Location: Sarasota , 34242
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5880 MIDNIGHT PASS RD #511, SARASOTA, FL 34242
$2,490,00092 Days on yellowkey MLS ID: A4684184
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2481 Built: 1982 Tax: $13,010 (2025)Community: CasarinaCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,010
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: You will be WOWED! by this Furnished 2400+ Sq Ft of Elegant BEACHSIDE LIVING with (3) Generously Sized Bedrooms & (3.5) Baths with STUNNING FINISHES THROUGHOUT!.....RARELY AVAILABLE Corner Unit in this Special Boutique Community---a Resort-Style PET FRIENDLY "low density" plush 7 acre residential complex with over 200 feet of Powdery Quartz sand frontage along with "Old Florida" Clubhouse; Courts; Beachside Pool & Cabanas and an Onsite Manager....Upon Entrance you will be Greeted with a Grand Hallway that leads to a BRIGHT & SPACIOUS Floor Plan, reminiscent of a Single Story Home...Each Bedroom is Privately Located, each with it's own Full Baths....ENTERTAINING is "Extra Special" with Expansive Living Areas and Ideally Centrally Located Wet Bar....WELL-APPOINTED INTERIORS, including: Porcelain Tile throughout; Quartz Countertops; Hurricane Impact Windows/Sliders; "Hotel Style" Primary Suite with Seating Enclave & Sumptuous Ensuite Bath; Abundant Storage & Closet Space; In-Unit Laundry and Importantly...ease of Indoor/Outdoor Living with Multiple Sliders leading to "Wrap-Around" Balcony/Lanai--Perfect for Morning Coffees or Indulging your Favorite Cocktails while Watching Majestic Sunsets over the Gulf....*****Deeded Beach Access, convenient for long strolls collecting Seashells or just "Toes in the Sand" relaxing at Top Rated Siesta Key Beach. Dining/Shopping and Nightlife of the main village are just minutes away...GARAGE PARKING...---Ideal as Second Home/Vacation, Investment or Year-Round Residence. Island Living @ It's Finest!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mike Martino (773-619-8593)
8779 MIDNIGHT PASS RD #502H, SARASOTA, FL 34242
$735,000171 Days on yellowkey MLS ID: A4673776
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1303 Built: 1980 Tax: $5,825 (2024)Community: Island Reef Ii Ph 1 2 & 3Condo
Taxes:$5,825
Tax Year: 2024
Remarks: A rare top floor opportunity in a quiet corner of Island Reef. Stunning views of Little Sarasota Bay and the Gulf from the always-shaded lanai or balcony where sunrises and sunsets are easily visible this time of year. Renovated from top to bottom, this is one of the few units with "Impact Glass" already installed in the lanai. This is a true turn-key opportunity allows you to move in immediately and start enjoying this little corner of paradise. Kitchen features granite countertops, and the unit includes an in-residence laundry. Furnished and complete with a carport! Island Reef is a serene waterfront community, and one of the few Gulf-to-Bay communities that offers many desirable amenities including a beach, boat docks (lifts allowed), two lit tennis courts, pickleball, two fitness rooms, kayak storage, a library, billiards, a game room, a clubhouse, two heated pools and gas grills. Pet friendly! Tropical gardens enhance the appeal of Island Reef and this wonderful community, conveniently located near two of Siesta Key's popular restaurants. A complimentary trolley provides access to Siesta beach, Siesta Village offering dining, shopping, ice cream, mini donuts, cute brunch spots, dancing, and live music every night of the week.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Marlene Marshall (941-539-8850)
5880 MIDNIGHT PASS RD #306, SARASOTA, FL 34242
$1,285,000253 Days on yellowkey MLS ID: A4665591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $8,594 (2025)Community: CasarinaCondo
Taxes:$8,594
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Welcome to Your Siesta Key Sanctuary. Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming clubhouse—all just steps from the famous crystal sands of Siesta Key Beach. Located on the third floor, this residence boasts a newly updated kitchen, luxury vinyl flooring, an updated guest bath, and a new AC unit. Enjoy serene garden views from your 17-foot screened balcony, with a peek-a-boo view of the Gulf and pool areas. Need extra space? The flexible 8’ x 8’ breakfast nook can easily be transformed into a home office or additional sleeping area. Casarina is a well-maintained 89-unit complex with fully funded reserves and recent complex renovations. Owners can bring one small pet, and enjoy the convenience of a covered carport and access to the free Siesta Key Trolley for dining, shopping, and entertainment. Whether you're paddle boarding, kayaking, biking, or simply relaxing on the beach, this condo offers the perfect blend of island lifestyle and resort-style amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
8779 MIDNIGHT PASS RD #401H, SARASOTA, FL 34242
$595,000297 Days on yellowkey MLS ID: A4661131
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1485 Built: 1980 Tax: $4,969 (2025)Community: Island Reef Ii Ph 1 2 & 3Spa: NoCondo
Taxes:$4,969
Remarks: ENJOY THE BAY VIEWS FROM THIS UPDATED HOME! Kitchen with Granite countertop, Laundry in Residence, office space off foyer. Partially Furnished! Carport! Island Reef is a serene waterfront community, one of the few Gulf to Bay community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed) two lit tennis courts, pickleball, 2 fitness rooms, Kayak Storage, Library, Billiards, game room, clubhouse, two heated pools and Gas Grills, PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key’s popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cut brunch spots and dancing and live music every night of the week!
6415 MIDNIGHT PASS RD #705, SARASOTA, FL 34242
$584,500103 Days on yellowkey MLS ID: A4683086
REDUCED by $15,300 (2.6%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1975 Tax: $3,669 (2025)Community: AnchorageSpa: NoCondo
Taxes:$3,669
Remarks: Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. Speaking of boats you can dock your boat on our giant seawall for $10.00... yes...ten dollars a month. Your new condominium is an open floor plan with living room/dining room combo. All three rooms have hurricane sliding doors. The main bedroom is very large and the master bath has a walk-in shower. The guest bedroom has 2 double beds with a tub/shower! You also have one covered parking space underneath the main building valued at $25,000.00. We have a beach easement to Siesta Key beach! Our Seawall was replaced in 2019. 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! There is a trolly that you could take to Siesta Key Village to enjoy more shopping, entertainment and dining options. The Anchorage is very conveniently located near Stickney Point Bridge to give you easy access to the mainland, including downtown Sarasota!
Listing is courtesy of: DELUCA REALTY INC (941-487-7162)
Listing Agent: Anthony Deluca (941-685-6001)
8710 MIDNIGHT PASS RD #203B, SARASOTA, FL 34242
$699,00061 Days on yellowkey MLS ID: A4688439
REDUCED by $36,000 (4.9%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1650 Built: 1980 Tax: $8,179 (2025)Community: Tortuga Beach ClubSpa: YesCondo
Taxes:$8,179
Remarks: Perfect Beach Life on Siesta Key! Tortuga Beach has so much to offer. Private 77 unit complex has the small intimate feel with a luxury with it's many offerings. Private Beachfront, Tennis, Clubhouse with kitchen, library and entertainment area, indoor/outdoor community pool, sauna, sun deck with grills and seating, and boat slips across the street on the bay. There are 3 slips open for rental for $300 a year. Just fill out your application. With the friendly residents you can enjoy the relaxing atmosphere with the wonderful views of the Gulf of Mexico from daytime sunbathing to sunset pleasures. Upon arrival to the condo you will find an enclosed lanai to offer more living space in the 1650 Square feet. Kitchen has plenty of space with it's wood cabinets and granite countertops with pass through breakfast bar. New AC. Split Floor plan. Primary bedroom closet contains the washer dryer but Tortuga also offers a laundry facility if you are in need. Separate dining room just off the kitchen for entertainment. Covered Parking spot very close to the entrance and elevator for easy loading and unloading.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
6480 MIDNIGHT PASS RD #503, SARASOTA, FL 34242
$1,199,00019 Days on yellowkey MLS ID: N6144252
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,073 (2025)Community: Siesta BreakersCondo
Taxes:$9,073
Middle School: Sarasota Middle
Remarks: Turnkey-furnished and move-in ready, experience the ultimate coastal lifestyle in this beautifully maintained beachfront condo located on the beautiful, world-famous Siesta Key. Enjoy the soft, white sand of Crescent beach, with a Beach Attendant managing a 200 ft section of private beach. Whether you’re searching for a full-time residence, seasonal getaway, or income-producing investment property, this luxury condo offers the perfect blend of comfort, convenience, and breathtaking Gulf views. Enjoy relaxing mornings and stunning sunsets from your private screened balcony overlooking the sparkling heated pool, tropical courtyard, and turquoise waters of the Gulf of Mexico. Inside, the condo features an open and airy floor plan filled with natural light, tile flooring throughout the main living areas, and tasteful coastal finishes. The kitchen offers ample cabinetry, stainless steel appliances, recessed lighting, tray ceiling detail, and space for entertaining guests with a breakfast bar & dining area. The spacious primary suite provides a peaceful retreat with pool view, plantation shutters and sliding doors that open to the balcony. The ensuite has been updated with dual granite vanities, large walk-in shower and abundant storage. Open the sliders to the balcony for a seamless indoor-outdoor living experience. Residents and guests enjoy resort-style amenities including a beachfront heated pool, direct private beach access with free beach lounge chairs, option to rent an umbrella or cabana, beautifully maintained grounds, covered parking, grills and lighted tennis / pickleball courts. This condo also offers excellent rental potential, making it a fantastic opportunity for investors seeking vacation rental income in one of Florida’s most desirable beach destinations. Ideally located, walk to restaurants, bars, grocery, boat/bike/kayak/jet ski rentals, gift shops and more! Wake up to the beautiful beach & ocean views, where every day feels like a vacation!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Heather Lakeman (941-412-6083)
6266 MIDNIGHT PASS RD #404, SARASOTA, FL 34242
$1,180,00040 Days on yellowkey MLS ID: A4691031
REDUCED by $10,000 (0.8%) on 05/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1263 Built: 1980 Tax: $10,169 (2025)Community: Excelsior Beach To BayCondo
Taxes:$10,169
Remarks: RARELY AVAILABLE INCOME PRODUCING EXCELSIOR GULF FRONT UNIT This large unit has been completely updated and renovated with Impact windows and new HVAC in 2025, Upgraded kitchen and all appliances, plantation shutters, and Hunter Douglas window shades, in-unit washer/dryer, custom tile throughout, tastefully appointed with fine furnishings and all the accoutrements for the Siesta Beach lifestyle. The under-building covered parking and elevators are conveniently located the spacious gulf front patio is the perfect place to relax and enjoy the fabulous views. Excelsior is your Gulf to Bay resort residence with a Private White Sand Beach, Two Large Heated Swimming Pools, Poolside Restrooms / Hot Water Showers, Shuffleboard, Two Heated Whirlpools, Two Lighted Tennis Courts, Two Pickle Ball Courts, Fitness Center, Large Gulfside Sun Deck, Beach Loungers and Chairs, Lounges & Sunbathing Parapets' Outdoor Barbecues / Picnic Areas, Intercoastal Fishing Pier / Shaded Viewing Area, Community Room and monthly community events', Library' Walk to Shopping, Dining, Bike & Boat Rentals Located just a half mile to the S village shops, dining and marina makes this a great spot to enjoy all the best that world famous Siesta Key has to offer.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Bob Stahlschmidt Ii (941-266-2684)
1080 W PEPPERTREE LN #305A, SARASOTA, FL 34242
$1,135,00041 Days on yellowkey MLS ID: A4690895
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1365 Built: 1974Monthly Fee: $1,239 Tax: $7,537 (2025)Community: Peppertree Bay IvSpa: NoCondo
Taxes:$7,537
Remarks: Rarely available beach-view residence with deeded access to the renowned shores of Siesta Key Beach. Located on the third floor, this bright and inviting unit features a versatile layout, including a pull-out sofa on the lanai with a privacy partition—perfect for creating a comfortable third sleeping area for guests. The well-designed split floor plan offers a spacious dining area, an eat-in kitchen with bar seating, two generously sized bedrooms, and two full bathrooms. Ample storage can be found throughout the home, along with the added convenience of in-unit laundry. Enjoy the ultimate coastal lifestyle with just a short stroll—approximately 70 steps—to the beach, as well as easy access to the community clubhouse, fitness center, and pool. Residents are treated to an array of resort-style amenities, including two heated swimming pools, two clubhouses ideal for entertaining, tennis courts, a fully equipped fitness center, and multiple BBQ areas. A scenic fishing pier invites you to cast a line or simply relax and watch boats and yachts glide by. Ideally located just minutes from shopping, dining, entertainment, golf courses, biking trails, boating, and the vibrant arts and culture of Sarasota. Beautifully updated in 2023 (to the studs, to include all new electric and plumbing) and offered turnkey furnished, this residence is move-in ready and perfectly suited as a primary home, vacation getaway, or income-producing investment.
Listing is courtesy of: PEPPERTREE BAY REALTY INC (941-914-3380)
Listing Agent: Eliza Miller (941-914-3380)
1203 SIESTA BAYSIDE DR #1203-D, SARASOTA, FL 34242
$498,00042 Days on yellowkey MLS ID: A4690769
REDUCED by $27,000 (5.1%) on 04/27/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $5,340 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$5,340
Remarks: Sellers Are Highly Motivated! Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
4900 OCEAN BLVD #304, SARASOTA, FL 34242
$685,00078 Days on yellowkey MLS ID: A4686177
REDUCED by $65,000 (8.7%) on 05/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1978Monthly Fee: $1,371 Tax: $9,084 (2025)Community: Sandy Cove IvCondo
Taxes:$9,084
Remarks: RECENTLY REDUCED -- TURNKEY FURNISHED -- WITH YOUR VERY OWN PRIVATE SHELL BEACH! Perched among the treetops in the beloved Sandy Cove community on Siesta Key, this beautifully renovated 2BR/2BA residence offers a rare blend of privacy, charm and authentic island living. With 1,200+/- sq. ft. of thoughtfully designed space and three private balconies, life here feels like a peaceful retreat surrounded by nature, where sunlight filters through the trees and the gentle sounds of the island become part of every day. Inside, the residence has been fully updated with a relaxed tropical style that feels both fresh and welcoming. The open floor plan centers around a spacious waterfall quartz island that anchors the kitchen and living areas, creating a natural gathering place for entertaining or quiet evenings at home. Large sliding doors open to the balconies, extending the living space outdoors and welcoming in the Gulf breezes. Morning sunrises fill the residence with soft light, creating an airy atmosphere as the trees rustle just beyond the windows. From the balconies, it is common to see mourning doves, egrets and osprey gliding overhead, with the occasional eagle soaring past. The primary suite features his-and-her closets and private balcony access, while the guest bedroom and bath provide comfortable accommodations for family or visitors. All sliders and windows come with custom room darkening shades. The unit also offers reserved covered parking, assigned storage unit, inside mail room and secured door code entry. The HOA covers sewer, water, pest control, trash, lounge chairs, umbrellas and tables at the pool and beach, and one Gig of fiber optic Internet. The stroll to the waterfront is part of the experience itself. A winding path lined with banyan and palm trees leads to Sandy Cove’s private Gulf-front lawn and beach area. When you turn the corner and the Gulf opens before you, the moment feels almost surreal, like you have just arrived in paradise. Located within Sandy Cove, a distinctive Old Florida community designed by Sarasota School of Architecture master Frank Folsom Smith, residents enjoy private beach access, kayak and paddleboard storage, clubhouse for entertaining, fishing pier and a quaint beach area with chairs and tables to relax, read a book, chat with friends and watch the dolphins play while enjoying magnificent sunsets and panoramic Gulf views that capture the timeless spirit of the island. Ideally positioned on the north end of Siesta Key, Sandy Cove IV sits just a short walk or bike ride from Siesta Key Village, where you can spend the afternoon browsing boutiques, enjoying fresh seafood and vibrant dining, catching live music drifting from open-air patios or simply taking in the laid-back rhythm that makes the Key such a beloved destination befitting its world-famous beach. Here, the feeling is unmistakable. The breeze, the water and the view become your own sanctuary, a place where it quietly feels like vacation is always waiting just outside your door.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Tracey Stetler (941-266-9001)
611 VENICE LN, SARASOTA, FL 34242
$1,072,00040 Days on yellowkey MLS ID: A4686684
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2168 Built: 1972Monthly Fee: $42 Tax: $9,119 (2025)Community: Siestas Bayside Waterside EastSpa: NoSingle Family
Taxes:$9,119
Remarks: Island living meets easy everyday comfort in this turnkey furnished Siesta Key pool home. With 3 bedrooms, 2 bathrooms, approximately 2,168 square feet of living space and a 2-car garage, there is room for full-time living, a vacation getaway, or a high-demand rental. Built of concrete block, this Ruth Richmond home offers peace of mind with major updates already done: brand new metal roof with warranty (April 2026), AC with warranty (August 2023), garage door (March 2025), front door (April 2025), and low-maintenance terrazzo flooring. Step inside to an inviting, well-planned layout with the primary suite on one side of the home with updated ensuite bath, and guest bedrooms on the other, offering privacy for family and visitors. The newly updated kitchen features granite countertops and modern finishes. The living room, dining area, and sunroom flow together seamlessly and overlook your private backyard oasis. Outside, enjoy your own sparkling, “sports pool” with a shallow area across the center, ideal for hosting friends for a game of pool volleyball, playing with the kiddos, or lounging. A brand-new fence with self-closing gates (April 2025) wraps the yard in privacy, creating a quiet retreat after a day at the beach. Located on world-famous Siesta Key with low HOA fees of just $500 per year, you’re just minutes from the white quartz sand beaches, charming village shops and restaurants, boating, kayaking, and all the island lifestyle has to offer. This home combines an incredible coastal location with everyday convenience. Turn the key, drop your bags, and start living the Siesta Key lifestyle at 611 Venice Lane.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
1249 DOCKSIDE PL #110, SARASOTA, FL 34242
$825,00067 Days on yellowkey MLS ID: A4687526
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1982 Tax: $7,705 (2025)Community: Harbour TowneCondo
Taxes:$7,705
Remarks: Welcome to your slice of paradise on Siesta Key! This beautifully maintained two-bedroom, two-bath first-floor end unit offers a blend of comfort, convenience and coastal living with no stairs to climb and easy access throughout. Ideally just a short two-block stroll to world-famous Siesta Key Beach, you’ll enjoy powdery quartz sand that stays cool underfoot, even on warmest days. This well-maintained island condominium features a roomy layout and comes fully furnished, making it move-in ready or ideal as an income-producing rental. The generous screened lanai overlooks the peaceful marina, creating a spot to relax with your morning coffee or unwind at sunset. Boating enthusiasts will appreciate the sought-after deeded boat dock, providing direct water access to the Intracoastal Waterway. The private garage with overhead storage offers plenty of extra space for beach, fishing gear and more. Within the desirable Harbour Towne community, residents enjoy a host of amenities including a heated swimming pool, spa, tennis and pickleball courts, plus a welcoming clubhouse known for its friendly, social atmosphere. Whether you're seeking a seasonal getaway or investment opportunity, this condominium checks every box. Enjoy the laid-back Siesta Key lifestyle with dining, shopping and entertainment just minutes away, all while living near one of the world’s celebrated beaches.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
5132 JUNGLE PLUM RD, SARASOTA, FL 34242
$5,985,000383 Days on yellowkey MLS ID: A4651663
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 6928 Built: 2008Monthly Fee: $247 Tax: $45,860 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$45,860
Remarks: Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
9150 BLIND PASS RD #206, SARASOTA, FL 34242
$999,00010 Days on yellowkey MLS ID: C7526359
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1710 Built: 1975 Tax: $9,204 (2025)Community: Fishermans HavenCondo
Taxes:$9,204
Remarks: Some photos have been virtually staged. Welcome to Fishermans Haven on South Siesta Key, where coastal comfort and modern updates come together in this beautifully renovated 3-bedroom, 3-bath waterfront condo. Offering over 1,700 square feet of bright, open living space, this residence has been fully updated from top to bottom with new flooring, a beautifully redesigned kitchen, updated bathrooms, and stylish finishes throughout. Natural light pours into the living areas, creating a warm and airy feel, while the private patio offers peaceful water views that perfectly capture the relaxed island lifestyle. Located right next to Turtle Beach and just a short drive from the world-famous Siesta Key Beach, you’ll enjoy easy access to beaches, boating, kayaking, restaurants, and shopping. The community features great amenities including a heated pool, sundeck, grilling area, kayak and bike storage, and elevator access. Additional updates include a new HVAC system and hot water tank replaced in 2026. Community improvements are also underway and expected to be completed this summer, including pool restoration, exterior painting, and parking lot repairs making this an even more attractive opportunity to own your piece of paradise on Siesta Key.
Listing is courtesy of: RE/MAX PALM REALTY (941-743-5525)
Listing Agent: Taylor Brady (239-896-6433)
5790 MIDNIGHT PASS RD #209, SARASOTA, FL 34242
$1,125,00024 Days on yellowkey MLS ID: N6144235
REDUCED by $25,000 (2.2%) on 05/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1433 Built: 1979 Tax: $9,389 (2025)Community: Gulf & Bay Club Ph 1Condo
Taxes:$9,389
Remarks: Welcome to highly sought-after "Building A" at the Gulf & Bay Club located on Siesta Key Beach! Where you'll be just steps to the No. 1 BEACH in the USA! As you enter the gated community, you will feel like you've landed in paradise as you make your way down the brick paved streets to the building closest to the beach. Offered TURN-KEY FURNISHED, this nicely updated 2-bedroom, 2-bathroom condo located on the second floor offers quick and easy access to the amenities and is just steps to private beach access! From the moment you enter you'll be drawn to the incredible views of the beach, gulf, pool, pond and beautiful grounds of the community! The kitchen features a large island, breakfast bar, granite countertops, new appliances and plenty of cabinetry for storage. The open floor plan is great for entertaining. Comfortably sleeps 6 people. Both bathrooms have been beautifully updated. New wood flooring follows throughout with tile in the kitchen. The unit offers an inside laundry room and an owner’s storage closet for your beach toys! Enjoy several upgrades including ceiling fans in each room, crown molding, custom trim woodwork and more! Amenities include 32 pristine acres, 800 feet of private beach on Siesta Key, a lush Tropical courtyard with a freshwater lake, 3 large heated pools, outdoor barbecuing areas, 6 tennis courts including 1 Har-Tru court, pickleball, basketball, shuffleboard, 2 clubhouses, media center, pool table and TV’s, fitness center and more! Schedule a showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-493-1000)
Listing Agent: Jamie Mullis (941-716-1375)
145 AVENIDA MESSINA #3, SARASOTA, FL 34242
$630,000242 Days on yellowkey MLS ID: A4667146
2 Days Off yellowkey (back on 3/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1025 Built: 1966 Tax: $5,561 (2024)Community: Villa NavarraCondo
Taxes:$5,561
Remarks: Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic tile flooring throughout. The guest bath was completely remodeled along with the primary bathroom that has been expanded for a little extra elbow room. This has a new water heater and HVAC system, new roof in 2025, all new doors, impact windows, ceiling texture and it doesn't stop there. This comes very tastefully turnkey furnished in a warm coastal theme! Relax on your screened patio and look out to palms and foliage and take in the gulf breezes. The pristine beach is 2/10 of a mile away and the SK Village is about 100 feet away with a large selection of restaurants, shopping, grocery, nightlife, and so much more! Don't miss this beautiful condo in the heart of all that Siesta Key has to offer in a very well-run complex.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joe Cleary (941-650-8485)
5103 WINDWARD AVE, SARASOTA, FL 34242
$3,549,000149 Days on yellowkey MLS ID: A4676707
REDUCED by $108,625 (3.0%) on 05/05/2026
Bed: 3 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3034 Built: 2026 Tax: $4,091 (2024)Community: Sara SandsSpa: YesSingle Family
Taxes:$4,091
Remarks: Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white sand beaches and charming Siesta Village easy and convenient. The free-flowing plan, offering 3,034 sq. ft. of open living, will seduce you with its inviting atmosphere wrapped in casual elegance and modern sophistication. With plenty of natural light, the great room boasts double-height ceilings adorned with rich architectural detail, an elaborate floor-to-ceiling fireplace wall, and see-through views to the expansive outdoor space and coveted canal setting. Beyond the great room’s glass doors, an entertaining lounge with wood ceiling accents, a professional grill station, and a heated pool/spa await your plans for spending cherished time with family and friends. As evening approaches, night lighting transforms the beautiful backyard and creates a timeless ambiance that encourages relaxation and reflection. A gorgeous kitchen is enhanced with an abundance of amenities including a premium Sub-Zero and Wolf appliance package, stone counters, stylized fixtures and finishes, a walk-in pantry, and adjoining laundry. The formal dining room features a built-in buffet and French doors leading to a brick paver patio, making it a wonderful spot for dining alfresco under the stars. The bonus room, with wet bar and pool bath, features two walls of glass sliders showcasing the extensive outdoors and picturesque water views. The primary suite is an oasis of serenity with an office outfitted with built-ins, a generous wardrobe for two, and an exquisite bath intended to pamper and spoil with a free-standing tub, a frameless glass shower with rain head, separate vanities with stone tops, and a water closet. Two additional en-suites offer plenty of room to unwind and rejuvenate in comfortable privacy. A brick paver drive, a 3-car garage, professional landscaping with timed irrigation, eye-catching curb appeal, and other notable customizations inside and out, complete this magnificent waterfront home. This fresh new residence, designed by the award-winning team at Allegra Homes, has been artfully designed and crafted to offer the highest quality to those who live here. An exciting opportunity to make this island paradise yours!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1700 COVE II PL #324, SARASOTA, FL 34242
$824,90073 Days on yellowkey MLS ID: A4686403
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $25,000 (2.9%) on 05/17/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $7,965 (2025)Community: Midnight Cove IiCondo
Taxes:$7,965
Remarks: Under contract-accepting backup offers. 3 BEDROOMS ON SIESTA KEY! ONE WEEK RENTALS! DEEDED BEACH ACCESS! WATER VIEWS! DOCKS AVAILABLE! Fantastic 3 bedroom townhouse at Midnight Cove II. 2nd and 3rd floor with lovely views and deeded beach access. Plenty of room for family and friends. Large sized living, dining and kitchen area. Perfect for family gatherings! Midnight Cove II offers deeded beach access directly across the street, marina with slips available, beautiful grounds, grilling area, tennis, pickleball, basketball court, fitness center and a large, heated pool. And bring the large pup too! Great association with onsite rental and management office. Fully funded reserves, milestone inspections complete! Turnkey furnished too! Walk to nearby dining, shopping, water sports and more. See this unit today!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Kim Sheridan (941-313-0262)
5073 HIGEL AVE, SARASOTA, FL 34242
$2,400,00017 Days on yellowkey MLS ID: A4693713
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2965 Built: 1958 Tax: $10,432 (2025)Community: Sara SandsSingle Family
Taxes:$10,432
Remarks: Welcome to luxury coastal living on Siesta Key. Perfectly positioned in the exclusive Sara Sands community, this fully remodeled 4-bedroom, 3.5-bath waterfront residence offers the ultimate blend of modern elegance, boating lifestyle, and relaxed Florida luxury. Situated on a deep-water canal with quick access to Sarasota Bay and the Gulf, this exceptional property features a private dock and boat lift, making it a dream for boaters and waterfront enthusiasts alike. Thoughtfully redesigned with high-end finishes and updated appliances throughout, the home showcases an open-concept layout filled with natural light, designer touches, and seamless indoor-outdoor living. The gourmet chef’s kitchen flows effortlessly into expansive living and entertaining spaces, while oversized impact glass doors open to your private tropical retreat. Step outside to a resort-style covered pool and lounge area designed for year-round entertaining, complete with multiple patio spaces and beautiful canal views. Whether hosting sunset gatherings, relaxing poolside, or taking your boat out for the day, this property delivers the best of the Siesta Key lifestyle. Additional features include a spacious 2-car garage, lush landscaping, generous bedroom suites, luxurious spa-inspired bathrooms, and a prime oversized lot on one of the island’s most desirable streets. Located just minutes from world-famous Siesta Key Beach — consistently ranked among the top beaches in the United States — as well as Siesta Village dining, shopping, and entertainment. Enjoy easy access to white quartz sand beaches, waterfront restaurants, marinas, and downtown Sarasota cultural attractions, all within approximately a 5–10 minute drive. Recently appraised at approximately $2.6 million and now offered at $2.4 million, this is an extraordinary opportunity to own a move-in-ready luxury waterfront home in one of Sarasota’s most sought-after coastal neighborhoods. Experience the perfect combination of modern sophistication, waterfront convenience, and island living at 5073 Higel Avenue.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Abraham Ruth (832-529-7370)
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