Lido Key Homes with Two Story Property Description

Lido Key Homes with Two Story Property Description

Welcome to Lido Key, Florida—a hidden gem nestled in the heart of Sarasota County. This picturesque barrier island is renowned for its stunning white sandy beaches, crystal-clear turquoise waters, and a vibrant community that captures the essence of coastal living. With its charming boutiques, eclectic dining options, and lush parks, Lido Key offers a unique blend of relaxation and recreation, making it an ideal destination for both residents and visitors alike.

One of the most captivating features of Lido Key is its diverse real estate market, particularly the stunning two-story homes that grace this idyllic landscape. These properties are designed to maximize both comfort and style, offering spacious living areas that seamlessly blend indoor and outdoor living. Imagine waking up to breathtaking views of the Gulf of Mexico or enjoying sunset cocktails on your private balcony. With generous floor plans, high ceilings, and modern finishes, these two-story homes provide the perfect backdrop for family gatherings or entertaining friends.

In addition to their aesthetic appeal, many of these homes come equipped with luxurious amenities, such as gourmet kitchens, expansive master suites, and outdoor living spaces that invite you to bask in the Florida sunshine. Living in a two-story home on Lido Key means embracing a lifestyle filled with adventure, from beach days and water sports to exploring nearby nature trails and cultural attractions.

Whether you're looking for a vacation retreat or a permanent residence, Lido Key’s two-story homes offer the perfect blend of elegance, comfort, and coastal charm. Discover your slice of paradise today!

Newest Lido Key Homes with Two Story Property Description

$14,900,000
6 Beds ⋅ 6 Baths ⋅ Lido C SubDv. ⋅ 34236 Zip Code
Some properties tell the story of Sarasota's evolution. Offered for the first time publicly in half a century, this waterfront estate in Lido Shores presents a rare opportunity to become the next steward of 1.34 acres with 247 feet of western shoreline. Held by only two families since 1974, both recognized for their lasting contributions to the Sarasota community, the property offers a unique connection to the people and vision that helped shape the city we know today. A rare slice of Sarasota's legacy is now ready for its next chapter. Designed by Seibert Architects, the residence reflects an important chapter in Sarasota's architectural heritage. The home encompasses more than 9,000 square feet with six bedrooms and six baths, including a library and billiards room. This home was thoughtfully designed to embrace its waterfront setting through expansive living spaces, gathering areas and water views throughout, including multiple terraces. The generous homesite presents exceptional possibilities for restoration, renovation or the creation of a new waterfront estate. Opportunities offering this scale of western-facing water frontage, private beach access and architectural provenance are increasingly rare along Sarasota's coastline. Offering a remarkable sense of privacy, yet just minutes from the boutiques and fine dining of St. Armands Circle, downtown Sarasota's renowned arts and cultural institutions, theaters, galleries and museums, this exceptional property also enjoys convenient access to international airports and multiple international gateways, connecting this storied waterfront setting to destinations around the world.

1157 Westway Drive, Sarasota
$4,380,000
5 Beds ⋅ 6 Baths ⋅ Lido Beach SubDv. ⋅ 34236 Zip Code
Pre-Construction. To be built. Stop searching for the perfect home and build it. This premium vacant lot is offered with a spectacular proposed luxury estate, featuring high-end architectural concepts, an expansive open-concept layout, and top-tier finishes designed for modern sophistication. Why this property stands out: The Canvas: A beautiful, ready-to-develop lot in a coveted enclave. There is a permit in place obtained by Eason Builders Group, projected cost of a complete build including pool , pavers landscaping is $2,900,000.00 with top of the line finsihes . The Vision: Seamless indoor-outdoor integration, gourmet chef’s kitchen concept, and a lavish primary retreat. The Location: Exceptional privacy without sacrificing proximity to top-tier dining, shopping, and entertainment and just 2 blocks to the Lido public beach. Survey, site plans, and proposed renderings are available upon request. Secure the land, finalize the details, and claim your piece of luxury. Ideally suited for weekly vacation rentals with annual income projected between $350,000.00 and $425,000.00

514 S Blvd Of The Presidents, Sarasota
$11,900,000
5 Beds ⋅ 8 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code
At the end of Westway Drive, where Lido Shores meets the open water of New Pass, 1435 Westway Drive occupies one of Sarasota’s most extraordinary waterfront settings. Private, gated, and set on a double lot, the estate captures sweeping views across New Pass toward Longboat Key while offering direct deepwater access to the Gulf of Mexico and Sarasota Bay. This is the rare property that delivers every element of elevated coastal living in one address: boating, privacy, architectural presence, beach access, proximity to St. Armands Circle, and a level of land rarely found on Lido Key. Designed by Brian Phipps and built in 2013, the British West Indies–inspired residence blends timeless coastal architecture with modern luxury. Inside, expansive living spaces are framed by tall ceilings, walls of glass, rich wood flooring, custom millwork, and a natural connection to the water beyond. The great room opens to the waterfront terraces, creating an effortless flow between interior comfort and outdoor living. The kitchen is designed for both daily living and large-scale entertaining, with premium appliances including Sub-Zero and Wolf, generous stone surfaces, custom cabinetry, and an open connection to the main living and dining areas. Whether hosting guests after a day on the boat or enjoying a quiet evening overlooking the water, the home feels equally suited to celebration and retreat. With five bedrooms, two primary suites, and elevator service, the floor plan offers rare flexibility for owners, family, and extended guests. The upper-level owner’s retreat is a private sanctuary, complete with a sitting area, wet bar, wine refrigeration, espresso station, study, dual walk-in closets, and a terrace overlooking New Pass, the Gulf, and the lights of Longboat Key beyond. The outdoor living experience is exceptional. Covered terraces, a summer kitchen, resort-style pool, waterfall feature, and waterfront lounge spaces create a private setting designed around the view. The dock includes a 24,000-lb boat lift and additional jet ski lift, placing premier boating waters directly at your door. From here, New Pass provides immediate access to the Gulf, Sarasota Bay, Longboat Key, and the surrounding barrier islands. What truly sets the property apart is its scale. The estate spans approximately three-quarters of an acre, including an adjacent parcel that has been transformed into a lush private garden with mature landscaping, open lawn, fire pit, pond, cascading waterfall, and meandering paths. It gives the home a sense of arrival and breathing room that is almost impossible to recreate in this location. With its own gated access and generous dimensions, this portion of the property also offers future flexibility for a guest house, wellness pavilion, additional structure, or further reimagining, subject to applicable approvals. Lido Shores remains one of Sarasota’s most coveted coastal enclaves, known for its architectural pedigree, quiet streets, private beach access, and rare positioning between the Gulf, New Pass, St. Armands Circle, downtown Sarasota, and Longboat Key. Residents enjoy the privacy of a true neighborhood while remaining moments from dining, shopping, boating, beaches, and culture. Previously recognized as an HGTV Ultimate House Hunt winner for waterside living, 1435 Westway Drive is more than a waterfront residence—it is a private Sarasota estate with presence, scale, and a setting that cannot be duplicated.

1435 Westway Drive, Sarasota
$4,300,000
4 Beds ⋅ 5 Baths ⋅ St Armands Division SubDv. ⋅ 34236 Zip Code
For Those Who See Home as an Expression of Art. 541 S Washington offers a rare blend of architectural character, quality craftsmanship, and waterfront living. Beautifully renovated to reflect the enduring principles of Mid-Century Modern design, where clean lines, natural light, and a connection to the outdoors shape the living experience. Set on 75 feet of canal frontage along prestigious South Washington Drive, just moments from St. Armands Circle, Lido Beach, and downtown Sarasota. From the moment you enter, expansive folding glass doors frame the water beyond. A striking gas fireplace anchors the main living spaces, while thoughtfully proportioned rooms balance openness with comfort. Offering four bedrooms, four-and-a-half baths, and a flexible bonus space, the 3,395-square-foot floor plan was designed for easy every day living. At the center of the home, a custom Poliform kitchen with premium Miele appliances combines clean design with exceptional functionality. The primary suite serves as a private retreat, complete with a spa-inspired bath and outdoor shower. Throughout the residence, the current owners have also enhanced the property with Control4 home automation, security system, new HVAC system, instant-on hot water heaters, whole-home water treatment, Icynene insulation, and a reinforced roof with tiedowns. Outside, curated tropical landscaping creates privacy around the heated saltwater pool. Multiple outdoor living spaces, including an expansive balcony and rooftop deck, provide beautiful settings for sunset views, while a private kayak launch offers direct access to Sarasota's waterways. A distinctive waterfront residence in one of Sarasota's most sought-after island neighborhoods, inspired by timeless design and a connection to the water. Inquire with the listing agents for a complete list of updates and to schedule your private showing.

541 S Washington Drive, Sarasota
$3,075,000
4 Beds ⋅ 4 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code
An exceptional opportunity awaits on one of Sarasota’s most coveted streets — 76 S Washington Drive, located on the lovely St. Armands Key. Welcome to a rare gem nestled within the prestigious John Ringling Estates. Framed by a stately row of regal palms and lush tropical landscaping, this enchanting residence captures the essence of refined coastal living with an irresistible blend of classic charm and modern sophistication. Nestled on an oversized lot, this home features 4 bedrooms and 3 1/2 bathrooms, with a thoughtfully designed open floor plan perfect for entertaining. Behind a graceful white privacy wall, the estate opens to reveal a picture-perfect private oasis, complete with a sparkling pool, spa, lush landscaping, and multiple lounge areas making it ideal for both relaxation and stylish entertaining. The resort-style backyard also features a guest cottage ready to be finished with your personal touches. The brick-paved walkways are all framed by manicured hedges and grand architecture that exudes Mediterranean Revival elegance. Step inside and be welcomed by soaring vaulted ceilings, rich hardwood floors, and an expansive open living area that seamlessly blends comfort with designer touches. Graceful archways, crown molding, and carefully curated fixtures echo the home’s timeless appeal, while large windows invite natural light and frame garden views. The gourmet kitchen is a chef’s dream—fitted with custom white cabinetry, a high-end gas range, farmhouse sink, and a striking patterned wood-and-marble floor that adds a bespoke touch of artistry. Just outside, an al fresco kitchen awaits under a wood-beamed ceiling—perfectly equipped for hosting summer evenings and sunset soirees. Located just moments from the luxury boutiques and fine dining of St. Armands Circle, this exceptional residence also offers proximity to Lido Beach, downtown Sarasota, and the cultural treasures of the Ringling Museum district. Whether you’re seeking a permanent residence, a vacation retreat, or an investment property, this home embodies the ultimate coastal lifestyle. Don't miss your chance to live moments from the circle, the beach, and all of Sarasota's best!

76 S Washington Drive, Sarasota
$5,895,000
10 Beds ⋅ 12 Baths ⋅ Lido Beach SubDv. ⋅ 34236 Zip Code
Coastal luxury meets exceptional investment opportunity on Lido Key. Just steps from the white sands and turquoise waters of Lido Beach, this custom one of a kind residence offers 10 bedrooms, 10 full baths, and 2 half baths in a beautifully designed turnkey furnished setting. Built with a sophisticated contemporary aesthetic, the home features an open concept floor plan spanning multiple living levels, designed for both effortless entertaining and comfortable everyday living. The chef’s kitchen is a true centerpiece, complete with a large quartz island, walk in pantry, panel ready refrigerator, premium appliances, and custom lighting. Each of the 10 bedrooms includes its own ensuite bath, creating a private and luxurious experience for guests and making the home ideal for large gatherings or vacation rental use. Thoughtful design elements, including unique accent walls and upscale finishes, add character and cohesion throughout. Outdoor living is equally impressive, with multiple balconies, an expansive patio, and a private pool and spa that create a true resort-style atmosphere. The upper level offers an additional entertaining space with a wet bar, while the rooftop terrace delivers stunning views and the perfect setting to relax or host guests. An elevator services the home for added convenience, and the spacious primary suite provides a serene retreat with a double vanity, walk-in shower, and a freestanding soaking tub. Located just minutes from St. Armands Circle and a short drive to downtown Sarasota’s dining, shopping, and cultural attractions, this property offers the best of coastal living with strong income potential.

119 Mckinley Drive, Sarasota
$12,987,000
5 Beds ⋅ 9 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code
Live your luxury at Casa Lido, a spectacular waterfront estate in the enclave of Lido Shores, offering sweeping, unobstructed views across Sarasota Bay to downtown Sarasota and iconic Ringling Bridge, while having private beach access. This is a rare opportunity to own a residence of extraordinary scale, presence and craftsmanship, where every detail has been custom-designed and executed at the highest level. A private, gated drive leads to a dramatic custom arched wooden double door entry opening to a two-story grand foyer, setting the tone for the home’s impressive proportions and architectural sophistication. Soaring ceilings, refined millwork, curated chandeliers and walls of glass frame the open bay views, while electric screens allow you to enjoy uninterrupted vistas throughout the day without sacrificing comfort or privacy. Spanning an exceptional amount of square footage, the residence offers five bedrooms, five full baths, four half baths and a thoughtfully designed layout that balances grandeur with livability. Two dedicated office spaces include a stunning wood-paneled office with a spiral staircase leading to a second-story library, complete with custom bookcases and a charming tucked-away nook, ideal as a child’s hideaway or creative retreat. The first-floor primary suite is a sanctuary, featuring oversized dual walk-in closets and a spa-inspired bath designed for effortless daily living. Wake each morning to tranquil water views and the gentle rhythm of the bay. An additional private office adjoining the suite offers an inspiring workspace with panoramic scenery. Designed for entertaining at every scale, the chef’s kitchen is anchored by premium appliances, an expansive island, a butler’s pantry, dual dishwashers and seamless flow into the family room. Pocketing sliders open to the outdoor living areas, blurring the line between indoors and out. Wellness and leisure are elevated throughout the home, including a private gym with sauna, a temperature-controlled wine room and storage, and a fully equipped entertainment room with theater seating, wet and dry bars, and game space. Upstairs, spacious guest suites enjoy refined finishes and access to wraparound balconies with a gas fireplace. ideal for sunset views over the water. Guests will appreciate the separate guesthouse, featuring a private entrance, living area, kitchenette, dedicated laundry, en-suite bath and serene water views, ideal for extended stays or multigenerational living. Outdoors, the estate continues to impress with upper and lower resort-style pools, a fire pit, outdoor kitchen, and multiple spaces for dining and relaxation. Boating enthusiasts will enjoy direct bay access from the private dock, complete with lifts and accommodations for watercraft and paddleboards. Every space in Casa Lido is oversized, intentional and undeniably grand, a home that must be experienced in person to fully appreciate its scale, finishes and commanding presence. Just minutes from St. Armands Circle, world-class beaches and downtown Sarasota, this is waterfront living without compromise.

1436 John Ringling Parkway, Sarasota
$5,795,000
4 Beds ⋅ 4 Baths ⋅ Lido Beach SubDv. ⋅ 34236 Zip Code
An Exquisite Bayfront Residence on Prestigious Lido Key, Sarasota. This meticulously reimagined two-story bayfront masterpiece embodies the pinnacle of sophisticated coastal living. Offering 3,832 square feet of thoughtfully designed interior space which was fully renovated in 2017, including impact-resistant doors and windows and a new roof. The residence features 4 ensuite bedrooms, a state-of-the-art 2025 gourmet kitchen, designed for discerning entertainers, showcases premium appliances, custom cabinetry, and an expansive island that serves as the heart of the open-plan living areas. The new elegant flooring unifies the bright, voluminous interiors. The second story includes a spacious home office with views over the pool to the bay. Beyond the interiors lies a private waterfront sanctuary: a heated saltwater pool overlooks an expansive floating dock, ideally suited for vessels of varying sizes, kayaks, or paddleboards. Unobstructed sailboat access invites effortless exploration of the bay and beyond. Additional conveniences include a spacious two-car garage, proximity to downtown Sarasota's vibrant cultural scene, a 15-minute drive to Sarasota-Bradenton International Airport. Close by is the pristine sands of Lido Beach with the most spectacular sunsets and moments away is St. Armands Circle's dining and shopping. Framed by the preserved mangroves of Otter Key, the sheltered waters host an abundance of marine life, dolphins, manatees, and graceful wading birds frequently enchant residents with their presence. This extraordinary property represents a rare harmony of tranquil waterfront serenity, impeccable modern enhancements, and unparalleled proximity to Sarasota's finest amenities—an enduring legacy of refined coastal elegance. Independently certified appraisal on 03/05/2026 by Birkholz Appraisal Group: Value by sales comparison approach $5.9M and Value by cost approach $6.2M

701 Tyler Drive, Sarasota
$7,250,000
5 Beds ⋅ 4 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code
An extraordinary expression of modern waterfront living, this custom-designed Sarasota residence seamlessly blends architectural distinction, refined interiors and a tranquil Bayou setting flowing directly into the Gulf of Mexico, creating a home that is visually striking and effortlessly livable. Thoughtfully conceived by the owners, this exceptional five-bedroom, three full-bath and one half-bath waterfront residence is on approximately .37 acres and was designed to honor its surroundings while embracing contemporary form, function and natural light. Offering 4,284 square feet under air and 6,416 total square feet, the home makes a striking yet calming first impression. A circular brick-paver driveway, decorative architectural elements, trellises accents, curated landscaping, and subtle exterior lighting establish a refined sense of arrival and architectural presence. Inside, a dramatic open-concept floor plan unfolds with intention and volume. The great room features ceilings approaching 20 feet, custom wire railings and expansive glass frame serene water views from every room. Natural materials, most notably warm cedar accents carried seamlessly from interior to exterior, create a cohesive modern design language. Beechwood flooring, refined finishes, automatic solar window treatments, imported European light fixtures, and integrated LED lighting enhance comfort and contemporary appeal. The gourmet kitchen is designed for everyday living and entertaining, featuring Porcelanosa Design cabinetry, a side-by-side paneled Sub-Zero refrigerator, Asko dishwasher, Wolf built-ins including wall oven, warming drawer, microwave, a U-Line under-counter wine cooler, illuminated onyx island, quartz countertops, seamless under-cabinet lighting and a walk-in pantry. A new Whirlpool top-load washer complements the Whirlpool Cabrio Platinum dryer, completing the home’s functional amenities. The residence offers exceptional flexibility with two private primary suites on the main and upper levels, each providing direct terrace access and tranquil water views. Spa-inspired baths, one features a steam shower and walk-in closets, creating serene retreats. Additional guest suites, office, a waterfront gym or flexible living space, and these multiple en-suite accommodations support a variety of lifestyles. Outdoor living is equally compelling. A saltwater infinity-edge pool with spa and planter waterfall feature anchors the waterfront setting, complemented by covered and enclosable lanais with automatic window and terrace screens. Existing posts for the hammock overlook the Bayou. The outdoor pavilion provides space for an outdoor kitchen, with room to add a built-in grill, ice maker or under-counter refrigerator with existing gas hookup and water supply. A private illuminated dock provides direct Bayou access leading into the Gulf of Mexico, enhancing the home’s connection to nature and offering multiple gathering spaces ideal for entertaining and cherished memories. Modern construction, impact-rated openings and integrated smart-home technology contribute to peace of mind and long-term value. In one of Sarasota’s desirable waterfront neighborhoods, with optional deeded Lido Shores beach access and proximity to downtown Sarasota, St. Armands Circle and Longboat Key, this residence offers privacy, elevation, serenity and refined expression of luxury coastal living, designed to be admired and lived in.

222 Morningside Drive, Sarasota
$5,200,000
9 Beds ⋅ 9 Baths ⋅ Lido Beach SubDv. ⋅ 34236 Zip Code
Motivated Seller! NEW PRICE! This custom-built NEW (2022) residence showcases refined craftsmanship and thoughtfully curated luxury upgrades throughout. The home features soaring ceilings and expansive floor-to-ceiling windows that create a dramatic architectural statement while maximizing natural light. Wide-open living spaces are enhanced by high-end tile flooring, sleek modern lines, and a seamless indoor-outdoor flow designed for upscale coastal living. The gourmet kitchen is outfitted with premium cabinetry, designer countertops, and high-end appliances, offering both elegance and functionality for entertaining. Designer-inspired bathrooms feature luxury tilework, glass-enclosed showers, floating vanities, and upscale fixtures, creating a resort-like experience in every en-suite (seven total). Custom lighting, contemporary finishes, and refined millwork elevate each space, while thoughtfully designed en-suite bedrooms provide hotel-style privacy and comfort. Multiple balconies, a private rooftop terrace, and an open upper-level lounge further enhance the home’s architectural appeal, offering elevated vantage points and sophisticated outdoor living spaces. Outdoors, the property is designed for luxury entertaining, featuring an outdoor gas fire pit, gazebo, private outdoor shower, and a fully fenced backyard—perfectly blending style with functionality. An outdoor kitchen, designed to the buyer’s specifications, will be provided at closing, offering a personalized extension of the home’s exceptional indoor-outdoor lifestyle. From the elegant owner’s suite to the panoramic rooftop retreat, every detail of this residence reflects modern coastal luxury and meticulous attention to design. Single-owner, fully custom home thoughtfully designed from plat to completion with exceptional attention to detail throughout. Call to schedule your private showing today. Generates a nice six figure rental income annually!

149 Mckinley Drive, Sarasota
$3,675,000
4 Beds ⋅ 4 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code
Experience refined coastal living in the heart of St. Armands Circle, Sarasota’s premier destination for luxury shopping, fine dining, and island living. This fully turnkey, furnished 4-bedroom, 3.5-bath residence is ideally located just steps from world-class amenities and a short stroll to Lido Beach. Extensively renovated with coastal elegance in mind, this home features impact-rated windows and doors, a new roof with skylights, updated HVAC systems, designer flooring, remodeled bathrooms, upgraded lighting, and premium finishes throughout. The chef’s kitchen showcases Wolf, Sub-Zero, and Bosch appliances, quartz countertops, and custom cabinetry. The private outdoor retreat offers a fully renovated pool, travertine decking, lush landscaping, modern fencing, copper gutters, and a custom privacy wall featuring ceramic artwork by a celebrated Florida artist. Located in one of Sarasota’s most iconic destinations, this rare turnkey residence offers a unique opportunity for full-time living, a seasonal retreat, or an exceptional rental opportunity. Embrace effortless access to Lido Beach, St. Armands Circle, and the best of Sarasota’s island lifestyle.

345 Madison Drive, Sarasota
$2,050,000
2 Beds ⋅ 2 Baths ⋅ St Armands Division SubDv. ⋅ 34236 Zip Code
Virtually Staged. Hidden behind lush plantings is this beautifully redesigned and amazingly private two-story home boasting over 3900 sq ft of interior living space all moments away from the shops & cafes of St. Armands Circle, the beaches of Lido Key & downtown Sarasota. As you enter this hideaway of peace and tranquility you are greeted by a fountained courtyard garden through gates of aged iron. From there the interiors will call to the imagination as it evokes the visions of a bastide in Provence or a country home in the hills of Scotland. Imperfection is curated and intentional. Rooms flow easily enhanced by wide plank reclaimed wood floors, white ship lap walls framed with wood accents, reclaimed wood beams artfully placed throughout, thick roughhewn interior doors with patinaed hardware, an eclectic kitchen design with soap stone counters, side tables and oven backsplash, a double farm sink, a new 10- burner dual fuel gas range with two ovens, a Sub-Zero fridge with a glass door & four bottom draws to name just a few of the many appealing details. A grand front room leads to a beautiful staircase of wood and clay tiles with a landing at the center of the house leading you to the primary suite, encompassing the entire second floor. Here we have a library/seating room lined with bookshelves, roughhewn wide plank wood floors, a spacious bedroom with a Julliet balcony, two walk-in closets and bath with a tub, large quartz shower with horizontal subway tiles, dual shower heads & handheld and two vanities with surface mount sinks and quartz counters sitting on retrofitted antique cabinets. There is a loggia spanning the width of the house opening on to an exceptionally large backyard bursting with lush tropical foliage. The nearly 12,000 sq ft lot is 160 ft deep. Intricately laid clay tiles form multiple walkways and an extensive lounging area. Beautifully weathered custom wrought iron gates abound not only on the drive entry but also on the courtyard and on the arched window openings of the loggia. Aged clay tiles surround windows and doors, even the garage door. Custom crafted metal awnings adorn the windows. Exterior custom metal lanterns and sconces echo the same intentional aging. There are two tankless water heaters, a whole house water purifier and a well for the yard. This home will captivate you.

41 S Adams Drive, Sarasota
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