Bay Isles Homes with Special Community Restrictions Community Features

Welcome to Bay Isles, an exclusive gem nestled in the heart of Longboat Key, Florida. This charming subdivision is renowned for its serene atmosphere and vibrant community spirit, making it an ideal destination for those seeking a peaceful coastal lifestyle. With its prime location in Sarasota County, Bay Isles offers residents easy access to the stunning beaches and lush landscapes that define this beautiful area.

Bay Isles features an array of exquisite homes, each designed with elegance and comfort in mind. The community is characterized by its unique architectural styles and meticulously landscaped gardens, creating a picturesque setting for families and retirees alike. However, it's important to note that Bay Isles has special community restrictions that help maintain the aesthetic integrity and tranquility of the neighborhood. These guidelines ensure that the beauty of the community is preserved, promoting a harmonious living environment for all residents.

Residents of Bay Isles enjoy a wealth of community features that enhance their lifestyle. From private access to pristine beaches to scenic walking trails and recreational facilities, the area is perfect for outdoor enthusiasts. The community also boasts a vibrant social scene, with events and gatherings that foster connections among neighbors.

Whether you're sipping coffee on your sun-drenched patio or taking a leisurely stroll along the waterfront, Bay Isles offers a unique blend of luxury and relaxation. Experience the charm of this extraordinary community where every day feels like a vacation. Discover your dream home in Bay Isles, where coastal living meets community spirit!

Newest Bay Isles Homes with Special Community Restrictions Community Features

$4,550,000

4 Beds ⋅ 4 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.

1571 Harbor Cay Lane, Longboat Key

$7,900,000

3 Beds ⋅ 4 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Longboat Key, this extraordinary peninsula estate delivers exceptional privacy, dramatic Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, the property features two private docks with water and electric, including one with a 15,000-lb lift designed for easy access. The Gulf is reachable through the nearby jetty with drawbridge, with an additional route via the John Ringling Bridge. The seawall was newly capped in 2020, and the pier deck and boat lift controls were replaced in 2025, ensuring superior waterfront infrastructure. Extensively rebuilt and structurally engineered, the residence is warm, refined, and filled with natural light, capturing sweeping bay views from nearly every room. The chef-inspired kitchen showcases custom rare wood cabinetry, an extended breakfast bar, a three-sink layout, double dishwashers, Sub-Zero refrigerator, Wolf warming drawer, standalone ice maker, and beautifully finished wood ceilings. The living and dining areas feature a custom jazz club floor and open seamlessly to a wraparound screened lanai, fully reconstructed with multilayer waterproof construction, a rich teak ceiling, and an open-sky section ideal for coastal breezes and stargazing. Multiple seating and dining areas create effortless indoor-outdoor living with uninterrupted water views. Outdoors, the pool area offers a private retreat surrounded by tropical landscaping and expansive travertine decking designed for both relaxation and entertaining. A custom palm-terrace garden enhances the tranquil ambiance along the east side of the deck. All bathrooms have been fully remodeled with premium finishes, floor-to-ceiling tilework, and frosted glass shower doors. The primary suite features an elegant, spa-like bath designed with refined materials. Additional upgrades include hurricane-rated windows and doors, 5-ton A/C units installed in 2024 and 2025, all-new plumbing, electrical, and HVAC ductwork, a whole-house water purification system, a full security camera system, and extensive structural improvements completed under engineering oversight. Exterior enhancements include landscape lighting, a resurfaced epoxy garage floor with mini-split A/C, and cell-foam insulation for efficiency. Residents of Bay Isles enjoy private Gulf beach access at the Bay Isles Beach Club, offering tiki huts, restrooms, BBQ areas, and gathering spaces. The gated community provides 24/7 security, community pools, and miles of shaded sidewalks ideal for walking and cycling. With its unrivaled peninsula setting, exceptional boating amenities, unmatched privacy, and sweeping water views at every turn, this estate represents one of Longboat Key’s most remarkable waterfront opportunities—an extraordinary residence defined by craftsmanship, luxury, and coastal elegance.

560 Harbor Cove Circle, Longboat Key

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