Lido Key Homes with Sailboat Water Water Frontage

Lido Key Homes with Sailboat Water Water Frontage

Welcome to Lido Key, Florida – a hidden gem nestled in the heart of Sarasota County, where sun-soaked beaches meet serene waterways. This vibrant barrier island is not only known for its stunning shoreline but also for its luxurious lifestyle and captivating natural beauty. With its soft, white sandy beaches and crystal-clear waters, Lido Key is a paradise for beach lovers, boating enthusiasts, and those who appreciate the finer things in life.

One of the most alluring features of Lido Key is the availability of homes with sailboat water frontage. Imagine waking up to breathtaking views of the tranquil waters, with direct access to the Gulf of Mexico right from your backyard. Whether you’re an avid sailor or simply enjoy the peaceful ambiance of waterfront living, these properties offer an unparalleled lifestyle. Picture yourself gliding through the gentle waves, exploring the beautiful coastline, or enjoying a sunset cruise with friends.

The community on Lido Key is as inviting as its natural surroundings, with charming boutiques, delightful dining options, and a welcoming atmosphere that makes you feel right at home. The nearby St. Armands Circle offers an array of shopping and entertainment, creating a perfect blend of relaxation and excitement.

If you’re seeking a slice of paradise where luxury meets leisure, Lido Key’s sailboat waterfront homes are a dream come true. Experience the ultimate Florida lifestyle in this enchanting coastal haven, where every day feels like a vacation. Come discover your perfect home on Lido Key – where the water meets your dreams!

Newest Lido Key Homes with Sailboat Water Water Frontage

$9,800,000
4 Beds ⋅ 6 Baths ⋅ The Beach Residences SubDv. ⋅ 34236 Zip Code
This Gulf-front coastal haven is where opulence is complimented by exclusivity. This lauded RITZ-CARLTON managed contemporary residence sets the standard for legendary white-glove service. Welcome to the coveted lifestyle at The Beach Residences. Atop this exquisite 88 residence high-rise sits a ONE-OF-A-KIND, SEAMLESSLY INTERCONNECTED DUAL PENTHOUSE SUITE with 4 bedrooms, plus 2 flex rooms (i.e.- media room, den or 2 more bedrooms) & 6 full bathrooms. Palatial & thoughtfully remodeled, this 12th-floor masterpiece blends world-class craftsmanship w/the natural light of soaring ceilings. As you step from one of two semi-private elevators into a welcoming Grand Salon, the spectacular 6,332 sqft home greets you with impeccable finishes, crown moldings, as well as timeless wood & marble flooring throughout. Each expansive residence boasts 3,000+ sqft flowing naturally into West, Northwest, & East-facing wraparound terraces. Double-paned floor to ceiling glass walls provide panoramic views of turquoise Gulf waters, epic sunsets, w/dynamic Sarasota skylines. The gourmet kitchens feature state-of-the-art appliances- stainless steel Sub-Zero refrigerator & wine fridge, Dacor natural gas cooktop, chef’s island, granite countertops, w/solid-wood cabinetry. Two gas fireplaces enhance the alluring interior setting, while generous 1,400 sqft terraces with BBQ offer alfresco dining among the clouds. This bespoke & customizable space is perfectly tailored for large events or intimate gatherings. Catered soirees are simplified by 2 generous kitchens, large pantries & spacious laundry rooms for post-events. This penthouse features 2 private garages in the garage for 4+ vehicles & 2 air-conditioned storage rooms on the elevated lobby level. This personal haven is a serene retreat featuring his & her walk-in closets, wet-bars, & 4 ensuite bathrooms where marble floors meet a spa-inspired bath w/jetted tubs and dual vanities. These EFFORTLESSLY INTERCONNECTED PENTHOUSES are joined by a one-of-a-kind hallway, lovingly & meticulously designed by a Nasa Engineer. The dual-unit layout offers flexible configuration choices whether you prefer ONE SPRAWLING UNIFIED SPACE OR TWO SEPARATE PENTHOUSES. The Ritz-Carlton managed Residences set the standard in resort-style maintenance-free living with a 24-hour concierge & 24-hour manned guard gate. Residents enjoy the heated pool & spa with a generous fire-pit to appreciate on cold evenings. Added comforts include a social room w/caterers’ kitchen, boardroom, massage room, sauna, fitness center, theater, ping-pong & yoga room, as well as 2 guest suites. Two large pets per unit can enjoy our dog run. The Ritz-Carlton Members Club is optional & immediately available to purchase. Complimentary shuttle buses escort you throughout the day to St Armands Circle with charming boutique shopping, bistro dining & walkable convenience. Lido Key boasts quartz-white sand beaches, elegant bistros, world-class restaurants, A short 10-minute drive away, you’ll find an award-winning tennis and pickleball center, the 2nd largest marina on Florida’s West Coast & 45 holes of exclusive & challenging PGA golf courses surrounded by shimmering Gulf waters. Nearby conveniences: Publix, CVS, & world-class doctors. Downtown Sarasota is a cultural hub offering entertainment and gourmet cuisine, art galleries, opera & theatre venues. Luxury, location and the Lido Key lifestyle- it doesn’t get any better than this.

1300 Benjamin Franklin Drive Unit 1205 & 1206, Sarasota
$585,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor East SubDv. ⋅ 34236 Zip Code
Enjoy a million-dollar view without a million dollar price tag! Sarasota Harbor East is one of the most sought-after locations in Sarasota, just minutes from St Armand's Circle, Lido Beach, downtown Sarasota, and directly across the street from the Sarasota Yacht Club. You'll fall in love with the spectacular views the turquoise waters of Sarasota Bay, the Ringling Causeway as it lights up at night, and be spellbound by the fireworks over Sarasota Bay during July 4th and New Year's Eve. This lovely 2-bedroom/2-bath condo is offered turnkey furnished, with ceramic tile, an open-concept floor plan, renovated kitchen/baths, and an enclosed lanai, with a shared laundry room right next door. Recent updates include new hurricane-impact windows and sliders, a Nest thermostat, keyless front-door entry, and newly refinished cabinetry. Each unit includes a covered parking space and a storage unit on the 3rd floor. Community amenities include a clubhouse, community pool with sweeping views of the bay, shuffleboard courts, a community gas grill, a secured bicycle shed, and a kayak storage rack. The community's free boat slips are available on a first-come, first-served basis, are commonly available, accommodating both sail boats and powerboats up to 30'. Sarasota Harbor East is a 55+ community that allows rentals after one year of ownership. The second floor unit is accessible by elevator and stairs.

777 John Ringling Boulevard Unit 24, Sarasota
$460,000
2 Beds ⋅ 1 Baths ⋅ Sarasota Harbor SubDv. ⋅ 34236 Zip Code
Brand new AC unit for the ultimate peace of mind. Few addresses in all of Sarasota deliver what 763 John Ringling Blvd offers every single day: direct, unobstructed views across Sarasota Bay with St. Armands Circle, Lido Key, and the sparkling Gulf of Mexico as your permanent backdrop. This is one of the most coveted waterfront corridors on the Gulf Coast, and this beautifully updated two-bedroom, one-bath residence puts you right in the middle of it. Step outside and you are standing on the bay seawall with private community boat docks at your feet and open water stretching to the horizon. Dolphins cruise the shoreline in the morning. The Ringling Causeway glows gold at sunset. The bayfront community pool, shuffleboard courts, and waterfront walkway give residents every reason to stay close to home, while St. Armands Circle sits just minutes away across the bridge with its world-class European-style dining, boutique shopping, and lush tropical gardens. Inside, the residence has been thoughtfully updated with hardwood floors, a refreshed kitchen with new appliances, and the rare convenience of an in-unit washer and dryer. The layout offers the right balance of comfort and ease, ideal for a full-time residence, seasonal retreat, or income-producing rental. The address itself carries genuine historical significance. Unit 22 sits within the Harding Circle Historic District, a landmark community envisioned by circus magnate John Ringling and listed on the National Register of Historic Places since January 2001. This is not just a home. It is a piece of Sarasota's founding story. Downtown Sarasota's waterfront arts district, marina, and restaurant scene are minutes away. Lido Beach is just over the causeway. For buyers relocating from the Northeast or Midwest, this property delivers the Gulf Coast lifestyle at an exceptional entry point: waterfront, walkable, and fully updated, with boat docking access and panoramic bay views that simply cannot be replicated at this price.

763 John Ringling Boulevard Unit 22, Sarasota
$565,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor East SubDv. ⋅ 34236 Zip Code
Virtually Staged. Sarasota Bay is your backyard in this stunningly remodeled, first-floor waterfront sanctuary located in the premier 55+ community of Sarasota Harbor East. This residence offers a front-row seat to nature’s theater with direct views of dolphins, manatees, and vibrant sunsets from your private lanai. The heart of the home is a brand-new kitchen featuring sleek quartz countertops, contemporary cabinetry, a stylish backsplash, a Bosch oven and premium induction cooktop, and new stainless appliances (refrigerator and dishwasher). Peace of mind is built-in with a 3-year-old AC unit, new water heater, and updated plumbing. Perfectly positioned between St. Armands Circle, Lido Key, and downtown Sarasota, the community offers an unparalleled lifestyle: enjoy a bayfront pool, a clubhouse with private changing facilities, and secured bike and kayak storage. A boater’s dream, the community provides boat slips (up to 30 ft) at no additional cost to residents—a rare and valuable find. The comprehensive HOA fee ensures a maintenance-free lifestyle, covering exterior grounds, building maintenance, cable, internet, water, sewer, and trash. Complete with covered parking, dedicated storage, and laundry facilities, this is turn-key coastal luxury at its finest.

769 John Ringling Boulevard Unit 2, 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
$599,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Harbor East SubDv. ⋅ 34236 Zip Code
Imagine living in a prime, unique waterfront community with an amazing location—maybe the best Bayfront community in Sarasota! You’re just a short walk from downtown, St. Armands Circle, Lido Beach, and the Sarasota Yacht Club. Sarasota Harbor East is a 55+ waterfront community with all the perks of maintenance-free living. This THIRD-FLOOR unit gives you stunning views of Sarasota Bay and the city. It has 2 bedrooms and 2 full baths, perfect for you to make your own. Plus, you’ll have an enclosed four-season glass lanai and high-impact sliding glass doors and windows. The clubhouse has been updated and includes a fully equipped kitchen, a new metal roof, a library, full bathrooms, and a large lap pool with Bayfront views. There’s even a designated area for storing kayaks and bicycles! You’ll have one covered parking space and plenty of guest parking. The community is very neat and tidy, and the maintenance fees cover everything from docks and exterior building to cable TV, a heated community pool, building insurance, internet, exterior maintenance, ground maintenance, a manager, exterior pest control, pool maintenance, sewer, trash, and water. Deep-water boat slips are available on a first-come, first-served basis, and all costs are included in the maintenance fee. (Slips are currently available.) The boat slip can accommodate up to a 30’ powerboat or sailboat. Leasing is not allowed for one year after purchase. Pets permitted with valid service or support animal documentation.

777 John Ringling Boulevard Unit 32, Sarasota
$339,000
2 Beds ⋅ 1 Baths ⋅ Sarasota Harbor SubDv. ⋅ 34236 Zip Code
Beautiful views of Sarasota Bay await you from this 2-bedroom, 1-bath, first-floor condo. Newer high impact windows installed 2016, and exterior doors being replaced by association. 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)34ft.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. Boatslips/docks currently being replaced.

761 John Ringling Boulevard Unit 5, Sarasota
$4,925,000
3 Beds ⋅ 4 Baths ⋅ Lido Shores SubDv. ⋅ 34236 Zip Code
Experience the epitome of island living in this luxurious three-bedroom, four-bath residence. With high-end finishes and spacious rooms featuring soaring ceilings, every detail exudes comfort and elegance. Enjoy leisure time with a ping-pong table, a theater room, and a pristine pool that basks in southern exposure, overlooking the tranquil open bayou. The kitchen, complete with a breakfast area, offers stunning views of the pool and bayou, while a cozy office space provides an ideal work-from-home environment. The home also features a beautiful dining room with a wet bar and a welcoming living room adorned with elegant wood floors throughout. Each bedroom offers luxurious en-suite baths, and the master bath is a true retreat. The expansive pool deck area and the convenience of a two-car garage and boat dock add to the home’s charm. Plus, with an elevator and a full-house generator, you’ll enjoy ultimate comfort and peace of mind.

340 Morningside Drive, Sarasota
$12,950,000
5 Beds ⋅ 7 Baths ⋅ Saint Armands Div John Ringling Estates SubDv. ⋅ 34236 Zip Code
Like a Picassos’ Mona Lisa, a true masterpiece. THIS home is the GEM of all jewels. It is one of a kind, created with artistry-imagination & craftsmanship that simply cannot be replicated. This is not your typical concrete block home. It has warmth, & timeless character. Every detail reflects the skill of master craftsmen whose work has become increasingly rare. Homes of this quality are no longer built, making this residence as exceptional as it is beautiful. In a world filled with contemporary “concrete boxes” that often lack warmth, personality & charm, this home stands apart. It invites you to slow down, sit back, stay awhile, and savor every moment. It doesn’t just provide shelter—it embraces you with comfort, elegance, & a sense of belonging. Warm, ageless, and unforgettable, this is more than a home. It is a work of art that quietly whispers, “Stay here…create new memories for a lifetime” Timeless Elegance, Effortless Living where HISTORY Meets MODERN LUXURY @ "Casa del Carnevale," an exquisite waterfront estate, situated in the prestigious St. Armands Key, a neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway & Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical home. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials & artisanship. Expanded from 4,000 to nearly 10,000 sq. ft. under roof & featuring over 7,800 sq. f.t of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis-kayaks, & breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats & entertaining areas, all complemented by stunning garden water vistas, a central courtyard, & an elegant 65' saltwater pool & spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny’s quarters, walk-in wine room, billiards room, office, & custom impact-glass arched windows designed to maximize unobstructed views. The chef’s kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range & hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, & curated artwork create an inviting, sophisticated atmosphere, offered furnished. Instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance & modern comfort on one of Sarasota’s most coveted waterfront estates. IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.

139 S Washington Drive, Sarasota
$6,945,000
5 Beds ⋅ 6 Baths ⋅ Saint Armands Division John Ringling Estates SubDv. ⋅ 34236 Zip Code
A boater's dream and RARE opportunity—One of just 39 homes on this EXCLUSIVE side of St. Armands Circle offering -DIRECT GULF ACCESS- NO FIXED BRIDGES - and NO OBSTACLES. True deep-water dockage that comfortably accommodates a vessel over 60 feet. Enjoy full waterfront views of Sarasota Bay and the iconic downtown Sarasota skyline from every north-facing room in this home. This stunning, gated waterfront estate showcases the timeless elegance of Mediterranean architecture, blending classical design with refined coastal living. Expertly engineered with solid poured concrete walls reinforced by structural steel beams, this residence offers unmatched strength, integrity, and long-term value—an ideal foundation for both luxury and peace of mind. This Venetian-inspired estate is a rare architectural masterpiece, showcasing meticulously hand-applied Venetian plaster walls that exude artisan-crafted elegance—both refined and truly one-of-a-kind. The home features unmatched fit and finish throughout the entire residence. The primary floor of this home is thoughtfully designed for seamless living and exceptional entertaining value. Take in full waterfront views of Sarasota Bay and the downtown skyline while preparing a meal in the master-crafted kitchen or relaxing on the expansive waterfront veranda. The kitchen is an authentic showpiece and a true chef’s dream, featuring professional-grade appliances, a robust gas range with multiple burners, hand-carved cabinetry, and marble flooring throughout. This four-story home is equipped with a whole-house elevator for effortless access to each level. With an expansive extended garage, it’s ideal for car enthusiasts, offering multiple storage bays and additional space for organization. Looking for ease of maintenance? Enjoy the recently installed, top-of-the-line polymer turf surrounding the home. The luxury pool and spa features all brand new equipment and water heater, a premium-grade saltwater chlorination system, complete with full automation and water features. Delivering crystal-clear water and low-maintenance convenience. St. Armands Circle is one of Sarasota’s most coveted and prestigious addresses. This home's premier location places you just steps from Lido Beach. Frequent festivals, classic car shows, and seasonal events make the area lively year-round. Choose from gourmet restaurants, boutique shops, and family-friendly activities as you stroll the Circle. Downtown Sarasota’s theaters, museums, and fine arts venues are just a short drive away. For golf enthusiasts, this home is minutes from The Longboat Key Club—one of Sarasota’s most prestigious private clubs. The club features 45 holes of championship golf across two beautifully maintained courses and a full-service, resort-style experience including a world-class tennis center, private beach, deepwater marina slips, full-service spa, upscale dining, and an active calendar of social events.

290 N Washington Drive, Sarasota
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