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$590,000
2 Beds ⋅ 2 Baths ⋅ A4683913 MLS ⋅ 35 BLDG.
Discover this impeccable, light-filled second-floor End unit in Peppertree Bay, offering serene views of the tranquil pond. Meticulously remodeled and lovingly maintained over 20 years, this residence exudes pride of ownership. Featuring two bedrooms and two bathrooms, the unit is complete with impact windows throughout, ensuring safety and comfort. Every square inch of this home has been tastefully enhanced, and the furnishings are included for your convenience. Enjoy the added convenience of an in-unit washer and dryer. Residents of Peppertree Bay benefit from a wealth of resort-style amenities, including a private beach with lounge chairs, two heated swimming pools, a fitness center, saunas, tennis and pickleball courts, barbecue grills, a fishing pier, and dedicated on-site management. Ideally located just a short stroll from Siesta Village’s shops and dining, and a quick drive to Sarasota’s cultural attractions, this property embodies coastal living at its best. Whether you’re seeking a full-time residence, a winter retreat, or an investment opportunity with rental income potential, this exceptional beachfront property meets all your needs. Don’t miss your chance to embrace the Siesta Key lifestyle—where every day feels like a vacation.

1169 W Peppertree Drive Unit 118A, Siesta Key
$590,000
2 Beds ⋅ 2 Baths ⋅ A4672795 MLS ⋅ 1 BLDG.
Find safety and security from possible inclement weather near your beach dwelling with a top floor unit with eastern exposure at this wonderful Midnight Cove II unit. Priced extremely competitively on Siesta Key, this nicely renovated unit overlooks the boat traffic and wildlife playground that is the intracoastal waterway that runs between Siesta Key and the mainland. A unique opportunity to capitalize on attractive income while utilizing this third-floor perch to drink in a saltwater breeze when your schedule permits. From your sun deck, a wall of glass sliders connects you to the main living space, flooded with cheerful Florida sunshine. Delight in low maintenance living with the handsome LVP flooring throughout the space. The kitchen offers updated cabinetry, chic stainless appliances and granite counters that shine under the recessed lighting. The dining area offers seating for six while the living area is the perfect place to kick up your feet after a day of Siesta Key adventures. The principal suite is bright and fresh with a beautifully renovated full bath. The second bedroom offers an attractive headboard wall. Guests and families will be quite comfortable with the unique, second full bath allowing for a private space to refresh. With amenities that rival or bests many communities, Midnight Cove II is a vibrant, welcoming place to call home with a marina, tennis courts, barbecue area, fitness room and heated pool. You will also enjoy deeded beach access to Crescent Beach, Siesta Key’s renowned beach with powdery white sands along the Gulf of Mexico. Take a stroll or a trolley to any one of the eateries and shopping opportunities along Siesta Key or venture off island and explore Sarasota and beyond!

1900 Cove Ii Place Unit 138, Siesta Key
$590,000
2 Beds ⋅ 2 Baths ⋅ A4639882 MLS ⋅ 6415 BLDG.
Real estate is always about location, and your new condominium has it. No need for a car when you live here! Leave your condo, down the elevator and walk out the front door of The Anchorage to the Daiquiri Deck, Captain Curt’s Crab & Oyster Bar, plus a variety of other restaurants and shops along with the Siesta Key Marina and private access to Siesta Key Beach! If you are looking for convenience, then you've found the perfect 2 bedroom, 2 bath condo! When you aren't using your condo, the HOA allows for weekly rentals throughout the entire year. Waste and water lines have been replaced 2 or 3 years ago. Alos our J wall aka seawall was replaced in 2019. beside tennis courts the building and ground are in great 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 private laundry room and you have your own car port. 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 508, Siesta Key
$590,000
2 Beds ⋅ 1 Baths ⋅ A4639755 MLS ⋅ Building A BLDG.
Siesta Key Beachfront Paradise – Rare Top-Floor Gulf View Condo! Location, location, location! This stunning 2-bedroom, 1-bathroom, 753 sq. ft. top-floor unit in La Siesta’s Building A offers unobstructed, direct Gulf views from both the private screened balcony and the spacious primary bedroom. Rarely available and highly sought after, this turn-key furnished condo is situated directly across from Siesta Key Public Beach, providing the perfect opportunity for vacation living or an income-producing rental - this is one of the few weekly rental properties on Siesta Key with on-site management. Designed for both comfort and style, this coastal-inspired retreat comfortably accommodates six guests. The primary suite features a king-size bed, walk-in closet, full dresser, and 48” wall-mounted TV, all with stunning beachfront views. The second bedroom offers a full-over-full bunk bed, dresser, walk-in closet, and 32” smart TV, while the living room provides a queen sleeper sofa, plush seating, a 55” smart TV. The fully equipped kitchen allows for home-cooked meals, but for those who prefer to explore, charming Siesta Key Village is just a short walk or free trolley ride away, offering restaurants, shops, and nightlife. La Siesta offers resort-style amenities, including a heated pool, fitness center, recreation room with pool table and ping pong, shuffleboard courts, grilling areas, laundry facilities, and assigned covered parking. The on-site full-time management team ensures easy rentals and a hassle-free experience. Whether you're looking for a dream vacation home or a high-performing rental property, this rare top-floor Gulf-view condo is an incredible opportunity—don’t miss out!

901 Beach Road Unit 402, Siesta Key
$590,000
2 Beds ⋅ 1 Baths ⋅ A4573940 MLS ⋅ 1 BLDG.
Escape to your own slice of Paradise with this enchanting 2-bedroom, 1-bath Waterfront Condo, nestled on the serene and secluded south end of Siesta Key. Offering a captivating cottage-style ambiance, a private BOATSLIP, and the possibility for SHORT TERM RENTALS, this property is a hidden gem for both personal retreats and investment ventures. Per the board vice-president of the HOA, the board unanimously agreed to the change for the rental minimum from 30 days to a 7 day minimum.

9022 Midnight Pass Road Unit 213, Siesta Key
$589,000
2 Beds ⋅ 2 Baths ⋅ O6183863 MLS
HUGE PRICE DROP! FULLY FURNISHED! Experience the epitome of absolute paradise with this beautiful turnkey, fully furnished and equipped 2BR/2BA villa just a 4 minute walk across the street to the famous siesta key beach. It features a private attached garage and a spacious storage room. Conveniently located right in front of the pool and only a short walk to the beach, you can enjoy all the amenities this villa has to offer. Step inside and be greeted by the stunning porcelain tile flooring that gives a modern travertine look. The tastefully furnished living room and dining room feature 5 inch floor moldings. There are flat screen TVs in the living room and both bedrooms. The kitchen countertop is quartz, complemented by charming tile backsplashes. You will also find quartz breakfast bar seating. Under cabinet lighting is provided in the kitchen, along with stainless steel Samsung appliances and a stainless steel Frigidaire refrigerator. Solid wood cabinets feature soft-close drawers. The villa is equipped with three fans throughout. The master bedroom offers a king-size bed with a custom headboard and furniture on each side. It also has a spacious walk-in closet and a beautiful master bath. The second bedroom features a queen-size bed and a single bed. Just three blocks south is Siesta Key Village, where you can enjoy the Tiki bar, a wide selection of restaurants and plenty of stores and businesses. Don't miss the opportunity to take the free trolley to the north side of town. Come relax and enjoy the beautiful sugar sand found at Crescent Beach on Siesta Key, voted #1 beach in the country!

113 Vista Hermosa Circle Unit 3-A, Siesta Key
$585,000
2 Beds ⋅ 1 Baths ⋅ A4685497 MLS ⋅ A13 BLDG.
Larger two-bedroom gulf-side/beach access, stand-alone villa in Casa Blanca--the gem of gems--and rarely available 980 total square feet floor plan. Just a few steps from the pure, white quartz sand of Siesta Key Beach, great restaurants, shopping, and entertainment. Total custom design renovation carefully planned and completed January 2026, with no details overlooked. Larger kitchen and dining area, induction stove top, stainless steel appliances, quartz countertops, custom cabinetry with self-close drawers, and new luxury vinyl tile flooring inside. The south-facing, screened lanai, with a composite floating floor, invites sunshine and warmth inside. Turn-key furnished and equipped. Wonderful on-site rental management office; historically generating approximately $40,000 annual rental income. 110-volt EV charger outside and wired for 220 volts; PVC plumbing lines replaced, electrical outlets raised; new raised water heater, HVAC air handler and condenser, new ducts. HVAC 2023. Casa Blanca is well-appointed community on the island, with the South Siesta Village and the Siesta Key Village just a short walk away, with charming shops, restaurants, and nightlife. Enjoy the pool, clubhouse, fitness center, yoga on the beach nearby, and the local cuisine. Casa Blanca Unit A13 is the top-of-the-line villa. Own your own piece of Siesta Key's paradise.

6154 Midnight Pass Road Unit A13, Siesta Key
$585,000
2 Beds ⋅ 2 Baths ⋅ A4683608 MLS ⋅ 1200 BLDG.
Set within Peppertree Bay on Siesta Key, 1200 E Peppertree Lane #307 offers a well-proportioned, turnkey, move-in ready two-bedroom, two-bath residence encompassing 1,466 square feet. The interior presents a bright, open layout anchored by a spacious great room, where crown molding, tile flooring throughout, and an expansive wall of impact glass windows create an airy, light-filled living environment. The adjoining dining area flows seamlessly into the kitchen, reinforcing the home’s functional, connected design. The kitchen features a tray ceiling with inner crown molding, recessed lighting, abundant wood cabinetry, granite countertops, a tile backsplash, and a full suite of stainless-steel newer Whirlpool appliances. A breakfast bar provides additional prep and serving space, supporting both everyday living and casual entertaining. The primary bedroom is generously scaled and benefits from strong natural light, crown molding, a walk-in closet, and direct access to the enclosed sunroom. The primary bath includes a granite-topped vanity, glass-enclosed walk-in shower, linen storage, and updated fixtures. A well-sized guest bedroom with an oversized window alcove and a nearby full bath maintains privacy and flexibility for visitors. An enclosed sunroom lined with windows extends the living space, offering versatility as a lounge, office, or secondary sitting area. A stacked washer and dryer are conveniently positioned within a dedicated closet. Newer HVAC system (2024) and Water heater (2025). Peppertree Bay is a Gulf-to-Bay community providing private deeded beach access, a fishing pier, two resort-style heated pools, clubhouses, a fitness center, saunas, tennis and pickleball courts, covered under building assigned parking with this unit that provides a bicycle rack and unit storage, and multiple outdoor gathering areas. This building has newer elevators along with stairwell access, with the building roof being replaced in 2020. The location places residents directly on Siesta Key, home to Siesta Beach, consistently ranked the #1 beach in the United States by TripAdvisor, further underscoring the appeal of both the setting and lifestyle offered by this residence.

1200 E Peppertree Lane Unit 307, Siesta Key
$585,000
2 Beds ⋅ 2 Baths ⋅ A4677365 MLS ⋅ Harbor Towers BLDG.
Experience the best of coastal living at Harbor Towers on Siesta Key in this beautifully appointed two bedroom, two bath residence with Intracoastal Waterway views. Offered fully furnished, this turnkey condominium is ideal as a full time residence, vacation getaway, or income producing investment.Enjoy seamless indoor outdoor living with brand new sliding glass doors that invite in natural light. Recent community and building enhancements include new exterior paint and updated windows, adding to both peace of mind and long term value. Harbor Towers is a highly sought after waterfront community that allows short term rentals with a minimum of two weeks, making ownership especially attractive for investors. The convenience of on site property management ensures effortless rental coordination and maintenance when you are away. Residents enjoy a resort style lifestyle with an impressive array of amenities, including a waterfront swimming pool, relaxing spa, fitness center, sauna, tennis courts, outdoor grilling areas, and boat slips available on a first come first served basis. Ideally located on the Intracoastal Waterway with easy access to boating, world famous beaches, dining, and shopping, this is a rare opportunity to own a move in ready, income friendly waterfront property in one of Siesta Key’s most desirable communities.

5855 Midnight Pass Road Unit 408, Siesta Key
$585,000
2 Beds ⋅ 1 Baths ⋅ TB8435270 MLS
Life is good at the beach! This light and bright coastal 2 bedroom, 1 bath villa is ready for you. Just drop your bag and head to the beach or pool. Largest heated pool on Siesta Key. This unit features new LVP flooring, Stainless steel appliances, solid wood kitchen & solid surface tops with an open floor plan. New metal roof 2025 Unit comes turn key ready for you to enjoy or rent. Aloha Kai is located on Siesta Key, a popular barrier island on Florida’s West Coast. Aloha Kai is a family friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and crystal clear waters & magnificent sunsets Siesta Key is one of Floridas top vacation destinations.

6020 Midnight Pass Road, Siesta Key
$585,000
2 Beds ⋅ 2 Baths ⋅ A4650688 MLS ⋅ 8911 BLDG.
Embrace waterfront living in this end-unit residence in Sunrise Cove, an updated, turnkey-furnished 2-bed/2-bath condo offering 1,228 sq ft of coastal style, just one shared wall, tile flooring and crown molding throughout, abundant closets, and a coveted in-unit washer-dryer. The granite kitchen features high-end stainless appliances, two pantries, and generous cabinetry, while impact-rated windows, plantation-shuttered in both bedrooms, capture spectacular sunrise panoramas over Little Sarasota Bay from the living area and screened lanai and serene sunset Gulf views from the kitchen and guest suite. Extra end-unit windows flood the primary suite and guest room with light; newer systems include an HVAC (2022) and water heater (2021). Community highlights: two heated pools (one Olympic length), lighted tennis/pickleball courts, a freshly renovated clubhouse, fitness and game rooms, barbecue area, kayak launch and optional boat docks, all tended by an on-site crew Monday, Friday, with a funded assessment for new roofs, carports, and dock upgrades under way. On-site management supports 30-day rentals for effortless income potential, while Turtle Beach, three restaurants, and the free Siesta Key Breeze trolley are just steps from your door, delivering the complete island lifestyle and an investment opportunity in one.

8911 Midnight Pass Road Unit 308, Siesta Key
$585,000
2 Beds ⋅ 2 Baths ⋅ A4645162 MLS ⋅ 1080 BLDG.
6th floor Gulfside Highrise facing East overlooking the peppertree grounds--High and Dry! Beautifully appointed with detail to owners care of the unit. Spacious open kitchen with extra storage, wood lament flooring throughout the living areas; tile in the baths and lanai. Lanai enclosed with hurricane windows and new murphy bed on lanai. Supersized utility room with washer and dryer. Underground parking space. Turnkey Furnished and Move in Ready!

1080 Peppertree Lane W Unit 602, Siesta Key
$585,000
2 Beds ⋅ 2 Baths ⋅ A4627089 MLS ⋅ 1 BLDG.
Immerse yourself in a world of elegance and serenity with this stunning condo in the sought-after Siesta Harbor 55+ community. This beautifully updated 2-bedroom, 2-bathroom retreat is a true gem, featuring luxurious vinyl flooring that exudes style and comfort. The recently remodeled kitchen is a showstopper, with sleek white cabinetry and marble countertops, creating a modern, sophisticated space perfect for any chef. The bright and inviting lanai offers a seamless transition between indoor and outdoor living, where you can bask in the refreshing coastal breeze while enjoying picturesque views. Resort-style amenities abound, including a sparkling pool, clubhouse, and private beachfront access, offering endless opportunities for relaxation and recreation. Stay active in the state-of-the-art fitness center, unwind in the saunas, or soak in the outdoor spa and heated pool. Convenience meets coastal charm with on-site laundry facilities and a private pier along the tranquil intracoastal waterway, ideal for fishing or peaceful waterfront walks. This is your chance to experience coastal living at its finest—don’t miss out on this exceptional opportunity!

1257 S Portofino Drive Unit 406, Siesta Key
$585,000
2 Beds ⋅ 2 Baths ⋅ A4580539 MLS
Welcome to Vista Hermosa, your ultimate maintenance-free, island retreat nestled just steps away from the powdery sands of Crescent Beach on Siesta Key! This beautifully appointed, free standing villa is turnkey-furnished and move-in ready with brand new upgrades including a new guest bathroom (2022), new kitchen appliances (2021), hurricane impact windows (2021), new front door (2021), HVAC system (2023), hot water heater (2023), and new flooring (2024) . This home features two spacious bedrooms and two full bathrooms, an office/lanai off of living room, a separate laundry room with washer/dryer, and a mud room off of kitchen with door to private carport. This tropical oasis also offers a heated pool, clubhouse w/kitchen and several grilling areas. Vista Hermosa is located just a short walk to restaurants, bars, shopping, entertainment and water sports. Enjoy the convenience of living close to Stickney Point bridge where you can venture off the island in minutes to visit Downtown Sarasota, St. Armand's Circle, Lido Key and Longboat Key. Great opportunity for a second home, vacation rental or full-time ownership. Emotional support and trained service animals are accepted. 2-week minimum, 26 times per year rental policy allows for great income potential! Don't miss this opportunity to own a piece of paradise and enjoy the laid-back, beach lifestyle of Siesta Key!

167 Vista Hermosa Circle, Siesta Key
$582,000
2 Beds ⋅ 2 Baths ⋅ A4690420 MLS ⋅ Island Reef BLDG.
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, Siesta Key
$582,000
2 Beds ⋅ 2 Baths ⋅ A4588606 MLS ⋅ Bldg 4/421 BLDG.
Prime second floor unit with views of the salt water canal and cascading oak trees. The unit features new luxury vinyl flooring and new 5 inch baseboard throughout. Other upgrades include a newer air conditioning system and water heater ( July 2020 water heater and 2021 a/c unit). Unit is sold unfurnished and is waiting for your designer touches. Midnight Cove II has a deeded access to Siesta key beach. Excellent rental complex with weekly rentals allowed. On site management provides you with piece of mind that the unit is looked after when you are not in town and provides you supplemental income to help offset your costs. Midnight Cove II has numerous amenities including tennis and pickleball courts, barbeque areas, a basketball court, car washing station, boat dockage, heated swimimg pool, exercize room, Kayak racks and bayfront seating area to watch the boats go by. Midnight Cove II allows 1 pet for owners only and is a close distance to the south village. Dont miss out and this prime opportunity. Priced to sell

1600 Cove Ii Place Unit 421, Siesta Key
$580,000
2 Beds ⋅ 2 Baths ⋅ A4654831 MLS ⋅ 101 BLDG.
Experience the pinnacle of coastal luxury in this completely updated, FULLY FURNISHED end-unit condo located in the relaxing community of Whispering Sands on Siesta Key. Overlooking a tranquil lagoon and offering private beachfront access, this 2-bedroom, 2-bath residence seamlessly blends modern comfort with serene island living. This rare end-unit offers extra privacy and natural light, along with two fully enclosed balconies that expand your living space and showcase beautiful views of the lagoon and the gulf. Updates include recessed lighting, updated light fixtures, luxury vinyl flooring throughout, fully redesigned kitchen with granite counter tops and stainless steel appliances, and both bathrooms have been thoughtfully redesigned with sleek, modern finishes that elevate the overall feel of the home. Every detail has been considered, from the open-concept layout to the quality craftsmanship found in every corner of this completely renovated unit. Set in one of Siesta Key’s most desirable communities, residents enjoy exclusive amenities including 800 feet of private beach on the Gulf, two heated pools, fitness rooms, clubhouses, and scenic walking paths around the lagoon. Just a short stroll away, Siesta Key Village offers dining, shopping, and vibrant island culture. Whether you're seeking a year-round residence or the perfect vacation getaway, this home offers the ultimate combination of luxury, location, and laid-back Gulf Coast lifestyle.

101 Whispering Sands Drive Unit 307, Siesta Key
$580,000
2 Beds ⋅ 2 Baths ⋅ A4602030 MLS ⋅ Sailfish BLDG.
3rd Floor CORNER END UNIT ON THE CANAL! Rarely available 2 bedroom 2 bath in the Sailfish Building! Welcome to this delightful remodeled, Turn-key furnished and ready to move in 2-bedroom, 2-bathroom canal front condominium, ideally situated on Siesta Key. Final Stages of a Full Kitchen remodel with raised recessed lighting Now Complete. Brand new Light Shaker Cabinetry, Gorgeous granite countertops, recessed lighting with a larger open kitchen area. New Ceramic Tile throughout the kitchen, living area, hallway and entry, entire ceiling just retextured and entire condo freshly painted. If you are looking for a remodel that is a Turn-Key Furnished end unit with Water Views - This is it! Within the last few years the bedrooms and bathrooms were also upgraded and retiled and the lanai was fully remodeled with new tinted Impact/Hurricane Glass Enclosures. All other windows are hurricane resistant with sun block. You'll love how conveniently located you are to exceptional restaurants, Siesta Key Village and the natural beauty of Siesta Key Beach. This condo boasts a spacious open floor plan adorned with large windows, bathing the dwelling in warm, natural light. The contemporary new flooring adds a classic touch to the modern layout. Among its foremost features, this unit comes with a dedicated parking spot and enjoys amenities like a community pool, fitness center, and on-site laundry. Elevate your living experience in this fully furnished beach 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! Immaculate and much larger than the other two bedroom units at Siesta Harbor. Storage room, covered parking, clubhouse, active community with lots of activities in season, private beach access directly across the street. The location is wonderful, walk to stores, scat and trolley right outside your door, easy on and off the key, this is an over 55 community! Close to the Heated pool, clubhouse, Grills, Exercise Room, Library and Shuffleboard Courts! Beautifully done! This is a great community lots of activities, fitness room, outdoor spa, heated pool, sauna, pier on the main intracoastal waterway to relax and fish. This is Paradise - You Deserve Paradise!

1300 N Portofino Drive Unit 301SAI, Siesta Key
$580,000
1 Beds ⋅ 1 Baths ⋅ A4591804 MLS ⋅ Jamaica Royale / 48 BLDG.
<I>**BE SURE TO VIEW THE <B>IMMERSIVE 3D FLOOR PLAN</B> BY VISITING OUR <B>STATE-OF-THE ART VIRTUAL TOUR.</B>**</I><BR>TURNKEY FURNISHED SIESTA KEY INCOME PRODUCER! This updated one bedroom, one bath residence is simply charming and is brimming with investment opportunity. Or, if you prefer, make this your year round island home! So close to a private section of Siesta Beach that you can smell the salt in the air and feel the sand in your toes. This light and bright great room plan has a nice open flow between the kitchen, living area and dining space. Beautiful granite counter tops complement the tiled backsplash in the kitchen with recessed lighting. Plenty of white paneled cabinetry blends seamlessly with all the customary appliances that are included. Easy to care for ceramic tiled flooring flows naturally throughout the entire residence. Next to the primary bedroom is an upgraded bathroom with a modern freestanding vanity with a sink. The tiled shower surround has gleaming glass doors. Completing the interior is a well-appointed laundry room. Sliding glass doors present the upgraded paver patio that is steps to the community pool, shuffleboard court and beach access. Residents and guests at Jamaica Royal also enjoy deeded carport parking, storage lockers, gas grilling stations, three pools, plus Tiki Huts and chairs on the private beach. The onsite management team ensures that you have a profitable beach retreat that enables you to relax and enjoy yourself. The mid-key location is poised on the #1 rated Siesta Beach, nearby pavilions, playgrounds, and picnic areas. It is less than two miles to Siesta Key Village with shopping, dining, entertainments, several annual events, and a Farmers market. Yet the perfect distance to preserve the serenity of an island lifestyle. It is also just a few minutes from Downtown Sarasota, St. Armands Circle & championship golf. Call Office for List of Items Excluded.

5830 Midnight Pass Road Unit 48, Siesta Key
$580,000
2 Beds ⋅ 2 Baths ⋅ A4583858 MLS ⋅ Sunset House BLDG.
Lowest priced condo in beautiful Whispering Sands. Located in the heart of Siesta Village, this open floor plan 2/2 condo is on the third floor of an elevator midrise building. Freshly painted with luxury vinyl flooring in the living area and ceramic tile on the extra-large glassed-in lanai. There is access to the lanai through large sliding glass doors from the living area and the primary bedroom. Lanai adds 286 additional square feet and can be used for relaxation, reading, and an office space. Newer kitchen cabinets and vanities plus updated ceiling fans. Stainless steel appliances. The community has deeded beach access to the world renown Siesta Key Beach with its crystal sand, two community pools plus two clubhouses where many fun activities take place. One pool is located directly on the beach and has a sun lounge deck. Kayak storage area, fitness center, tiki bar, barbeque/ picnic area plus shuffleboard. A short stroll to Siesta Village where there are many restaurants, bars and shops. Large walk-in closet in primary bedroom. second large closet in guest bedroom, linen closet and storage closet inside condo. There is also an additional storage area for this condo down the hall. Coin operated laundry is also down the hall. Dedicated carport parking space plus guest parking. This is an active 55+ community. Sorry, no pets allowed.

225 Hourglass Way Unit 308SUN, Siesta Key
$578,000
2 Beds ⋅ 2 Baths ⋅ A4645637 MLS ⋅ Anchorage BLDG.
Discover this beautifully renovated and fully furnished 1,287 square foot condominium on Siesta Key, featuring 2 spacious bedrooms and 2 modern bathrooms. Nestled in the prestigious Anchorage Yacht and Tennis Club, this southern-exposure gem offers breathtaking views of both the Gulf and the Intercoastal Waterway. Ideal for both personal use and investment, the HOA permits weekly rentals year-round when not owner-occupied. Step inside unit 607 to find a bright, open-concept living area that connects to a private, condo-width balcony through sliding glass doors. The fully-equipped kitchen, adorned with elegant granite countertops, opens onto the dining area and living space, perfect for entertaining or enjoying quiet evenings at home. The expansive master suite features an ensuite bathroom with a luxurious walk-in shower, a separate dressing area, a generous walk-in closet, and its own access to the balcony. The inviting guest bedroom also includes a walk-in closet and balcony access, ensuring comfort for all your visitors. This unit comes with a deeded carport, along with ample guest parking for your convenience. The Anchorage offers an impressive array of amenities, including an Olympic-sized heated swimming pool, a state-of-the-art fitness center, lighted pickleball and tennis courts, a clubhouse, BBQ and picnic areas, and kayak storage facilities. With private beach access to the renowned Siesta Key Crescent Beach, The Anchorage combines the luxury of resort-style living with the comforts of a residential community. Enjoy living or vacationing in this prime location condominium on beautiful Siesta Key. Don’t miss your chance to own this exceptional property!

6415 Midnight Pass Road Unit 607, Siesta Key
$577,500
2 Beds ⋅ 1 Baths ⋅ A4630299 MLS ⋅ Yoder Homes BLDG.
PRICED to Sell! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision whether you’re seeking a full-time residence, vacation retreat, or long-term investment. The existing cottage, which holds no contributory value due to hurricane flooding, creates a true blank slate for new construction. As an added benefit, this property is being offered with the option to build a thoughtfully designed custom home by Yoder Construction. The proposed plan, The Oceana, is part of an exclusive ISLAND SERIES, developed with sustainability and the unique coastal conditions of Siesta Key in mind. Buyers may choose to build this elevated 2,735-square-foot home, or collaborate with the builder on a personalized design through the available design center. Commonwealth Drive is ideally located just minutes from the powdery sands of Siesta Key Beach and the vibrant charm of Siesta Village, with its shops, restaurants, and island lifestyle. Opportunities to build new in this highly sought-after location are increasingly rare. To explore this offering further, request details on the optional build package, and schedule a walk of the lot.

5019 Commonwealth Drive, Siesta Key
$575,000
2 Beds ⋅ 1 Baths ⋅ A4680397 MLS ⋅ D BLDG.
Tucked within the Gulf-front Casa Blanca community on Siesta Key, this thoughtfully restored villa offers an effortless blend of comfort and coastal style just steps from the white sand beaches and crystal clear waters that make Siesta world famous. From the moment you enter, the open living space feels welcoming and well-balanced, designed for easy everyday living and relaxed entertaining. The remodeled kitchen serves as the heart of the home, featuring modern finishes that connect naturally to the dining and living areas, which have also recently been revamped with updated flooring and fresh interior paint, creating a clean and inviting atmosphere throughout. From the main living area, sliding glass doors lead to a spacious lanai that extends the home outdoors, offering a private setting to relax, entertain, or enjoy the island air. The bedrooms are thoughtfully positioned to provide comfort and privacy, enhanced by new carpeting that adds warmth and a fresh feel, making the layout well-suited for full-time living or seasonal stays for up to six guests. Casa Blanca is a gated community known for its beautifully maintained grounds, peaceful atmosphere, and inviting pool area designed for relaxed coastal living. With convenient access to Siesta Village dining and entertainment via the public Breeze trolley or tips-only shuttle service, this property offers both lifestyle and flexibility. Whether you are seeking a long-term rental investment with in-house management, a seasonal retreat, or a personal island residence, this villa presents a compelling opportunity in one of Siesta Key’s most sought-after communities. *A 1% RATE BUY-DOWN IS AVAILABLE TO QUALIFIED BUYERS WHO WORK WITH THE SELLER'S PREFERRED LENDER.*

6154 Midnight Pass Road Unit 10 D, Siesta Key
$575,000
1 Beds ⋅ 1 Baths ⋅ A4679051 MLS ⋅ Gulf Haven BLDG.
Located in the highly sought-after Gulf Haven Community, this beautifully renovated residence offers a rare opportunity to enjoy private beachfront living on the sugar-white sands of world-famous Siesta Key Beach, shared exclusively by just 50 owners. No crowds, no competition for space for your beach chair or blanket, just pure relaxation. With over 1,000 square feet of air-conditioned living area, the unit features a brand-new kitchen showcasing stainless steel appliances, shaker-style cabinetry, and elegant quartz countertops. The chef’s kitchen is complemented by an oversized living area with soaring vaulted ceilings and enlarged windows that flood the space with natural light. The fully renovated bathroom includes a custom glass-enclosed shower, new cabinets, and stunning countertops. Major upgrades such as a new HVAC system and water heater provide peace of mind and leave nothing for an owner to do but enjoy the beach. Additional features include an air-conditioned Florida room protected by exterior block construction, a spacious bedroom with a walk-in closet, second closet, and attic storage. Additionally, there is a fully enclosed carport with ample attic storage, parking for three vehicles, and an outdoor storage shed. Finally, there is a in residence laundry room with stacked washed and dryer, very rare for beach front condominiums. This ground floor residence is ideally located close to the sand while overlooking the lush grassy courtyard that leads directly to the beach. Residents enjoy access to a beachfront club room, community outdoor gathering area, and a sparkling community pool, delivering the ultimate Siesta Key lifestyle that you’ve been waiting for. A short ride to dining, shopping, and non-stop entertainment at either the north or south villages. Come and live the life you deserve in this ultimate beach getaway.

5860 Midnight Pass Road Unit 40, Siesta Key
$575,000
2 Beds ⋅ 2 Baths ⋅ A4673783 MLS ⋅ Na BLDG.
One or more photo(s) has been virtually staged. Siesta Key Beachfront Living at Jamaica Royale--Experience the best of coastal Florida in this fully renovated two-bedroom, two-bath condominium, perfectly situated on world-famous Siesta Key Beach. With 300 feet of private, powder-white quartz sand just steps away and no roads to cross, this Jamaica Royale residence delivers true beachfront living on a quiet, private lane. Step inside to a bright, open-concept layout featuring luxury flooring throughout. The gourmet kitchen shines with stainless steel appliances, quartz countertops, custom soft-close cabinetry, and stylish finishes. The spacious primary suite offers a serene retreat with a beautifully updated en-suite bath and walk-in shower, plus extra-deep double closets in both bedrooms for abundant storage. Recent upgrades include a new roof (2022), new water heater, new A/C, new appliances, updated plumbing, contemporary interior doors, and hardware—everything has been thoughtfully refreshed for move-in-ready comfort. Enjoy your morning coffee on the private patio, take advantage of convenient in-unit laundry, and park right outside your door. Resort-style amenities include three heated pools, plenty of lounge chairs, and lush tropical landscaping. Whether you’re relaxing to the rhythm of the Sunday drum circle, watching breathtaking sunsets, strolling the cool-to-the-touch white sand, or hopping on the free shuttle to Siesta Key Village for dining and shopping—this is relaxed, turnkey beach living at its finest.

5830 Midnight Pass Road Unit 94, Siesta Key
$575,000
2 Beds ⋅ 2 Baths ⋅ A4672885 MLS ⋅ Island Reef BLDG.
Have It All in This Beautifully Remodeled & Fully Furnished "Beach House" style Condo! Welcome to one of Siesta Key’s most desirable pet-friendly communities, perfectly positioned Gulf-to-Bay with quiet, deeded beach access just steps away. This impeccably updated residence offers a smart split floor plan that provides ideal privacy between the main bedroom suite and the guest room. Enjoy morning coffee or evening cocktails on the gorgeous, enclosed lanai, overlooking lush tropical gardens and the sparkling community pool. The well-appointed kitchen features room for a cozy breakfast table and has been completely renewed with high-quality finishes. No detail has been Overlooked: Impact windows, New electric and plumbing, All-new kitchen, Beautifully renovated bathrooms, New flooring throughout, Tasteful, neutral furnishings—move-in ready with no contractor visits needed! Step outside and live the resort lifestyle with multiple pools, boat docks (lifts permitted), tennis and pickleball courts, a fitness center, and grilling areas. After a day at the beach or pool, cast a line from the dock—fish are plentiful! The Siesta Key trolley stops right at your door, offering easy access to shopping, dining, and all the island’s best attractions. First time on the market and truly a must-see—this property checks every box. Let the beach life begin!

8773 Midnight Pass Road Unit 204G, Siesta Key
$575,000
1 Beds ⋅ 1 Baths ⋅ A4597133 MLS ⋅ 901 BLDG.
Location, Location, Location! The allure of having an up-to-the-minute, move-in-ready furnished condo is beyond compare! Imagine waking up to breathtaking full Gulf of Mexico views from your screened lanai, living room, and bedroom, unhindered by any obstructions. This top-floor unit has modern updates, with all features remodeled within the last five years. There are gorgeous upgraded quartz countertops and new vinyl plank flooring that add an extra touch of class and durability. Hurricane impact windows and sliders are included. This unit also offers a reserved covered parking space. Whether it's an investment or a lifestyle, La Siesta Condominiums offers the option of being part of a weekly rental program that is managed by a full-time on-site management staff. The clubhouse at La Siesta is a place for gathering, as it's the heart of this condo community. With a pool table, ping pong table, fitness center, and a library, the clubhouse is your go-to haven for leisure and enrichment. For outside activities, there are shuffleboard, cornhole, and BBQ grills on-site as well an inviting heated pool! The trolley stop is located right in front of the building and is more than just a convenience; it's a lifeline to seamless connectivity. With the free trolley, you can ride whenever the mood strikes, without worrying about driving or finding parking. Location is key in real estate; this condo takes it to heart! Perfectly positioned on the key, it's nestled amidst everything you could want or need. A short stroll from the front door and you're ready to swim, kayak, play tennis or volleyball, and power boat or sailing are all steps away from the complex. The world-famous #1 rated Siesta Key beach with beautiful quartz crystal sand is directly across the street. In this stunning, move-in-ready updated condo, life isn't ordinary - it's a symphony of extraordinary experiences, waiting to be enjoyed.

901 Beach Road Unit 403, Siesta Key
$570,000
2 Beds ⋅ 1 Baths ⋅ C7524394 MLS ⋅ 915 BLDG.
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
$570,000
2 Beds ⋅ 2 Baths ⋅ A4678463 MLS ⋅ 6415 BLDG.
Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. This condominium is on the 7th floor facing north. Wait till you see the sunsets. Even a lightning storm is going to be fantastic from your large lanai perfect for entertaining. The main bedroom is big lots of with a walk-in shower. Guest bedroom is a generous size as well and also has a walk in shower. ****TURNKEY FURNISHED…WEEKLY RENTALS…It’s all about convenience and living the good life. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. 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. Yes, have are own easement to the beach… If you have a boat, The Anchorage also offers dockage along the Seawall! “$10.00 per month” There is a trolly that you can 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 702, Siesta Key
$570,000
2 Beds ⋅ 2 Baths ⋅ A4670071 MLS ⋅ Waterside Manor BLDG.
PRICE IMPROVEMENT!! Step into relaxed coastal living at the premiere GULF FRONT property of Whispering Sands on world famous Siesta Key! This lovely, immaculately maintained 2 bed/2 bath, 2nd floor retreat instantly embraces you with its soft, soothing, aqua hues and comfortable, inviting layout. One of the best features of this unit is its spectacular 34’ screened and glassed lanai running the entire length of the unit, offering RARE WATER VIEWS of both the sparkling clubhouse pool and shimmering lagoon, with a peekaboo view of the Gulf! Framed by graceful palms and gentle Gulf breezes, your lanai is perfect for enjoying peaceful morning coffee or sunset cocktails. The updated kitchen features granite counters, stainless Whirlpool appliances, and crisp subway tile backsplash. SELECTED LIVING & DINING ROOM FURNISHINGS ARE BEING OFFERED with this unit including an entertainment center with remote controlled electric fireplace. The spacious primary bedroom includes a walk-in closet and ensuite bath with glassed shower. Equally spacious, the guest bedroom is large enough to hold 2 queen beds. When you’re not gazing from your lanai, take the elevator down one floor for a swim in the pool or an invigorating workout in the clubhouse right next door! The clubhouse is currently undergoing complete remodeling and will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. This unit also comes with an assigned storage locker for all of your beach essentials. The common laundry room just steps from this unit features 2 sets of W/Ds, enabling you to complete your laundry in half the time so you can spend more time outdoors enjoying the Florida lifestyle! Ideally located right next to the colorful boutiques & restaurants of Siesta Key Village, Whispering Sands is an exceptional 55+ Gulf front community offering 800' of PRIVATE beach, two heated pools, clubhouse, new beachside Tiki Hut, gas grills, shuffleboard, & canoe/kayak storage. Experience the perfect blend of tranquility, community, and coastal charm. Your island retreat awaits!

199 Whispering Sands Drive Unit 201, Siesta Key

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