Bay Isles Homes with Trail(s) Amenities

Welcome to Bay Isles, a stunning and exclusive subdivision nestled in the picturesque Longboat Key, Florida. This charming community offers a perfect blend of luxurious living and serene natural beauty, making it a coveted destination for those seeking a tranquil coastal lifestyle.

Bay Isles is renowned for its beautifully designed homes, each exuding elegance and sophistication. The architecture reflects the quintessential Floridian style, with lush landscaping and stunning water views that enhance the overall aesthetic appeal. Residents enjoy spacious layouts, modern amenities, and private outdoor spaces ideal for entertaining or unwinding after a long day.

One of the standout features of Bay Isles is its extensive network of trails that meander through the community, providing residents with ample opportunities for outdoor activities. Whether you enjoy leisurely strolls, invigorating runs, or biking amidst nature, these scenic trails are perfect for staying active while soaking in the beautiful surroundings. The community's commitment to preserving its natural beauty ensures that you can enjoy the tranquility of the lush landscapes and serene waterways right at your doorstep.

In addition to its stunning homes and trail amenities, Bay Isles boasts a vibrant community atmosphere. Residents can partake in various social events, fostering connections with neighbors and creating lasting friendships. With its prime location in Longboat Key, you're just moments away from pristine beaches, upscale dining, and boutique shopping, making it the perfect place to call home.

Discover the allure of Bay Isles, where luxurious living meets nature's serenity, and experience the best that Florida's coastal lifestyle has to offer!

Newest Bay Isles Homes with Trail(s) Amenities

$1,798,000

2 Beds ⋅ 3 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code ⋅ R4910478 MLS ⋅ Active Status ⋅ Grand Bay One BLDG.

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

3060 Grand Bay Boulevard Unit 174, Longboat Key

$7,900,000

3 Beds ⋅ 4 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code ⋅ A4672059 MLS ⋅ Active Status

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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