Location: Sarasota , 34242
Do Not Show Listings
901 BEACH RD #205, SARASOTA, FL 34242
$639,00045 Days on yellowkey MLS ID: A4686468
REDUCED by $10,000 (1.5%) on 04/21/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972 Tax: $5,156 (2025)Community: La Siesta CondominiumsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,156
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to the iconic La Siesta Condominiums, directly across from the main beach access of Siesta Key where coastal charm meets effortless beach days. Perfectly positioned just 100 steps from the powdery sands of Siesta Key Beach, this beautifully appointed turnkey furnished second floor condo offers breathtaking Gulf views and an unmatched connection to one of the nation’s most iconic shorelines. Designed for prime vacationing, this income producing vacation rental features an updated interior with coastal-inspired finishes including a modern kitchen, luxury vinyl plank flooring and a dining area. The primary bedroom has a king bed, secondary bedroom features two twin beds, and a queen sleeper sofa in the living room. The open-concept living space is filled with that special Siesta Key sunshine that just hits differently. You are met with a seamless flow between indoors and out featuring a hurricane rated slider door that leads you to a private balcony that becomes your front-row seat to unforgettable sunsets over the Gulf of Mexico. Ideal for both personal enjoyment and income potential, this investor-friendly property allows for up to 52 weeks of rentals annually, offering exceptional flexibility and the opportunity to maximize returns in one of Florida’s most sought-after beach destinations utilizing the professional full-time rental management program. At La Siesta, you’ll enjoy resort-style amenities including a heated pool, fitness center, clubhouse, grilling stations, on-site laundry, a covered parking space and additional storage are also included. With a seven-day rental minimum and strong demand year-round, this unit offers excellent income potential, with bookings already secured into 2026. Located just minutes from the vibrant charm of Siesta Key Village and the south bridge, you’ll have easy access taking the Siesta Key trolley to boutique shopping, waterfront dining, and experience the laid-back island nightlife. Let’s make this coastal paradise a part of your story!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Ann Allen (407-949-4457)
847 FREELING DR, SARASOTA, FL 34242
$3,950,0006 Days on yellowkey MLS ID: A4690268
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4034 Built: 1954 Tax: $40,498 (2025)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$40,498
Remarks: Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
5924 MIDNIGHT PASS RD #507, SARASOTA, FL 34242
$1,250,0006 Days on yellowkey MLS ID: A4689477
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1971 Tax: $12,802 (2025)Community: Sarasota Surf & RacquetSpa: NoCondo
Taxes:$12,802
Remarks: An exceptional opportunity to secure a Gulf-front residence in the highly sought-after Sarasota Surf & Racquet Club on Siesta Key. Positioned on the 5th floor, this two-bedroom, two-bath condominium offers sweeping, unobstructed views of the Gulf of Mexico?the kind of breathtaking backdrop that defines true beachfront living. With 1,195 square feet of interior space plus an expansive 200-square-foot lanai, the layout provides the perfect canvas to create a custom coastal retreat tailored to your personal vision. From sunrise reflections to vivid sunset skies, the panoramic water views take center stage from the main living areas and outdoor space, delivering an ever-changing coastal experience. Sarasota Surf & Racquet Club is known for its prime beachfront location and resort-style setting, offering residents access to a wide array of amenities including tennis courts, swimming pools, fitness facilities, and direct access to Siesta Key?s world-renowned white sand beach. The community?s established reputation and desirable location continue to make it a favorite for both personal enjoyment and long-term investment. Offered at a compelling value reflective of its unique opportunity, this residence presents a rare chance to sec
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
4708 OCEAN BLVD #E7, SARASOTA, FL 34242
$2,350,000219 Days on yellowkey MLS ID: A4665893
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,841 (2025)Community: Windward PassageCondo
Taxes:$16,841
Remarks: Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence ideally positioned on the Gulf of Mexico at Big Pass. This exceptional 3-bedroom, 3-bath condominium offers unobstructed panoramic views of the Gulf, Sarasota Bay, and distant vistas of Lido Key and downtown Sarasota. Encompassing 2,277 square feet with miles of Gulf-front views, the residence has been thoughtfully redesigned with wide-plank European engineered oak flooring, impact-rated windows and doors, and integrated smart-home technology throughout. The chef’s kitchen is a statement in both form and function, featuring custom cabinetry, Milano Dolomite countertops, a striking Macaubas Quartzite island, and premium GE Café appliances—perfect for entertaining against a backdrop of endless blue water. The primary suite is a private retreat with direct access to a Gulf-front balcony and a spa-inspired bath complete with dual vanities, rainfall shower, and bidet. Two additional guest suites provide comfort and privacy, each finished with designer details. Additional highlights include a two-car tandem garage with hurricane-rated door, new HVAC systems, electric hurricane shutters, and an integrated sound and entertainment system. Amenities include a heated pool, guest parking, and direct walking access to the sugar-white sands and vibrant Village of Siesta Key. This residence blends timeless coastal elegance with modern luxury—an extraordinary Gulf-front retreat on one of Siesta Key’s most coveted stretches of shoreline.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Stacey King (646-734-5014)
116 GARDEN LN, SARASOTA, FL 34242
$1,995,000174 Days on yellowkey MLS ID: A4671064
REDUCED by $155,000 (7.2%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2971 Built: 2017 Tax: $20,113 (2024)Community: Siesta Rev OfSingle Family
Taxes:$20,113
Tax Year: 2024
Remarks: Effortless Island Living on Siesta Key’s Coveted North End. Discover the perfect blend of modern luxury and low-maintenance living in this contemporary coastal retreat, ideally located on the quiet North End of Siesta Key. Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortless proximity to Siesta Village, the North Bridge, and downtown Sarasota. Built in 2017 to the highest standards by MGB—My Green Building—this four-level residence was designed for comfort, efficiency, and peace of mind. Solid construction, energy-smart design, impact-rated materials, and a brand new A/C system (March 2026) make it the ideal lock-and-leave home for those seeking a worry-free coastal lifestyle. Light-filled living spaces flow seamlessly between the gourmet kitchen, dining, and family areas, all centered on the third floor for optimal views and connection. The private primary suite spans the top level with its own balcony retreat, while three guest bedrooms on the second floor offer space for family or friends. An elevator connects all four floors for easy access, and the flexible lower level provides extra room for a fitness area, studio, or media lounge. Designed for those who value quality, comfort, and ease, this home offers all the benefits of coastal living—without the upkeep. From morning beach walks to sunset cocktails overlooking the Gulf, every day here feels like a vacation.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Gerard Healy (941-961-2240)
1200 E PEPPERTREE LN #307, SARASOTA, FL 34242
$669,00062 Days on yellowkey MLS ID: A4683608
REDUCED by $30,000 (4.3%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1466 Built: 1973 Tax: $7,547 (2025)Community: Peppertree Bay IiCondo
Taxes:$7,547
Remarks: Set within Peppertree Bay on Siesta Key, 1200 E Peppertree Lane #307 offers a well-proportioned, turnkey, move-in ready two-bedroom, two-bath residence encompassing 1,466 square feet. The interior presents a bright, open layout anchored by a spacious great room, where crown molding, tile flooring throughout, and an expansive wall of impact glass windows create an airy, light-filled living environment. The adjoining dining area flows seamlessly into the kitchen, reinforcing the home’s functional, connected design. The kitchen features a tray ceiling with inner crown molding, recessed lighting, abundant wood cabinetry, granite countertops, a tile backsplash, and a full suite of stainless-steel newer Whirlpool appliances. A breakfast bar provides additional prep and serving space, supporting both everyday living and casual entertaining. The primary bedroom is generously scaled and benefits from strong natural light, crown molding, a walk-in closet, and direct access to the enclosed sunroom. The primary bath includes a granite-topped vanity, glass-enclosed walk-in shower, linen storage, and updated fixtures. A well-sized guest bedroom with an oversized window alcove and a nearby full bath maintains privacy and flexibility for visitors. An enclosed sunroom lined with windows extends the living space, offering versatility as a lounge, office, or secondary sitting area. A stacked washer and dryer are conveniently positioned within a dedicated closet. Newer HVAC system (2024) and Water heater (2025). Peppertree Bay is a Gulf-to-Bay community providing private deeded beach access, a fishing pier, two resort-style heated pools, clubhouses, a fitness center, saunas, tennis and pickleball courts, covered under building assigned parking with this unit that provides a bicycle rack and unit storage, and multiple outdoor gathering areas. This building has newer elevators along with stairwell access, with the building roof being replaced in 2020. The location places residents directly on Siesta Key, home to Siesta Beach, consistently ranked the #1 beach in the United States by TripAdvisor, further underscoring the appeal of both the setting and lifestyle offered by this residence.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Sharon Chiodi (941-809-0380)
1192 HORIZON VIEW DR, SARASOTA, FL 34242
$13,900,000349 Days on yellowkey MLS ID: A4652708
Bed: 6 Bath: 7.0 Gar: 2 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)
6154 MIDNIGHT PASS RD #A13, SARASOTA, FL 34242
$615,40052 Days on yellowkey MLS ID: A4685497
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 875 Built: 1966 Tax: $4,775 (2025)Community: Casa Blanca VillasVilla
Taxes:$4,775
Remarks: Under contract-accepting backup offers. Larger two-bedroom gulf-side/beach access, stand-alone villa in Casa Blanca--the gem of gems--and rarely available 980 total square feet floor plan. Just a few steps from the pure, white quartz sand of Siesta Key Beach, great restaurants, shopping, and entertainment. Total custom design renovation carefully planned and completed January 2026, with no details overlooked. Larger kitchen and dining area, induction stove top, stainless steel appliances, quartz countertops, custom cabinetry with self-close drawers, and new luxury vinyl tile flooring inside. The south-facing, screened lanai, with a composite floating floor, invites sunshine and warmth inside. Turn-key furnished and equipped. Wonderful on-site rental management office; historically generating approximately $40,000 annual rental income. 110-volt EV charger outside and wired for 220 volts; PVC plumbing lines replaced, electrical outlets raised; new raised water heater, HVAC air handler and condenser, new ducts. HVAC 2023. Casa Blanca is well-appointed community on the island, with the South Siesta Village and the Siesta Key Village just a short walk away, with charming shops, restaurants, and nightlife. Enjoy the pool, clubhouse, fitness center, yoga on the beach nearby, and the local cuisine. Casa Blanca Unit A13 is the top-of-the-line villa. Own your own piece of Siesta Key's paradise.
Listing Agent: Linda Holley (941-914-4914)
5400 OCEAN BLVD #8-05, SARASOTA, FL 34242
$690,000176 Days on yellowkey MLS ID: A4670371
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 522 Built: 1970 Tax: $6,969 (2025)Community: Beach TerraceCondo
Taxes:$6,969
Remarks: BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERRE Discover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise. Whether you call Sarasota or Lakewood Ranch home, imagine having your own Siesta Key retreat just moments away, a place to unwind, recharge, and embrace the coastal lifestyle whenever you need it. The private balcony frames stunning Gulf views, while the thoughtfully designed interior maximizes space and comfort. Covered parking provides convenient, weather-protected access to your beach escape, while the residence's prime location puts you steps from all the dining, shopping, and entertainment that Siesta Key Village has to offer. No need to drive once you arrive, everything is at your fingertips. Resort-style amenities elevate the experience: enjoy the elevated heated saltwater pool with its spectacular sunset views (truly the best amenity besides the unbeatable location), stay active in the fitness center, gather in the community room, and access the world-renowned Siesta Key Beach directly from the property. The powdery white sand and crystal-clear waters are quite literally your backyard. More than a weekend residence, this is your personal gateway to the Gulf-front lifestyle. Whether it's a spontaneous Friday escape or a planned coastal retreat, your Siesta Key sanctuary awaits. This is the effortless beach lifestyle you've been dreaming of, close to home, yet worlds away.
Listing Agent: Mickey Kiernan (941-402-9115)
5400 OCEAN BLVD #6-4, SARASOTA, FL 34242
$1,250,000240 Days on yellowkey MLS ID: A4663880
REDUCED by $50,000 (3.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1970 Tax: $10,071 (2025)Community: TerraceCondo
Taxes:$10,071
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. The Beach Terrace building is one of the most desirable addresses on Siesta Key with a direct Gulf of Mexico location and nestled at the end of the village. This 2 bedroom / 2 full bath corner residence offers panoramic views of the Siesta Key beach, village and aqua water of the Gulf of Mexico. The condominium offers 3 spacious balconies to enjoy morning coffee, evening sunsets and the skyline of downtown Sarasota in the distance. Enter the split floor plan residence through the entry with tiled flooring into the kitchen. The kitchen boasts updated cabinetry, appliances, lighting, granite countertops. The large living area offers dual sliders that provide expansive views throughout Siesta Key and the beach. You can enjoy just relaxing on the couch and viewing the sparkling waters of the gulf. The dining area also provides ample space for entertaining. The primary bedroom has a private balcony with views of the gulf and village. There are two full size beds and an ensuite bath and vanity area including updated tile, cabinetry and granite countertops. The second bedroom offers a full bed with an additional full sliding door for and dazzling views of the gulf. This bedroom also provides an additional bathroom with updated cabinetry, tile shower and granite. The onsite amenities include elevated heated saltwater pool, fitness center, community room all steps from private beach.
777 BEACH RD #1E, SARASOTA, FL 34242
$765,000176 Days on yellowkey MLS ID: A4670832
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1970 Tax: $8,392 (2024)Community: Crescent Royale 3Spa: NoCondo
Taxes:$8,392
Remarks: Get ready to be wowed by this completely reimagined 2-bedroom, 2-bath coastal gem in the highly sought-after Crescent Royale! Step inside to discover a stunning transformation where modern luxury meets timeless coastal charm. The new kitchen, now seamlessly integrated into the great room by the removal of a wall, creates a spacious and inviting open-concept layout perfect for entertaining or relaxing in style. Both bathrooms have been beautifully redesigned, featuring fresh, contemporary finishes. As an end unit, this residence shines with upgrades from top to bottom – including new plumbing, electrical, and flooring – ensuring every detail has been thoughtfully addressed. Enjoy the ease of first-floor living with no elevators or stairs to navigate, plus the convenience of a covered parking space located just steps from your door. From your living room and lanai, take in breathtaking Gulf views and relish the unbeatable location directly across from world-renowned Siesta Key Beach. Crescent Royale’s amenities complete the picture of resort-style living, featuring a vibrant clubhouse with a fitness center and game room, a sparkling heated pool, and a grilling/picnic area perfect for outdoor gatherings. All this, and you are just a short stroll or bike ride to Siesta Key Village, where dining, shopping, and entertainment await. Whether you are seeking your own beachside retreat or an exceptional investment property, this condo truly has it all. With outstanding rental potential, you can enjoy it when you wish and generate income while you are away. Don’t miss this rare opportunity to own your slice of paradise at Crescent Royale — where luxury, location, and lifestyle come together beautifully.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Scott Rickards, Pa (941-356-7040)
6157 MIDNIGHT PASS RD #B12, SARASOTA, FL 34242
$500,000104 Days on yellowkey MLS ID: A4678073
REDUCED by $80,000 (13.8%) on 04/24/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1332 Built: 1974 Tax: $3,024 (2025)Community: Bay OaksSpa: NoCondo
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)
5855 MIDNIGHT PASS RD #404, SARASOTA, FL 34242
$645,00038 Days on yellowkey MLS ID: A4687131
0 Days Off yellowkey (back on 3/31/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976 Tax: $5,981 (2025)Community: Harbor Towers Y & RCondo
Taxes:$5,981
Remarks: Under contract-accepting backup offers. Experience elevated coastal living at Harbor Towers Yacht & Racquet Club, where this beautifully updated 2-bedroom, 2-bath residence offers a seamless blend of comfort, style, and breathtaking waterfront scenery. Perfectly positioned along the Intracoastal Waterway in sought-after Siesta Key, this light-filled condo showcases an open-concept layout with expansive windows that frame stunning views of the marina, sparkling pools, and lush tropical surroundings. The thoughtfully designed interior features a modernized kitchen and sleek flooring throughout, creating a fresh and inviting atmosphere ideal for both everyday living and entertaining. The spacious primary suite offers a private retreat with an en-suite bath and generous closet space, while the guest accommodations provide comfort and privacy for visitors. Residents enjoy a gated, resort-style community with exceptional amenities, including multiple pools, tennis courts, fitness center, sauna, private marina, and scenic waterfront spaces perfect for relaxing or watching boats glide by. With easy access to Siesta Key’s world-renowned beaches, dining, and entertainment—plus convenient trolley service just outside the community—this property presents an outstanding opportunity for both personal enjoyment and investment in one of Florida’s most desirable coastal destinations.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Anna Lee Williams (240-315-4672)
6006 MIDNIGHT PASS RD #51, SARASOTA, FL 34242
$575,00022 Days on yellowkey MLS ID: P4938368
Bed: 1 Bath: 0.0 Liv Area Sq Ft: 600 Built: 1960 Tax: $3,999 (2025)Community: Casa MarSpa: NoApartment
Taxes:$3,999
Remarks: PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!
Listing is courtesy of: HUT REALTY, LLC (407-559-2929)
Listing Agent: Daniel Hut (863-400-6090)
1400 COVE II PL #631, SARASOTA, FL 34242
$660,00080 Days on yellowkey MLS ID: A4681753
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,509 (2025)Community: Midnight Cove IiCondo
Taxes:$5,509
Remarks: Welcome to the most adorable condo on world famous SIESTA KEY. Start enjoying the island lifestyle in this TURNKEY condo with GREAT WATER VIEWS and pool views! ***WEEKLY RENTALS***Very comfortable open floor plan with balcony to sip your cocktails and relax. The PRIVATE DEEDED BEACH ACCESS to the quartz sand Siesta beach in priceless. Midnight Cove offers tennis, pickleball, barbecue areas, fitness, pool, on site management, boat docks and more. Very importantly, there was no storm damage. Take the free trolley to Siesta Village or walk to the south village restaurants and shops. Downtown Sarasota and St Armand's Circle just a short drive away. An excellent opportunity for your vacation getaway or investment property.
Listing Agent: Livya Hament (941-735-1227)
22 SANDY COVE RD #APT 203, SARASOTA, FL 34242
$639,0007 Days on yellowkey MLS ID: A4691011
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 532 Built: 1969 Tax: $4,204 (2025)Community: Sandy CoveCondo
Taxes:$4,204
Remarks: Introducing a charming one-bedroom, one-bathroom condo in the heart of Siesta Key, where Old Florida charm meets modern coastal living. This elevated second-floor unit offers a bright, inviting living space set within a secluded, tropical oasis designed by the renowned Frank Folsm Smith of the Sarasota School of Architecture. Enjoy peace of mind with no history of storm damage in this elevated location, and savor private access to a community beach and fishing pier just steps away. From the private beach, you can watch dolphins play in the Gulf as you unwind to sea breezes and tranquil sunsets. This distinctive enclave blends architectural pedigree with lush, mature landscaping and a resort-like atmosphere, providing a rare combination of privacy and coastal convenience. The property is perfectly positioned within easy reach of Siesta Key Village, where you’ll find a vibrant mix of restaurants, live music, and boutique shopping. Whether you’re seeking a full-time residence or a carefree vacation getaway, this condo offers a low-maintenance lifestyle without sacrificing character or location. Why you’ll love it: a compact, stylish retreat with direct beach access, private coastal views, and proximity to village amenities all in one package. It’s an excellent option for year-round living or a tropical getaway, combining unique architecture, serene grounds, and a distinctive Siesta Key experience. Schedule a private tour to experience this exceptional property firsthand.
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
19 WHISPERING SANDS DR #201, SARASOTA, FL 34242
$950,00096 Days on yellowkey MLS ID: A4679748
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1464 Built: 1973Monthly Fee: $1,440 Tax: $3,007 (2025)Community: Whispering SandsCondo
Taxes:$3,007
Middle School: Heron Creek Middle
Remarks: Front row FULL Gulf views—just one floor above the sand! Priced below market, this lovely 2 bed/2 bath GULF FRONT tower residence in the premiere Siesta Key property of Whispering Sands represents an opportunity to move right in, and if desired, ultimately take your time to create your own vision and make it your own - and enjoy a lifetime of memories. Don’t hesitate - this is currently the best priced Gulf front tower unit in Whispering Sands. Upon entry, you’re greeted with spectacular, unobstructed 180-degree views of the shimmering aquamarine Gulf. Along with its direct FULL GULF VIEWS, this unit is just one floor away from the sparkling beachside pool and 800’ of Whispering Sands' own private beach. This unit features a nicely remodeled kitchen and great OPEN CONCEPT floor plan, enabling easy interaction between you and your guests. The kitchen includes granite countertops & backsplash, an 8’ breakfast bar, recessed LED & under cabinet lighting, convenient built-in desk, and an abundance of cabinet storage. Experience true Florida living by opening the floor to ceiling sliders in the living room and primary bedroom and take in the fresh salt breezes and the gentle sound of the surf. Both sets of sliders include remote controlled shades. The primary bedroom includes a custom walk-in closet, large vanity area, and ensuite bath with marble countertops, glassed walk-in shower, and linen closet with pullout drawers. A set of glassed French doors with privacy shades opens into the guest bedroom, which can serve as both an office and a bedroom with a fantastic SICO wall bed, desk, and built-ins. This unit is being sold As Is. Whispering Sands is a premiere 55+ Gulf front community offering 2 heated pools, Tower Lounge, Clubhouse – both of which are undergoing remodeling with a completion date in 2026 – beachside Tiki hut and grills, shuffleboard, canoe/kayak storage, and 800’ of private beach on the Gulf. In one of the best locations on Siesta Key, Whispering Sands is right around the corner from the colorful boutiques and restaurants of Siesta Key Village. Don’t miss this opportunity!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
6512 MIDNIGHT PASS RD #504, SARASOTA, FL 34242
$2,495,000405 Days on yellowkey MLS ID: A4643532
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1991 Built: 2006 Tax: $20,738 (2024)Community: Crescent Siesta KeyCondo
Taxes:$20,738
Remarks: This rare and exceptional turnkey Siesta Key residence offers an unparalleled blend of space, style, and sweeping Gulf views. Spanning nearly 2,000 square feet, this 3-bedroom, 2.5-bath coastal retreat features two expansive terraces—one overlooking the serene elevated pool and spa area, and the other offering unobstructed sunset vistas across the Gulf. Each of the three bedrooms enjoys private balcony access via sliding glass doors, creating a seamless indoor-outdoor living experience. Designed with a modern coastal aesthetic, the interior features full-thickness bamboo flooring in the main living areas, premium custom cabinetry, and sleek quartz countertops. Soaring 11.5-foot ceilings and clerestory windows with remote-controlled shades enhance the home’s light-filled, airy ambiance. The gourmet kitchen is equipped with top-of-the-line GE appliances, bar-height seating, and a pass-through window that frames the Gulf beyond. The open-concept living and dining areas are ideal for entertaining or quiet reflection, anchored by a Gulf-facing terrace and thoughtfully appointed with a Stressless reclining sofa and captain’s chairs—all perfectly positioned to take in the view. The spacious primary suite offers high ceilings, expansive windows with Gulf views, and blackout draperies for restful nights. The spa-style bath includes a multi-head oversized shower, a large vanity with quartz countertops, a dedicated makeup area, and tile flooring. Two additional bedrooms are configured for comfort and versatility, including a dedicated office in the third bedroom with a Murphy bed. A host of upgrades includes a Schlage Smart Entry Lock, Arlo security camera system, hardwired mesh network for seamless connectivity, a deck-mounted hot water dispenser, and an 80-gallon hot water heater with recirculating system. Additional conveniences include two dedicated parking spaces located on the first floor under the building and an air-conditioned storage cage (#4) on the fifth floor. Crescent offers an elevated beachfront lifestyle with private, direct access to Crescent Beach. The community is meticulously maintained, with newly renovated pools—including an elevated second-floor spa and a completed beachside pool and hot tub—fresh exterior painting, new landscaping, and a host of upscale amenities including a fitness center, social room, upgraded security system, and onsite manager. Ideally situated just off Stickney Point Bridge, this residence offers effortless access to Sarasota’s renowned dining, shopping, and cultural attractions. With Siesta Beach just steps away—recently named the No. 1 beach in America by Tripadvisor—this property captures the essence of Gulf-front living, whether as a full-time home, luxurious getaway, or investment opportunity.
Listing Agent: Joel Schemmel (941-587-4894)
9397 MIDNIGHT PASS RD #405, SARASOTA, FL 34242
$475,000257 Days on yellowkey MLS ID: A4662312
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1975 Tax: $5,514 (2024)Community: Pointe On Midnight PassCondo
Taxes:$5,514
Remarks: Here’s is your chance to live on the SOUTHERNMOST TIP OF SIESTA KEY and enjoy STUNNING SUNRISES & SUNSETS all year long. In fact, this is the CLOSEST CONDO to MIDNIGHT PASS and LOWEST PRICED 2-bedroom unit in the entire complex! This one-of-a-kind gated community encompasses over 5+ acres of PRIME WATERFRONT real estate and is loaded with amenities including tennis, pickleball, fitness center, heated lap pool, spa, dry sauna, kayak launch, clubhouse and more. Boat docks are also available for a small fee on a first come first serve basis. Rather go to the beach? No problem…Turtle Beach access is just about a half-mile away. And let’s not forget, just a few miles up the road are all the amazing restaurants and shops of Siesta Village. The first thing you’ll notice when you enter this turnkey-furnished, 2bed/2bath condo, is how the living area leads right out to an expansive 30-foot lanai overlooking Little Sarasota Bay and the Jim Neville Nature Preserve…a perfect spot for entertaining or just sitting back and enjoying the view and the wildlife. The primary bedroom also has access to the lanai and features an ensuite bathroom, finished closets, and of course, spectacular sunrise views. Engineered hardwood floors throughout give the home a cozy, beachy feel. Unlike other condos in the area, a washer/dryer is conveniently located within the unit. Recent updates include 5 new ceiling fans, new blinds, new range, newer dishwasher, and new furniture in the dining room and living room. AC was replaced in 2019. There is also additional storage space on the ground floor for all your beach and boating gear. Don’t miss out on your chance to own a piece of paradise! Schedule your showing today! Before you know it, you could be floating around the crystal blue waters of Midnight Pass and enjoying STUNNING SUNRISES & SUNSETS right from your own condo.
Listing is courtesy of: UKEEPCOMMISSION REAL ESTATE (941-465-9206)
Listing Agent: Adam Waxler (941-465-9206)
4822 OCEAN BLVD #11E, SARASOTA, FL 34242
$419,00015 Days on yellowkey MLS ID: TB8498225
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 820 Built: 1973 Tax: $4,517 (2025)Community: Siesta TowersSpa: NoCondo
Taxes:$4,517
Remarks: 11th-floor Gulf views, Siesta Key Beach right down the road, and a price point that gives you real upside. This the kind of condo/value comination people hope for. The unit has modest finishes as it sits, but the real play here is the value. You get a front-row seat to the Gulf, a private balcony for sunsets every night, and the chance to update it the way you want without paying a premium for someone else’s remodel. This is a bright west-facing 1-bedroom in Siesta Towers, so the natural light and water views are the star of the show. Whether you want a full-time place, beach getaway, or investment hold, this one checks the box for location and long-term potential. Siesta Towers is a well-kept beachfront community with a community pool, covered parking assigned by seniority, updated lobby/amenities, and beautifully maintained grounds. The building completed its milestone inspection in 2024, major exterior repairs were done in 2023, the roof was replaced in 2018, and the association fully funds both mandatory structural reserves and general reserves. You are also right in the middle of what makes this area so desirable. Siesta Key Beach is close by, and Siesta Key Village is right there for dining, shopping, and nightlife. It is hard to beat this combination of views, location, and value on Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Nathan Shirk (585-356-2197)
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