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408 Jackson Drive, Lido Key
$2,750,000
4 Beds ⋅ 4 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
Better than new and upgraded to perfection! Steps from St. Armands Circle, this spacious and quiet 4BR/4BA home offers tranquility in its simplicity, while still walkable to a bevy of options for activities and entertainment. The fenced-in garden, pool, and covered outdoor eating area make this nearly new home a gem of all jewels. Walk to St Armands Circle in minutes, a short distance to Lido Beach, and Sarasota’s bustling downtown. Perfect for family living or entertaining on any scale. Nothing was overlooked when this home was meticulously renovated recently! Remarkable touches and style are visible in every room, from soaring tray ceilings and recessed lighting, to the seamless indoor/outdoor flow that’s created by a wall of double-paned sliders, and a shady poolside outdoor eating/grilling space. The open and light-filled Great Room effortlessly connects to a welcoming dining area and exquisite new chef’s kitchen, boasting waterfall quartz countertops and backsplash, as well as an extended breakfast bar, SS appliances, convenient pot-filler, and updated neutral sage-tone solid wood cabinets on display. The Casita with a separate (keyless) entryway would delight any overnight visitors! This private suite boasts its own mini-kitchen, bathroom, walk-in closet, and French doors leading guests directly into a hidden and relaxing pool area. Just 2 blocks to St. Armands Circle, minutes from the heart of downtown Sarasota and its Bayfront, where a sprawling cultural hub offers: theaters, Opera, museums, restaurants, boutique shopping, dining, and plenty of entertainment venues. Finally a place where you can relish in the peace and luxury of quiet comfort near St Armands Circle, while enjoying the best entertainment and activities that downtown Sarasota can share. Come see it for yourself!

408 Jackson Drive, Lido Key

156 Emerson Drive, Lido Key
$3,450,000
4 Beds ⋅ 5 Baths ⋅ Lido Beach SubDv.
Wake up to the sound of waves and fall asleep to Gulf breezes in this extraordinary three-story residence, perfectly positioned just steps from the white sands of Lido Beach. With direct access to the nature trails along Pansy Bayou and sweeping views of the water, sunsets, and the tranquil shores beyond, this is not simply a home, it is a lifestyle. Custom-built in 2003 by the current owner and meticulously maintained ever since, this 4,486 sq. ft. masterpiece was constructed for the long term. Masonry materials, a piling foundation, and fortress-quality construction have protected this home through every season, with no history of storm damage or water intrusion, offering exceptional peace of mind. Inside, every detail reflects thoughtful craftsmanship. Rich solid wood floors and staircases flow throughout, complemented by soaring ceilings and walls of windows that flood the home with natural light. A private elevator connects all three levels with ease. The layout is designed with both privacy and elegance in mind, featuring a serene master retreat on the second level, dedicated guest accommodations, and a stunning artist's studio outfitted with generous storage and bathed in light. The upper living level is the crown jewel, an entertainer's dream open to sky, water, and nature. The chef's kitchen impresses with thoughtful design and a generous walk-in pantry, while the showstopping terrace delivers breathtaking panoramic views that must be seen to be believed. Tucked at the end of a quiet private drive, the home offers rare seclusion without sacrifice. St. Armands Circle's world-class dining and upscale shopping are just a leisurely stroll away. An oversized attached garage plus additional off-street parking complete this exceptional offering. Homes of this caliber, in this location, simply do not come available often.

156 Emerson Drive, Lido Key

424 Bowdoin Circle, Lido Key
$13,375,000
5 Beds ⋅ 6 Baths ⋅ Lido Shores SubDv.
Set against Sarasota’s coveted bayfront in Lido Shores, this extraordinary waterfront estate captures sweeping views of Sarasota Bay, the downtown skyline, Ringling Bridge, and City Island, offering an unparalleled luxury lifestyle with effortless access to boating, beaches, and downtown Sarasota. More than a residence, this is a statement property—an iconic example of West Indies–inspired architecture executed with exceptional craftsmanship and modern sophistication. A private gated entry introduces a home where over $1 million in enhancements and more than 2,000 hours of custom design are evident throughout. Advanced smart home automation allows seamless global control, blending innovation with refined living. The custom front door opens to a dramatic foyer and a great room defined by a coffered ceiling, media wall, linear fireplace, and expansive bay views. The dining space features a quartz-topped bar with wine storage and flows into a chef’s kitchen appointed with Thermador appliances, a large floating island with quartz waterfall edges, and a walk-in pantry with an additional Bosch refrigerator. The primary suite is a tranquil sanctuary with floor-to-ceiling glass, sliders, and breathtaking water views. Two custom walk-in closets complement a spa-inspired bath featuring floating vanities, a soaking tub, a custom multi-head shower, and sliders leading to a private Zen garden with an outdoor shower. A sculptural staircase and glass-enclosed wine wall lead to an upper-level loft with a wet bar and waterfront terrace. A refined office with custom built-ins and four en-suite guest bedrooms, each with custom closets, projector screens, and private balconies, ensure comfort and privacy throughout. Outdoors, the estate transforms into a resort-style waterfront retreat. An infinity-edge pool with sun shelf, in-pool table, and cascading spa anchors the setting, surrounded by multiple seating areas, a firepit, and an outdoor shower. The fully equipped outdoor kitchen—featuring a smoker, grill, wok, and side burner—makes alfresco entertaining effortless, while a spiral staircase leads to an upper terrace with panoramic views. The newer deepwater dock is designed for serious boating, offering a 20,000-pound boat lift, jet ski lift, water and power, ambient lighting, and a dedicated fishing area. With direct access to Sarasota Bay just steps from the backyard, this property delivers exceptional boating and waterfront living. Additional features include a three-car garage, two laundry rooms, an elevator, a garage drop zone, and a hidden utility closet. The home is fully integrated with Control4 automation, security cameras, a 48-kilowatt generator, 20-kilowatt battery backup, high-end audio-visual systems, automated shades, circadian lighting, outdoor theater, app-controlled pool and irrigation, Wi-Fi-enabled appliances, EV charger prewiring, Starlink backup internet, motion-activated lighting, and voice control via Josh AI. Lido Shores is one of Sarasota’s most sought-after and architecturally significant waterfront communities, offering residents exclusive access to the north end of Lido Beach and close proximity to St. Armands Circle, Longboat Key, City Island, and downtown Sarasota. This remarkable bayfront estate is an architectural triumph, designed for sophisticated entertaining, advanced living, and extraordinary waterfront luxury.

424 Bowdoin Circle, Lido Key

409 N Washington Drive, Lido Key
$1,631,000
2 Beds ⋅ 2 Baths ⋅ Saint Armands Division John Ringling Estates SubDv.
What if you could own a fully renovated beach house on St. Armands Circle for the price many buyers are paying for an outdated condo… while being surrounded by $3M-$10M homes just blocks from the Gulf? Welcome to 409 N Washington Drive, an exceptionally rare opportunity to own one of the least expensive fully renovated homes to become available on St. Armands in years. Perfectly positioned just two blocks from the world-famous boutiques, restaurants, and cafés of St. Armands Circle, and only three blocks from the beautiful beaches of Lido Key, this charming single-story bungalow captures the kind of lifestyle most only experience on vacation. And here, vacation never has to end. Tucked away on one of the quietest streets on the Key, this beautifully updated 2-bed, 2-bath residence spans about 1700 SF and has been thoughtfully designed to deliver effortless coastal living with a resort-style feel. Lush tropical landscaping creates a sense of privacy rarely found this close to the beach and Circle, while multiple outdoor patios, lounging areas, and a sparkling resort-style pool invite year-round indoor-outdoor living and entertaining. Behind the charming exterior is a completely updated residence designed for effortless ownership, low-maintenance living, and maximum enjoyment. The home has undergone extensive renovations including updated PVC plumbing, updated electrical systems, hurricane-rated impact windows and doors, renovated kitchen and bathrooms, upgraded flooring, modern finishes, updated appliances, and refreshed indoor-outdoor living spaces. Every detail was intentionally curated to create a bright, inviting atmosphere that feels relaxed, elevated, and move-in ready from day one. Unlike many older island properties that become renovation projects disguised as opportunities, 409 N Washington removes the uncertainty, expense, and disruption buyers often fear when purchasing near the coast. There is no looming “what will break next?” anxiety here. The heavy lifting has already been done. For investors, this property checks nearly every box that drives premium short-term rental performance: an iconic walkable location, proximity to the beach, strong luxury rental demand, a fully furnished turnkey setup, and a proven St. Armands address that has historically outperformed many Sarasota County markets in appreciation and desirability. Offered furnished, including household goods, linens, décor, and months of future bookings in place, this is the type of property capable of generating strong occupancy with minimal downtime while also serving as a long-term appreciation play in one of Florida’s most supply-constrained markets. For lifestyle buyers, the appeal becomes even more personal. Imagine morning walks to coffee on the Circle, afternoons at Lido Beach, sunset dinners without needing a car, and evenings entertaining poolside after a day on the water. Whether used as a seasonal retreat, a lock-and-leave second home, or a full-time residence for a buyer seeking a lower-maintenance alternative to condominium living, this home delivers the rare combination of freedom, convenience, privacy, and coastal charm. In an area where many properties require extensive updating or command significantly higher prices, this home represents a rare opportunity to own a turnkey St. Armands residence with lifestyle appeal, income potential, and long-term investment strength wrapped into one exceptionally charming property.

409 N Washington Drive, Lido Key

1300 Benjamin Franklin Drive Unit 501, Lido Key
$4,750,000
3 Beds ⋅ 4 Baths ⋅ The Beach Residences SubDv.
Rarely available and highly coveted, Residence 501, a private corner residence, at The Beach Residences offers world-class coastal living with sweeping views of the Gulf of Mexico, Intracoastal Waterway, Siesta Key, and the downtown Sarasota skyline. This premier corner floorplan is filled with natural light and wrapped in glass with expansive terraces that bring the outdoors into every room. Directly below lies Lido Key’s world-famous, diamond-like crystal sand—soft as baby powder—and the recently completed beach renourishment has added exceptional width and depth to this already stunning shoreline. Spanning 4,196 square feet under air, the 3-bed/3-bath layout features two private ensuite bedrooms on opposite wings plus a versatile third suite. Rich wood floors, 10' ceilings, and floor-to-ceiling glass define the modern coastal aesthetic, while the gourmet kitchen with an oversized island is ideal for both intimate dining and entertaining. Massive terraces to enjoy sunrise to sunset, the residence delivers unforgettable moments—morning light over the Intracoastal and Siesta Key, the rhythm of Gulf waves throughout the day, and cinematic sunsets each evening. Views encompass the Gulf of Mexico, downtown Sarasota’s sparkling skyline,Sarasota Bay, Big Pass, Siesta Key, Bird Key and a protected bird sanctuary and ecological lagoon, creating a panoramic backdrop alive with nature. A private elevator foyer, two premium parking spaces, and pet-friendly living enhance comfort. Managed by The Ritz-Carlton, the building offers signature services and resort-style amenities including social lounges, theater, sauna, massage room, fitness center, ping-pong/yoga studio, boardroom, and two guest suites. Enjoy effortless access to St. Armands Circle’s world-class dining, shopping, and entertainment just moments away. Downtown Sarasota is a quick ride over the Ringling Bridge to enjoy the cultural hub of Sarasota.

1300 Benjamin Franklin Drive Unit 501, Lido Key

1300 Benjamin Franklin Drive Unit 701, Lido Key
$4,708,000
3 Beds ⋅ 4 Baths ⋅ Beach Residences SubDv.
Unparalleled luxury in this 4,196 sq. ft. 7th-floor corner residence at The Ritz-Carlton Beach Residences. Offered FULLY FURNISHED & TURNKEY. Arrival is via a private elevator opening into an exclusive foyer, leading to a massive living area with floor-to-ceiling glass. This rare "flow-through" floor plan features two massive wrap-around balconies: one facing East for sunrises over the John Ringling Bridge/Downtown, and one facing West for spectacular Gulf sunsets. INVESTOR ALERT: Property is sold with an active 2-month lease, providing immediate income. Residents enjoy world-class Ritz-Carlton amenities: private beach, resort pool, and 24-hour concierge. Minutes from St. Armands Circle, this is the ultimate move-in-ready property on Lido Key. luxury in this 4,198 sq. ft. 7th-floor corner residence at The Ritz-Carlton Beach Residences. Offered FULLY FURNISHED & TURNKEY for immediate enjoyment. Arrival is via a private elevator opening into your exclusive foyer, leading to a massive living area framed by floor-to-ceiling glass. This rare "flow-through" floor plan features two massive wrap-around balconies: one facing East for sunrises over the John Ringling Bridge/Downtown Sarasota, and one facing West for spectacular Gulf of Mexico sunsets. Residents enjoy world-class Ritz-Carlton amenities: private beach, resort pool/spa, and 24-hour concierge. Minutes from St. Armands Circle, this is the ultimate move-in-ready legacy property on Lido Key.

1300 Benjamin Franklin Drive Unit 701, Lido Key

765 John Ringling Boulevard Unit 23, Lido Key
$367,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor SubDv.
Beautiful views of Sarasota Bay await you from this 2-bedroom, 1.5-bath, second-floor condo. Newer high impact windows installed 2021. Sarasota Harbor is a maintenance-free, 55+ community. Enjoy watching manatees and dolphins from the condo. This unit has the ultimate waterfront lifestyle that offers a leisurely walking path along the seawall, a fishing pier, swimming pool, community room, and more. Launch your kayak onto Sarasota Bay or take advantage of the available boat docks ($1,200 a year)30ft. maximum length. Perfectly positioned between the world-class destinations of St. Armand’s Circle and downtown Sarasota, you can enjoy the five-minute walk to the boutiques and restaurants that line St. Armand’s Circle or the vibrant arts, culture, shopping, and dining of downtown Sarasota across the iconic Ringling Bridge. ***Boat slips, sidewalks, and carports recently damaged from the hurricanes.

765 John Ringling Boulevard Unit 23, Lido Key

1001 Benjamin Franklin Drive Unit 403, Lido Key
$385,000
1 Beds ⋅ 2 Baths ⋅ Lido Towers SubDv.
Experience the charm of Lido Towers, a highly sought-after coastal community set on world-famous Lido Beach. This refreshed and inviting 1-bedroom, 1.5-bath residence delivers effortless coastal living with deeded beach access just steps away. The residence comes beautifully furnished, allowing for a fully turnkey experience—ideal for personal use or immediate rental income. Monthly rentals are permitted, and the on-site management company makes ownership truly hassle-free. Inside, the unit is bright and comfortable with fresh paint, new water heater and dishwasher with updated finishing touches, and a private screened balcony—perfect for enjoying the warm Gulf breeze. The building itself is known for its secure, well-maintained environment, offering beautifully landscaped tropical grounds, soundproof walls, individually controlled heating and air, and reserved covered parking for convenience and peace of mind. Residents enjoy a full suite of amenities designed to enhance everyday living. The heated pool, spa, and sauna create a relaxing retreat, while the poolside card and party room, outdoor BBQ area, and lush gathering spaces encourage a true community atmosphere. Practical features such as two elevators, a laundry room on each floor, an emergency electrical generator, and included water, sewer, trash, and common-area WiFi further elevate the ease of ownership. Beyond the building, the location is exceptional. Step across the street to your private deeded beach access, take a stroll to either end of Lido Beach, or walk/bike less than a mile to the shops, cafés, and restaurants of St. Armands Circle. Directly across from the community is South Lido/Ted Sperling Park, a beloved destination for kayaking through mangroves, paddleboarding, birdwatching, or exploring nature trails. Quick trolley access offers a direct link to Sarasota’s Bayfront and vibrant downtown district. This is a rare opportunity to own a beautifully maintained, turnkey condominium in one of the most sought-after beach destinations on Florida’s Gulf Coast—ideal for full-time living, seasonal use, or investment.

1001 Benjamin Franklin Drive Unit 403, Lido Key

170 Roosevelt Drive Unit 2, Lido Key
$300,000
1 Beds ⋅ 1 Baths ⋅ Pelican Gardens SubDv.
Part of a 5 unit portfolio in Pelican Gardens. See MLS #A4670924. Turnkey Lido Key Income Property | Remodeled & Airbnb-Ready Welcome to 170 Roosevelt Dr. Unit #2, nestled in the sought-after Pelican Gardens—just steps from the sugar-white sands of Lido Beach and a short stroll to St. Armands Circle’s upscale shopping and dining. This beautifully renovated studio/efficiency unit offers the perfect blend of beachside charm and modern luxury. Updated in 2024, the space features durable luxury vinyl plank flooring, crisp shaker-style cabinetry, and a fully redesigned bathroom with contemporary fixtures and finishes. Whether you're seeking a vacation home or a revenue-generating Airbnb asset, this condo delivers. With a proven rental history and strong demand, it's ideal for investors looking for reliable cash flow in one of Sarasota’s premier locations. Enjoy morning beach walks, vibrant sunsets, and the arts and culture of nearby downtown Sarasota. The low HOA fees, pet-friendly policy, and well-maintained complex round out this exceptional opportunity. Fully furnished, move-in ready, and primed for income—Unit #__ is your gateway to the ultimate Gulf Coast lifestyle.

170 Roosevelt Drive Unit 2, Lido Key

204 N Adams Drive, Lido Key
$1,600,000
Saint Armands Division John Ringling Estates SubDv.
Prime Vacant Lot in the Heart of St. Armands Circle – Rare Opportunity. Seller will entertain offering owner financing. Discover one of the most coveted pieces of real estate in Sarasota – a large 17,588 SF vacant lot perfectly positioned in the heart of St. Armand’s Circle. Surrounded by multi million dollar homes, world-class restaurants, boutique shopping, and vibrant nightlife, this location offers the ultimate Sarasota lifestyle. Lido Beach is just moments away, while the cultural attractions and waterfront beauty of downtown Sarasota are a short drive over the Ringling Bridge. Whether you envision a luxury coastal retreat or a savvy investment in one of Florida’s most sought-after areas, this rare offering is your chance to own a piece of paradise in an iconic location.

204 N Adams Drive, Lido Key

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