and granite countertops. The guest bedroom offers a full bed and private sliding door to dazzling Gulf views, plus an updated full bathroom with modern finishes and tile shower. Elevated heated saltwater pool with sunset views, modern fitness center, community room, covered parking, and gated security with onsite management. Private beach access puts you steps from world-renowned Siesta Key Beach. Nestled at the end of the village, enjoy tranquility and convenient access to Siesta Key Village shops and restaurants—no car needed once you arrive. Beach Terrace represents the pinnacle of Gulf-front living. With the lowest pricing for a 2-bedroom in over 8 years, this move-in ready split-floor plan residence is your once-in-a-decade opportunity to own paradise where stunning views, luxury amenities, and coastal elegance unite.

5400 Ocean Boulevard Unit 6-4, Sarasota

3455 Flamingo Avenue, Sarasota
$1,100,000
3 Beds ⋅ 2 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code
Welcome to Flamingo Avenue, one of Sarasota's most coveted streets. Set on Bay Island, this classic Sarasota home presents an excellent opportunity to own on a street accompanied by iconic estates. You'll feel the ocean breeze at this location, and even enjoy partial water views from balconies! This Key West style home offers an elevated living area with features such as wood floors, fireplace, plantation shutters and much more! From the moment you arrive at this property, you'll notice the walled-in pool and patio area which creates a private island oasis with covered seating area. The first level of the home features a two-car garage and abundant storage. The main living level is on the second story and features a generously-sized living area, dining room, kitchen and two bedrooms with access to the hall bath. The primary bedroom is on the third level and features its own west facing balcony for incredible sunset viewing. This spacious suite offers plenty of room, an oversized walk-in closet, and spacious bathroom. This home has a metal roof and two brand new HVAC units for low maintenance peace of mind. This small and private dead-end street is unique to Bay Island and presents a fine opportunity to own in one of Sarasota's best neighborhoods. Easy access off the north bridge to downtown Sarasota is yours, and as well as just a short distance to amazing Gulf beaches. Schedule your private showing today!

3455 Flamingo Avenue, Sarasota

420 Beach Road Unit 203, Sarasota
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
Paradise Found on Siesta Key! Wake up to Gulf breezes and end each day with a sunset over the water from this direct beachfront condo at Siesta Gulf View. This 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened and glass-enclosed balcony, accessible from the living room, kitchen, and primary suite. From here you can enjoy both the beauty of the shoreline and the natural dune vegetation that makes this second-floor perspective feel close and connected to the beach. This floor level offers an ideal balance of easy access and elevated views: take the stairs for quick trips to the beach, pool, or parking garage, or use the elevator if preferred. No long waits, no hassle, just effortless access to every amenity. The TURNKEY FURNISHED layout includes a light-filled open kitchen with eat-in nook (perfect as a dinette or office), two spacious walk-in closets, separate laundry room, and generous storage throughout. Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping nearing completion, with no special assessments. Siesta Gulf View is a sought-after, gated, 59-unit community offering private boardwalk access to the quartz sands of Siesta Key Beach, plus resort-style amenities: a 25’x40’ heated pool, tennis and pickleball courts, fitness room, grilling areas, and clubhouse. Assigned under-building parking, ample guest parking, first-floor storage, and an on-site management office add convenience. Pet lovers will appreciate that up to two small pets are welcome. Best of all, you’re just blocks from vibrant Siesta Key Village: restaurants, shops, and live music are a short stroll away. Whether you’re seeking a vacation retreat, investment property (one-month minimum rentals allowed up to 12 times/year), or full-time Gulf-front living, this condo delivers the ultimate island lifestyle. Don’t miss this opportunity to claim your piece of paradise.

420 Beach Road Unit 203, Sarasota

5760 Midnight Pass Road Unit 404, Sarasota
$1,094,550
2 Beds ⋅ 2 Baths ⋅ Gulf N Bay SubDv. ⋅ 34242 Zip Code
Welcome to your dream fully furnished coastal retreat! This beautiful newly renovated 2-bedroom, 2-bathroom condo, complete with a versatile bonus room, is nestled in the exclusive Gulf and Bay Club on Siesta Key. The owners poured their hearts into renovating this home with sleek, modern furnishings, creating a space that feels both luxurious and inviting. Imagine unwinding on your screened-in lanai, soaking in stunning beach views and serene sunsets that make every evening special. With the convenience of an in-unit washer and dryer, plus a flexible bonus room perfect for your home office or personal sanctuary, this condo is designed for effortless living. As a resident, you’ll have access to multiple sparkling pools, a lively club room, tennis and pickleball courts, and a private beach along Siesta Key’s world-famous shoreline. This is more than a home—it’s your gateway to refined coastal living. Schedule a tour today and see why this gem is the perfect place to call your own!

5760 Midnight Pass Road Unit 404, Sarasota

4822 Ocean Boulevard Unit 9D, Sarasota
$1,090,000
2 Beds ⋅ 2 Baths ⋅ Siesta Towers SubDv. ⋅ 34242 Zip Code
Welcome to Siesta Towers on Siesta Key, where breathtaking Gulf views meet luxurious modern living. Positioned high above on the 9th floor, this stunning 2-bedroom, 2-bath residence showcases sweeping vistas of the Gulf waters, Big Sarasota Pass, and Downtown Sarasota from its expansive private lanai. Completely remodeled with no expense speared, from the studs out in 2024. This 1,440 sq. ft. condo is brand new in every sense of the way. Updates include all new drywall, texture and paint, new plumbing, new electrical, new electrical panel, new hurricane-rated impact windows and sliding glass doors, new air conditioner, and a new hot water heater. Inside new high-end interior finishes, with no expense spared. The chef's inspired kitchen is equipped with custom cabinetry with soft close doors and drawers, beautiful quartz countertops, large island, undermount single bowl kitchen sink, designer tile backsplash, top-of-the-line GE stainless steel appliances, built-in island microwave, and a wine/beverage refrigerator. All new interior doors, closet doors, all new interior millwork to include crown molding, all new lighting and fixtures, new luxury vinyl flooring throughout. Beautifully re-designed bathrooms to include high-end porcelain tile, custom cabinetry with soft close doors and drawers, lighted mirrors, and glass enclosure showers, create a sophisticated yet inviting coastal ambiance. Also, a new in-unit full size washer & dryer with folding table, for ultimate convenience. This beautiful residence comes completely turnkey-furnished with designer-quality furnishings and carefully curated décor, kitchenware, bedding, bathroom linens, and even high-end "Art Frame" TVs making it move-in ready for you to enjoy the Siesta Key lifestyle immediately. Siesta Towers itself has been thoughtfully updated throughout the building and grounds, offering resort-style amenities, including a state-of-the-art club room, fitness center, heated waterfront swimming pool, fishing pier, and a social pier perfect for sunset cocktails. Additional conveniences include storage room for beach equipment, bike storage and a very secure building environment. Whether you're seeking a full-time residence or a perfect beachside retreat, this pristine condo delivers the best of island living. Modern luxury, panoramic views, and resort-style amenities, all just minutes from the world-famous white sands of Siesta Beach. And with Siesta Key Village dining, shopping, and entertainment just a short walk away, this condo truly offers it all.

4822 Ocean Boulevard Unit 9D, Sarasota