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$685,000
2 Beds 2 Baths A4569085 MLS Beachway Apts BLDG.
Fantastic Siesta Key sunsets await from this spacious and updated two-bedroom, two-bath condominium facing west overlooking Siesta Key Beach. You can be on the sugary sands in seconds from your front door. Beautifully finished with an open floor plan, amazing natural light, neutral ceramic tile throughout, large kitchen island bar complete with granite countertops and beverage refrigerator, stainless steel appliances, spacious walk-in finished closets, custom built-ins, crown molding, plantation shutters, and all impact glass windows and sliders. This unit has a new air conditioning system, and the building has just been freshly painted. Beach Way allows monthly rentals 12 times a year, and has a large heated pool with an outside grilling area, social room with a kitchen for entertaining, elevator to your floor and a separate storage closet for all your beach needs. A carport just outside this condominium is included but there is no need for a car as you are minutes from the shopping and dining of Siesta Key Village, or a short ride to the arts and culture of downtown Sarasota. A great Island getaway, full-time residence or a highly desirable investment property as this condominium has a good rental history, allowing you to still enjoy the benefits of personal use when not renting. A truly unique property.

5600 Beach Way Drive Unit 213, Siesta Key

$684,000
2 Beds 2 Baths A4577238 MLS Turtle Bay BLDG.
PRICE IMPROVEMENT! Bay and gulf views, boat docks and beach access! Who could ask for more? Welcome to this rare opportunity on the southern end of Siesta Key: Turtle Bay. Enjoy beautiful views of Sarasota Bay sunrise in the morning. Deeded beach access makes it easy to watch the sunset at the end of the day! This spacious 2 bedroom, 2 bath condominium offers an updated kitchen with granite counters, tile backsplash, stainless steel appliances and large tile flooring on the diagonal. No carpet! The owner's suite is spacious with a private bath, walk-in closet and access to the enclosed terrace. The second bedroom is serene and private with plenty of storage! Laundry in residence with full size washer/dryer. Enclosed lanai to enjoy year-round. Unique feature: private garage and storage under the building. This is a pet friendly condo! Turtle Bay amenities include a heated pool and spa, lighted tennis courts, pickleball courts, a grilling and picnic area, shuffleboard and a variety of activities for residents to enjoy. On site management, secure entry and two elevators. Boat slips are available to all owners on a first come first serve basis. Explore Siesta Key and enjoy the many restaurants, shopping and island lifestyle. Memories are made here!

8701 Midnight Pass Road Unit 505A, Siesta Key

$683,000
2 Beds 2 Baths A4582041 MLS 8767 BLDG.
BEACH! BOATS DOCKS! SPECTACULAR BAY VIEWS! Come experience Siesta Key living just steps from the gentle bay waters at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedroom, plus Den with 2 bunk beds. 2 baths, laundry in residence, carport, and guest parking. Newer Appliances , light fixtures and porcelain tile flooring in both bathrooms, Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks (lifts allowed), two lit tennis courts, pickleball, 2 fitness rooms, kayak Storage library, Billiards, game room, clubhouse, two heated swimming pools and more. Pet friendly! Imagine rising each day to panoramic vistas of Bay to view sunrises and coastal wildlife. Stroll over to the Gulf side of Island Reef to enjoy the refreshing breezes and magnificent sunsets. Tropical gardens add to the appeal of Island Reef and this wonderful community is close to three of Siesta Key's most popular restaurants and all of the Your new social life awaits a perfect 3-5 minute walk from a trio of Siesta Key’s favorite restaurants (casual & waterfront fine dining) or enjoy a complimentary trolley to Siesta Village for dining, shopping, ice cream, mini-donuts, cute brunch spots, yoga, dancing and live music every night of the week! Enjoy the cultural activities Sarasota has to offer.

8767 Midnight Pass Road Unit 304F, Siesta Key

$682,000
2 Beds 2 Baths A4580407 MLS Tortuga BLDG.
Tortuga Club is a private beachfront community located on the South end of Siesta Key directly on the Gulf of Mexico. This two bedroom beach-front residence presents opportunity for immediate rental income and is offered turnkey furnished, has tile floors throughout, Impact windows and door, newer HVAC. The lanai is the perfect place to relax and enjoy majestic colorful sunsets with direct views of the Gulf of Mexico. The Tortuga Club supports an active island lifestyle with deeded beach access, tennis, pickleball, boat docks, fishing pier, indoor/outdoor heated pool, saunas, clubhouse, gas grills, and library. Secured building entry and on-site Manager. Ground level secure garage with parking space and storage for kayaks or paddle boards. Easy access to all of Siesta Key restaurants, shops, public beach and nightlife and the Sarasota Mainland is located just minutes away.

8730 Midnight Pass Road Unit 203, Siesta Key

$680,000
2 Beds 2 Baths A4666702 MLS Na BLDG.
One or more photo(s) has been virtually staged. Private deeded 32 foot boat dock. Private beach access to Siesta Key Beach. Waterfront community on Sarasota Bay. Updated in 2019. Set on the bay side of Siesta Key, this beautifully renovated two bedroom two bath residence at Boca Siesta offers a lifestyle that feels both rare and natural. Located within a waterfront community on Sarasota Bay, the residence includes a private deeded 32 foot boat dock and private access to Siesta Key Beach, creating an exceptional balance of boating, beach access, and bayfront living. Located in the understated bayfront enclave of Boca Siesta, this residence enjoys peaceful bay views and a quieter sense of retreat, while Siesta Key Beach sits just across the street, known for its expansive shoreline and world famous quartz crystal sand. Updated in 2019, the residence features a more open and inviting floor plan with solid wood cabinetry offering generous storage, granite countertops, plantation shutters, crown molding, impact windows, new ceiling fans, and fresh interior paint. The open kitchen and great room combine living and dining areas oriented toward the bay and flow seamlessly into a screened private patio with impact windows overlooking Sarasota Bay. The primary suite offers calming bay views and a spacious ensuite bath with a jetted soaking tub, large walk in shower with rain shower head, dual vanities, and a generous walk in closet. The second bedroom and bath provide flexibility for guests, a home office, or additional living needs. Boating enthusiasts will appreciate the private deeded 32 foot boat dock that accommodates a larger vessel and provides direct access to Sarasota Bay. Additional conveniences include covered carport parking, private storage under the building, and an in unit full size washer and dryer located in a large utility room. Community amenities include a heated bayfront pool, tennis and pickleball courts, fishing pier, kayak launch, grilling areas, and a bayside clubhouse overlooking the bay with kitchen, bar, sauna, and fitness area. Private beach access is provided through the association, with access just across the street through Sarasota Surf & Racquet Club. From this location, Siesta Village, South Village dining, and downtown Sarasota are easily accessible by bike, free ride services, or the Siesta Key trolley. For those who choose Siesta Key for the water as much as the beach, Boca Siesta offers an effortless boating lifestyle where Sarasota Bay and Siesta Key Beach are part of everyday life. Experience life at Boca Siesta. To view a 360 walk through go to: https://funkypalmproductions.hd.pics/5911-Midnight-Pass-Rd-unit-206/idx

5911 Midnight Pass Road Unit 206, Siesta Key

$680,000
2 Beds 2 Baths A4660431 MLS 1055 BLDG.
Welcome to Peppertree Bay, one of Siesta Key’s most coveted Gulf to Bay communities, where island living meets effortless elegance. This turnkey, beautifully reimagined 2 bedroom, 2 bathroom residence is nestled within the desirable midrise building on the beach side of the complex, offering the perfect combination of privacy, convenience, and resort style amenities. Just steps from Siesta Key’s world renowned quartz sand, this home embodies the island lifestyle. From the moment you enter, you’ll be captivated by the peaceful view of the tranquil pond and fountain, setting the tone for relaxation. This updated unit has been thoughtfully redone, showcasing a spacious open concept floor plan that seamlessly blends form and function. The gourmet kitchen is a showstopper, featuring granite countertops, stainless steel appliances, soft close cabinetry, and a breakfast bar perfect for casual dining or entertaining. Elegant ceiling fans and updated fixtures enhance the coastal vibe, while the dining and living areas flow together effortlessly, creating a bright and inviting space for family gatherings or quiet evenings. The primary suite is a serene retreat with a walk in closet and ensuite bath, and the guest bedroom provides a comfortable haven for visitors. With a strong rental history, this property is as appealing to investors as it is to those seeking a full time residence or seasonal escape. At Peppertree Bay, residents enjoy private deeded beach access, two heated swimming pools, tennis courts, a fitness center, clubhouse, fishing pier, and professional onsite management. Covered parking and extra storage add convenience to this lock and leave lifestyle. Situated close to Siesta Key Village, eclectic dining, boutique shopping, and vibrant cultural experiences, this home truly offers it all. Whether you are looking for an income producing investment, a sun soaked seasonal retreat, or a luxurious full time residence, this residence at Peppertree Bay delivers the very best of Siesta Key living.

1055 W Peppertree Drive Unit 106AA, Siesta Key

$680,000
2 Beds 2 Baths A4650747 MLS 1155 BLDG.
Professionally Redesigned, Renovated & Updated in 2021, this lake-front Contemporary Coastal Chic townhouse is sure to delight! Located just steps away from the cool quartz sand on Siesta Key Beach this open, light & bright townhouse lives large with high ceilings & 4 sets of glass sliders. This 2-bedroom, 2-full bathroom home has a 1-car garage under the unit with extra storage space for the equipment to enjoy sand, pool & tennis/pickleball activities. Start your day with coffee & sunrise on the Eastern balcony & wind down on the 21 ft. covered porch with long-lake views & sunsets over the Gulf! The remodeled kitchen with soft-close hardwood cabinets, Quartz Countertops, & detailed tile backsplash is well equipped for efficiency to serve the adjacent dining table or kitchen dinette. The Primary Ensuite has a long-lake view from the King bed & large screen TV. The spa-like Ensuite has a solid-wood double vanity w/ Quartz top, detailed porcelain flooring, a walk-in shower w/ Frameless Glass Enclosure & 2 large closets. Bedroom #2 is separated on the 2nd floor, has 2 twin beds & enjoys the morning Sunrise over the balcony. The 2nd full bathroom, also on the 2nd floor has an enlarged tub, dual showerheads, folding glass shower curtain & solid wood single vanity w/Quartz top. The solid-surface floors throughout & the full-sized in-house washer & dryer provide easy maintenance. Onsite amenities include tennis, a resort-style pool, BBQ & picnic area. Across the street, the Siesta Key Public Beach offers Pickleball, Tennis, a Kid’s Playground, Lifeguards, wheelchair access & Sand Volleyball on the beach. A FREE Trolley runs up & down the Key to a variety of restaurants, bars, small boutiques & shops. Being sold turn key, this is a wonderful opportunity for a new owner and/or also a great investment property. The owners currently have the home in an Airbnb and there is also an onsite, short-term Rental Company with a waiting list for 2026 reservations. Siesta Key Beach was Ranked in 2025 by Tripadvisor #1 beach in the U.S. & #4 in the world. The Townhomes at Our House on The Beach do not last long on the market, so don’t miss your opportunity!

1155 Lake House Circle Unit C119, Siesta Key

$680,000
2 Beds 2 Baths A4631853 MLS Harbor Tower Yacht & Racquet BLDG.
You have found your oasis! Harbor Towers Yacht & Racquet Club recently completed a four-year hurricane hardening and structural upgrade program in 2024, meeting all new safety standards for hurricane/wind protection. Copies of the funded upgrade program are available for your review. This no-worries furnished, updated unit, has all new hurricane-rated windows and doors, two small balconies, a beautiful granite kitchen with under-counter lighting, updated baths with granite counters and walk-in showers for your ease of use. The well-proportioned living and dining area completes the ideal getaway. Harbor Towers is in a class of its own, with a bayside marina, a fishing area and easy access to the gulf with no fixed bridges. The community offers its residents two heated resort-style pools, barbecue areas, kitchen prep area, a fitness center with a great array of workout equipment, three Har-Tru tennis courts, a sauna, a clubhouse, a fabulous marina with areas to sit along the intercoastal to watch sea life and boats float by you. If interested, the association has rental slips for personal watercraft. Want an investment, this unit can be rented for two-week minimums, 25 times a year plus you can utilize the on-site property management company for potential rentals, or you can do it yourself. Join this amazing community where the residents are eager to meet you.

5855 Midnight Pass Road Unit 225, Siesta Key

$680,000
2 Beds 2 Baths A4592139 MLS 5963 BLDG.
Your NEW Investment awaits ~ Consistent Rental Business with reservations to transafer/Milestone Inspection completed and passed! Why wait? Explore this fantastic 2 Bedroom/2 Bath, Top-Floor unit in the exclusive community of Palm Bay Club. Imagine enjoying daily sunrises/sunsets including panoramic views of nature, boats, and sea life; while lounging at the private Bay-Side pool. If you are looking to have the BEST of two Worlds; Bay and Gulf experiences, then this is the community for you. Enjoy convenience to Siesta Key Village, shops & restaurants with Gulf-to-Bay access. Privately launch water crafts, take pleasure in fishing, and benefit from the abundance of amenities this property and its surround has to offer. Not many do, but Condo can be warmly used as your first or second-home residence. The upgraded appliances, countertops, flooring and furnishings will add peace of mind for guests utilizing the rental program or equally for Owner relaxation. Impeccably maintained and sold TURN-KEY/ Suitcases are all that you bring! One-Year home warranty is provided at closing for the lucky Buyer. It's a must see, so call today to get your private tour and get ALL the deets on this unit. It' Summer, Let's GO!! All measurements are approximate, Buyer to verify if important

5963 Midnight Pass Road Unit 359, Siesta Key

$675,000
2 Beds 2 Baths N6136071 MLS 8635 BLDG.
Stunning 2-Bedroom 2-Bathroom Condo with Breathtaking Intracoastal Views Welcome to an oasis in the sky! Situated on the 4th floor of the highly sought-after Bay Tree Condo Complex, this exquisite residence offers an open, modern design, enhanced by panoramic Intracoastal water views. Sit in your living room or at your dining table and bask in the tranquility of the majestic oaks in a park-like setting and the peaceful water views of Sarasota Bay and the Intracoastal waterway. Additionally, relish in the luxury of having deeded private BEACH ACCESS directly across the road, complete with your own cabana nearby. During a total custom renovation, everything was replaced from the drywall, electrical wiring, to kitchen, bathrooms, and more. Some of the key features include: Impact windows and tempered glass sliders for safety, security, and energy efficiency. Low-maintenance, high-end finishes throughout, including custom cabinetry, designer flooring, and sleek countertops. Two spacious ensuite bedrooms and bathrooms provide ultimate privacy and comfort. This condo has a range of built-in features designed to maximize both space and convenience. In the spacious living room, an elegant entertainment unit is integrated into the wall, providing a sleek, clutter-free space for all your media essentials. The bedroom includes thoughtfully crafted built-in dressers, offering ample storage while maintaining a clean, streamlined aesthetic. For versatility, the second bedroom features a cleverly designed Murphy bed, perfect for accommodating guests or optimizing the space when not in use. In addition, a built-in desk creates a dedicated workspace, ideal for working from home or pursuing hobbies. With these smart, built-in features, this home provides both comfort and efficiency, making it the perfect choice for modern living. Bay Tree is a 25-acre gulf and bay community with beautiful old oak trees on well-manicured grounds. Every condo owner has a private storage cabana near the beach to stow their beach essentials, bikes, umbrellas, and chairs. Unique to this complex, for added convenience there are restrooms for owners just off the beach. Bay Tree also has fishing piers with boat docks on the Intracoastal available on a first come basis (owners can install lifts). Bay Tree has two heated pools for year-round relaxation, along with two patios with grills for easy outdoor dining and social gatherings. This community offers the perfect blend of beachside luxury and modern living, with every amenity you need for a laid-back, yet active lifestyle. Whether you're enjoying the stunning water views from your condo or lounging at the beach or by one of the pools, this is Florida living at its finest. Located a few miles from popular Siesta Key Beach, and Siesta Village with its multiple restaurants, music venues, and entertainment means you’re near the action, but away from the major hustle and bustle of it.

8635 Midnight Pass Road Unit 405C, Siesta Key

$670,000
2 Beds 2 Baths A4669286 MLS West Tower BLDG.
Price Drop of 20K - best price for a Tower Unit in Our House at the Beach !Strong Rental Income – Across from Siesta Beach! Totally updated 2 bed / 2 bath condo in the West Tower of “Our House at the Beach”, directly across from Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor in 2024. This second-floor unit offers incredible natural light and nearly 270 degrees of wraparound views thanks to 46 feet of sliding glass doors in the living and dining areas. This unit is turnkey furnished (excluding some artwork and personal items) and features luxury plank vinyl flooring throughout, with updated bathrooms and a gorgeous, remodeled kitchen with granite countertops, stainless steel appliances, and a pass-through to the main living area. The spacious primary bedroom offers abundant windows and a bright, airy feel. Both bathrooms have been tastefully upgraded. Enjoy two oversized balconies, perfect for relaxing after a day at the beach or hosting guests. This is not just a beach retreat—it’s a solid investment: • $32,900 gross rental income in 2023 • $28,000 in 2024 (despite storms) • Projected $40,000+ in 2025 with owner use! Weekly rentals allowed, boosting occupancy and revenue potential. The $45,000 special assessment (impact glass & more) is fully paid by the seller. Community amenities include: • Heated pool • 2 tennis courts • Grilling pavilion • Assigned covered parking • In-unit full-size washer/dryer • Pet-friendly (owners may have 1 pet up to 15 lbs) Units in the West Tower rarely come on the market—last year’s sale went for significantly more. This is your chance to own a beautifully maintained, income-producing condo across from one of the world’s most beautiful beaches!

1001 Beach Road Unit A203, Siesta Key

$670,000
2 Beds 2 Baths A4644896 MLS 1113 BLDG.
Rarely available, this recently fully-renovated lake-front townhome is steps away from the crystal sands of Siesta Key Beach! Beautifully updated with a Coastal Chic interior, this end unit townhouse lives large. Light & bright with high ceilings, an open floor plan & four sets of glass sliders inviting the Gulf breezes inside makes each new day a delight. This 2-bedroom, 2-full bathroom home has a 1-car enlarged garage with ample storage for the water & sunshine toys, a covered balcony for coffee at sunrise & a 21’ long covered porch to celebrate evening sunsets! The kitchen with soft-close, hard-wood cupboards, granite counters & bar top is well equipped for efficiency to serve the adjacent dining table, bar seating or rattan cozy coffee table for two! The Primary Ensuite has a lake-view from the King bed, walk-in shower, dual vanities and 3 separate closets. Bedroom 2 is separated on the 2nd floor and enjoys the morning sunrise & adjacent 2nd full bath. The solid-surface floors & the full-sized inhouse washer & dryer provide easy maintenance & electric power shades on all windows provide closure at the end of the day. This unit was totally remodeled with high-end furnishings & interior finishes several years ago & has been lightly used, reserved for only Family & Friends. Onsite amenities include tennis, a resort-style pool, BBQ & picnic area. Across the street, the Siesta Key Public Beach offers Pickleball, Tennis, a Kid’s Playground, Lifeguards, wheelchair access & Sand Volleyball on the beach! A FREE Trolly runs up & down the Key to a plethora of restaurants, bars, small boutiques & shops. Being sold turn-key, this is a great opportunity for a new owner and/or is also a great investment property. There is an on-site, short-term Rental Company with a waiting list for 2026 reservations. Siesta Key Beach was Ranked in 2025 by Tripadvisor #1 in the U.S. & #4 in the World. Don’t miss this opportunity for a fabulous townhome across the street at Our House at The Beach!

1113 Lake House Circle Unit C110, Siesta Key

$670,000
2 Beds 2 Baths A4584122 MLS 9011 BLDG.
Welcome to the perfect Siesta Key WATERFRONT PARADISE !! This condo is located directly on the Intercoastal Waterway. Fabulous unobstructed views of Little Sarasota Bay. It's the closest building to the water. Sunrise Cove has all the amenities you will need. Boat Slips are available right outside your door!! Freshly painted and fully turn-key furnished. Two Bayside Pools, Fitness Center, Lighted Tennis and Pickleball courts, Clubhouse, Rec Room with Kitchen, Picnic and BBQ Grills right at the water's edge. Second BBQ area just across the parking lot from the unit. Tastefully decorated with no expense spared. The unit has wood floors in the Living room and Dining room, 18"ceramic tile floors in the kitchen, lanai, bathrooms. Walk-in closets, granite countertops, stainless steel appliances, great room and enclosed lanai. New plantation shutters. Built-in mini bar next to Kitchen great for entertaining. Dining area has been completely updated. Unit has been updated to open up the Kitchen area and Lanai for additional living space. The carport is right at the bottom of the stairs. Ophelia's on the Bay, voted best waterfront restaurant is right next door or jump on the trolley stop across the street for shopping and dining in the Siesta Key Village. Add this to your investment portfolio, in-house management offers low fees. Great rental Income. The roof and carports were recently done and the seawall is very new. 2004 Saturn included with full price offer.

9011 Midnight Pass Road Unit 230, Siesta Key

$665,500
2 Beds 2 Baths A4582875 MLS Harbor Towers Yacht & Racquet BLDG.
Whether you are looking for an investment property, a vacation home, or a place to call your own, this completely remodeled, turn key furnished, two-bedroom, two-bath condo in the beautiful Harbor Towers Yacht and Racquet Club is perfect for you! The views from the balcony are stunning as you look over to see the intercoastal waterways, Palm trees, and the pool. The gallery-style kitchen features an oversized stainless steel refrigerator, range, and dishwasher. Plus plenty of counter space and cabinets! The Primary Bedroom includes a walk-in closet with shelving to help stay organized and has an En suite bathroom. Unwind in the privacy of your custom walk-in shower with beautiful tile work after a long day. New A/c, Washer, Dryer, and remote-controlled blinds. The Harbor Towers Community offers luxury amenities including a community pool that stays at 85 degrees all year, a grilling patio and shaded seating area, a Fitness center, three tennis courts, a marina with the option to rent boat slips so you can set sail without having to drive anywhere, Kayaking racks, bike racks, and Island Gazebo to watch the dolphins and manatees swim. Located on 1/4 of a mile from the famous Siesta Key Beach! Schedule your showing today! Minimum 2 week rental, potential gross rent during season is $8500/month

5855 Midnight Pass Road Unit 203, Siesta Key

$665,000
2 Beds 2 Baths A4698700 MLS
Beach, comfort, and privacy all in one standalone villa. This 2-bed, 2-bath escape sleeps the whole group with a king primary ensuite, two twins in the guest room, and a living-area sofa bed. Ideal for families or friends. Inside: roomy living and dining areas, a fully equipped kitchen with updated counters and modern appliances, three flat-screen TVs, central heat and air, and a private screened lanai for winding down. Outside: you're part of Island House Beach Resort, a short walk from the Gulf's powdery sand and turquoise water. Enjoy a beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating for legendary Siesta Key sunsets, plus two beach cabanas, a heated pool, and a game room with ping pong and air hockey. Ride the Siesta Key Trolley to Siesta Village's dining and shops, or explore Myakka River State Park, island bike routes, and paddleboarding through the mangroves and reopened Midnight Pass. Sarasota's museums, gardens, golf, and world-renowned Mote Marine Aquarium round out everything you need for a memorable stay. Your unforgettable Siesta Key getaway starts here.

Siesta Key

$660,000
2 Beds 2 Baths A4670329 MLS
Discover coastal luxury on Siesta Key with this beautifully renovated and fully turnkey-furnished condominium at the prestigious Anchorage Yacht and Tennis Club. Featuring two spacious bedrooms and two modern baths, this residence blends comfort, style and investment potential. Ideal for personal enjoyment and potential rental income, Anchorage allows weekly rentals, 52 weeks per year, and offers onsite management and a rental office for effortless ownership. The sellers have never rented the property, as it has been used exclusively as their private residence, reflecting the utmost care and pride of ownership. Enter to find a tastefully remodeled interior showcasing fresh, neutral tones and modern coastal design. The condominium is handsomely appointed with coastal furnishings and décor, just two years old. creating a light, inviting atmosphere throughout. The open-concept living area flows seamlessly to a private, condominium-width balcony, accessible through impact glass sliding doors. Enjoy southern exposure and all-day sunshine with views of the waterway and marina. The chef’s kitchen is fully equipped with elegant quartz countertops, white cabinetry and stainless steel appliances, opening to the dining and living areas, ideal for entertaining or relaxing evenings at home. The expansive primary suite features a luxurious ensuite bath with a walk-in shower, a customized walk-in closet and private balcony access. Additional highlights include a deeded under-building parking space and ample guest parking. The HOA fees conveniently cover insurance, water, sewer, trash, cable TV and internet. Residents of The Anchorage enjoy an impressive array of resort-style amenities, including an Olympic-sized heated swimming pool, fitness center, lighted pickleball and tennis courts, clubhouse, barbecue and picnic areas, shuffleboard, kayak storage and launch area, and dock access for fishing or boating. Along a saltwater canal with boat dockage, Anchorage offers easy access to the Intracoastal Waterway via the south Siesta Key bridge (no fixed bridge). Plus, residents enjoy private beach access to the world-famous Siesta Key Crescent Beach. Combining resort-style living with the comfort of a residential community, this exceptional condominium is ideal for full-time living, a vacation retreat or a proven income-producing investment. Don’t miss the opportunity to own your piece of paradise on Siesta Key!

6415 Midnight Pass Road Unit 505, Siesta Key

$660,000
1 Beds 1 Baths A4665033 MLS 797 BLDG.
PENTHOUSE" OPPORTUNITY on the 5th Floor of Building 797 in Sought After & Gated CRESCENT ROYALE! As you walk through the door you will be astounded with the beautiful views of the Gulf of Mexico & Siesta Beach! Own your own piece of Siesta Key and enjoy the gorgeous nightly sunsets on the top floor. This updated unit has been well maintained and tastefully furnished, updated with a functional kitchen, updated bath and Hurricane sliding glass doors leading out to the lanai. The screened lanai will give you balmy breezes and will also provide a 180 degree view of the Gulf of Mexico. Security Gates & a beautiful paved entryway will greet you upon entering and you'll have your own, assigned covered carport space. There is plenty of guest parking available as well. There is also a storage area assigned to this unit for beach chairs, coolers, etc. on the same floor. You will be greeted with a professional and friendly staff from management to maintenance on site who handle all aspects of property management. Crescent Royale also features a new state-of-the-art fitness center, gas grills & tables with umbrellas for a cookout, shuffleboard court, Olympic style heated pool, pool table in the air conditioned lounge, elevators, recreation room & a handicap accessible banquet room with a kitchen. A short ride to siesta village with lots of shopping and nite life

797 Beach Road Unit 509, Siesta Key

$660,000
2 Beds 2 Baths N6137253 MLS 6415 BLDG.
Stunning Intracoastal and Gulf views from this rare 9th-floor corner unit on Siesta Key. Welcome to Unit #909 at The Anchorage—a beautifully updated condo offering breathtaking panoramic views of the Intracoastal Waterway and Gulf glimpses from three private balconies. This light-filled corner unit is perched on the 9th floor and designed to capture peaceful coastal living from every angle. Inside, you'll find a newly renovated kitchen with updated finishes, premium vinyl flooring throughout, and hurricane-rated windows and sliders that let in abundant natural light. The spacious owner’s suite includes a large closet, a private bathroom, and its own balcony overlooking the water. The second bedroom also features its own en-suite bathroom and private balcony, providing comfort and privacy for guests or additional residents. An extra laundry room and storage space are located just outside the unit, and there's also an in-unit washer and dryer for added convenience. The Anchorage allows one-week minimum rentals, making it a fantastic option for full-time living, a vacation retreat, or a lucrative investment. HOA fees cover insurance, water, sewer, trash, cable TV, internet, and concierge services. Amenities include a heated Olympic-size pool, outdoor barbecue grills, fishing spots, a boat slip, tennis courts, dual saunas, shuffleboard, a clubhouse, and a fitness center. Pickleball courts are also being added soon. Conveniently located near the Stickney Point Bridge, The Anchorage offers easy access to the mainland and downtown Sarasota, while being just steps from the beach, shops, restaurants, and everything Siesta Key has to offer. Unit is currently undergoing some upgrades. New Carpet is being installed in all bedrooms and closets. New upgraded vanities will be installed in all bathrooms. Renovations will be completed by the end of June. Updated Photos will be done after completion.

6415 Midnight Pass Road Unit 909, Siesta Key

$660,000
2 Beds 2 Baths A4628484 MLS 1291-A BLDG.
Deeded Beach access on Siesta Key! This immaculate corner unit condo is the perfect blend of serenity and modern living, boasting breathtaking views and top-notch amenities. Tucked away amidst lush tropical landscaping, this single-level ground floor condo offers a peaceful pond and fountain view right from your private lanai. It’s an ideal retreat for those seeking tranquility and a connection to nature. Upon entering, you’re greeted by a bright, warm ambiance that flows throughout the condo. The entire unit features stylish ceramic tile flooring, creating a seamless and crisp aesthetic. The kitchen is a culinary dream, equipped with granite countertops, stainless steel appliances, and a chef-inspired faucet and sink. Whether preparing a casual meal or hosting guests, this kitchen provides both functionality and elegance. The master suite is a true sanctuary, featuring a luxurious bathroom with dual sinks, granite countertops, and a walk-in shower. The second bathroom matches this standard of beauty, ensuring comfort for family and guests. Relax and unwind in the hurricane glass lanai, which serves as a peaceful retreat, perfect for enjoying your morning coffee or evening sunsets. This condo is not only beautiful but also practical, featuring a full-size washer and dryer for added convenience. For your vehicle, a single car garage provides secure parking. Gulf & Bay Club Bayside boasts a variety of exceptional amenities, including two heated pools, an exercise room, tennis courts, and pickleball courts. The clubhouse, available for reservations, features kitchen facilities perfect for celebrations and gatherings. Beach lovers will be thrilled with deeded beach access, just a short stroll across the street and down a scenic path leading to the powdery sands of the Gulf of Mexico. Plus, a trolley service runs every 15 minutes for easy transport. Perfectly situated near Siesta Key Village, this condo offers the best of both worlds: a peaceful sanctuary and access to shopping and dining. Don't miss out on this slice of paradise!

1291 Siesta Bayside Drive Unit 1291A, Siesta Key

$660,000
2 Beds 2 Baths A4618730 MLS Sandy Cove Iv BLDG.
.Enjoy Siesta Key in the tropical Gulf side community of Sandy Cove IV. This 2 bedroom, 2 bath unit comes turnkey furnished with many upgrades. New plumbing, vinyl plank flooring, refrigerator, washer/dryer, interior painting and newer AC unit. Located on the 3rd floor this bright and open floor plan will allow you to enjoy views of the pool, lush well maintained grounds and a peek at the Gulf of Mexico. The many amenities include a heated pool, kayak rack and historic clubhouse. Enjoy magnificent sunsets and city views from the private fishing pier and shell beach located in the park like setting along the Gulf coast. Sandy Cove is pet friendly and steps from the vibrant Siesta Key Village offering restaurants, shopping and entertainment. There is also easy access to downtown Sarasota to enjoy the arts district, theater, gourmet dining and more. Don't miss this opportunity to have all that Siesta Key has to offer! Great rental or call it home.

4900 Ocean Boulevard Unit 303, Siesta Key

$659,000
2 Beds 2 Baths A4680527 MLS Sea Village BLDG.
STUNNING FULL GULF VIEWS!..... STUNNING UPDATES THROUGHOUT!..... STUNNING SUNSETS!----You will be WOWED by this FURNISHED Siesta Key residence....just moments to the "baby powder" quartz white sands of TOP RATED Siesta Key Beach. This WELL-APPOINTED Spacious & PET FRIENDLY Two Bedroom/2 Bath condo has many desired UPDATES & FEATURES: Impact Windows/Sliders; Elevated Coastal Furnishings; Indulgent Primary Suite with Sumptuous Ensuite "Spa-Like" Bathroom; Custom Closets & BUILT-INS THROUGHOUT; Continuity of Materials & Finishes; In Unit Washer/Dryer; and a Large Kitchen with solid wood cabinetry; stainless appliances, glass tile backsplash & Generous amounts of Counter Space & Storage! You will ENJOY your morning coffee Dolphin Watching and your evening cocktails soaking in the Amazing Colors of Sunset over the Gulf.....Sea Village, conveniently located to dining/shopping/nightlife of the Main Village, features (2) gulfside Pools; fishing pier; Bike Storage & additional Storage Lockers. Perfect as Investment; Vacation or Year-Round Residence.

4660 Ocean Boulevard Unit O2, Siesta Key

$659,000
2 Beds 2 Baths A4647328 MLS
Built in 2009, this fully renovated first-floor 2-bedroom, 2-bathroom condo at The Beach Club at Siesta Key is a rare opportunity offering both personal enjoyment and strong rental income. Just steps from the world-famous Siesta Key Beach, the property has a proven history of short-term rental success, with owner usage permitted up to 120 days per year—making it an ideal balance of leisure and investment. Uniquely positioned within the community, the unit feels like an end unit thanks to the way the buildings are angled, offering enhanced privacy and natural light. It’s also the only first-floor condo in the complex with its own private covered balcony, surrounded by lush tropical greenery. This exclusive outdoor space provides a peaceful retreat with serene views of the pool while maintaining privacy through natural landscaping. Inside, the updates are extensive. The condo features fresh interior paint, brand-new living room furniture, modern lighting, a new dining set, flat-screen TVs in every room, and a brand-new washer and dryer. The open layout includes a bright and fully equipped kitchen with stainless steel appliances, offering a turnkey living space that is comfortable and inviting for both owners and guests. The property is fully furnished and professionally managed on-site, providing a hands-off experience with services including guest bookings, communication, cleaning, and maintenance. Amenities include a heated pool, hot tub, complimentary Wi-Fi, and free beach chairs and umbrellas. The Beach Club offers direct access to the cool white sands of Siesta Key Beach just steps away through a shared community gate—making beach days effortless and convenient. Located mid-island and just minutes from the Stickney Point Bridge, this unit provides easy access on and off the island and close proximity to shopping, dining, and outdoor recreation in the vibrant Siesta Key Village. With a combination of premium upgrades, a rare private balcony, and a stellar rental track record, this condo stands out as one of the premier offerings on Siesta Key.

1020 Sun N Sea Drive Unit 104B, Siesta Key

$657,000
2 Beds 2 Baths A4601287 MLS Unit 206b BLDG.
Welcome to Beach Club at Siesta Key, where an exceptional investment opportunity awaits mere steps from the iconic Siesta Key Beach. This 2-bedroom, 2-bathroom second-floor condo boasts a proven track record in short-term rentals, ensuring a steady income stream for potential investors. With the owner's personal use restricted to 120 days per calendar year, this provides an ideal balance between generating revenue and providing opportunities for leisurely retreats. Upon entering the fully turnkey unit, guests are greeted by sea-inspired decor that sets a serene coastal ambiance. Each living space is equipped with a TV for entertainment, while the modern kitchen features stainless steel appliances and convenient in-unit laundry facilities cater to guests' comfort and convenience. Forget about the hassles of property management; a professional on-site property management team handles everything from bookings to maintenance to cleaning, ensuring a worry-free experience for owners. Guest amenities include a heated pool, a relaxing hot tub, free wi-fi, and complimentary chairs and umbrellas for enjoying beach days. Situated mid-island and just moments away from the Stickney Point Bridge, this condo offers easy access to explore beyond the island. Whether guests seek thrilling adventures like parasailing or prefer activities such as scenic trails, biking, or kayaking, there's something for everyone to enjoy. When it's time to immerse in the vibrant Siesta Key lifestyle, Siesta Key Village beckons with its shopping, dining, and entertainment options, completing the perfect coastal getaway.

1020 Sun N Sea Drive Unit 206B, Siesta Key

$655,000
2 Beds 2 Baths A4691019 MLS 2 BLDG.
This stunning 2-bedroom, 2-bath retreat is steps from Siesta Key’s renowned powdery white sand. Fully renovated with premium, top-to-bottom upgrades (new plumbing, electrical, HVAC, and high-end appliances), this turnkey property is rental-ready. This unit has been completely redone with quality everything and no expenses spared! Enjoy immediate income and income potential with easy access to Village dining and shopping via walking or a free trolley. Jamaica Royale is a well-maintained beachfront community known for its private deeded beach and resort-style amenities, including three pools (one beachfront), newly renovated beachside restrooms and changing facilities, and an outdoor kitchen with grills and seating. With onsite rental management, this condo provides an easy, low-maintenance investment opportunity. Whether you’re searching for a turnkey vacation rental, income-producing investment property, or coastal retreat, this Jamaica Royale condo offers location, luxury, and beach good times!

5830 Midnight Pass Road Unit 86, Siesta Key

$655,000
2 Beds 2 Baths A4685194 MLS 1054 BLDG.
Siesta Key investment property and nightly rental opportunity at Beach Club at Siesta Key, approved for true nightly vacation rentals near world famous Siesta Key Beach. Historical rental income approaches $83,000 annually, with modeled revenue potential exceeding $103,000 if owner use nights were made available for rental. Historical bookings show approximately 209 reserved nights annually with average nightly rates between $397 and $450, creating a strong income producing profile relative to the $660,000 list price. Detailed rental history, booking records, and revenue analysis are available for review. Few properties on Siesta Key combine true nightly rental eligibility, documented rental performance approaching $83,000 annually, modeled revenue potential exceeding $103,000, extensive renovation, and resort style amenities within this price range. Unit 106D is the largest floor plan in the community and is positioned as a private corner residence overlooking the heated resort style pool with minimal foot traffic. Built in 2009 with elevated construction, the building sustained no storm related damage. This Unit has been recently and extensively renovated beyond prior community finishes. While some online rental marketing may reflect earlier interiors, the unit now features luxury vinyl plank flooring throughout, matching quartz countertops in the kitchen and bathrooms, updated cabinetry, stainless steel appliances, modern fixtures, and renovated kitchen and bath spaces. A full size washer and dryer supports guest convenience and longer stays. From entry, the space presents more like a boutique resort suite than a typical beach rental. Upgrades were selected for both visual appeal and rental durability. Offered fully furnished and turnkey, the property is positioned for immediate continuation of nightly rental operations. A detailed 3D virtual tour is included with the listing to allow buyers to explore the residence remotely. Due to consistent guest bookings, showing availability may require advance coordination. Ownership allows up to 120 days of personal use annually while maximizing income through nightly rentals. Professional on site management handles reservations, guest communication, cleaning, and maintenance. Community amenities include a heated pool, hot tub, grilling areas, shared patio spaces, complimentary beach chairs and umbrellas, on site office support, and gated beach access to Siesta Key Beach. Located near the South Bridge with Crescent Market and the restaurants, bars, and shops of Siesta Key’s South Village just around the corner. Recent interior updates and the residence’s desirable pool view location create additional opportunity for increased booking activity and nightly rates as updated photography and marketing are introduced. Historical booking data demonstrates consistent guest demand and strong occupancy, while analysis of owner use nights indicates additional revenue potential depending on preferred usage strategy. Properties offering true nightly rental flexibility with Siesta Key Beach access, documented rental performance approaching $83,000 annually, modeled revenue potential exceeding $103,000, and extensive renovation rarely become available within this price range on Siesta Key. Detailed rental history, booking records, and full revenue analysis are available upon request.

1054 Sun N Sea Drive Unit 106, Siesta Key

$655,000
2 Beds 2 Baths A4646075 MLS Harbor Towers Yacht & Racquet BLDG.
Coastal living at it's best at Harbor Towers Yacht & Racquet Club. You will fall in love from the moment you enter this gated premier waterfront paradise on Siesta Key which recently completed a $13 million, four-year hurricane hardening and structural upgrade program in 2024, meeting all new safety standards for hurricane/wind protection. WOW this beautifully furnished 2-Bedroom, 2-Bathroom condo INCLUDES IT'S OWN CARPORT (A RARE COMMODITY!!) and two balconies with unobstructed views of the intracoastal, marina, and pool. This unit has been tastefully renovated, plantation shutters and freshly painted through out including all new 6 panel interior doors, new furnishings 11/24, new A/C 2023, new water heater 2022, and 20" tile flooring on the diagonal through out. The amenity rich Harbor Towers is in a class of its own, offering boating, fishing, kayaking, bayfront gazebo, two heated pools, large BBQ area, kitchen prep area, state of the art fitness center, an active three Har-Tru tennis courts, a sauna, a clubhouse, high-speed WIFI, a fabulous marina with new docks, pilings, electrical pedestals and water. If interested, the association has slips available on a first come first serve basis at $3 a foot. The property is conveniently located moments from Siesta Key Village with an abundance of shopping, dining, and nightlife options. Enjoy getting around Siesta Key on the free trolley that stops right outside the community or you can walk to the World-Famous Siesta Key Beach! If you are not planning on living here full time or just want an investment, this unit can be rented for a two-week minimum rental period plus you can utilize the on-site rental program or manage rentals yourself.

5855 Midnight Pass Road Unit 204, Siesta Key

$655,000
2 Beds 2 Baths A4597411 MLS 101 Whispering Sands BLDG.
Discover the perfect blend of breathtaking VIEWS and an unbeatable LOCATION at this waterside haven on Siesta Key! Nestled in the heart of the Village of Siesta Key, Whispering Sands presents an exclusive opportunity with 800 feet of PRIVATE BEACH front along the Gulf of Mexico. Step into luxury with a recently updated and meticulously cared-for open floor plan featuring brand-new flooring, a state-of-the-art AC unit, ceiling fans, and a fresh coat of paint throughout. This charming two-bedroom, two-bathroom condo boasts an expansive lanai overlooking a serene lagoon – providing a tranquil retreat that spans the entire length of the residence. The modern kitchen is a chef's delight, showcasing granite countertops, stylish wood cabinetry, and a top-of-the-line Bosch dishwasher. The guest bath has been tastefully renovated to perfection. Store your beach essentials and accessories securely in the individual locked storage area. Whispering Sands goes beyond just a residence; it's a vibrant community with meticulous upkeep. Enjoy a plethora of amenities, including 2 heated swimming pools (one right on the beach), a tiki hut with a community picnic area, grills, an updated fitness center, and 2 recreational buildings. Venture on a brief stroll to the renowned Siesta Key Village, offering an array of dining options, entertainment, and shopping opportunities. Your dream home awaits – seize the chance to make Whispering Sands your own!

101 Whispering Sands Drive Unit 204TRO, Siesta Key

$655,000
2 Beds 2 Baths A4578759 MLS
Welcome to your dream coastal retreat! this 2-bedroom, 2-bathroom home has undergone a complete and exquisite remodel, ensuring a luxurious and comfortable living experience. Located within prestigious Whispering Sands, this property provides unparalleled access to a private beach and not one but two private pools, making it an idyllic retreat for those seeking an exclusive coastal lifestyle. Step inside this thoughtfully designed haven, and you'll be captivated by the tasteful and contemporary finishes throughout. Every detail has been carefully considered, creating an inviting ambiance that immediately makes you feel at home. The recently added secluded and hurricane impact four seasons room with privacy glass is a true standout feature keeping you comfortable in any weather. This versatile space boasts its own split cooling system, making it an ideal spot to relax and unwind year-round. Step outside, and you'll be greeted by a paradise of amenities. The private beach access is just a short stroll away, allowing you to savor the white sandy shores and gentle waves anytime you desire. In addition to the beach, the community offers two private pools, and a workout facility. Whether you prefer to relax poolside with a refreshing drink or take a revitalizing dip, these pools provide the perfect setting to unwind and bask in the coastal ambiance. You also have a private gate-access across the street to walk directly into the Siesta key shopping center and restaurants. Back inside, the masterfully remodeled interior boasts a spacious and airy layout that effortlessly blends living, dining, and kitchen areas. The gourmet kitchen is a chef's delight, featuring top-of-the-line stainless steel appliances, elegant cabinetry, and gleaming countertops. Create culinary masterpieces while enjoying the company of loved ones in the open and inviting space. Both bedrooms are generously sized, offering a peaceful retreat to rest and recharge. The modern bathrooms exude sophistication with premium fixtures, stylish tiling, and contemporary lighting. Seize the opportunity to make this coastal haven your own. Embrace the unparalleled comfort, convenience, and exclusivity that this 2-bed, 2-bath gem has to offer. With its newly remodeled interiors, private beach access, and two private pools, this property represents the epitome of coastal living at its finest. Don't miss out on your chance to experience the ultimate in coastal luxury! Fully remodeled from studs out in 2017; see attached improvements sheet for details

111 Whispering Sands Circle Unit V-38, Siesta Key

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