Hidden Harbor Homes with Sailboat Water Water Frontage

Hidden Harbor Homes with Sailboat Water Water Frontage

Welcome to Hidden Harbor, an enchanting subdivision nestled in the heart of Siesta Key, Florida, where coastal living meets tranquil elegance. This picturesque community is a haven for those seeking the ultimate waterfront lifestyle, boasting homes with sailboat water frontage that provide direct access to the stunning Gulf of Mexico. Imagine waking up to the gentle sound of waves lapping against your dock and the promise of a sun-soaked day ahead, whether you're setting sail or simply enjoying the breathtaking views from your patio.

Hidden Harbor is characterized by its lush tropical landscaping, charming streets, and a friendly neighborhood atmosphere that invites you to relax and unwind. Each home is uniquely designed, featuring modern amenities while preserving the timeless charm that makes Siesta Key so special. With properties that range from spacious family homes to intimate waterfront retreats, there is something for everyone in this idyllic community.

Living in Hidden Harbor means embracing a lifestyle filled with outdoor adventures, from boating and fishing to kayaking and paddleboarding. The nearby Siesta Key Beach, renowned for its powdery white sands and vibrant sunsets, is just minutes away, offering endless opportunities for recreation and relaxation. Additionally, the local dining and shopping scene is rich with options, ensuring that you never run out of delightful experiences to enjoy.

Discover the allure of Hidden Harbor, where every day feels like a vacation. Your dream home awaits in this serene slice of paradise, where the beauty of nature and the luxury of waterfront living come together in perfect harmony.

Newest Hidden Harbor Homes with Sailboat Water Water Frontage

$8,500,000
4 Beds ⋅ 5 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Privately positioned on a tropical peninsula on Siesta Key in the coveted community of Hidden Harbor, this extraordinary bayfront estate captures sweeping views across Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline. Set on 0.62 acres with 125 feet of panoramic waterfront, the residence was masterfully built by luxury builder M. L. Collingwood and thoughtfully designed to celebrate both architectural craftsmanship and the beauty of its remarkable setting. A protected deep-water harbor, a private 50-foot dock and 20,000-pound lift create an exceptional opportunity for the serious boater, while the home’s privacy, scale and resort-style outdoor living make it equally ideal as a serene waterfront retreat. From the moment you arrive, custom mahogany doors, beveled glass transoms, lush landscaping and a gracious entry introduce the timeless character found throughout the residence. Inside, soaring ceilings, generous room proportions and walls of glass frame magnificent water views from many of the principal living areas. Rich architectural details include coffered and tray ceilings, bentwood arches, crown molding, custom millwork and travertine inset flooring. The formal living and dining rooms flow beautifully for entertaining and are complemented by a fully outfitted cherrywood-paneled bar and wine room. The executive office and library are a showpiece, featuring cherrywood paneling, an 18-foot coffered ceiling and a spiral staircase leading to upper bookshelves. The well-appointed island kitchen offers Wood-Mode cabinetry, quartzite countertops, stainless steel appliances, paneled Sub-Zero refrigeration, a Viking six-burner gas range, dual ovens, a walk-in pantry and a spacious breakfast bar. Open to the bayfront breakfast and gathering rooms, the space features an electric fireplace, adding warmth and ambiance, and connects effortlessly to the outdoor living areas. The primary suite is a private waterfront sanctuary with a bayfront sitting room and a generous bath with dual vanities, a two-person shower, a soaking tub and private water closets. Two additional guest suites are privately positioned in their own wing on the main level, along with a powder bath and laundry room. Upstairs, a fourth bedroom or game room includes a full bath, walk-in closet and private western balcony overlooking the harbor, ideal for taking in evening sunsets. Designed for relaxed Florida living, the expansive lanai features a heated saltwater infinity-edge pool, travertine decking and a shaded outdoor living space with custom ceiling detail, creating an inviting setting for alfresco dining and waterfront entertaining. Frequent dolphin and manatee sightings add to the magic of this rare waterfront setting. Additional features include a side-entry three-car garage, a paver drive and walkways, landscape lighting, a walk-in attic and abundant storage. Hidden Harbor is one of Siesta Key’s most treasured boating communities, offering exceptional privacy just one mile from the powdery white sands of Siesta Beach and close to Siesta Village’s dining, shopping and island charm. Mainland Sarasota’s cultural venues, restaurants, shopping, medical facilities and schools, including nationally acclaimed Pine View School, are also within easy reach.

1280 Hidden Harbor Way, Sarasota
$2,650,000
3 Beds ⋅ 2 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Now is your opportunity to own this waterfront tropical oasis on Siesta Key in the highly sought after exclusive community of Hidden Harbor. Comprised of just 36 homes, Hidden Harbor located on the North end of Siesta Key, is one of the most unique developments in Sarasota with its tropical landscaping reminiscent of old Florida. Most known for its waterfront lots and brick paver streets shaded by a magnificent canopy of lush greenery. This home has been beautifully reimagined to showcase its contemporary design and is situated on over half acre lot enjoying 119’ of deep-water canal front, making this a boater’s dream. The dock spans almost 40 feet and features a 10,000lb boat lift (installed in 2020) and has both electric and water supplies. No bridges to obstruct your journey out to Roberts Bay, which is just a turn of a corner away. The home features a new metal roof (2023), 4 new HVAC units that includes a garage unit (2024), and new hurricane impact sliders and windows (2021). On the inside you will find a floor plan that is flooded with natural light thanks to large sliders and tall architectural style windows that truly bring the Florida landscape inside. The first floor has all new luxury flooring and woodwork, including new solid core doors. The kitchen was recently renovated with European style cabinetry, stone counters, and a luxury Fisher & Paykel appliance package including range hood and induction cooktop. The two light-filled bedrooms on the East side of the home both feature access to outdoor spaces and walk-in closets. The shared bathroom, which also acts as a pool bath with its door to the outside, was renovated with a new seamless glass shower, European style vanity with LED mirror, and all new fixtures and hardware. Throughout the home, you will find restored original fixtures keeping with the home’s integrity. The primary suite dominates the second floor with a loft area, a light filled bedroom that enjoys the cross breeze when both walls of sliding windows are open, and a custom installed closet. There is an updated en-suite bathroom with another seamless glass shower and floating vanity with new upgraded fixtures. Outside the yard is truly a Florida paradise with fire pit area, stunning tropical landscaping with professionally installed low voltage lighting system, pest control misting system, and an impressive heated pool that was resurfaced and upgraded with a travertine deck. This property offers extreme privacy, architectural character and significance, and water views, all within one of the most unique neighborhoods on Siesta Key. The Hidden Harbor canal offers deep water for your boat or sailboat. Enjoy true island life, whether you find yourself relaxing by your pool, boating, fishing, kayaking, and even paddle-boarding all from your property. There is a natural seawall of mangroves, and the riprap was installed by the reputable Duncan Seawall. The world-famous Siesta Key Beach is just a short 1.5-mile bike ride, golf cart ride, or leisurely walk away. Enjoy local restaurants, boutiques, and live music at the island's lively Siesta Village. Close to the mainland and downtown Sarasota, this is a prime location for island living. If you are looking for your own piece of paradise, and a property that is truly unique, set up a private tour today!

5303 Hidden Harbor Road, Sarasota
$11,975,000
5 Beds ⋅ 8 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Under Construction. Introducing one of Hidden Harbor’s most significant new offerings—a waterfront estate meticulously crafted by Dynan Construction Co. one of Sarasota’s most respected and sought-after luxury builders. Known for their uncompromising standards, Fortified Gold engineering, and elite coastal construction methods, Dynan Construction Co. has earned a prestigious reputation across Florida for delivering residences that marry innovative design with enduring structural integrity. This home represents a rare level of elevated coastal living, where artistry and engineering come together in flawless harmony. This bay front property’s unique footprint extends across to a deep saltwater canal, allowing unobstructed panoramic Bay views while still providing protected harbor docking—an extraordinary combination rarely found in Sarasota. Just beyond the resort-level pool and terraces, a stretch of private white-sand shoreline delivers a true barefoot-beach experience, steps from your outdoor living spaces. Designed for both grand entertaining and effortless everyday living, the home features a full outdoor kitchen, covered dining pavilion, outdoor shower, and an expansive poolscape that blends seamlessly with the surrounding water and sky. Inside, every surface, finish, and detail has been curated to reflect a standard of luxury that defines Sarasota’s elite design culture—custom millwork, designer lighting, elevated stone selections, and a palette inspired by refined coastal sophistication. The estate plan offers 5 bedrooms, a dedicated office, gym with built in Sauna, plus additional wellness/lifestyle spaces, and thoughtful livability throughout. The primary suite is conveniently located on the main level, offering privacy, water views, and immediate access to the outdoor living areas. Two laundry rooms, an elevator, and multiple flexible-use rooms create convenience for multigenerational living, extended guests, or long-term functionality. Car enthusiasts and coastal adventurers will appreciate the 4-car garage plus a golf cart/motorcycle garage, providing exceptional storage and flexibility. Located just minutes from Siesta Key, this home not only offers immediate access to world-renowned beaches but beyond the waterfront lifestyle, the estate is a short drive to Sarasota’s vibrant cultural scene—from performances at the Van Wezel and Sarasota Opera House to exhibitions at The Ringling Museum. A rare convergence of architectural pedigree, luxury construction, and irreplaceable waterfront setting—this Hidden Harbor estate stands as a defining example of elevated coastal living on Florida’s Gulf Coast.

1290 Hidden Harbor Way, Sarasota
$4,500,000
6 Beds ⋅ 7 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Majestic waterfront home nestled in one of Siesta Key's most exclusive neighborhoods. Prime waterfront location with direct access to the inter-coastal (no bridges) and features a 16,000 pound vertical lift and a jet ski lift. This Waterfront home features wraparound decks on multiple levels composed of Brazilian Ipe decking, wood ceilings, a private grill area with a dramatic view up the canal and a resort like swimming pool and spa featuring a rock waterfall and paver patio to fill your sun filled afternoons. Upon entering the home, you will see the amount of detail and craftsmanship that was put into this home. Hand-scraped wood flooring, coffered tongue-n-groove ceilings, huge baseboard and crown molding throughout. Expansive windows let the natural light in and an aquarium glass wall in the kitchen/family room overlooks your lower deck, swimming pool, spa and water view. The home has well over 6000 square feet of living area with the master suite occupying the first-floor level. This home affords 6 bedrooms, 5 full baths, 2 half baths, a private office with built-in cabinetry, 2 wet bars one on each level, 2 laundries with one on each level, a Sports room/ man cave with a built-in entertainment center. Upstairs has 4 bedrooms, two of which are suites, a second family room/playroom, theater/entertainment room which connects to your second level deck. The main level of the home incorporates your kitchen, family room, pantry, wet bar, dining room, private office, master suite and laundry. The kitchen features a huge walk-in pantry with entry door, a huge center island with a granite top, Subzero refrigerator, a Wolf 6 burner/griddle stove, a Wolf warming drawer, a Wolf microwave, 2 drawer Fisher Paykel dishwasher and a second Miele dishwasher for all your entertainment needs. Each level has a wet bar with the lower level having a subzero wine refrigerator and a drink refrigerator and the upstairs level has a Fisher Paykel dishwasher, an ice-maker, microwave, and a refrigerator. For the car enthusiast you have two 2 car garages with separate drives which provides additional parking as well. This spectacular home is hard to match, and you won't be disappointed. The home has an elevation of 15 feet and also has a home generator to provide comfort and a sense of security during any power outages that may occur. Schedule an appointment to see your future home!

5309 Hidden Harbor Road, Sarasota
$5,685,000
5 Beds ⋅ 7 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code
Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.

5132 Jungle Plum Road, Sarasota
$2,995,000
Hidden Harbor SubDv. ⋅ 34242 Zip Code
An exclusive opportunity awaits on Siesta Key—a .6-acre homesite in the prestigious Hidden Harbor community. With 144 feet of prime canal frontage, this property offers direct access to the sparkling waters of Sarasota Bay, making it a boater’s paradise. As you arrive, a tree-canopied, pavered street winds through a secluded enclave of luxurious estate homes, setting the stage for the ultimate waterfront retreat. This is a rare chance to build your dream home in one of the island’s most coveted neighborhoods. The existing structure sustained flood damage from recent hurricanes and is being offered at lot value only—an incredible opportunity to create a custom masterpiece in this serene, private setting. Opportunities like this are few and far between—secure your slice of Siesta Key paradise today.

5225 Hidden Harbor Road, Sarasota
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