Location: Sarasota , 34242
Do Not Show Listings
915 SEASIDE DR #611, SARASOTA, FL 34242
$2,950,00038 Days on yellowkey MLS ID: A4697522
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2625 Built: 2009 Tax: $33,482 (2025)Community: Siesta Key Beach Residences IiSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$33,482
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Experience elevated Gulf-front living from the 6th floor of this exceptional four-bedroom, four-bath residence at The Residences on Siesta Key Beach. Perfectly positioned to capture breathtaking, unobstructed views of the Gulf of Mexico, this luxury condominium offers a front-row seat to Sarasota's legendary sunsets, the soothing sounds of the waves, and the ultimate beachfront lifestyle. Spanning more than 2,600 square feet, the thoughtfully designed interior blends sophisticated coastal elegance with effortless comfort. High-end finishes, designer furnishings, premium appliances, spa-inspired baths, and an expansive open-concept floor plan create an ideal setting for both everyday living and entertaining. What truly sets this residence apart is the unparalleled ownership experience. Residents enjoy exclusive access to the world-class amenities and services associated with the neighboring Hyatt Residence Club, including concierge services, a beachfront pool and spa, valet parking, an owners' lounge, daily breakfast service, fitness facilities, towel and chair service, and attentive resort-style hospitality. For those seeking flexibility and income potential, the property benefits from an established onsite management and rental program, making ownership as effortless as it is rewarding. Whether enjoyed as a primary residence, seasonal retreat, or luxury investment property, this residence offers a rare opportunity to combine personal enjoyment with strong rental appeal. Located on the highly sought-after south end of Siesta Key, you're just moments from waterfront dining, shopping, entertainment, the marina, and all the charm of island living, while still enjoying a private beachfront setting. Offered turnkey furnished, this is a seamless opportunity to step into one of Siesta Key's most prestigious Gulf-front addresses and begin enjoying the luxury resort lifestyle.
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)
Listing Agent: David Lehrman (941-321-5595)
420 BEACH RD #203, SARASOTA, FL 34242
$1,249,000587 Days on yellowkey MLS ID: A4631493
0 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1980 Tax: $10,693 (2025)Community: Siesta Gulf ViewCondo
Taxes:$10,693
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Paradise Found on Siesta Key! Wake up to Gulf breezes and end each day with a sunset over the water from this direct beachfront condo at Siesta Gulf View. This 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened and glass-enclosed balcony, accessible from the living room, kitchen, and primary suite. From here you can enjoy both the beauty of the shoreline and the natural dune vegetation that makes this second-floor perspective feel close and connected to the beach. This floor level offers an ideal balance of easy access and elevated views: take the stairs for quick trips to the beach, pool, or parking garage, or use the elevator if preferred. No long waits, no hassle, just effortless access to every amenity. The TURNKEY FURNISHED layout includes a light-filled open kitchen with eat-in nook (perfect as a dinette or office), two spacious walk-in closets, separate laundry room, and generous storage throughout. Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping nearing completion, with no special assessments. Siesta Gulf View is a sought-after, gated, 59-unit community offering private boardwalk access to the quartz sands of Siesta Key Beach, plus resort-style amenities: a 25’x40’ heated pool, tennis and pickleball courts, fitness room, grilling areas, and clubhouse. Assigned under-building parking, ample guest parking, first-floor storage, and an on-site management office add convenience. Pet lovers will appreciate that up to two small pets are welcome. Best of all, you’re just blocks from vibrant Siesta Key Village: restaurants, shops, and live music are a short stroll away. Whether you’re seeking a vacation retreat, investment property (one-month minimum rentals allowed up to 12 times/year), or full-time Gulf-front living, this condo delivers the ultimate island lifestyle. Don’t miss this opportunity to claim your piece of paradise.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jennifer Russo (212-683-1173)
8555 HERON LAGOON CIR, SARASOTA, FL 34242
$2,725,000483 Days on yellowkey MLS ID: A4646820
INCREASED by $1,350,000 (98.2%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2568 Built: 1951Monthly Fee: $75 Tax: $12,703 (2024)Community: Heron Lagoon LodgesSingle Family
Taxes:$12,703
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Rare Opportunity on Siesta Key – Expansive Corner Lot with Private Beach Access + Custom Coastal Estate by SeaSafe Homes. A truly rare opportunity to build your dream home on one of the largest privately owned parcels on Siesta Key. Situated on an expansive over ¾-acre corner lot with nearly 37,000 square feet, this exceptional homesite offers private beach access via an exclusive pedestrian bridge leading directly to your own slice of Siesta Key’s sugar-sand shoreline. Located within an intimate enclave of only 13 homes along Heron Lagoon, this hidden gem offers unmatched privacy, serenity, and exclusivity on the south end of the island, while remaining just minutes from Siesta Key Village Featured here is the Wave Crest Model by SeaSafe Homes, thoughtfully designed for elevated coastal living. Built for luxury and resilience, this home features a superior 2x12 floor system and 2x6 wall construction, engineered to withstand winds up to 180 MPH, exceeding typical coastal building standards and providing peace of mind. With advanced off-site construction methods, build time can be reduced by up to 75%, minimizing weather-related construction delays and allowing you to enjoy your new home sooner. The thoughtfully designed floor plan offers 4 bedrooms, 3.5 bathrooms, and an open-concept layout ideal for full-time living, seasonal enjoyment, or luxury rental potential. The spacious kitchen flows seamlessly into the living and dining areas and includes a large walk-in pantry and extended island, perfect for entertaining. The primary suite features direct porch access, a spa-inspired bath and walk-in closet. A secondary en-suite bedroom with optional private exterior entrance offers ideal flexibility for guests or lockout rental use. Every SeaSafe home also includes energy-efficient sealed systems and upgraded insulation as standard, combining strength, efficiency, and thoughtful design. Whether you envision a legacy family estate, luxury island getaway, or investment opportunity, this extraordinary homesite paired with a premier coastal build offers a once-in-a-lifetime chance to own something truly special on Siesta Key. Private tours, lot walks, and builder consultations available upon request.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Conner Ashley (941-374-1024)
3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242
$2,290,000136 Days on yellowkey MLS ID: A4685652
REDUCED by $100,000 (4.2%) on 04/02/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2856 Built: 1989Monthly Fee: $1,400 Tax: $15,416 (2025)Community: Hamilton ClubSingle Family
Taxes:$15,416
Remarks: Welcome to coastal luxury living in the exclusive Hamilton Club community on Siesta Key. This beautifully updated 3-bedroom, 3.5-bath waterfront residence offers an exceptional blend of elegance, comfort, and boating convenience in one of the island’s most desirable locations. Designed for effortless everyday living and entertaining, the home features a private elevator, impact-rated windows and doors, and a private 10,000-lb boat lift with quick access to Sarasota’s waterways and the Gulf beyond. A spacious screened lanai overlooking the water provides the perfect setting for morning coffee, evening cocktails, and year-round enjoyment of peaceful coastal breezes. Each spacious bedroom includes its own en-suite bath, offering privacy and comfort for both residents and guests. Thoughtfully updated throughout, the residence showcases renovated bathrooms completed in 2022–2023, kitchen enhancements in 2023, updated lighting, and beautiful new wood flooring, all contributing to a refined coastal aesthetic. Additional improvements include a new water softener and water pressure pump installed in 2025 for added functionality and peace of mind. Offered furnished or unfurnished, the home provides flexibility for immediate enjoyment or personalization to suit your style. Hamilton Club residents will also benefit from upcoming community landscaping improvements this summer and exterior building painting scheduled for 2027, both covered by HOA dues. Ideally located just minutes from Siesta Key’s world-renowned beaches, dining, shopping, and entertainment, this exceptional waterfront residence delivers the ultimate combination of modern upgrades, private boating access, and relaxed island living.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
548A BEACH RD, SARASOTA, FL 34242
$1,725,00087 Days on yellowkey MLS ID: A4691951
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2080 Built: 1981Monthly Fee: $1,500 Tax: $16,762 (2025)Community: Tiffany SandsTownhouse
Taxes:$16,762
Remarks: Beautifully renovated Tiffany Sands townhome offering the perfect combination of coastal elegance, spacious living, and an exceptional Siesta Key location with tranquil beach views. This 3-bedroom, 3.5-bath residence features an open, light-filled floor plan designed for effortless island living. Each generously sized bedroom includes a walk-in closet, providing ample comfort and storage. A versatile first-floor bonus room with a full bath and private entrance offers endless possibilities as a guest suite, home office, media room, or additional living space. The home also features a one-car garage with extra storage, multiple expansive decks, and a private patio ideal for enjoying Gulf breezes and picturesque views of Siesta Key's turquoise waters. Just steps away, deeded beach access leads to the world-famous quartz sand beaches of Siesta Key. Ideally situated near Siesta Key Village, residents enjoy convenient access to boutique shopping, acclaimed restaurants, entertainment, and everyday conveniences. Move-in ready and impeccably updated, this is a rare opportunity to own a stylish coastal retreat in one of Siesta Key's most desirable beachfront communities.
4185 ROBERTS POINT CIR #LOT 19, SARASOTA, FL 34242
$3,400,000274 Days on yellowkey MLS ID: A4669769
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3200 Built: 2026Community: Roberts Point 2Spa: YesSingle Family
Taxes:$0
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, masterfully designed in timeless West Indies coastal style and located in the exclusive Roberts Point enclave on Siesta Key. This exquisite residence blends architectural elegance with modern coastal engineering, offering both refined beauty and peace of mind in one of Sarasota’s most desirable island settings. Constructed to the highest coastal standards, this home exemplifies Noah Thomas Builders’ commitment to craftsmanship and durability. With solid concrete block construction, hurricane-rated impact windows and doors, metal roofing, and elevated foundation systems, it’s designed to withstand Florida’s most demanding coastal conditions while maintaining unmatched elegance. The interior features open-concept design, soaring ceilings, and expansive glass sliders that invite natural light and connect seamlessly to the outdoor living spaces. The chef’s kitchen is a showpiece with premium appliances, custom cabinetry, and a large center island ideal for entertaining. The primary suite offers a spa-like retreat with a luxurious bath with freestanding soaking tub, dual vanities, and a spacious walk-in shower. Additional guest suites each feature designer finishes and en-suite baths, while a flexible bonus room provides space for an office, gym, or media retreat. Designed for year-round enjoyment, the outdoor living area includes a fully equipped kitchen, outdoor dining terrace and a resort-style pool and spa. Every space has been designed to take full advantage of Siesta Key’s gentle breezes and year-round sunshine — creating a true outdoor sanctuary that’s both private and unforgettable. The rooftop deck, however, defines this residence. This elevated sanctuary invites you to experience Siesta Key from a completely new perspective. Imagine sunrise yoga sessions with bay breezes, afternoon lounging under a canopy, or unforgettable sunset gatherings framed by fiery Gulf skies. The rooftop deck creates a one-of-a-kind open-air retreat that feels both private and cinematic. Whether hosting guests or escaping for solitude, this rooftop oasis is where the rhythm of island life meets the art of design. Situated on the quiet north end of Siesta Key, Roberts Point is prized for its natural beauty, privacy, and proximity to Siesta Beach, Siesta Village, and downtown Sarasota. Experience West Indies coastal luxury at its finest — where superior design, outdoor living, and hurricane-rated craftsmanship unite in this extraordinary new home by Noah Thomas Builders. All images, renderings, and descriptions illustrate the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
749 SIESTA DR, SARASOTA, FL 34242
$750,00099 Days on yellowkey MLS ID: O6399340
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1978 Built: 1952 Tax: $11,062 (2025)Community: Bay IslandSingle Family
Taxes:$11,062
Remarks: Investor Special!!Welcome to your next amazing project! Known damage with full or partial rehab. Excellent renovation opportunity on an oversized lot in a highly desirable Siesta Key area. Sold AS-IS with significant upside potential.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Yisbel Bera Damiron (239-265-5102)
1356 POINT CRISP RD, SARASOTA, FL 34242
$4,495,00082 Days on yellowkey MLS ID: A4692551
2 Days Off yellowkey (back on 5/12/2026)
Bed: 5 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 7443 Built: 2005 Tax: $61,095 (2025)Community: Point Crisp AddSpa: YesSingle Family
Taxes:$61,095
Remarks: Virtually Staged. Ideally positioned on the exclusive Point Crisp Peninsula of Siesta Key, this waterfront estate offers a rare blend of privacy, scale, and direct boating access, with sweeping views spanning both Little Sarasota Bay and the Intracoastal Waterway. Set on over 230 feet of water frontage, the property features a newly constructed T-shaped dock (2025) and allows for effortless arrival by land or water, all complemented by the rare advantage of nearby beach access. Spanning more than 7,400 square feet of interior living space, the five-bedroom residence is designed for elevated coastal living, where expansive entertaining areas and walls of glass frame panoramic water views throughout. Freshly painted and ready for personal customization, the two-story interior is defined by high coffered and tray ceilings, crown molding, solid-core doors, and a blend of marble and wood flooring. A grand double-door entry opens to a soaring living area with a cathedral ceiling and statement fireplace, while floor-to-ceiling sliding glass doors create a seamless connection to the outdoor living spaces. The multi-level outdoor setting is designed for both gathering and relaxation, featuring an extended travertine deck, covered lounge areas, an outdoor gas fireplace, a summer kitchen with built-in grill and wraparound bar, an additional grilling station, and a heated pool and spa—all overlooking the tranquil waterfront. At the center of the home, the gourmet kitchen was redesigned in 2022 with quartzite countertops, custom cabinetry, professional-grade appliances, and an oversized island with seating. The adjacent family room offers built-in features and direct access to the outdoor entertaining areas, creating a natural flow for everyday living. The primary suite, located on the main level, serves as a private retreat with expansive water views, a custom walk-in closet, and a spacious en-suite bath. An additional guest suite on this level provides flexibility for a study, fitness room, or nursery. The second level is dedicated to guest accommodations and recreation, offering a home theater, an oversized game room with wraparound bar, multiple terraces, and three additional bedroom suites—one of which is generously scaled to function as a second primary suite—each with access to outdoor living spaces. The ground level includes a six-car split garage with multiple storage and utility rooms, supporting both functionality and flexibility. Located within one of Siesta Key’s most sought-after enclaves, this residence offers the unique combination of close beach access and protected boating waters. Just minutes away, Siesta Key Village provides dining and boutique shopping, while downtown Sarasota offers a vibrant cultural scene with theaters, galleries, waterfront parks, and marinas—delivering a lifestyle that balances coastal tranquility with everyday convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
5830 MIDNIGHT PASS RD #32, SARASOTA, FL 34242
$449,90061 Days on yellowkey MLS ID: A4694962
REDUCED by $50,000 (10.0%) on 06/16/2026
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 392 Built: 1962 Tax: $2,441 (2025)Community: Jamaica RoyaleSpa: NoCondo
Taxes:$2,441
Remarks: Welcome to Jamaica Royale, a Gulf-side development on Siesta Key, with its award-winning, crystal powder soft sandy beach, just nearby. This studio offers a main-floor villa that has been renovated for comfort and durability. Enjoy the new kitchen with new stainless steel appliances, quartz counters throughout and a new bath. All furnishings have been tastefully replaced with a focus on quality and functionality. The water heater is new, freshly painted, and waiting for its new owner. The location of the rear patio is conveniently near one of three pools. An on-site office offers an optional rental program, so you may generate potential income when not in residence. While you go out your rear patio to the beach, you will pass Jamaica Royale's additional pools, beach cabana and white sands of Siesta Key. The clubhouse offers a full kitchen, a meeting room, on-site association services and rental management. Outside offers barbecue grills, a table and chairs, a lounging area and shuffleboard, a great area to gather with family and friends. Siesta Key offers public transportation to many of the area's local coastal attractions, restaurants, shopping and Sarasota, with all that it offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
316 BEACH RD, SARASOTA, FL 34242
$5,249,000152 Days on yellowkey MLS ID: A4683801
REDUCED by $250,000 (4.5%) on 06/16/2026
Bed: 8 Bath: 9.0 Gar: 2 Liv Area Sq Ft: 4681 Built: 1996 Tax: $37,822 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$37,822
Remarks: Just steps from the shoreline, this coastal home offers deeded beach access and sweeping panoramic views of the Gulf. Completely remodeled in 2021, the property lives and performs like new construction, blending modern coastal design with durable, rental-ready finishes throughout. Thoughtfully designed across three living levels and serviced by a private elevator, the home features 8 bedrooms, 8 full baths, and 2 half baths, with expansive gathering spaces suited for both everyday living and hosting. With a proven track record as a high-performing short-term rental, the property generates approximately $400,000 to $500,000 annually, offering strong income potential alongside its lifestyle appeal. The top floor serves as the heart of the home, where the main kitchen and primary living area open directly to a Gulf-facing balcony showcasing breathtaking, unobstructed water views. This elevated vantage point creates a stunning backdrop for daily living, with the kitchen, dining space, and great room all positioned to take in the scenery. A secondary club room with wet bar provides an additional space to gather, while multiple balconies throughout the home frame the coastal setting from different vantage points, including select bedroom suites. Below, the outdoor living space features a private pool and integrated spa surrounded by lush landscaping, along with a fully equipped outdoor kitchen with built-in grill, refrigeration, and dining area. All eight bedroom suites offer ensuite baths and generous accommodations, with several enjoying Gulf views and private balcony access. Located near beach access and Siesta Key Village, this is a rare opportunity to own a fully renovated coastal home that delivers both luxury living and compelling investment performance.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
814 PARADISE WAY, SARASOTA, FL 34242
$1,945,000143 Days on yellowkey MLS ID: TB8483961
REDUCED by $50,000 (2.5%) on 06/15/2026
Bed: 4 Bath: 2.0 Gar: 2 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)
6312 MIDNIGHT PASS RD #305S, SARASOTA, FL 34242
$775,000145 Days on yellowkey MLS ID: A4684866
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 894 Built: 1968 Tax: $5,871 (2025)Community: Crescent ArmsCondo
Taxes:$5,871
Remarks: Positioned directly on the sands of world-famous Siesta Key, this 2-bedroom, 2-bath en-suite condominium offers the perfect blend of personal getaway and income-producing investment. Fully furnished and thoughtfully configured for vacation living, this residence is already an active vacation rental with proven historical returns, making it an ideal opportunity for buyers seeking a property that can help offset ownership costs while providing their own beachfront retreat. Inside, tile flooring throughout creates an easy-care coastal interior designed for high-traffic vacation use, while the split layout with two en-suite bedrooms provides privacy and comfort for guests. A large storage closet dedicated to beach gear and recreational “toys” makes it simple to keep everything needed for effortless days on the sand. From the residence, enjoy views of the Gulf of Mexico and the convenience of direct walk-out access to Siesta Key’s powdery white beach, where beach chairs are available for guests, perfect for owners and vacation renters alike. The location places you in one of the most desirable areas of the island, within walking distance to nearby restaurants, shops, and local favorites, or simply hop on the Siesta Key trolley for easy access up and down the island. With its prime beachfront setting, turnkey furnishings, and established rental performance, this property presents a compelling opportunity to own a slice of Siesta Key that can generate income while serving as your personal coastal escape.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Ryndie Brusco (941-809-6913)
1320 MOONMIST DR #B-11, SARASOTA, FL 34242
$1,200,000185 Days on yellowkey MLS ID: A4679270
REDUCED by $100,000 (7.7%) on 04/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1790 Built: 1968 Tax: $5,819 (2025)Community: Polynesian GardensCondo
Taxes:$5,819
Remarks: Rarely available direct bayfront 2/2 maintenance free villa in Polynesian Gardens. Magnificent views of the Intracoastal/Little Sarasota Bay. Watch the manatees and boats go by from your paved patio directly on the water. Spacious 2 bedrooms/2 full baths with very large great room. Updated kitchen and baths with new cabinetry, granite and stainless-steel appliances. Plenty of closet space. Garage with plenty of storage plus an extra driveway allows for 2 parking spaces. Newer washer/dryer in garage. Beautiful landscaping. Community has a heated pool, clubhouse and fishing pier. Close to shops, dining and America's #1 Beach - Siesta Key. Free trolley stops directly in the front of the community on Midnight Pass Road. Two pets allowed any size.
Listing Agent: Helene Hyland (941-685-2274)
SARASOTA, FL 34242
$2,895,00045 Days on yellowkey MLS ID: A4694972
Bed: 5 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2966 Built: 2021 Tax: $24,633 (2025)Community: Point Of Rocks TerraceSpa: YesApartment
Taxes:$24,633
Middle School: Sarasota Middle
Remarks: There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
5073 HIGEL AVE, SARASOTA, FL 34242
$2,400,00073 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)
1800 COVE II PL #213, SARASOTA, FL 34242
$595,00056 Days on yellowkey MLS ID: A4695562
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,863 (2025)Community: Midnight Cove IiCondo
Taxes:$5,863
Remarks: Fully Funded Reserves & Passed SIRS Inspections! 2 Bedroom, 2 Bath First-Floor Condo with Screened Lanai on fabulous Siesta Key Across from Crescent Beach – Just Steps from Siesta Key Beach! This turnkey furnished, beautifully maintained 2-bedroom, 2-bathroom condo is located on the first floor and offers the perfect blend of comfort and convenience. Enjoy stunning views of the Intracoastal Waterway right from your screened lanai. The property is fully funded for reserves and has passed the required SIRS inspections, providing peace of mind for the new owner. Key Features: Turnkey Furnished: Move-in ready with everything you need. Location: Prime location on Siesta Key, just across the street from Crescent Beach and an easy walk to world-renowned Siesta Key Beach. Views: Enjoy picturesque views of the Intracoastal Waterway from your lanai. Community Amenities: Marina with dock space available for rent or purchase. Fitness center and basketball court for active living. Heated pool for year-round enjoyment. Rental Opportunities: Midnight Cove II allows 1-week rentals, offering great potential for short-term rental income. The on-site office is optionally available to handle rentals on your behalf, making it a hassle-free investment. This property is an excellent opportunity for investors or those seeking a relaxing retreat in one of Florida’s most desirable locations. Schedule your private showing today!
Listing is courtesy of: EXCEPTIONS REALTY (941-536-8378)
Listing Agent: Peter Lev (941-536-8378)
6910 MIDNIGHT PASS RD #B, SARASOTA, FL 34242
$2,895,00047 Days on yellowkey MLS ID: A4694978
Bed: 5 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2801 Built: 2021 Tax: $22,665 (2025)Community: Point Of Rocks TerraceSpa: YesApartment
Taxes:$22,665
Remarks: There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.
5855 MIDNIGHT PASS RD #420, SARASOTA, FL 34242
$745,000257 Days on yellowkey MLS ID: A4671788
REDUCED by $20,000 (2.6%) on 06/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976 Tax: $4,975 (2024)Community: Harbor Towers Y & RCondo
Taxes:$4,975
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)
6157 MIDNIGHT PASS RD #F22, SARASOTA, FL 34242
$529,90059 Days on yellowkey MLS ID: A4692762
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1332 Built: 1974 Tax: $5,274 (2025)Community: Bay OaksSpa: YesCondo
Taxes:$5,274
Remarks: This property is a rare find, featuring two master suites upstairs, each with its own private balcony. The home is tastefully decorated and is being sold Turnkey, making it an excellent opportunity for immediate use or investment. Notably, the property already has a strong track record of rental income with several future bookings already in place. The Bay Oaks community offers a serene setting with mature landscaping and a wide array of amenities, including a heated pool, tennis courts, recreation room and a fishing pier. It also provides the convenience of on-site management and a picnic area with Barbeques for your enjoyment. Located less than a mile from Crescent Beach, the property offers easy access to the world-renowned powdery, quartz sand of Siesta Key, recently ranked as the #4 beach in the world by Tripadvisor in 2025. The area is a premier destination spot. Additionally, the trolley stops directly in front of the complex providing easy transportation to the various dining, shopping and nightlife options Siesta Key is famous for.
Listing is courtesy of: BECKMANN REAL ESTATE (941-346-3500)
Listing Agent: Josh Beckmann (941-321-3500)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000124 Days on yellowkey MLS ID: A4687301
REDUCED by $200,000 (3.7%) on 06/11/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$25,684
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
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