Sarasota County Homes with Three+ Story Property Description

4 Beds ⋅ 7 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code

Meticulously designed and flawlessly executed, this exceptional 6,700-square-foot palatial estate on iconic Westway Drive is majestic. Nestled in Lido Shores, the property spans an impressive 1.67 acres—making it among the largest and most desirable waterfront holdings in the Lido/Longboat area. With a premier western exposure and sweeping waterfront frontage, the property offers unobstructed, panoramic views of Sarasota’s legendary sunsets and the Gulf of Mexico's ever-changing beauty. Architectural brilliance is evident in every aspect of the estate’s design, as classic Mediterranean influences blend with graceful elegance. Security and exclusivity are paramount, ensuring that every moment in this sanctuary is one of tranquility and distinction. A regal, gated entrance creates a dramatic sense of arrival, while the privileged location ensures seclusion and prominence along spectacular waterways and pristine Gulf Coast shorelines. The long driveway winds through mature, manicured landscaping—lush with live oaks, sabal palms, palmettos, and ferns, all illuminated by dramatic night lighting. The home’s brick-paved courtyard presentation is adorned with stately columns and intricate detailing, setting a tone of timeless sophistication that echoes throughout the property. A stately portico welcomes with a monumental carved-wood entry door that sets the tone for sophisticated interiors. Inside, grand rooms feature exquisite fixtures, polished finishes, and rich furnishings, unified by an elegantly styled aesthetic and an atmosphere of refined opulence. Every detail reflects a commitment to luxury, comfort, and timeless style. Stunning examples include exquisite marble and wood flooring, a sweeping curved staircase with iron railing, arched windows and doors, artisan millwork, high ceilings with custom details, triple crown molding, and bespoke cabinetry that embellish the home throughout. With three expansive levels, the residence boasts four en suite bedrooms, an attached 770-square-foot VIP apartment secluded from the rest of the house, two additional baths, dual living rooms, three formal and casual dining areas, three offices, a vast recreation room, a gym, two laundry rooms, an elevator, two fireplaces, a three-car garage, and dozens of French doors and glass sliders that open to invite the incredible outdoors in. Expansive covered terraces and upper-level balconies stretch along the rear façade, offering multiple spaces for outdoor living and entertaining—perfect for both lavish celebrations and intimate gatherings. Outdoor living unfolds effortlessly with a sleek pool and spa, inviting lounges, open-air dining areas, and voluminous acreage that add to the options and appeal of waterfront living. Every aspect of the residence, from its expansive footprint to its gilded amenities, has been thoughtfully designed to deliver a lifestyle of unrivaled sophistication, comfort, and exclusivity. This coastal refuge offers an irreplaceable opportunity in Sarasota’s elite waterfront market. The estate’s enviable location offers easy access to Sarasota’s world-class beaches, the downtown’s vibrant cultural scene, and the boutique shopping and fine dining venues of St. Armands Circle. This exceptional listing is truly stunning, perfect for a luxurious lifestyle in a magnificent setting. A must-see in person to fully appreciate its wonderful allure and unique characteristics.

1083 Westway Drive, Sarasota

$5,750,000

4 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

At the water’s edge of Sandspur Lane sits one of Casey Key’s best-kept secrets: a stunning estate offering unmatched privacy, tranquility, protected waterfront, and bespoke contemporary coastal architecture. A multi-year renovation completed in 2024 reimagined the property, adding more than 2,000 square feet of interior and exterior living space and transforming an already exceptional waterfront home into a truly distinctive residence. Tucked at the end of this quiet, private lane, the home’s structural features and sheltered location provide proven storm-resilient advantages. Ownership of both sides of the canal protects the mature trees and vegetation along the opposite shoreline, preserving natural privacy. The main level features vaulted ceilings and an open floor plan connecting the modern kitchen with dining, living, and family rooms, while wraparound aquarium glass windows and sliding glass doors flood the space with natural light and offer views of the water and the parcel’s expansive waterfront setting. A floating staircase rises through a circular glass stair tower to the primary suite, featuring a spacious bath, sitting room, and a private balcony with long water views. An adjoining casita with its own private entrance and water views provides luxurious accommodations for family, guests, or in-home staff. Two dedicated offices with built-in cabinetry and granite desks offer long ICW views, creating an inspiring setting for work or personal pursuits. A new elevator connects every level, from the garage to the rooftop deck. Designed for recreation and entertaining, the property features a cabana with bar and outdoor kitchen, a new waterfall spa and remodeled pool with water features, a home gym, firepit, indoor-outdoor Sonos sound system, and multiple balconies, terraces, and decks. After sunset the extensive outdoor lighting, including dock and underwater fish lights, transforms the property. The long driveway and motor court accommodate parking for 12–15 vehicles— a rarity on Casey Key. The 200 feet of protected waterfront includes a newly added 45-foot dock, 20,000-lb. boat lift, and two PWC lifts. And when the Gulf beckons, deeded beach access leads to its warm waters and shoreline. From sunrises over the ICW to Gulf sunsets from the rooftop deck and illuminated evenings poolside, the home embraces its waterfront setting from virtually every angle. This residence offers a package increasingly hard to find: extraordinary privacy, tranquility, and protected waterfront living—all wrapped in a beautifully reimagined contemporary coastal estate on one of Florida’s most exclusive islands.

3718 Sandspur Lane, Nokomis

1975 Gulf Of Mexico Drive Unit G4-203, Longboat Key

$795,000

2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code

Virtually Staged. Wake up to breathtaking, unobstructed views of the Gulf of Mexico from this two-bedroom, two-bath condominium in beautiful Seaplace. The screened-in lanai provides the perfect setting to relax, take in spectacular sunsets and enjoy the azure waters of the Gulf. On the lanai there is an additional large retractable screen for protection from the sun along with a hurricane impact sliding glass door. Offered unfurnished and a clean slate ready for updating, this residence presents a wonderful opportunity to bring your own style and vision to a prime Gulf-facing property. This residence offers spacious and comfortable living space, while the spectacular views provide a backdrop that is truly hard to replicate. Additional features include electric hurricane shutters on the bedroom windows, two assigned parking spaces, including one covered space, offering convenience and value. The Seaplace community on Longboat Key has 42 acres of magnificent grounds, 1/2 mile of beautiful beach and a mile walking trail around the property. Included in the amenities are two swimming pools with spas, kiddie pool, fitness room, sauna, fire pit and kiddie playground. Located very close to famous Saint Armand's Circle and downtown Sarasota where you will find an abundance of restaurants, boutique shopping, art galleries, live theatre, ballet and an opera house. Don't miss this chance to live in paradise on unique Longboat Key. BE SURE TO SEE THE VIRTUAL TOUR!

1975 Gulf Of Mexico Drive Unit G4-203, Longboat Key

$3,400,000

5 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Set along the coveted waterways of Siesta Key, this exceptional newer-construction home is a refined coastal sanctuary where sophisticated design, effortless boating, & the relaxed beauty of island living come together. Thoughtfully designed for everyday enjoyment, the home offers a rare opportunity to embrace the Siesta Key lifestyle from a private waterfront setting, complete with a boat lift & kayak launch. The home reveals an elevated level of craftsmanship & thoughtful design. Soaring ceilings, engineered hardwood floors, plantation shutters, crown molding, and carefully considered architectural details create an atmosphere of understated elegance & comfort. An elevator provides access to all levels while expansive sliders open the main living spaces to the balcony, pool & tropical surrounds. The beautifully appointed kitchen combines sophisticated finishes w/exceptional functionality. Luxurious quartz countertops, oversized island w/seating, custom soft-close cabinetry, tile backsplash, farmhouse sink, KitchenAid appliances, Vitafresh refrigeration & under-cabinet lighting create an inviting culinary environment suited to quiet mornings & memorable gatherings. The dining area elevates with a beautifully appointed wet bar, wine/beverage fridge, dedicated wine storage & distinctive hammered sink. The family room offers an inviting gathering space centered around a Dimplex electric fireplace w/marble surround, illuminated custom cabinetry & electric sunshades. Pocket sliders open to the covered balcony, where tongue-and-groove wood cypress ceiling & ceiling fans create a warm & sophisticated setting for enjoying the tropical surroundings. The primary suite is designed as a private retreat w/engineered hardwood flooring, plantation shutters, crown molding & direct balcony access. The spa-inspired primary bath features elegant quartz & marble detailing, statement pendant lighting, a glass marble shower & luxurious soaking tub. A walk-in closet with custom built-ins completes this serene sanctuary. Upstairs, beautifully appointed guest accommodation provides privacy for family & visitors. A charming music/reading nook framed by a stained-glass window adds a unique sense of character, while an expansive bonus room with built-in desk, wine fridge & dramatic open-to-below design offers an extraordinary space for an office, lounge, or additional entertaining. The outdoor spaces transform the property into a private retreat. A fully enclosed, 2 story caged pool & lanai are surrounded by lush tropical landscape and thoughtfully designed gathering spaces. The outdoor living area features a tongue-and-groove cypress ceiling, ceiling fans, minimalist stone landscaping, and a crystal fire pit, creating an inviting setting for long afternoons by the pool. The private boat lift provides effortless access to the surrounding waterways, while the kayak launch invites leisurely exploration of Siesta Key beach coastal landscape only .3 miles away. An oversized garage w/epoxy non-slip flooring, hanging storage & convenient elevator access provides exceptional functionality of the home's elevated lifestyle. Mornings can begin on the waters of Siesta Key, afternoons can unfold along the powder-soft sands of world-renowned Siesta Key Beach & evenings can be spent wandering through Siesta Village where charming boutiques, restaurants & cafés capture the spirit of island living.

70 Island Circle, Sarasota

$1,295,000

3 Beds ⋅ 4 Baths ⋅ Valencia At Prestancia SubDv. ⋅ 34236 Zip Code

Welcome to 1262 May Lane, a beautifully appointed townhome at Valencia in Sarasota’s vibrant Rosemary District. Thoughtfully designed with refined finishes and functional upgrades throughout, this residence offers en-suite bedrooms, hardwood floors, crown molding, custom closets, and abundant storage. The gourmet kitchen is equipped with solid-wood cabinetry, a waterfall-edge quartz island, Sub-Zero refrigerator, and Wolf dual-fuel range and oven. Large windows with Hunter Douglas Silhouette shades bring in generous natural light, while upgraded fixtures and finishes create a polished, cohesive feel. The primary suite opens to a private balcony with bamboo-composite flooring and a built-in cabinet with sink, an inviting spot to enjoy Sarasota’s open air. The laundry area includes a smart washer and dryer with quartz countertop, and the mudroom offers bench seating, extensive cabinetry. Practical features include a whole-house water-treatment system, central vacuum with Hide-A-Hose outlets on each level, impact windows, and a spacious two-car garage with epoxy flooring, storage systems, service door, and Wi-Fi battery-backup door opener. Conveniently located near The Bay Park and downtown Sarasota, this home is also walkable to the Rosemary District’s excellent dining, shopping, and neighborhood energy.

1262 May Lane, Sarasota

$150,000

2 Beds ⋅ 2 Baths ⋅ Japanese Gardens Of Venice SubDv. ⋅ 34293 Zip Code

Dog Friendly & Move-In Ready! Welcome to this updated 2-bedroom, 1.5-bath home in Japanese Gardens, a resident-owned, active 55+ community with no lot rent! Located in the community’s dog-friendly section, this home is ideally situated directly across the street from the clubhouse, pool, and hot tub. Inside, you’ll find an open floor plan with laminate and tile flooring throughout, upgraded windows, and plenty of comfortable living space. The former Florida room has been opened to the main living area, creating a larger, more open feel that’s perfect for everyday living and entertaining. And there’s even more space to enjoy with a large enclosed sunroom at the rear of the home. Outside the sunroom if a private outdoor shower. Additional updates include a new roof, making this home truly move-in ready. With its expanded living space, great location, pet-friendly setting, and access to all the amenities Japanese Gardens has to offer, this home is ready for its next owner! Updates: 2022: a/c, duct work professionally cleaned and inspected, flooring in FL room and sunroom completely replaced. 2024: The add on living room was rebuilt including wall, window, flooring, and doors. 2025: new water heater, new garbage disposal, replaced shed and improved carport with attachments and stanchions, 100% new roof including the new construction, the sunroom, and the older section of the home with carport and shed.

6150 Teahouse Road, Venice

5450 Bentgrass Drive Unit 5-108, Sarasota

$179,900

1 Beds ⋅ 1 Baths ⋅ Las Palmas SubDv. ⋅ 34235 Zip Code

LOCATION, LOCATION, LOCATION! Welcome to this charming first-floor condo in the highly desirable gated community of Las Palmas! This spacious 1-bedroom, 1-bath residence offers nearly 1,000 square feet of comfortable living space and is ideally located approximately 1 mile from UTC Mall, offering an incredible selection of shopping, dining, and entertainment just minutes away. Step inside to a bright, open floor plan featuring a spacious great room accented with crown molding. The kitchen overlooks the main living area and features granite countertops, a tiled backsplash, and plenty of workspace, making it ideal for everyday living and entertaining. The generously sized primary bedroom provides a comfortable retreat, while the bathroom features a remodeled shower. An inside laundry room with a newer full-size washer and dryer. You’ll also love the location within the community—this building is conveniently situated closest to the large pool and clubhouse! Las Palmas is a pet-friendly, gated community with approximately 450 residences and an impressive array of amenities, including a clubhouse, fitness center, tennis courts, two heated swimming pools, hot tub, dog park, playground, and picnic areas. The community is NOT age-restricted, and the monthly maintenance fee is $373. The condo is located in a non-flood zone and offers several important updates, including A/C condenser (2020), water heater and refrigerator (2021), air handler (2022), and air duct cleaning (2024), per seller. Whether you're looking for a full-time residence, seasonal Florida getaway, or investment opportunity, this first-floor condo offers the perfect combination of location, amenities, convenience, and low-maintenance Florida living—all just minutes from everything the UTC area has to offer!

5450 Bentgrass Drive Unit 5-108, Sarasota

$4,695,000

6 Beds ⋅ 5 Baths ⋅ Gedney Richard H Inc SubDv. ⋅ 34275 Zip Code

Experience effortless luxury in this exceptional Gulf-front estate on the pristine shores of Casey Key, where the Gulf is your backyard and privacy, tranquility, and sweeping water views await! Originally built in 1951 and tastefully renovated in 2016 and 2025, this beach-front residence seamlessly blends classic character with refined modern updates. Offering nearly 4,000 square feet of living space under air, this home features 6 bedrooms and 4.5 bathrooms across three levels, designed for both comfort and entertaining. Generous room for hosting/gathering throughout with three expansive balconies inviting you to enjoy both breathtaking Gulf and intracoastal waterway views! Thoughtfully designed in-law quarters on the first level with the second level featuring a gourmet chef’s kitchen, family room and additional guest rooms/baths. The chef's kitchen is equipped with a Wolf six-burner gas range with griddle and double oven, a Sub-Zero PRO refrigerator/freezer, granite countertops, soft-close cabinetry, and a large centerpiece island perfect for casual dining with a view. The Owner's level on the third floor is to die for! Tremendous views of the Gulf from the substantial primary suite with this level also featuring a sitting area and den/office/bonus room that has views of the intracoastal waterway! The primary bathroom includes a stand-alone garden tub with skylight over, large walk-in glass and tile shower, dual vanities, and solid wood cabinets with granite countertops. Additional highlights include impact windows and doors, travertine flooring throughout (with the exception of engineered hardwood in the kitchen), marble-tiled baths, and a 2-car garage. Recent improvements include a new metal roof (2025), fresh paint inside and out (2025), a new septic system (2025) and A/C system (2023), offering peace of mind for years to come. Offered turnkey furnished. With private beach access steps away, this is a rare opportunity to own a truly remarkable waterfront retreat on one of Florida’s most desirable barrier islands! Call today for more information or to set up a private tour! **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

412 S Casey Key Road, Nokomis

$1,599,000

3 Beds ⋅ 4 Baths ⋅ Tiffany Sands SubDv. ⋅ 34242 Zip Code

Exceptional opportunity to own a slice of heaven on Siesta Key Beach. The sparkling turquoise water and quartz sand beach await you. This sought after renovated townhouse has lovely Gulf Views and fabulous deeded Beach front access for everyday enjoyment. TURNKEY furnished & spacious with 3-bedrooms and 3.5 baths. Open floor plans to capture great light and an airy feeling created by coastal living. Enjoy the magnificent decks off the Primary Suite and Living Room to capture beautiful sunsets and Gulf breezes. Also, it is a great place just to relax on a lounge chair in the Florida Sunshine. The Gourmet Kitchen has a lovely wood painted cabinetry, granite counters cook-top island, Breakfast Bar with counter seating and all Stainless Appliances. The main level offers a bonus room that is very versatile with a full bath & separate entrance. Perfect for guests, home office or media room. The Primary Suite has Views of the Gulf from Sliders that opens to a great deck. The Master Bath has dual marble vanities and a large frameless glass shower & separate water closet. The other two bedrooms share a Full Bath. Laminate flooring and Plantation Shutters throughout. So close to Siesta Key Villate for boutique shopping, fabulous restaurants & island entertainment. Ready for the next buyer to own this spectacular beach retreat. Motivated Seller.

548 Beach Road Unit A, Sarasota

$1,500,000

3 Beds ⋅ 3 Baths ⋅ Mangroves Sub The SubDv. ⋅ 34242 Zip Code

Virtually Staged. Old Florida Charm on Siesta Key's Quiet South End Hidden beneath a canopy of mature tropical trees on one of South Siesta Key's most desirable residential streets, this distinctive three-story home captures the timeless character and charm that make island living so special. Located within a small enclave of established homes where short-term vacation rentals are restricted, the neighborhood is known for its lush landscaping, beautiful waterfront residences, and authentic sense of community that has become increasingly rare on Siesta Key. Thoughtfully spread across three levels, the home blends timeless coastal architecture with modern updates. Exposed wood beams, a fireplace, and an abundance of outdoor living spaces give the residence a sense of warmth and character rarely found in newer construction. Multiple terraces provide private places to relax throughout the day, while the newly built Trex rooftop deck elevates the experience with sweeping sunset views and refreshing Gulf breezes. Offering 3 bedrooms, 3 bathrooms, a two-car garage, a newer metal roof, high-velocity HVAC system, Hardi board siding, and a generously sized fenced yard, the property strikes a balance between charm, functionality, and laid-back island living. Just a short walk to Point of Rocks, beach access, South Siesta Village, Captain Curt's, Crescent Beach Market, the Crescent Club, and other local favorites, the location places the best of Siesta Key at your doorstep. Spend your days exploring the island by bike, trolley, or on foot, with Siesta Key Beach, Turtle Beach, waterfront dining, and endless coastal activities all nearby. Whether it's a morning walk along the shore, an afternoon spent enjoying the island's vibrant beach culture, or sunset from the rooftop deck, this home is perfectly positioned to experience everything that has made Siesta Key one of Florida's most beloved destinations. Properties like this are becoming increasingly difficult to find on Siesta Key. Combining architectural character, modern improvements, walkability to the beach and dining, a large private yard, and a neighborhood centered around homeowners rather than vacation rentals, this is a rare opportunity to enjoy the authentic charm of island living on the quieter south end of the Key.

1209 Sea Plume Way, Sarasota

8701 Midnight Pass Road Unit 304A, Sarasota

$649,000

2 Beds ⋅ 2 Baths ⋅ Turtle Bay SubDv. ⋅ 34242 Zip Code

Experience the ultimate Bayfront lifestyle on Siesta Key in this turnkey furnished 2BR/2BA residence at Turtle Bay. Tucked away on the serene south end of the island, this spacious condo blends modern coastal luxury with vibrant island living. Wake up to spectacular sunrises over the Intracoastal from your private, enclosed lanai, and wind down with sunsets via deeded beach access directly across the street. The generous primary suite features a walk-in closet, and a private entrance to the lanai. An in-unit laundry room includes a full-size washer/dryer and extra storage—a rare luxury on the Key! Additional upgrades include hurricane-impact windows to perfectly frame the water views. One of the most valuable features is the private, oversized 1-car garage providing secure parking and ample gear storage. Pet-friendly Turtle Bay offers premium amenities: brand-new boat docks/slips (just $300/year and you can add your own hoist), an updated fishing pier, kayak launch/storage, heated pool/spa, lighted tennis/pickleball courts, shuffleboard, clubhouse, and grilling area. Enjoy maintenance-free ease with on-site management, secure entry, and elevators. Leave your car behind and take the free trolley to nearby Siesta Village, South Village, or Point of Rocks snorkeling. Just minutes to Stickney Point Bridge and 20 minutes to downtown Sarasota. Perfect as a full-time residence, seasonal escape, or a great investment income opportunity.

8701 Midnight Pass Road Unit 304A, Sarasota

$2,175,000

4 Beds ⋅ 6 Baths ⋅ Coronas Park SubDv. ⋅ 34242 Zip Code

Architectural masterpiece tucked away in one of Siesta Key’s most coveted, private gated communities. Masterfully renovated, this executive estate seamlessly blends modern elegance with unparalleled coastal convenience. Positioned just one block from the water, the residence boasts beautiful views of the Gulf of Mexico and the glittering Sarasota skyline—offering front-row seats to world-class Florida sunsets every single evening. Built with peace of mind in mind, both the home and the community's ground level are significantly elevated to minimize flood risk, meaning this property has never flooded. Soaring high ceilings and impact-resistant windows and doors throughout. Convinent elevator providing effortless access to all levels. Chef’s kitchen equipped with premium Viking appliances, double convection ovens, and sleek quartz countertops.4 large bedrooms, each featuring private en-suite baths and spacious walk-in closets. Flexible bonus room perfect for a dedicated home office or a 5th bedroom. Extra-high ceilings throughout the entire house, creating an incredibly open, airy, and grand feel. Grand primary suite offering an extra-large layout, ocean and city views, and a spa-like bath. Convenient elevator servicing the living levels. Multiple private balconies that effortlessly expand your living space outdoors. Fully fenced backyard framed by lush, mature landscaping—ideal for pets. Outdoor oasis featuring a sparkling pool and a relaxing water fountain. Extra-large 3-car garage supplemented by a climate-controlled storage unit. Bonus ground-floor space, perfect for a secondary climate-controlled office or gym, complete with a half bath. Two nearly brand-new A/C units ensuring optimal climate comfort. Recently insulated attic with premium spray foam for maximum energy efficiency. Located just 5 minutes from the vibrant dining and shopping of Siesta Village and only 8 minutes from the sugar-white sands of world-famous Siesta Key Beach. This estate offers the ultimate balance of secluded privacy and immediate coastal accessibility.....Please Note-Some Photos Virtually Staged.

6900 Bochi Circle, Sarasota

Sarasota County Homes with Three+ Story Property Description

Newest Sarasota County Homes with Three+ Story Property Description