Location: Sarasota , 34242
Do Not Show Listings
5855 MIDNIGHT PASS RD #420, SARASOTA, FL 34242
$765,000159 Days on yellowkey MLS ID: A4671788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976 Tax: $4,975 (2024)Community: Harbor Towers Y & RCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,975
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Location, location & views! Enjoy and experience luxury living at the Harbor Towers located just steps away from the world-famous Siesta Key beach. Highly desirable 4th floor unit, 2BR/2BTH with spectacular Gulf of America views from every room. Fully updated unit with new windows, new pipes, quartz countertops, new kitchen cabinets doors, new bathrooms and luxury vinyl flooring throughout. This turnkey furnished condo features an open floor plan, two suites split plan bedrooms and provides one parking space & additional storage room. New electrical panel and new water heater. Delight yourself at the HT amenities including heated resort style pools, 3 Har-Tru tennis courts, fitness center, sauna, clubhouse and a superb Marina & seating along the intercoastal waterway. HT has newly renovated building facade, common area including the lobby, spa area and hallways. A fantastic investment opportunity to own a rental income while enjoying the unit whenever you wish. Two-week minimum rentals are allowed 26 times/ year. Buyer can use the on-site property management company for rentals, or others.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Mihaela Dragan (630-330-8903)
777 BEACH RD #1B, SARASOTA, FL 34242
$649,995363 Days on yellowkey MLS ID: A4649455
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1174 Built: 1970Monthly Fee: $1,098 Tax: $8,125 (2024)Community: Crescent Royale 3Condo
Taxes:$8,125
Remarks: PRICED TO SELL! 100K PRICE IMPROVEMENT!! THE SEASON IS HERE! Don't miss your chance to secure a great investment with this consistently rented condo. Welcome home to the GOOD LIFE in Siesta Key Beach! This turn-key condo is ready for you to experience the epitome of beachside living year 'round as you awaken to the scent of salt air and the sound of waves rolling in, all from the comfort of your living room! This fully furnished, OPEN FLOOR PLAN, two-bedroom, two-bath condominium is positioned in the sought-after community of Crescent Royale directly across from Siesta Key’s world-renowned powdery sand beaches. Designed for those who value luxury and laid-back coastal elegance combined with smart investment potential, this prime, first-floor, turnkey condominium offers the ideal combination of luxury, convenience and relaxation. There is no need to take the stairs or search for beach parking when you live steps from the beach with an assigned parking space. Wake to panoramic views of turquoise water and unwind on your private lanai with stunning gulf sunsets. Inside, you’ll be greeted by bright, light-filled spaces with floor-to-ceiling sliders that invite in ocean breezes. The tastefully renovated home has newly installed white oak (LVP) floors throughout. A stylish kitchen complete with granite countertops, newer appliances, and a breakfast/wine bar that flows into the dining and living area creates a space for hosting with ease. Each bedroom is a serene retreat complete with a walk-in closet and a sophisticated en-suite bath, ideal for guests and owners alike. Crescent Royale pampers their residents and guests with resort-style amenities including a sparkling heated pool, fully equipped fitness center, game room, shuffleboard court, and a picnic/barbecue area. Just minutes away, Sarasota adds a cultural heartbeat with art galleries, theaters and gourmet dining. The pace here is relaxed but vibrant! Farmer’s markets, waterfront cafes and year-round sunshine create the ideal blend of sophisticated living and coastal charm. Living near Siesta Key and Sarasota means every day feels like a vacation, and every moment feels like home. Whether you're looking for a personal retreat, a seasonal escape or an income-generating asset, this property delivers because it works while you relax. Beyond its beauty, this residence is a savvy investment, offering strong rental income potential, friendly leasing policies and on-site management, creating a rare opportunity for a passive income stream in one of Florida’s most desirable beach communities. No pets or smoking allowed in this community! Location, luxury and income potential! Live the dream, earn while you’re away and invest in a lifestyle that pays you back. This condominium delivers the lifestyle you’ve been dreaming of, just across from Siesta Key Beach so don’t miss this rare chance to own a slice of Siesta Key’s desirable beachfront real estate, with income potential to match. Call us today to schedule your private showing and begin living the Florida Lifestyle you have dreamed of.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-907-9541)
Listing Agent: Trish Chandler (941-306-9533)
4644 HIGEL AVE, SARASOTA, FL 34242
$6,300,00088 Days on yellowkey MLS ID: A4679392
0 Days Off yellowkey (back on 2/26/2026)
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3482 Built: 2026 Tax: $15,244 (2025)Community: Ocean Beach RepSingle Family
Taxes:$15,244
Tax Year: 2025
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Under construction. This new Siesta Key residence is a masterpiece of innovative design and flawless craftsmanship, offering unparalleled luxury and coastal elegance, with a water view backyard and private boat dock. Designed and developed by the renowned Pham Development team, this home is ready for tours, with still the opportunity to customize finishings. Nestled on a nearly 14,000-square-foot lot with 118 feet of prime canal frontage, this waterfront home blends modern elements with timeless coastal charm. Featuring 4 spacious bedrooms, 4 full and 1 half impeccably designed bathrooms, and a 3-car garage, the home is thoughtfully designed for both comfort and style. At the heart of this residence is a well appointed kitchen, with an open-concept layout. The stunning quartz island with waterfall edges takes center stage, accentuated by elegant pendant lighting. Sleek, custom cabinetry complements the state-of-the-art stainless steel appliances, making this space ideal for both entertaining. The light-filled living areas are designed to maximize the breathtaking water views, offering a seamless connection to the outdoors. Step outside to your private oasis, where a resort-style pool is surrounded by lush landscaping. The outdoor spaces are designed in harmony with the natural surroundings, creating a tranquil retreat framed by swaying palms and shimmering waters. A private boat dock with a 10,000-pound lift and seating area provides unparalleled access to the Gulf Coast's azure waters, making this home a boater’s paradise. Located in one of Sarasota’s most desirable neighborhoods, this extraordinary property offers a blend of privacy, convenience, and luxury. A short distance away from world-class beaches, fine dining, and entertainment, this is a rare opportunity to own a slice of paradise in an exceptional location.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
1192 HORIZON VIEW DR, SARASOTA, FL 34242
$13,900,000339 Days on yellowkey MLS ID: A4652708
Bed: 6 Bath: 7.0 Liv Area Sq Ft: 8358 Built: 1980Monthly Fee: $33 Tax: $30,303 (2024)Community: Tortoise EstatesSingle Family
Taxes:$30,303
Elementary School: None
High School: None
Middle School: None
Remarks: Exclusive Gulf Coast Luxury Beachfront Estate with Private Gulf Access and Endless Ocean Views Welcome to one of the Gulf Coast’s most private and luxurious beachfront estates—an extraordinary opportunity to own a rare stretch of direct Gulf frontage in Florida. Tucked away at the end of a quiet cul-de-sac and secured behind dual gated entrances, this expansive oceanfront property is enveloped in lush tropical landscaping and designed for those who value seclusion, sophistication, and long-term legacy. Boasting 233 feet of pristine beachfront along the Gulf of Mexico, this remarkable estate spans over 8,000 square feet under air and has been completely reimagined through a meticulous, high-end renovation. It artfully blends timeless elegance with resort-style comfort, offering panoramic water views from nearly every room. Here, no neighbors interrupt the horizon—only serene coastal breezes and iconic Florida sunsets that feel like they belong to you alone. Designed for multi-generational living or grand-scale entertaining, this coastal residence features five private bedroom suites—including a separate in-law or nanny suite—as well as a dedicated home office that can serve as a sixth bedroom. Two full gourmet kitchens, five expansive balconies, and an elevator servicing all three levels ensure exceptional comfort and convenience throughout. The main living areas showcase open-concept design, natural light, and breathtaking vistas that define luxury Gulf Coast living. Resort-level amenities abound, including a heated, saltwater pool that reaches 10 feet deep, a hot tub with massage jets, a full steam room, and an infrared sauna for ultimate relaxation. A whole-home Sonos audio system, a 12-camera security network, and a powerful 60 kW natural gas generator provide modern convenience and peace of mind. Water quality is managed by an advanced reverse osmosis filtration system and whole-house conditioner, while a 70-foot private well supplies multi-zone irrigation for the manicured grounds. The property also features a unique drive-through two-car garage with an air-conditioned storage loft, three HVAC zones plus a mini-split system, LED color-changing lighting throughout, and outdoor enhancements such as a built-in gas grill, a fire pit, and an illuminated waterfall feature—ideal for entertaining under the stars. An adjacent buildable lot expands your opportunity for growth, allowing space for a future guest house, expanded estate grounds, or added privacy. This is more than a home—it's a one-of-a-kind legacy property offering privacy, luxury, and an irreplaceable position along Florida’s Gulf Coast. Now available exclusively by private appointment, this luxury beachfront retreat is the ultimate in coastal real estate. Don’t miss your chance to own a slice of Gulf-front paradise.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Brandy Loebker (941-404-4737)
814 PARADISE WAY, SARASOTA, FL 34242
$1,995,00045 Days on yellowkey MLS ID: TB8483961
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1996 Built: 1962Monthly Fee: $17 Tax: $14,830 (2025)Community: Siesta IslesSingle Family
Taxes:$14,830
Remarks: Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is the expansive Florida room, a light-filled living space designed for year-round comfort with floor-to-ceiling windows and seamless views of the water and surrounding greenery—ideal for relaxing or entertaining. The home has been thoughtfully maintained and is in excellent condition, allowing for immediate occupancy or rental income potential. Additional highlights include a heated pool, open and functional layout, and spacious living areas. Located just minutes from Siesta Key Beach and Siesta Key Village, this property combines prime location, generous living space, and waterfront charm, making it ideal as a primary residence, vacation home, or investment property. The house did not get flooded from the recent 2024 storms, a new roof was replaced in 2024, A/C was replaced in 2023, a pool heat pump was installed in 2023, re-piped and remodeled in 2022.
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
700 TROPICAL CIR, SARASOTA, FL 34242
$1,699,00048 Days on yellowkey MLS ID: A4684757
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2341 Built: 1977Monthly Fee: $54 Tax: $5,315 (2025)Community: Siesta BeachSingle Family
Taxes:$5,315
Remarks: Welcome to your private waterfront oasis, a meticulously renovated home set on a super private .41-acre lot defined by lush, mature greenery in one of Siesta Key’s most sought-after neighborhoods. The residence sits at a 9 foot elevation!! The interior features two primary bedroom suites, including a main retreat with a custom-built in closet. The open-concept layout has wide-plank light oak flooring and a kitchen with Italian cabinetry, waterfall quartz countertops, and a custom floor-to-ceiling built in cabinet pantry. Extensive structural and functional UPGRADES include a NEW ROOF, NEW STORM RATED WINDOWS AND SLIDERS, NEW DRAIN PIPES, and NEW PVC water lines. Transition through impact-rated glass sliders to a sun-drenched lanai and a new paver deck featuring a pool with all-new pool equipment. The backyard is a secluded tropical retreat bordered by a thick mangrove canopy for total privacy, offering direct water access for kayaking. Beyond the property, you are just minutes from the world-famous white sands of Siesta Key Beach, the vibrant dining and boutique shopping of Siesta Key Village, and a short drive to the cultural heart of Downtown Sarasota. From the designer finishes to the total structural renewal, this home offers security and luxury in a premier, verdant location. Call to set up a showing ~
Listing is courtesy of: CHIC PROPERTIES II LLC (941-302-0134)
Listing Agent: Ilona Davidovich (941-302-0134)
3360 HIGEL AVE, SARASOTA, FL 34242
$1,549,00068 Days on yellowkey MLS ID: A4682008
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2006 Built: 1960 Tax: $13,348 (2025)Community: Siesta Rev OfSingle Family
Taxes:$13,348
Remarks: Welcome to the home you've been waiting for! Your opportunity to own a fully updated island retreat pool home on world-famous Siesta Key. Imagine waking up minutes from powdery white quartz sand beaches, spending your afternoons poolside under the Florida sun, and ending your evenings with sunset walks along the water. This four-bedroom, three-bathroom home offers the flexibility, comfort, and lifestyle today’s buyers are looking for — whether as your primary residence, second home, or income-producing weekly rental. Inside, the home has been completely updated and thoughtfully designed for modern coastal living. With three separate living room areas, there is space for everyone to gather, relax, and spread out comfortably. Whether hosting friends, accommodating extended family, or welcoming vacation guests, the multiple living spaces provide both connection and privacy — a rare and valuable feature in Siesta Key homes. Natural light fills the interiors, creating a bright and inviting atmosphere that reflects the relaxed elegance of island life. Step outside to your new private pool and expansive outdoor living space designed for year-round enjoyment. Lounge poolside with morning coffee, host dinners, or unwind after a day at the beach. The seamless indoor-outdoor flow captures what Siesta Key living is all about. One of the most compelling features of this property is the one-week minimum rental allowance — a highly sought-after benefit on Siesta Key. Weekly rental flexibility allows you to generate strong short-term rental income while still enjoying personal time in your island home. With Siesta Key consistently ranked among the top beaches in the world, demand for updated weekly rental properties remains strong throughout the year. Residents of this neighborhood also enjoy private access to a beach area on the Pass — a peaceful waterfront setting perfect for sunset strolls, kayaking, paddle boarding, fishing, or simply relaxing away from the main beach crowds. Located just minutes from Siesta Key Village, you are close to dining, boutique shopping, live music, and vibrant island culture. Downtown Sarasota, marinas, golf courses, and Sarasota-Bradenton International Airport are all within easy reach. Whether you are searching for your own Siesta Key escape, a turnkey beach home with a pool, or a high-performing weekly rental investment in Sarasota, 3360 Higel Avenue offers the rare combination of lifestyle, flexibility, and location in one of Florida’s most coveted coastal communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
8534 HERON LAGOON CIR, SARASOTA, FL 34242
$1,299,00025 Days on yellowkey MLS ID: A4687653
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1153 Built: 1949Monthly Fee: $75 Tax: $5,695 (2025)Community: Heron Lagoon LodgesSingle Family
Taxes:$5,695
Remarks: A 2-minute walk across your private footbridge to secluded beach access, this 12,684-square-foot property in Heron Lagoon presents a rare opportunity to own in one of Siesta Key’s most intimate waterfront communities. The existing residence offers the potential to renovate or personalize, all while enjoying a tranquil lagoon setting. The property features a resort-style pool already in place which will need rehabbed, creating a strong foundation for an upgraded outdoor living space. With thoughtful improvements, this home can be transformed into a private coastal retreat that embraces indoor-outdoor living. Set within an exclusive enclave of just 13 homes — while this is 1 of 6 located on the water — residents enjoy a quiet, low-HOA community with direct access to kayaking, paddleboarding, fishing, and birdwatching. Private bridge access leads to a short stroll to Siesta Key’s world-renowned quartz-crystal beaches. Conveniently located just minutes from Siesta Key Village’s shops and dining, this property offers a unique opportunity to create your own island getaway. 3D renderings are available upon request for those seeking design inspiration.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Karlenn Peluso (941-356-5345)
450 BEACH RD #3, SARASOTA, FL 34242
$1,685,00061 Days on yellowkey MLS ID: A4682792
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1386 Built: 1977 Tax: $10,325 (2025)Community: Place 450Condo
Taxes:$10,325
Remarks: NEW 3-Day RENTAL APPROVED INVESTOR ALERT! SELLER MOTIVATED RECENT BUILDING IMPROVEMENTS! Experience refined Gulf-front living in this exquisitely renovated and fully furnished 3-bedroom, 2-bath coastal residence just steps from the powdery-quartz sand of world-renowned Siesta Key Beach. With deeded beach access and sweeping Gulf panoramas, this boutique retreat captures the essence of cosmopolitan island living. Professionally managed with flexible weekly rentals and proven year-round income potential, this property offers both lifestyle and investment appeal. A short stroll leads to the vibrant dining, live music, and charming boutiques of Siesta Key Village, while a peaceful path through the coastal preserve brings you directly to the shoreline and its mesmerizing turquoise waters. Located within an intimate five-residence enclave, the condominium has been thoughtfully renovated to reflect effortless coastal elegance. The open-concept interior showcases warm wood finishes, stainless steel appliances, and a beautifully designed kitchen that flows seamlessly into the living and dining spaces. Gulf views from the kitchen and a private balcony for sunset evenings elevate the experience even further. This charming boutique building, perfectly located for convenience, has been fully upgraded with major safety and community improvements! A new grill and lounge area are underway, alongside exciting game and entertainment spaces making it the ultimate spot to relax, socialize, and have fun. Additional features include an enclosed one-car garage, an assigned open parking space, and access to a beautifully maintained community pool and outdoor entertainment area complete with grilling space, lawn games, and a convenient private storage unit. Whether as a private seaside sanctuary, legacy family retreat, or high-performing investment, this exceptional property blends prestige, privacy, and prime location on coveted Siesta Key. An extraordinary coastal jewel exclusively presented.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Anne Schneider (310-562-9710)
1700 COVE II PL #324, SARASOTA, FL 34242
$849,90031 Days on yellowkey MLS ID: A4686403
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $7,965 (2025)Community: Midnight Cove IiTownhouse
Taxes:$7,965
Remarks: 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)
1374 MOONMIST DR #B1, SARASOTA, FL 34242
$1,000,000389 Days on yellowkey MLS ID: A4642845
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1996 Built: 1968 Tax: $2,989 (2025)Community: Polynesian GardensVilla
Taxes:$2,989
Middle School: Sarasota Middle
Remarks: A $500K price reduction - don't wait! A rarely available bayfront opportunity to create your dream retreat on Siesta Key. Experience the allure of waterfront living in this detached bayfront villa, poised for a fresh vision in the desirable Polynesian Gardens community on Siesta Key. One of only 11 exclusive bayfront residences, this end-unit villa offers sweeping, unobstructed views of the Intracoastal Waterway from nearly every room, where sunrises paint the sky in breathtaking hues. Go outside to your expansive private waterfront deck, where you can unwind to the sights of boats gliding by, playful dolphins in the distance, and the peaceful rhythm of the bay. A natural beachfront at your doorstep invites you to dip your toes in the water and embrace the tranquil coastal lifestyle. Professionally remediated following Hurricane Helene, this residence is a blank canvas, ready for transformation. With a spacious two-bedroom, two-bath layout that exceeds the size of many three-bedroom villas in the community, the potential for a luxurious, customized retreat is limitless. Enjoy the privacy and convenience of your own garage and private entrance, delivering the feel of a single-family home, yet with the ease of villa living. The location is unbeatable, just minutes from the world-famous Siesta Beach, renowned for its soft quartz sands and mesmerizing Gulf waters, where mango-hued sunsets cap off each day. Centrally located on the island, you're moments from the vibrant dining, boutique shopping, and lively atmosphere of Siesta Key Village and South Siesta Village, and just a short drive to downtown Sarasota’s cultural arts scene, theaters, and fabulous dining. This is a rare opportunity to reimagine and create your custom bayfront sanctuary in one of Siesta Key’s sought-after communities. Don’t let this one-of-a-kind coastal gem slip away.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5727 RIEGELS POINT RD, SARASOTA, FL 34242
$4,595,000628 Days on yellowkey MLS ID: A4618421
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 3616 Built: 1982Monthly Fee: $125 Tax: $19,884 (2024)Community: Riegels LandingSingle Family
Taxes:$19,884
Remarks: When home feels like a permanent vacation, every day becomes a tropical escape where time slows down, the water is always nearby, and every day begins and ends with a coastal breeze. That’s the essence of 5727 Riegels Point—a casually luxurious, resort-style property where the lifestyle is as effortless as it is extraordinary. Nestled within the gated enclave of Riegels Landing on Siesta Key, an exclusive community with fewer than 30 estate homes, this unique property offers a lifestyle where outdoor living is as exceptional as the interior. Step into your own island sanctuary, surrounded by 357 feet of deep-water shoreline on a private basin with direct Intracoastal access. It’s a true boater’s paradise, complete with two 10,000-lb boat lifts, a floating kayak launch, water and electricity at the dock, and lit pilings perfect for nighttime fishing. The water is deep enough for a large-scale yacht to sit comfortably at your dock. Expansive Shellstone patios wrap around the home, offering countless spaces to relax, dine, and entertain. The saltwater pool and raised spa, framed by fire and water features anchor this private resort experience. Remote smart controls make it easy to unwind in the pool and spa after a sunset cruise. The front entry showcases coastal curb appeal with double frosted glass doors, leading into an interior that blends casual sophistication with the ease of turnkey living. The great room is open and airy, with engineered wood floors and abundant natural light. Large sliders provide seamless access to the outdoor amenities, creating a perfect space for both entertaining and casual relaxation. The chef’s kitchen is designed for both form and function, featuring Wolf cooking appliances, a Sub-Zero refrigerator, a Miele dishwasher, a galley sink, and custom cabinetry throughout. Hidden outlets at the cabinet base and multiple pantries, plus clever storage built into the island, keep everything organized with ease. The primary suite is a serene retreat with engineered hardwood floors, a access to a waterfront terrace with Trex decking that wraps around the entire home, and well-thought-out blind and electrical automation. The luxurious bath features lighted mirrors, dual sinks, a makeup vanity, a free-standing tub, a walk-in shower, and a Toto commode. The suite also includes a spacious walk-in closet with custom built-ins. Upstairs, two generous guest suites share a well-appointed full bathroom. Two loft areas provide the perfect space for reading, working, or relaxing. The lower level offers a multifunctional space, featuring a living space, fitness room, sliders to access the outdoor space, and a wine room with plumbing for a cooler. Additional features include a spacious 2-car garage with custom built-ins, Control4 smart home technology for lighting, AV, security, and more, four HVAC zones for comfort, turnkey furnishings, a whole-house water softener system (salt and carbon filters), a whole house generator and an oversized laundry room with custom organization. At 5727 Riegels Point, enjoy island living with easy access to Sarasota and Siesta Key Village’s dining, shopping, and entertainment. Siesta Key Beach, recently named the No. 1 beach in America by Tripadvisor, is just moments away, offering powdery sand, clear waters, and stunning sunsets. From dockside mornings to poolside evenings, this is coastal living at its best—a full-time escape where your dream lifestyle unfolds.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
6157 MIDNIGHT PASS RD #B12, SARASOTA, FL 34242
$580,00094 Days on yellowkey MLS ID: A4678073
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1332 Built: 1974 Tax: $3,024 (2025)Community: Bay OaksCondo
Taxes:$3,024
Remarks: One or more photo(s) has been virtually staged. Waterfront Siesta Key condo with breathtaking Sarasota Bay intracoastal views and weekly rentals allowed. This rare 2BR/2.5BA Bay Oaks residence is a remarkable opportunity for a buyer with vision to transform a diamond in the rough into a spectacular waterfront getaway, full-time residence, or investment property. Positioned directly on the water, this two-level condo offers the kind of panoramic bay views that are hard to find and impossible to forget. The first floor includes the living room, dining area, kitchen, in-unit laundry, and guest half bath. Upstairs, both bedrooms feature ensuite baths and walk-in closets, including one suite with a private covered balcony overlooking the bay. Bay Oaks residents enjoy a heated waterfront pool, fishing pier, tennis, pickleball, clubhouse, picnic and grill areas, covered parking, bike storage, guest parking, onsite management, and 24-hour video surveillance. Just 1 mile to Siesta Key Beach, with trolley access directly outside the community, this location combines waterfront serenity with easy access to dining, recreation, and the best of Siesta Key.
Listing is courtesy of: LOYD ROBBINS & CO. LLC (941-957-9300)
Listing Agent: Jessica Burdick (941-302-4641)
225 HOURGLASS WAY #303, SARASOTA, FL 34242
$499,00025 Days on yellowkey MLS ID: TB8489788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $5,476 (2025)Community: Whispering Sands Sec 2Condo
Taxes:$5,476
Remarks: 3RD FLOOR FLOODPROOF CORNER UNIT TOP FLOOR PENTHOUSE PRIVATE BEACH RESORT APPROX.1,665 sf. The Treehouse at Beautiful Whispering Sands Siesta Key the World's Finest White Sand Beach. This is a unique opportunity to own a rare corner unit on the green belt Not a Parking Lot View, double Lanai flood proof no damage from Hurricanes. The breeze you get going through this condo is incredible, also there is brand new AC unit for the hotter months this is a must see condo. 800 ft of PRIVATE BEACH two private heated pools Clubhouse workout facility and more.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
3799 FLAMINGO AVE, SARASOTA, FL 34242
$18,500,000332 Days on yellowkey MLS ID: A4653658
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 8138 Built: 2016 Tax: $109,657 (2024)Community: Siesta Key / Bay IslandSingle Family
Taxes:$109,657
Remarks: Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with thousands of square feet of patio and pool area. An outdoor oasis offering an infinity-edge pool with a swim-up bar, a sunken fire pit lounge within the pool, a spa, an outdoor kitchen, a dining pavilion with a living plant wall and an open-air living room with a fireplace. A koi pond with stunning built-in footbridges stretches nearly the entire length of the home, enhancing the serene ambiance of the outdoor space. Spanning over an acre with more than 700 feet of waterfront, the property is a masterpiece of luxury, designed for effortless relaxed living or island-style entertaining. A custom-designed driveway welcomes you to a breathtaking entrance, where waterfalls and fire features set the tone for the experience that awaits inside. Expansive walls of glass, seamless indoor-outdoor transitions, and rich wood and stone flooring throughout create a striking, cohesive aesthetic. The thoughtfully designed interior boasts multiple living spaces, including a game room, home theater, fitness room, meditation space and an impressive 8-plus-car garage. For the waterfront enthusiast, a well-equipped boat dock, a separate waterfront garage, and a paddleboard/canoe launch provide unparalleled access to pristine waters. This exceptional residence also features a newer seawall, full-house generator, Crestron home automation, a three-stop elevator and a whole-house reverse-osmosis water filtration system, ensuring convenience and peace of mind. An island paradise, this estate offers unmatched privacy while remaining just moments from Sarasota’s vibrant shopping, dining and world-renowned cultural attractions. Don’t miss this rare opportunity to own a move-in-ready masterpiece on Siesta Key – home to the #1 beach in the USA (Tripadvisor).
3460 FLAMINGO AVE, SARASOTA, FL 34242
$7,749,00052 Days on yellowkey MLS ID: A4683051
3 Days Off yellowkey (back on 3/30/2026)
Bed: 5 Bath: 6.5 Liv Area Sq Ft: 6030 Built: 2026 Tax: $30,144 (2025)Community: Bay IslandSingle Family
Taxes:$30,144
Remarks: Under Construction. An extraordinary opportunity awaits on the coveted north end of Siesta Key. Currently under construction and scheduled for completion in late 2026, this magnificent waterfront estate offers the rare chance to personalize finishes and create a truly bespoke coastal masterpiece—without the years-long process of designing, permitting, and building. Set on a remarkable and rarely available 1.25-acre estate-sized lot with direct sailboat water frontage, the property provides unobstructed access to Sarasota Bay and the open waters of the Gulf of Mexico. Boating enthusiasts will appreciate the deep-water access with no bridges to the bay, offering seamless days on the water from your own backyard. The custom-designed residence encompasses over 6,000 square feet of refined living space, thoughtfully planned to blend grand scale with effortless coastal elegance. Expansive indoor-outdoor living areas, soaring ceilings, and walls of glass are designed to capture tranquil water views and Gulf breezes. Buyers have the exclusive opportunity to select interior finishes, fixtures, and design elements—tailoring the home to their personal vision while benefiting from the expertise and timeline already in place. Complementing the main residence is a private guest house, ideal for hosting family and friends in comfort and style. The true estate setting is further enhanced by a full-sized tennis court, lush grounds with room for additional amenities, and the privacy rarely found on waterfront properties. This is a once-in-a-generation opportunity to own a newly built waterfront compound in one of the Gulf Coast’s most sought-after locations—where luxury, space, convenience and converge. These images are architectural renderings created for illustrative purposes only and are based on preliminary plans and design concepts. Renderings are intended to convey the overall vision, layout, and design intent but are not exact representations of the final constructed residence. Actual materials, finishes, dimensions, landscaping, fixtures, furnishings, ceiling details, lighting, views, and architectural elements may vary. All features, specifications, and details are subject to change without notice.
Listing Agent: Jennifer Linehan (941-266-7555)
1054 SUN N SEA DR #106, SARASOTA, FL 34242
$660,00042 Days on yellowkey MLS ID: A4685194
0 Days Off yellowkey (back on 3/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 800 Built: 2009 Tax: $6,023 (2025)Community: Beach Club At Siesta KeyCondo
Taxes:$6,023
Remarks: Under contract-accepting backup offers. 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.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Josie Cline (941-266-6661)
1500 COVE II PL #524, SARASOTA, FL 34242
$849,900110 Days on yellowkey MLS ID: A4676444
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $8,269 (2025)Community: Midnight Cove IiCondo
Taxes:$8,269
Remarks: RARE OPPORTUNITY TO OWN A 3 BEDROOM ON SIESTA KEY! With Deeded beach access and one-week rentals! Maximize your investment while enjoying this fantastic 2 level townhouse in Midnight Cove II. Enjoy the views from your screened lanai or open air balcony on the second level. This unit offers space! Great sized living and dining areas, nice large, bright kitchen with updated appliances, powder room on the main level plus 2 more full baths upstairs. In unit laundry, deeded covered parking and offering a great rental history! Ideally located for quick deeded access to Crescent Beach just across the street! Midnight Cove II is a highly desirable community offering a marina with slips available and direct access to the intracoastal. Other amenities include tennis, pickleball, basketball court, fitness center and large heated pool. In addition, there is a grill and picnic area, car wash, pet walk, canoe storage and more! The property features beautiful mature landscaping with frontage on the intracoastal with paths and seating throughout the property. Midnight Cove II offers fully funded reserves, onsite rentals and management, and a rental friendly environment to maximize your income. Milestone Report is complete. Roof was replaced in fall of 2025 as well. Offered turnkey furnished with a small list of exceptions. Great opportunity - don't miss it!
6285 MIDNIGHT PASS RD #406, SARASOTA, FL 34242
$799,000172 Days on yellowkey MLS ID: A4670228
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1456 Built: 1981 Tax: $3,221 (2024)Community: Excelsior Beach To Bay 5Condo
Taxes:$3,221
Remarks: Welcome to this beautiful Penthouse end unit at the highly desirable Excelsior Beach to Bay community. Perfectly positioned on the Bay side, this 2 bedroom, 2.5 bath condo offers an open, airy layout enhanced by vaulted ceilings, abundant natural light, and impact windows throughout for peace of mind and energy efficiency. The living and dining areas flow seamlessly together, creating an ideal setting for entertaining or relaxing. The dining area features a mirrored accent wall, a built-in cabinet under the stairs, and another built-in at the end of the room for elegant storage and display. A wood staircase leads to the loft, a rare feature in this complex. The spacious loft includes a half bath, and 2 generous closets, offering flexibility as a guest retreat, office, or media room. The loft expands your living options beautifully. The kitchen is both functional and stylish, featuring wood cabinetry, Cambria quartz countertops, marble floors, a tray ceiling and a built-in eat-in area/desk. A window over the sink provides a charming peek of the Bay. The Primary Bedroom impresses with soaring vaulted ceilings, custom built-in furniture, and a bright, open feel, while the Primary Bath offers two separate sink areas with granite counters, built-in cabinetry, and a wall of closets-providing abundant storage and space. Pella sliding glass doors lead to the Florida room/lanai, enclosed in glass and framed by vaulted ceilings invites you to relax and enjoy tranquil views year-round. Residents of Excelsior enjoy private beach access, along with two heated pools, fitness center, tennis and pickleball courts, and clubhouse. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this Penthouse condo offers a rare blend of comfort, style, and location.
Listing Agent: Stacy Liljeberg (941-544-6103)
5569 CAPE LEYTE DR, SARASOTA, FL 34242
$4,495,00039 Days on yellowkey MLS ID: A4685577
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3654 Built: 2016 Tax: $32,419 (2025)Community: Siesta IslesSingle Family
Taxes:$32,419
Remarks: LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage on the Grand Canal leading to the ICW (only one bridge with about 15’ clearance to the Gulf). Oversized 16,163 sf Lot, elevated concrete block home and spectacular pool in your view from most every room! Not just the best location, but this custom-built in 2016 West Indies style home is a fortress all on one level, including the pool, and is well above the FEMA flood zone. High and dry through the "storms of the century" in 2024. Beautiful, engineered hardwood floors, custom cabinetry throughout by Elite Woodworking in the Kitchen, all Bathrooms and Great Room. The entire house has been freshly painted inside & out. Three large en-suite bedrooms. Additional rooms currently utilized as office with Murphy Bed as well as very large Bonus Room could be utilized as additional bedrooms #4 & 5, if desired. Even the powder bath has a shower for guest convenience. Large walls of sliding glass doors in all waterfront rooms extend living spaces to a huge, screened Lanai which adds over 500 sf to living space under roof, and much more in the screened Lanai area.. All hurricane rated extra heavy duty PGT doors and windows. The total A/C space is 3,654 sf, with a overall total of 5,075 under roof. The oversized 3-car garage with an Epoxy floor has a very high ceiling which allows 2 more cars to be added on lifts for a total of 5 vehicles for the enthusiast. Isonene insulated and floored attic storage space is available above the garage. New in the past year: A/C Condenser & Air Handler system in 1 (of 2) zones, water heater, refrigerator, ice maker, boat lift control boxes on both Lifts. The large free form pool and spa have new (wifi) Pentair pool pump & heater & auto chlorinator. Both boats as well as professional decorator staged furniture, decor and pictures may be available for separate purchase for "Turn-Key" possession. DEFINITELY check out the Virtual Tour, since it provides “3D walk through any direction” photos which can really give you the flow of the house as you manipulate your way around.
Listing Agent: Steve Hagan (941-900-4126)
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