Sarasota Homes with Three+ Story Property Description

Sarasota Homes with Three+ Story Property Description

Welcome to Sarasota, Florida, a vibrant coastal city that beautifully blends the allure of sun-soaked beaches with a rich cultural tapestry. Nestled on the Gulf Coast, Sarasota is renowned for its pristine shoreline, including the award-winning Siesta Key Beach, which boasts powdery white sands and crystal-clear waters. Beyond the beach, this city is a haven for art lovers, featuring the famous Ringling Museum of Art, a lively performing arts scene, and an array of galleries that showcase local talent.

Sarasota is not just a paradise for relaxation; it’s also a thriving community with top-rated schools, lush parks, and a diverse dining scene that caters to every palate. Whether you’re exploring the historic downtown area or indulging in fresh seafood at a waterfront restaurant, there’s always something new to discover.

For those seeking a unique living experience, Sarasota offers an impressive selection of homes with three or more stories. These properties provide an unparalleled lifestyle, often featuring breathtaking views of the Gulf, spacious floor plans, and luxurious amenities. Imagine waking up to panoramic sunsets over the water or entertaining guests on your expansive rooftop terrace. Many of these stunning homes are located in exclusive neighborhoods that offer both privacy and proximity to the vibrant heart of Sarasota.

Whether you’re looking for a permanent residence or a seasonal retreat, Sarasota’s three-plus story homes promise a lifestyle of elegance, comfort, and breathtaking beauty. Discover your dream home in this enchanting city, where every day feels like a vacation!

Newest Sarasota Homes with Three+ Story Property Description

1240 Hillview Drive, Sarasota
$14,950,000
4 Beds ⋅ 4 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code
Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’s most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood paneled library, formal dining with 12-foot ceilings, and a wet bar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand-new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.

1240 Hillview Drive, Sarasota
8846 Fishermens Bay Drive, Sarasota
$2,795,000
4 Beds ⋅ 6 Baths ⋅ Fishermens Bay SubDv. ⋅ 34231 Zip Code
Virtually Staged. An exceptional waterfront opportunity in the sought-after Fishermens Bay community, this impressive Jonas Yoder custom-built residence offers 5,764 square feet of living space on over half an acre with direct boating access to Little Sarasota Bay. Featuring five bedrooms, four full bathrooms, two half bathrooms, and expansive water views from every level, the home combines quality craftsmanship, generous living spaces, and a beautiful waterfront setting. Thoughtfully designed with an emphasis on lasting construction and functionality, the residence features soaring ceilings, spacious living and entertaining areas, abundant natural light, and an extraordinary amount of closet space and storage throughout. A metal roof, double-pane windows, and a generator add to the home's appeal, providing valuable features for Florida waterfront living. The substantial floor plan offers flexibility for a variety of uses, with multiple areas to gather, entertain, or simply enjoy the surrounding water views. Outside, the property offers a private swimming pool, expansive grounds, and a waterfront dock with direct boating access to Little Sarasota Bay and the surrounding Sarasota waterways. Enjoy beautiful views from multiple levels of the residence, whether relaxing poolside, spending time outdoors, or heading out on the water. The generous half-acre-plus homesite provides a sense of space and privacy that complements the home's impressive size. Well maintained and showcasing the craftsmanship of its original custom construction, the residence presents an excellent opportunity to personalize the kitchen, bathrooms, and select interior finishes while preserving the quality and character of the home. Its substantial square footage, established waterfront setting, and thoughtful design provide a strong foundation for creating a truly exceptional coastal residence. Located in the desirable Fishermens Bay community, the property offers convenient access to Siesta Key's renowned beaches, shopping, dining, and the many attractions of Sarasota. With its custom construction, expansive waterfront homesite, private pool, dock, and impressive views, this distinctive property offers a compelling combination of space, craftsmanship, and waterfront lifestyle.

8846 Fishermens Bay Drive, Sarasota
3210 Higel Avenue, Sarasota
$11,950,000
4 Beds ⋅ 5 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Under Construction. Set along the coveted north end of Siesta Key, this waterfront residence overlooks the aquamarine waters of Big Pass and the Gulf of Mexico, where dolphins and manatees swim just beyond your backyard. Being built by Trend Homes and designed in collaboration with Blu Interiors, the home is anticipated to be complete by the end of summer 2027, with a thoughtfully curated selection of finishes and materials already in place. Offering over 4,500 square feet of living space, the residence includes four bedrooms, four and a half bathrooms, and a four-car garage. Expansive windows frame water views from nearly every room and bring natural light into the open living spaces. The kitchen features custom cabinetry and top-of-the-line appliances, complemented by a walk-in pantry with a Miele coffee maker. Natural gas service adds to the home’s amenities, while elegant stonework and refined millwork carry throughout the interiors. The spacious primary suite offers generous walk-in closets. Outside, a saltwater swimming pool with both a heater and chiller provides comfort throughout the seasons, while a private boat dock and seawall complete the waterfront setting. Spend afternoons on the water and evenings overlooking the pass, just minutes from shopping, dining, and Siesta Key’s celebrated white-sand beaches.

3210 Higel Avenue, Sarasota
304 Calle Miramar Unit 304S, Sarasota
$2,495,000
4 Beds ⋅ 4 Baths ⋅ Beach Villas At The Oasis SubDv. ⋅ 34242 Zip Code
Experience exceptional Siesta Key living in this distinctive two-level penthouse, crowned by an expansive private rooftop terrace with Gulf glimpses, spectacular sunsets and refreshing coastal breezes. Ideally situated in the heart of Siesta Village, just a short stroll from the world-renowned sands of Siesta Beach, this turnkey furnished residence offers 3,236 square feet of beautifully appointed living space, four bedrooms, four baths and multiple private outdoor terraces. The rooftop terrace is a true highlight, creating an extraordinary setting for sunset gatherings, entertaining under the stars or simply relaxing above the vibrant Village atmosphere. Inside, spacious open-concept living areas are designed for comfort and entertaining, complemented by a well-appointed kitchen with a generous center island, breakfast bar and seamless access to outdoor terraces. A separate entertainment room features a wet bar and expansive terrace, providing additional space for family and guests. The inviting primary suite offers a private terrace and spacious bath with soaking tub and walk-in shower, while a second en-suite bedroom and two additional guest bedrooms provide comfortable accommodations. A private elevator connects the oversized attached two-car garage to the living levels, offering convenience and ample storage for beach and recreational gear. Within an intimate, gated community of just 12 residences in three four-unit buildings, each building enjoys its heated pool and spa. Offered turnkey furnished for immediate enjoyment, this exceptional penthouse places the boutiques, restaurants and lively atmosphere of Siesta Village nearby, with Siesta Beach an easy distance from home. Whether enjoyed as a full-time residence, luxurious island retreat or vacation property with rental potential, subject to community restrictions, this remarkable offering combines generous living spaces, exceptional outdoor retreats and one of Siesta Key's desirable locations.

304 Calle Miramar Unit 304S, Sarasota
5531 Rosehill Road Unit 203, Sarasota
$250,000
2 Beds ⋅ 2 Baths ⋅ Admirals Walk SubDv. ⋅ 34233 Zip Code
Virtually Staged. Welcome to Admirals Walk, a gated townhome community in Sarasota where this end unit has been completely redone and is ready for its next owner. It offers 2 bedrooms, 2 bathrooms, a third-level loft and 1,316 square feet. Every space has been updated with today’s buyer in mind, so you can move in and start enjoying it from day one. From the private ground-level entry, refinished stairs lead to a bright, open main level with vaulted ceilings, clerestory windows, new laminate flooring and sleek black track lighting. The new kitchen anchors the space, with crisp cabinetry, quartz countertops and a fluted peninsula with breakfast bar seating. It also has a new microwave and a reverse-osmosis filtered water tap. Just off the dining area, a built-in dry bar with a wine fridge makes hosting easy. The two bedrooms sit on opposite sides of the home for privacy, and each has its own en-suite bath and walk-in closet. That makes the layout ideal for co-owners, visiting family or a dedicated guest suite. The primary bath has been refreshed with new marble-look shower tile. The third level adds a versatile loft that is perfect as a dedicated home office or an additional guest space, set apart from the main living area. New light fixtures, ceiling fans, mirrors and AC vents run throughout, along with a 2026 water heater, 2020 AC system, and with the washer and dryer included in the sale! Admirals Walk residents enjoy a clubhouse, community pool and fitness center in a pet-friendly setting. Clark Road shopping and dining are minutes away, with easy access to I-75, downtown Sarasota and Siesta Key Beach. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

5531 Rosehill Road Unit 203, Sarasota
1023 Tocobaga Lane, Sarasota
$2,995,000
3 Beds ⋅ 4 Baths ⋅ Tocobaga Bay SubDv. ⋅ 34236 Zip Code
Sophisticated gated living just moments from the heart of downtown Sarasota. Evoking the timeless elegance of Palm Beach with the warmth of Old Florida charm, this exceptional Spanish Mediterranean residence is tucked within the exclusive gated waterfront enclave of Tocobaga Bay. One of only 9 private residences in the community, ideally positioned just moments from Sarasota's renowned dining, arts, shopping and waterfront attractions. Surrounded by lush tropical landscaping and tranquil water views, the home is thoughtfully designed for both sophisticated entertaining and relaxed everyday living. Expansive interiors are filled with natural light, highlighted by a grand foyer, travertine flooring, oversized floor-to-ceiling picture windows, motorized shades, and custom window treatments throughout. The residence features 3 bedrooms, each with its own en-suite bath, along with a media room or private office and a private 3-stop elevator. The oversized 4-car garage offers exceptional storage and ample spaces for vehicles, golf carts, kayaks, and recreational equipment, while the air-conditioned bonus room appointed with premium finishes including a La Cornue gas cooktop, Sub-Zero refrigerator, custom Campbell Cabinetry, spacious walk-in pantry, oversized center island and Taj Mahal quartz countertops and backsplash. The oversized living room offers an inviting atmosphere for gathering, while the separate formal dining room is perfectly suited for elegant dinners and entertaining. The primary suite serves as a peaceful sanctuary complete with its own Juliette balcony, dual custom walk-in closets, and a spacious en-suite bath. Two additional guest suites occupy the third floor, each with private baths, offering ideal comfort and separation for family and guest. Designed to embrace Sarasota's indoor-outdoor lifestyle, the open-air heated saltwater pool is surrounded by lush tropical landscaping and expansive patio space for lounging and dining. Additional improvements: new tile roof (2023), new irrigation system (2024), updated water heaters (2023 & 2024), electrical panels (2024), and updated A/C units. Residents enjoy access to the community day dock with direct bay access, perfect for boating and waterfront enjoyment. Perfectly located near Sarasota's renowned beaches, St. Armanda Circle, The Bay Park, and the iconic Ringling Bridge, this remarkable residence offers an exceptional lifestyle just minutes from the energy and culture of downtown Sarasota. Offered fully furnished and ready for immediate enjoyment.

1023 Tocobaga Lane, Sarasota
315 S Shore Drive, Sarasota
$4,950,000
4 Beds ⋅ 4 Baths ⋅ Sapphire Shores SubDv. ⋅ 34234 Zip Code
House never flooded, including during Hurricanes Milton and Helene, and protected by a generator! Built as a solid concrete structure on concrete pilings, this home was engineered for the Florida waterfront. Lavishly embellished with Old World authenticity, this exceptional waterfront estate evokes the grandeur of a 17th century Tuscan farmhouse. Custom built by John Cannon, the home is set on what was once Ringling’s personal yacht basin, offering protected sailboat water, 178 feet of seawall, a private dock, two boat lifts (24,000 lbs & 10,000 lbs), and a dedicated kayak lift platform, all framed by sweeping panoramic water views. From the moment of arrival, the level of craftsmanship is unmistakable. Walls are finished in aged plaster, hand made terra cotta floors have been acid washed and stained to reflect centuries of wear, and authentic frescoes and ceiling beams inspired by the Renaissance period add depth and character throughout. The great room provides a dramatic setting for entertaining with soaring 22 foot ceilings, a gas fireplace, and a wet bar accented by a hammered copper sink. The chef’s kitchen is equipped with an Italian eight burner gas range and Brazilian soapstone countertops, while the dining room features a rare brick vaulted ceiling that reinforces the home’s Mediterranean soul and creates a truly immersive dining experience. The primary suite is a romantic retreat with his and hers walk in closets and a spa like bath wrapped in rich wood and stone finishes. Additional spaces include two to three guest bedrooms, dual offices, a bonus room, and a wine room. A private elevator connects every level, offering effortless access from the garage to the living spaces above. A true 2,500 square foot ground level garage offers tandem parking for four plus vehicles, making it a dream for car collectors. Outdoor living is exceptional, with stone and wrought iron terraces, an outdoor kitchen and bar on the main level, all designed to capture natural breezes and expansive water views. The newly completed infinity edge pool and spa create a striking visual effect, with the water appearing to seamlessly spill into the bay. This storybook residence is ideally located near Sarasota’s beaches, dining, and cultural attractions, offering a rare blend of architectural artistry, privacy, and timeless elegance.

315 S Shore Drive, Sarasota
775 John Ringling Boulevard Unit 24, Sarasota
$575,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor East SubDv. ⋅ 34236 Zip Code
Fall in love with breathtaking views of the turquoise waters of Sarasota Bay, the illuminated Ringling Causeway at night, and spectacular fireworks displays over the bay on the Fourth of July and New Year’s Eve. This charming 2-bedroom, 2-bathroom condo is offered turnkey with optional furnished, making it easy to move in and start enjoying the Florida lifestyle. The inviting open-concept floor plan features ceramic tile flooring, a renovated kitchen and bathrooms, and an enclosed lanai where you can relax and take in the beautiful surroundings. A shared laundry room is conveniently located right next door. Enjoy an impressive selection of community amenities, including a clubhouse, a waterfront community pool with sweeping bay views, shuffleboard courts, a community gas grill, secured bicycle storage, and kayak storage. Even better, complimentary boat slips are available on a first-come, first-served basis and can accommodate sailboats and powerboats up to 30 feet, subject to availability and community rules. Located in a prime Sarasota waterfront setting, Sarasota Harbor East offers an exceptional opportunity to enjoy boating, beach days, vibrant downtown dining, and unforgettable sunsets. Rentals are permitted after one year of ownership, subject to community restrictions. Whether you're looking for a seasonal escape, a waterfront retreat, or your next Florida home, this Sarasota gem is one you won't want to miss!

775 John Ringling Boulevard Unit 24, Sarasota
1250 May Lane, Sarasota
$1,050,000
3 Beds ⋅ 4 Baths ⋅ Rosemary Park SubDv. ⋅ 34236 Zip Code
Set in Sarasota’s increasingly sought-after Rosemary District, this tri-level townhome offers a distinctly urban take on Florida living—where polished interiors, abundant natural light, and an enviable in-town address come together with remarkable ease. Built in 2019, this end-unit residence offers nearly 2,200 square feet of beautifully considered living space, with a sense of volume and privacy rarely found in a downtown setting. The architecture is complemented by a restrained palette of elevated finishes: warm hardwood floors, high ceilings, crisp crown molding, premium plaster-finished walls, plantation shutters, custom closets, and thoughtfully integrated storage. Every element feels intentional, creating elegant, interiors without sacrificing comfort. At the home's center, the chef’s kitchen serves as both a visual anchor and a natural gathering place. Solid wood cabinetry is paired with luminous quartz countertops, refrigerator, gas range, generous island with seating, and a well-appointed pantry. A nearby powder room adds convenience, while the kitchen’s open connection to the dining and living spaces creates an effortless flow for both intimate evenings and larger gatherings. In the dining room, a sculptural chandelier adds drama, while expansive windows on the north and south elevations draw daylight deep into the interiors, subtly changing the home's character from morning through late afternoon. The primary suite occupies the third level, offering a private retreat above the home's activity. Its generous bath and exceptionally large walk-in closet offers the space and separation more often associated with a single-family residence. A second bedroom suite, complete with its own bath, shares this level, along with a dedicated laundry room. On the first floor, a beautifully proportioned third suite—with a walk-in closet and en-suite bath—offers a quiet guest retreat or an especially desirable home office. Outside, a covered sitting area extends the home’s living spaces into the open air. It is an intimate setting for morning coffee, an alfresco dinner, or an evening glass of wine beneath Sarasota’s expansive skies. Valencia at Rosemary Place is an intimate gated enclave of Tuscan-inspired luxury townhomes positioned within a short distance of the restaurants, boutiques, galleries, and cafés that have made the Rosemary District one of Sarasota’s most dynamic neighborhoods. Main Street and Palm Avenue are nearby, while The Bay and Sarasota’s waterfront are just minutes away. Less than a quarter mile from the residence, the expansive 53-acre Bay Park is a signature public park along Sarasota Bay and adds another dimension to the lifestyle, with nature trails, a boardwalk, kayak launch, splash pad, fitness opportunities, concerts, and community events. Marina Jack, the Van Wezel Performing Arts Hall, Whole Foods, Marie Selby Botanical Gardens, and the district’s boutique hotels are all close at hand, with Lido Key and Siesta Key beaches within easy reach. Across the street, The Modern offers another amenity-driven extension of the lifestyle, with access to its pool, fitness center, restaurant, and bar available for a nominal monthly fee. Ultimately, this residence is defined as much by its setting as by its design. Refined but relaxed, highly considered yet wonderfully livable, it captures a distinctly Sarasota way of life.

1250 May Lane, Sarasota
1256 Riegels Landing Drive, Sarasota
$1,895,000
3 Beds ⋅ 4 Baths ⋅ Riegels Landing SubDv. ⋅ 34242 Zip Code
Designed by Sarasota School of Architecture.

1256 Riegels Landing Drive, Sarasota
35 Watergate Drive Unit 804, Sarasota
$2,845,000
3 Beds ⋅ 3 Baths ⋅ The Tower Residences SubDv. ⋅ 34236 Zip Code
Inspired by the luminous glamour of New York’s Baccarat Hotel, Tower Residence 804 is a dazzling expression of elevated living at The Ritz-Carlton, Sarasota. A private elevator opens directly into your own foyer, where nine custom crystal chandeliers set the tone for a residence designed to captivate. The open split floor plan unfolds across three exceptionally spacious bedrooms and three baths, with a gracious dining room, full kitchen, and separate laundry room. Rich hardwood floors, exquisite architectural millwork, custom doors, and an embellished fireplace bring warmth and distinction to every space. Walls finished in high-gloss Fine Paints of Europe Hollandlac reflect the light with a polished, jewel-like sheen. Every room opens onto an enormous private terrace, where sweeping views of Sarasota’s skyline and sparkling marina create a spectacular backdrop for year-round dinner parties and effortless outdoor living. Generous in scale and seamlessly connected to the interiors, the terrace feels like a grand extension of the home—an extraordinary setting for gathering with friends as the city lights shimmer across the water. Beyond your door, enjoy the signature comforts of Ritz-Carlton living, including 24-hour in-residence dining and attentive hotel services. On the third floor, an exceptional collection of amenities awaits: two social rooms, a movie theater, a fully equipped fitness center, sauna and steam baths, a massage room, and an expansive outdoor oasis with a heated lap pool, spa, fire table, and barbecue grills. All of this is moments from Sarasota’s celebrated theater, opera, ballet, galleries, fine dining, beaches, and Marie Selby Botanical Gardens—and conveniently close to Sarasota-Bradenton International Airport. Tower Residence 804 is more than a home: it is a private world of crystal-lit elegance, gracious service, and extraordinary coastal views.

35 Watergate Drive Unit 804, Sarasota
420 Beach Road Unit 507, Sarasota
$1,695,000
2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code
Siesta Key Beach paradise! Wake up to Gulf breezes and end each day with a sunset on the beach from this direct beachfront condo at Siesta Gulf View. This fifth floor center unit 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened balcony, accessible from the living room, kitchen, and primary suite. This beautifully updated unit with open floor plan, newly installed 2026 air conditioner with coastal coil, reverse osmosis both refrigerator water/ice, full granite counter tops, all stainless steel appliances, shaker cabinets throughout and beach decor with Restoration hardware custom leather sectional. Primary bedroom has his/her walk in closets and built-in linen closet. This income producing TURNKEY FURNISHED with Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping., 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. 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 Beach resort living this is a MUST SEE! Land, Site, and Tax Information

420 Beach Road Unit 507, Sarasota
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