Siesta Key Homes with Boatable Water Water Frontage

Siesta Key Homes with Boatable Water Water Frontage

Welcome to Siesta Key, Florida – a tropical paradise nestled within Sarasota County, known for its pristine beaches, vibrant culture, and laid-back lifestyle. This charming barrier island is famous for its powdery white sand beaches, particularly the award-winning Siesta Beach, where the sand is 99% pure quartz, making it cool to the touch even under the Florida sun.

Siesta Key is not just a beach lover's dream; it’s also a haven for those seeking a waterfront lifestyle. The island boasts an impressive collection of homes with boatable water frontage, allowing you to embrace the ultimate coastal experience. Picture yourself stepping out onto your private dock, ready to set sail into the shimmering Gulf of Mexico, where you can explore nearby islands, enjoy world-class fishing, or simply soak in breathtaking sunsets.

The real estate market in Siesta Key offers a diverse range of properties, from luxurious waterfront estates to charming beach cottages, each with its unique character and charm. Whether you’re looking for a primary residence, a vacation getaway, or an investment property, Siesta Key has something for everyone.

In addition to its natural beauty, the community is rich in culture and activities. Enjoy local dining, boutique shopping, and vibrant nightlife, all within a short distance from your home. Embrace the Siesta Key lifestyle – where every day feels like a vacation, and the allure of waterfront living is just a step away. Discover your dream home today in this idyllic coastal haven!

Newest Siesta Key Homes with Boatable Water Water Frontage

$729,500
2 Beds ⋅ 2 Baths ⋅ Contntls Sea Club SubDv. ⋅ 34242 Zip Code
Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an "Old Florida" feel. Sea Club II has private access to Siesta Key beach sand and the Gulf of America, with a 5-minute walk down community path. This Unit is on the second floor with stair access only. Discover the beauty of Siesta Key from this superb 2-bedroom condo. One bedroom has a 1 king bed and one with a 1 queen bed, queen sofa bed in living room. Cozy Electric Fireplace, Heated Pool, Area for lounging in the sun, dock area for fishing, Tiki Hut with chairs & charcoal grills. This fabulous property offers a comfortable and inviting space for guests- enclosed lanai and a large private deck overlooking the Bay with a gas grill and outdoor furniture. You'll find all the essentials you need, including 2 yr. old AC, hair dryer, Wi-Fi, an iron, coin laundry, beach chairs, wagon and umbrella, beach towels included in this turn-key sale! Move in and enjoy your new purchase. Laundry hook-ups but there are coin laundry machines on the 1st floor. Pets are not allowed. Minutes from Restaurants, Shopping, Entertainment, Grocery Store and Downtown Siesta Key Village. Public Stop for the Trolly is steps from the Condo Entrance! The views are exceptional of the ICW and bay as this the bayfront unit on the second floor, the only one with the large patio. This unit comes with a one car garage that only a few units are lucky enough to have. This two-bedroom unit has a deluxe bathroom and a half bathroom as well. Nice kitchen with granite tops and island L bar seating. Dinig table next to kitchen for those family dinners to make memories at. There is a community marina to bring your boat and enjoy this true Florida Beach and Bay lifestyle!!

5955 Midnight Pass Road Unit 21E, Sarasota
$299,000
1 Beds ⋅ 1 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code
Discover one of Siesta Key's best values at White Sands Village, where island living meets exceptional affordability. This beautifully furnished one-bedroom, one-bath condominium is ideally located just across the street from world-famous Siesta Key Beach and only a short stroll to the public beach access. One of the few pet-friendly communities on Siesta Key, White Sands Village welcomes well-behaved pets, making this an outstanding opportunity for full-time residents, seasonal owners, or investors seeking strong rental appeal. The community also offers an optional on-site rental management program, providing owners with flexibility to self-manage or utilize professional rental services. Residents enjoy a heated community pool, community boat docks available on a first-come, first-served basis, and convenient on-site laundry facilities. Siesta Key Public Beach is just moments away, offering tennis, pickleball, volleyball, nature trails, a playground, pavilion, and food concessions. Crescent Beach, Turtle Beach, Siesta Key Village, and downtown Sarasota's renowned dining, shopping, arts, and entertainment are all within easy reach. Whether you're searching for a personal beach getaway, a seasonal retreat, or an investment property with excellent rental potential, this furnished condominium delivers an exceptional combination of location, lifestyle, flexibility, and value at one of Siesta Key's most attractive price points.

5641 Midnight Pass Road Unit 902, Sarasota
$8,190,000
5 Beds ⋅ 5 Baths ⋅ Elliot M A Property Siesta Key SubDv. ⋅ 34242 Zip Code
A double waterfront, rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.

4034 Roberts Point Road, Sarasota
$11,900,000
5 Beds ⋅ 6 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. The lot is also available as vacant land (MLS #A4682294) ($6.7M). Introducing the Miller Floorplan designed by award winning Konstant Architecture (plans complete and available), a to be built waterfront estate set on one of the most extraordinary parcels on the north end of Siesta Key, one of only 10 properties with water access on the east and west. This award-winning luxury custom build plan is the example of architectural excellence at the highest level. Positioned on over three quarters of an acre with 175 feet of pristine water frontage, this rare offering captures sweeping panoramic views from Big Pass to Bayou Louise. With unobstructed access to Sarasota Bay and the Gulf, boating enthusiasts can enjoy effortless days of fishing, cruising, or island hopping directly from their backyard. This is coastal living without compromise. Designed for both elevated beauty and resilience, the Miller Floorplan features approximately 4,325 square feet of conditioned living space with a raised main living level, private elevator access, and a multi-bay garage with dedicated boat storage below. The thoughtfully designed layout includes five bedrooms, five full bathrooms, and a powder room. The primary suite is privately positioned offering a spa-inspired bath with separate water closet, expansive closet space, and seamless connection to outdoor living. The heart of the home is an open-concept living and dining space anchored by a designer kitchen with pantry and butler’s area, all oriented toward breathtaking water views. Expansive porches, screened outdoor living areas, and a resort-style pool with integrated spa and swim-off areas create a true waterfront retreat. A standing seam metal roof and sophisticated coastal architectural detailing reflect timeless style while complementing the surrounding natural beauty. Located on the coveted north end of Siesta Key, this estate offers both privacy and convenience. The beach, boating, waterfront dining, and Sarasota’s vibrant cultural and entertainment scene are moments away. Large parcels of this caliber with 175 feet of frontage and water access on the east and west side of the property, are rarely available, making this an exceptional opportunity to secure a refined blend of modern luxury, prime location, and long-term value. Where coastal beauty, architectural sophistication, and thoughtful design converge, this residence delivers an unparalleled Siesta Key lifestyle.

3550 Bayou Louise Lane, Sarasota
$17,650,000
4 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Four Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparalleled craftsmanship, and the restorative beauty of nature exist in perfect harmony. Offered fully furnished, the residence has been curated to provide an effortless, move-in-ready lifestyle, where every detail has been thoughtfully considered and every space evokes a sense of calm, balance, and understated luxury. Spanning more than 8,000 square feet, the home embraces the philosophy of seamless indoor-outdoor living. Expansive walls of glass dissolve the boundaries between the interiors and the surrounding tropical landscape, filling the home with natural light, gentle coastal breezes, and mesmerizing waterfront views. Rich exotic woods, natural stone, tranquil water features, and handcrafted architectural elements create an atmosphere reminiscent of an exclusive Balinese resort, where every room serves as a peaceful retreat. Designed as a private wellness oasis, the grounds are nothing short of breathtaking. Lush tropical gardens, mature specimen palms, fragrant flowering plants, and winding pathways lead through a series of serene outdoor spaces that inspire quiet reflection and effortless entertaining. A tranquil koi pond, crossed by picturesque footbridges, gently meanders alongside the residence, filling the air with the soothing sound of flowing water and creating a Zen-inspired tranquility throughout the estate. The resort-caliber outdoor living spaces are exceptional. An infinity-edge pool appears to merge effortlessly with the sparkling bay beyond and features a swim-up bar, spa, expansive sun shelves, and multiple terraces for lounging in the Florida sunshine. A dramatic sunken fire pit provides the perfect setting for evening gatherings beneath the stars, while the outdoor kitchen, covered dining pavilion, and numerous seating areas invite unforgettable alfresco entertaining against a backdrop of spectacular sunsets and panoramic waterfront vistas. With more than 700 feet of waterfront frontage, the property offers an extraordinary connection to the water that is rarely found. Whether setting out for a morning paddle through calm mangrove-lined waters or enjoying effortless boating from the private dock, every day begins and ends immersed in Sarasota's extraordinary coastal beauty. A dedicated waterfront garage, newer seawall, and abundant shoreline further enhance this exceptional waterfront lifestyle. Inside, every space has been thoughtfully designed to nurture both relaxation and recreation. A private theater, game room, fitness studio, and dedicated meditation room create an environment centered around wellness, entertainment, and everyday enjoyment. An oversized garage accommodating more than eight vehicles provides ample space for collectors and enthusiasts alike. Modern technology complements the home's timeless design with Crestron smart home automation, a three-stop elevator, whole-house generator, reverse osmosis water filtration system, and numerous additional upgrades that deliver effortless comfort, security, and peace of mind. This one-of-a-kind estate represents one of Siesta Key's most extraordinary luxury offerings and an exceptionally rare opportunity to own a true legacy property.

3799 Flamingo Avenue, Sarasota
$2,800,000
4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Privately set on Palm Island in the heart of Siesta Key, this residence offers an exceptional combination of generous living space, thoughtful design and effortless access to the island’s most celebrated destinations. Just a short distance from the powdery, white quartz sands of Siesta Beach and the boutiques, dining and lively atmosphere of Siesta Village, this beautifully reimagined waterfront residence presents a rare opportunity to enjoy a relaxed coastal lifestyle without compromising comfort, privacy or quality. Nearly every aspect of the home was transformed, creating a fresh, modern interior, designed for both everyday living and gracious entertaining. Soaring ceilings, abundant natural light, a contemporary custom staircase and impact-rated windows and doors establish an open, airy atmosphere, while luxury vinyl and engineered hardwood flooring, recessed lighting and thoughtfully integrated storage add warmth and architectural interest. The expansive kitchen serves as the centerpiece of the home, featuring custom cabinetry, stone countertops, upgraded stainless steel appliances, wine storage and an oversized quartz island with generous seating. Designed to accommodate everything from casual mornings to larger gatherings, the kitchen flows naturally into the surrounding living and dining spaces and continues outdoors to the pool, lawn and waterfront beyond. The main-level primary suite provides a serene private retreat with direct access to the pool area, a spacious custom-fitted closet and a beautifully appointed spa-inspired bathroom. Three additional bedrooms offer comfortable accommodations for family and guests, while an upstairs, separate flex space is ideally suited for a private office, exercise room or personalized retreat. A sunroom and conveniently positioned pool bath further enhance the home’s easy indoor-outdoor connection. Outside, the property reveals one of its most distinctive features: an unusually spacious backyard for Siesta Key. A broad lawn surrounds the heated pool, creating room for outdoor dining, recreation, pets and relaxed afternoons beneath the Florida sun. Beyond the pool, peaceful canal views and a private dock provide a tranquil waterfront setting with boating access. A well supplies the irrigation system, helping maintain the lush tropical landscape. A detached two-car garage offers valuable parking and additional storage for beach equipment, bicycles, paddleboards and other island essentials to enjoy the Siesta Key lifestyle. Morning walks along Siesta Beach, afternoons beside the pool and evenings dining in Siesta Village can all become part of everyday life. Spacious, extensively remodeled, and ideally positioned near the beach, Village and boating water, 430 Island Circle is a sophisticated yet wonderfully comfortable island retreat designed for those who want to experience the very best of Siesta Key.

430 Island Circle, Sarasota
$1,150,000
Roberts Point SubDv. ⋅ 34242 Zip Code
An exceptional opportunity to create a custom waterfront residence in one of North Siesta Key’s most desirable neighborhoods. Surrounded by substantial luxury homes, this property offers a peaceful bayou setting with direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards. The site is enhanced by mature tropical landscaping and tranquil water views, providing an inviting natural backdrop for a thoughtfully designed new home. Multiple outdoor living areas, terraces and elevated gathering spaces could be incorporated to take full advantage of the waterfront setting and relaxed Siesta Key lifestyle. An existing residence currently occupies the property, offering flexibility for use, rental or renovation while future building plans are developed. The home includes a roof completed in August 2023, hurricane shutters and completed storm remediation; however, the property’s compelling value lies in its land, location and potential to build new within a neighborhood known for impressive coastal residences. Conveniently positioned on North Siesta Key, the property provides easy access to Siesta Beach, Siesta Village, downtown Sarasota, shopping, dining and entertainment. Whether envisioned as a full-time residence or private island retreat, this is a rare opportunity to design a home tailored to your lifestyle in an established waterfront community.

4114 Roberts Point Circle, Sarasota
$1,150,000
4 Beds ⋅ 3 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code
Set along a quiet bayou in Roberts Point, one of North Siesta Key’s most coveted and established neighborhoods, this well-cared-for waterfront residence offers an appealing combination of immediate livability, flexible space and exceptional future potential. Enjoy the home as it is, thoughtfully update it over time or create an entirely new island retreat among the neighborhood’s impressive luxury residences. The primary living spaces are positioned on the upper level, where vaulted ceilings and an open layout create a bright, comfortable setting for everyday living and entertaining. Multiple decks extend the living areas outdoors, offering peaceful views of the water and surrounding tropical landscape. A hot tub overlooking the bayou provides a relaxing place to unwind at the end of the day. The legal ground level (non-conforming) adds valuable versatility with a private bedroom and bath, bonus room, screened lanai and two-car garage, well suited for guests, extended family, a home office or a recreational space. A new roof completed in August 2023, hurricane shutters and completed storm remediation provide added peace of mind. The property offers direct water access to Sarasota Bay for motorized craft, kayaks and paddleboards, making it easy to enjoy Siesta Key’s natural surroundings from your own backyard. Ideally located near Siesta Beach, Siesta Village, shopping, dining, and entertainment, and easy access to mainland Sarasota, this is a distinctive opportunity to live, renovate or rebuild in a coveted North Siesta Key setting.

4114 Roberts Point Circle, Sarasota
$2,600,000
4 Beds ⋅ 3 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
Stroll to the Village. Walk to the Beach. Cruise to the Gulf of Mexico. Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience, and the quintessential Siesta Key lifestyle are prepared for you to move in ready. A brief stroll from the vibrant energy of Siesta Key Village and the quartz sands of Siesta Beach. With an astounding approximately 240 feet of private seawall and offering long-range canal views creating a lagoon-like setting, this opportunity simply cannot be replicated. While offering crisp, clean lines of modern contemporary style, the infrastructure is strictly 2026-ready. This unique residence provides both luxurious aesthetic appeals, featuring a fully updated chef’s kitchen and designer baths, and "invisible luxury". The peace of mind that comes from the resilience of a durable metal roof, new seawall, and all-new high-velocity hurricane windows and doors, new flooring, wood burning fireplace, and new electrical, plumbing, as well as new three-zone HVAC and mechanical systems, has been thoughtfully provided. And, for your peace of mind, professional night vision high-tech security cameras and systems were installed in 2026. The preferred split plan offers three additional bedrooms, including a private guest suite with its own separate entrance and ensuite bath. Life at 339 Treasure Boat Way centers around the water. Venture out onto the paved, open-air pool deck to find a 2026 freshly re-finished Aqualink-controlled, saltwater, heated pool and spa with LED lighting. Enjoy gentle, golden morning sun and cool, shaded afternoons—perfect for entertaining and alfresco dining. An oversized detached two-car air-conditioned garage, fenced yard for pets, and ample guest parking.

339 Treasure Boat Way, Sarasota
$549,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Experience the best of Siesta Key living in this beautifully updated 2 bedroom, 2 bath 3rd floor condo in Sunrise Cove, offered turnkey furnished and ready for you to move in and start enjoying island life immediately. Enjoy next level comfort with a brand-new 2026 A/C system and an LED whole home in duct air purifier cool, refreshing comfort and cleaner, fresher indoor air all year long. Take in stunning back bay views from your home and enjoy an unbeatable location directly across from Turtle Beach and Park, with boat, kayak, and canoe launches, a playground, and a convenient trolley stop. Sunrise Cove delivers an exceptional amenity lineup, including two community pools, a fitness center, tennis and pickleball courts, kayak and bike storage, bayside BBQ grills, and picnic areas overlooking the water. Boat slips are available for rent with water and electric hookups, and the community includes full-time onsite facility and maintenance managers for added peace of mind. Step outside to Turtles Pub & Café, Turtles Restaurant, and a nearby marina right next door. Plus, you’re moments away from world famous Siesta Key Beach, known for its powdery quartz sand, sparkling water, and unforgettable sunsets.

9011 Midnight Pass Road Unit 329, Sarasota
$509,000
2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code
Opportunities to own in Sandy Cove are rare—and this residence presents the perfect chance to create your own island retreat in one of Siesta Key's most sought-after waterfront communities. Bring your vision and transform this well-located residence into the coastal getaway you've always imagined. Whether you're looking for a winter escape from the cold, a seasonal home to enjoy for years to come, or an investment in one of Florida's premier beach destinations, the value here lies in the location, lifestyle, and potential. Designed by renowned Sarasota architect Frank Folsom Smith, Sandy Cove is a boutique waterfront community celebrated for its timeless mid-century architecture, lush tropical landscaping, private shell beach, fishing pier, heated pool, kayak launch, and Gulf-front sunsets. Best of all, you're just a short stroll from Siesta Key Village, where local restaurants, boutiques, live music, and island charm await. Unlike buying someone else's renovation, this home offers the rare opportunity to update the interior to reflect your own style while investing in a community where demand remains consistently strong. Enjoy the property today, renovate at your own pace, and own a piece of Siesta Key in a location that continues to attract vacationers, seasonal residents, and investors alike. When the address is this exceptional, the possibilities are endless. Schedule your private showing today!

220 Pass Key Road Unit 220, Sarasota
$5,690,000
5 Beds ⋅ 5 Baths ⋅ Archibald Resub SubDv. ⋅ 34242 Zip Code
Virtually Staged. Exquisite new construction on Siesta Key redefines island luxury! Substantial progress has already taken place to complete this masterpiece. This is a rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. Siesta Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its famous powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. Just moments from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity: your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock—a true island luxury! This thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate incredible craftsmanship and fine detail, the home offers 4,195 square feet of interior living space and an additional 3,756 square feet of outdoor living, seamlessly blending indoor and outdoor environments. The chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. Two beautifully appointed bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or the private elevator one level up to access the primary suite, featuring a truly custom bath with bespoke tile, designer finishes, a soaking tub, and a spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper level. Flexible, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any lifestyle, from multi-generational living to a dynamic entertainer’s paradise. Imagine a home where the luxuries of island beach life blend perfectly with a private, resort-style retreat. Step outside to your inground pool and spa for cooling off or casual lounging, head up to the rooftop deck for sunset cocktails and starlit conversation, or enjoy your private boating access just steps from your front door. When you are ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. This is more than a home; it is an invitation to own your piece of the new Siesta Key lifestyle—elevated, effortless, and extraordinary!

539 Avenida Del Norte, Sarasota
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