Bay Isles, FL Luxury Real Estate & Waterfront Homes
Bay Isles is Longboat Key's premier 24-hour gated bayfront community — 16 neighborhoods, deeded private Gulf beach club access.
Bay Isles is Longboat Key's premier 24-hour gated bayfront community — 16 neighborhoods, deeded private Gulf beach club access.
Behind the 24-hour guarded gates of Bay Isles, every street feels like a private resort that never empties out at the end of the season. This is Longboat Key's most coveted gated community — a bayfront enclave on the southern half of the island where roughly 1,100 to 1,200 residences live across 16 distinct neighborhoods, all united by one of the most extraordinary amenity packages in Florida.
I'm Danielle Gladding — I live here in Queens Harbour, and I've been selling luxury real estate on Longboat Key since 1981. Every morning I walk these streets, greeting neighbors and their dogs, and I can tell you what Bay Isles is really like at every price point and in every neighborhood. The short version: from grand bayfront estates with private deep-water docks to maintenance-free villas perfect for a lock-and-leave second home, Bay Isles is built so that the right home exists here for almost any luxury buyer.
What sets Bay Isles apart isn't any single feature — it's how the pieces fit together. A private beach club on the Gulf of Mexico that comes with every home. A deep-water marina inside the gates. A world-class resort club next door. A grocery-anchored shopping center inside the community. And a security gate that's manned 24 hours a day, 365 days a year. You don't have to leave to live well.
Every Bay Isles owner has deeded private access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive — a residents-only Gulf-front retreat with covered pavilions, picnic areas, barbecue grills, a volleyball court, restrooms and showers, beach storage bins (allocated by biannual lottery), and secure parking right on the sand. It's the kind of amenity most buyers expect to pay Gulf-front prices to access. In Bay Isles, you live on the bay side — more privacy, better value — and the Gulf is still yours by deed.
“You live on the bay side — more privacy, better value — and this beach is still yours by deed.” — Danielle Gladding
The Longboat Key Club Moorings sits inside Bay Isles — a full-service deep-water marina with 291 storm-protected slips that can accommodate vessels up to 150 feet, designated a Clean Marina by the State of Florida. For the serious boater, the Harbor Section's 67 architect-designed waterfront estates offer direct, bridge-free Gulf access from private docks. Other neighborhoods inside Bay Isles offer dockage on navigable canals connecting to Sarasota Bay.
Membership at the Resort at Longboat Key Club is optional — but it's the lifestyle multiplier that draws many buyers here. Members enjoy 45 holes of championship golf across two PGA-approved courses (including Harbourside, inside Bay Isles), 20 Har-Tru tennis courts plus pickleball, an award-winning spa, a state-of-the-art fitness center, and multiple restaurants including the farm-to-table Tavern & Whiskey Bar.
Just outside the north gate, the Shoppes of Bay Isles at 525 Bay Isles Parkway anchors daily life — a Publix Super Market and Publix Liquors, CVS Pharmacy, Chase and Truist banks, a fitness center, salons, and casual dining. It's the kind of quiet convenience that makes full-time and seasonal living feel effortless. Just outside the gates you'll also find Longboat Key's town offices, library, post office, and community tennis center.
Bay Isles isn't one neighborhood. It's 16 distinct communities, each with its own character, price range, and lifestyle. Here's a quick orientation:
• The Bayou — 126 custom single-family homesites — many on the Bay Isles Waterway, others with golf course, lake, or garden views. Bay Isles' largest single-family neighborhood.
• Bay Isles Harbor Section — 67 architect-designed waterfront estates on deep-water canals with private docks and direct, bridge-free Gulf access. The most exclusive enclave inside Bay Isles.
• Corey's Landing — 61 homes — many with direct Sarasota Bay or lagoon frontage. Community pool, spa, and tennis.
• Queens Harbour — 102 maintenance-assisted single-family homes with Mediterranean and coastal-contemporary architecture, harbour and lagoon views, community pool and cabana. My own neighborhood.
• Sabal Cove — An intimate enclave with lake, preserve, and golf course views. Nearly all homes have private pool and spa.
• Harbour Court — Ultra-exclusive bayfront villas. Some of the most coveted addresses in all of Bay Isles. Rarely on the market.
• Winding Oaks — 56 units in 28 duplex villas on 14.5 acres — tree-lined, private courtyards, pools/spas, and a 4-acre nature park.
• Weston Pointe — 15 small, gated courtyard villas — 2,000 to 3,000+ sq ft. Community pool. True lock-and-leave luxury.
• Harbour Oaks — Single-story, two-story, and stacked villas — 3 bedrooms, 2,100+ sq ft, vaulted ceilings. One of the best values in Bay Isles.
• Harbour Circle — 42 contemporary Spanish-style villas — mostly 3-bedroom, intimate scale.
• Emerald Pointe (North & South) — 22 freestanding maintenance-free villas built around 2000.
• Harbour Links — 20 condominium units with golf course views, garages, and quality interiors.
• The Atrium — 80 condominium units in two mid-rise towers with spectacular Sarasota Bay views — part of Fairway Bay.
• Fairway Bay I & II — 208 condominium and townhouse units across 22 acres on Sarasota Bay.
• Grand Bay — Bay Isles' largest condominium community — 271 to 272 spacious units across six mid- and high-rise buildings with bay and Gulf views.
• Marina Bay — Approximately 60 condominium units in three buildings just south of the Moorings Marina.
Bay Isles tends to attract a specific kind of buyer — typically successful professionals and retirees in their late 50s through their early 70s who have done their homework. They've owned other Florida properties. They've vacationed at the Resort at Longboat Key Club. They want privacy without isolation, luxury without ostentation, and a community where they actually know their neighbors. Many become full-time residents. Many keep Bay Isles as a winter home and travel from Chicago, New York, Boston, Atlanta, Dallas, or Nashville. Either way, the lifestyle is the same — quiet, gated, walkable, and connected.
Honest trade-offs — because I tell clients what I'd tell my best friend: Bay Isles' inventory is limited and turnover is slow, which is wonderful for resale value but means the right home doesn't always exist on the market the day you start looking. Some neighborhoods have stronger HOAs than others. Some buildings allow short-term rentals; others restrict them. Some homes need updating, and some have been brilliantly renovated. The honest answer to almost every Bay Isles question is — it depends on the specific neighborhood, the specific building, the specific home. That's where having someone who lives here, walks here every morning, and has been a broker on Longboat Key since 1981 actually matters.
If you're considering Bay Isles — whether for a primary home, a winter retreat, or a long-term investment — I'd be honored to walk you through it personally. My daughter Alison Kanter and I work as a mother-daughter team at Danielle Gladding & Co. Realty, and between us you get two generations of Sarasota market knowledge, with the kind of insider community access only a Bay Isles resident can provide.
Visit DanielleGladdingCo.com or reach out directly for a private, no-pressure conversation about Bay Isles homes for sale. Call Danielle
Behind the 24-hour guarded gates of Bay Isles, every street feels like a private resort that never empties out at the end of the season. This is Longboat Key's most coveted gated community — a bayfront enclave on the southern half of the island where roughly 1,100 to 1,200 residences live across 16 distinct neighborhoods, all united by one of the most extraordinary amenity packages in Florida.
I'm Danielle Gladding — I live here in Queens Harbour, and I've been selling luxury real estate on Longboat Key since 1981. Every morning I walk these streets, greeting neighbors and their dogs, and I can tell you what Bay Isles is really like at every price point and in every neighborhood. The short version: from grand bayfront estates with private deep-water docks to maintenance-free villas perfect for a lock-and-leave second home, Bay Isles is built so that the right home exists here for almost any luxury buyer.
What sets Bay Isles apart isn't any single feature — it's how the pieces fit together. A private beach club on the Gulf of Mexico that comes with every home. A deep-water marina inside the gates. A world-class resort club next door. A grocery-anchored shopping center inside the community. And a security gate that's manned 24 hours a day, 365 days a year. You don't have to leave to live well.
Every Bay Isles owner has deeded private access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive — a residents-only Gulf-front retreat with covered pavilions, picnic areas, barbecue grills, a volleyball court, restrooms and showers, beach storage bins (allocated by biannual lottery), and secure parking right on the sand. It's the kind of amenity most buyers expect to pay Gulf-front prices to access. In Bay Isles, you live on the bay side — more privacy, better value — and the Gulf is still yours by deed.
“You live on the bay side — more privacy, better value — and this beach is still yours by deed.” — Danielle Gladding
The Longboat Key Club Moorings sits inside Bay Isles — a full-service deep-water marina with 291 storm-protected slips that can accommodate vessels up to 150 feet, designated a Clean Marina by the State of Florida. For the serious boater, the Harbor Section's 67 architect-designed waterfront estates offer direct, bridge-free Gulf access from private docks. Other neighborhoods inside Bay Isles offer dockage on navigable canals connecting to Sarasota Bay.
Membership at the Resort at Longboat Key Club is optional — but it's the lifestyle multiplier that draws many buyers here. Members enjoy 45 holes of championship golf across two PGA-approved courses (including Harbourside, inside Bay Isles), 20 Har-Tru tennis courts plus pickleball, an award-winning spa, a state-of-the-art fitness center, and multiple restaurants including the farm-to-table Tavern & Whiskey Bar.
Just outside the north gate, the Shoppes of Bay Isles at 525 Bay Isles Parkway anchors daily life — a Publix Super Market and Publix Liquors, CVS Pharmacy, Chase and Truist banks, a fitness center, salons, and casual dining. It's the kind of quiet convenience that makes full-time and seasonal living feel effortless. Just outside the gates you'll also find Longboat Key's town offices, library, post office, and community tennis center.
Bay Isles isn't one neighborhood. It's 16 distinct communities, each with its own character, price range, and lifestyle. Here's a quick orientation:
• The Bayou — 126 custom single-family homesites — many on the Bay Isles Waterway, others with golf course, lake, or garden views. Bay Isles' largest single-family neighborhood.
• Bay Isles Harbor Section — 67 architect-designed waterfront estates on deep-water canals with private docks and direct, bridge-free Gulf access. The most exclusive enclave inside Bay Isles.
• Corey's Landing — 61 homes — many with direct Sarasota Bay or lagoon frontage. Community pool, spa, and tennis.
• Queens Harbour — 102 maintenance-assisted single-family homes with Mediterranean and coastal-contemporary architecture, harbour and lagoon views, community pool and cabana. My own neighborhood.
• Sabal Cove — An intimate enclave with lake, preserve, and golf course views. Nearly all homes have private pool and spa.
• Harbour Court — Ultra-exclusive bayfront villas. Some of the most coveted addresses in all of Bay Isles. Rarely on the market.
• Winding Oaks — 56 units in 28 duplex villas on 14.5 acres — tree-lined, private courtyards, pools/spas, and a 4-acre nature park.
• Weston Pointe — 15 small, gated courtyard villas — 2,000 to 3,000+ sq ft. Community pool. True lock-and-leave luxury.
• Harbour Oaks — Single-story, two-story, and stacked villas — 3 bedrooms, 2,100+ sq ft, vaulted ceilings. One of the best values in Bay Isles.
• Harbour Circle — 42 contemporary Spanish-style villas — mostly 3-bedroom, intimate scale.
• Emerald Pointe (North & South) — 22 freestanding maintenance-free villas built around 2000.
• Harbour Links — 20 condominium units with golf course views, garages, and quality interiors.
• The Atrium — 80 condominium units in two mid-rise towers with spectacular Sarasota Bay views — part of Fairway Bay.
• Fairway Bay I & II — 208 condominium and townhouse units across 22 acres on Sarasota Bay.
• Grand Bay — Bay Isles' largest condominium community — 271 to 272 spacious units across six mid- and high-rise buildings with bay and Gulf views.
• Marina Bay — Approximately 60 condominium units in three buildings just south of the Moorings Marina.
Bay Isles tends to attract a specific kind of buyer — typically successful professionals and retirees in their late 50s through their early 70s who have done their homework. They've owned other Florida properties. They've vacationed at the Resort at Longboat Key Club. They want privacy without isolation, luxury without ostentation, and a community where they actually know their neighbors. Many become full-time residents. Many keep Bay Isles as a winter home and travel from Chicago, New York, Boston, Atlanta, Dallas, or Nashville. Either way, the lifestyle is the same — quiet, gated, walkable, and connected.
Honest trade-offs — because I tell clients what I'd tell my best friend: Bay Isles' inventory is limited and turnover is slow, which is wonderful for resale value but means the right home doesn't always exist on the market the day you start looking. Some neighborhoods have stronger HOAs than others. Some buildings allow short-term rentals; others restrict them. Some homes need updating, and some have been brilliantly renovated. The honest answer to almost every Bay Isles question is — it depends on the specific neighborhood, the specific building, the specific home. That's where having someone who lives here, walks here every morning, and has been a broker on Longboat Key since 1981 actually matters.
If you're considering Bay Isles — whether for a primary home, a winter retreat, or a long-term investment — I'd be honored to walk you through it personally. My daughter Alison Kanter and I work as a mother-daughter team at Danielle Gladding & Co. Realty, and between us you get two generations of Sarasota market knowledge, with the kind of insider community access only a Bay Isles resident can provide.
Visit DanielleGladdingCo.com or reach out directly for a private, no-pressure conversation about Bay Isles homes for sale. Call Danielle
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