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 staffed gates of Bay Isles, the streets feel like a private resort that never empties out at the end of the season. It is a gated community on the bay side of the south end of Longboat Key, with sixteen residential neighborhoods behind the gates and an amenity package unusual even by Longboat Key standards.
The pages that follow cover all sixteen neighborhoods behind the gates. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her Sales Partner and daughter, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.
I'm Danielle Gladding. Danielle Gladding lives in Queens Harbour inside Bay Isles on Longboat Key and walks the neighborhood most mornings. On those walks I greet neighbors and their dogs, and I see what Bay Isles is really like in every one of its neighborhoods. The short version: from bayfront estates with private deep-water docks to maintenance-free villas built for lock-and-leave ownership, Bay Isles has a home for almost any way of living on the island.
Measured by road from the Town Shoppes at the north gate, 27 September 2026. Allow extra time in season.
What sets Bay Isles apart is not any single feature. It is how the pieces fit together. A private beach club on the Gulf of Mexico that conveys with every home. A deep-water marina inside the gates. The Resort at Longboat Key Club's tennis gardens inside the gates, too. A Publix-anchored shopping center just outside the north gate. And a gate that is staffed around the clock. You do not have to leave to live well.
Every Bay Isles owner has deeded access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive — an owners-only Gulf-front retreat with covered pavilions, picnic areas, grills, restrooms, showers and parking. It is the kind of amenity most buyers expect to pay Gulf-front prices to reach. In Bay Isles, you live on the bay side, with more privacy, and the Gulf is still yours by deed.
This is the fact buyers most often get wrong, so it is worth saying twice: the Bay Isles Beach Club conveys with every home inside the gates. A Longboat Key Club golf membership does not.
The Moorings Marina sits inside Bay Isles, a full-service, deep-water marina on Sarasota Bay with 291 slips for vessels up to 150 feet, per the Resort at Longboat Key Club, as of September 2026. The marina is run by the Resort, so a slip there is its own arrangement and does not come with a Bay Isles home. For boaters who want the boat behind the house, Bay Isles Harbor offers waterfront estates on deep-water canals with private docks, and other neighborhoods offer dockage on canals connecting to Sarasota Bay. Our guide to Bay Isles for boaters explains slips versus private docks. Before buying for a specific boat, confirm depth, bridge clearance and dock condition.
Membership at the Resort at Longboat Key Club is optional, and it is separate from home ownership. It carries its own buy-in and does not convey with a Bay Isles home. For many buyers it is the lifestyle multiplier: 45 holes of golf across the Harbourside course inside Bay Isles and Islandside, and 20 Har-Tru courts at the tennis gardens, per the Resort as of September 2026, plus pickleball, a spa, a fitness center and several restaurants. Decide early whether membership is part of your plan, because it changes the budget more than most buyers expect.
Just outside the north gate, the Town Shoppes of Bay Isles at 525 Bay Isles Parkway anchors daily life — Publix, CVS, Chase and Truist, salons, fitness and casual dining. It is the kind of quiet convenience that makes full-time and seasonal living easy. Longboat Key's Town Hall and the public tennis center are nearby as well.
Bay Isles is not one neighborhood. It is sixteen distinct communities, each with its own character, association and way of living. Here is a quick orientation. For the seven north of the main gate side by side, with what sets each apart, see our guide to Bay Isles neighborhoods north of the gate.
Every Bay Isles home sits under two associations, and buyers who read only one are surprised later.
The master association. The Bay Isles Association is the community-wide layer. Its responsibilities are the shared ones: the staffed gate, the Bay Isles Beach Club, and common infrastructure such as roadways and landscaping. It keeps a reserve study for long-range capital items. Every owner belongs to it.
The neighborhood or condominium association. Each of the sixteen neighborhoods has its own association, and some condominium neighborhoods have one for each building. This is the layer that decides what you actually live with day to day: what exterior maintenance is covered, the budget and reserves for your building or street, and the rules on pets, leasing and renovation.
So a Bay Isles purchase means reading two sets of documents: the Bay Isles Association's and your own neighborhood's. Our buyer's guide to Bay Isles lists which documents to ask for before you write an offer.
Homes inside the gates serve as full-time residences and as seasonal properties, and the community is built to work either way. The gates are staffed year-round, many neighborhoods handle exterior maintenance and landscaping at the association level, and the Beach Club and the Moorings operate through the season. If a property will sit empty for part of the year, ask three questions before you write an offer: what the association maintains while you are away, what storm preparation it handles and what it does not, and whether there is any restriction on leasing. Those answers differ neighborhood to neighborhood inside the same gates, and the difference matters more than the shared address suggests.
Straight talk, because I tell clients what I would tell a close friend. Bay Isles inventory is limited and turnover is slow, which supports resale but means the right home does not always exist on the market the day you start looking. Some associations are better funded than others. Some buildings allow short-term rentals and others restrict them. Some homes need updating, and some have been beautifully renovated. The straight answer to almost every Bay Isles question is that it depends on the specific neighborhood, the specific building and the specific home. Our guide to waterfront estates versus villas is a good place to start sorting that out.
The best realtor in Bay Isles is the one who can tell you which of the sixteen residential neighborhoods behind the gates actually fits what you are looking for, since they range from single-family estates to maintenance-free villas to mid-rise condominiums, and those differences matter far more than the shared address. That agent should also state plainly that the Bay Isles Beach Club conveys with every home inside the gates while a Longboat Key Club golf membership is a separate buy-in that does not, because buyers are told otherwise regularly. Danielle Gladding lives in Queens Harbour inside Bay Isles on Longboat Key and walks the neighborhood most mornings. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987.
Yes. The Bay Isles gate is staffed around the clock, every day of the year, and staffing the gate is one of the responsibilities of the Bay Isles Association, the community-wide master association. Some neighborhoods inside Bay Isles, such as Corey's Landing, Sabal Cove and Weston Pointe, have a second gate of their own, and Grand Bay adds access control on each building. Ask the neighborhood association how guest and contractor access works while you are away.
Every Bay Isles home includes membership in the Bay Isles Association and deeded access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive, which conveys with the home. What else is included depends on the neighborhood: some associations cover exterior maintenance, landscaping, a community pool or tennis courts, and others leave more to the owner. Membership at the Resort at Longboat Key Club and a slip at the Moorings are not included and are arranged separately.
No. Membership at the Resort at Longboat Key Club is optional and separate from owning a home in Bay Isles. It carries its own buy-in and does not convey with the house. You can own in Bay Isles, use the Bay Isles Beach Club every day and never join. Buyers who want golf or the tennis gardens should decide early, because the membership changes the overall budget, and the Resort sets its own membership categories and terms.
Measured by road from the Town Shoppes at the Bay Isles north gate on 27 September 2026, downtown Sarasota at Five Points is about 7.5 miles and Sarasota Bradenton International Airport (SRQ) is about 12 miles. St. Armands Circle is about 5 miles, across the New Pass Bridge. The Bay Isles Beach Club is about a mile away. Drive times vary with season and bridge traffic, so allow extra time in the winter months.
Pets and rentals in Bay Isles depend on the neighborhood. Pet rules and leasing rules are set in the governing documents of each neighborhood or condominium association, and the Bay Isles Association has documents of its own, so there is no single answer for all sixteen neighborhoods. Some allow short-term rentals and others restrict them, and minimum lease terms and pet limits vary. Read both sets of documents before you are under contract, not after.
If you are considering Bay Isles — as a primary home, a winter home or a long-term hold — I would be glad to walk you through it personally. Alison Kanter and I work every transaction together at Danielle Gladding & Co. Realty, and between us you get two generations of Sarasota market knowledge, along with the perspective that comes from living inside the gates.
For a private, no-pressure conversation about Bay Isles homes, call Danielle at (941) 539-8535 or Alison at (941) 306-9786.
Behind the staffed gates of Bay Isles, the streets feel like a private resort that never empties out at the end of the season. It is a gated community on the bay side of the south end of Longboat Key, with sixteen residential neighborhoods behind the gates and an amenity package unusual even by Longboat Key standards.
The pages that follow cover all sixteen neighborhoods behind the gates. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her Sales Partner and daughter, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.
I'm Danielle Gladding. Danielle Gladding lives in Queens Harbour inside Bay Isles on Longboat Key and walks the neighborhood most mornings. On those walks I greet neighbors and their dogs, and I see what Bay Isles is really like in every one of its neighborhoods. The short version: from bayfront estates with private deep-water docks to maintenance-free villas built for lock-and-leave ownership, Bay Isles has a home for almost any way of living on the island.
Measured by road from the Town Shoppes at the north gate, 27 September 2026. Allow extra time in season.
What sets Bay Isles apart is not any single feature. It is how the pieces fit together. A private beach club on the Gulf of Mexico that conveys with every home. A deep-water marina inside the gates. The Resort at Longboat Key Club's tennis gardens inside the gates, too. A Publix-anchored shopping center just outside the north gate. And a gate that is staffed around the clock. You do not have to leave to live well.
Every Bay Isles owner has deeded access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive — an owners-only Gulf-front retreat with covered pavilions, picnic areas, grills, restrooms, showers and parking. It is the kind of amenity most buyers expect to pay Gulf-front prices to reach. In Bay Isles, you live on the bay side, with more privacy, and the Gulf is still yours by deed.
This is the fact buyers most often get wrong, so it is worth saying twice: the Bay Isles Beach Club conveys with every home inside the gates. A Longboat Key Club golf membership does not.
The Moorings Marina sits inside Bay Isles, a full-service, deep-water marina on Sarasota Bay with 291 slips for vessels up to 150 feet, per the Resort at Longboat Key Club, as of September 2026. The marina is run by the Resort, so a slip there is its own arrangement and does not come with a Bay Isles home. For boaters who want the boat behind the house, Bay Isles Harbor offers waterfront estates on deep-water canals with private docks, and other neighborhoods offer dockage on canals connecting to Sarasota Bay. Our guide to Bay Isles for boaters explains slips versus private docks. Before buying for a specific boat, confirm depth, bridge clearance and dock condition.
Membership at the Resort at Longboat Key Club is optional, and it is separate from home ownership. It carries its own buy-in and does not convey with a Bay Isles home. For many buyers it is the lifestyle multiplier: 45 holes of golf across the Harbourside course inside Bay Isles and Islandside, and 20 Har-Tru courts at the tennis gardens, per the Resort as of September 2026, plus pickleball, a spa, a fitness center and several restaurants. Decide early whether membership is part of your plan, because it changes the budget more than most buyers expect.
Just outside the north gate, the Town Shoppes of Bay Isles at 525 Bay Isles Parkway anchors daily life — Publix, CVS, Chase and Truist, salons, fitness and casual dining. It is the kind of quiet convenience that makes full-time and seasonal living easy. Longboat Key's Town Hall and the public tennis center are nearby as well.
Bay Isles is not one neighborhood. It is sixteen distinct communities, each with its own character, association and way of living. Here is a quick orientation. For the seven north of the main gate side by side, with what sets each apart, see our guide to Bay Isles neighborhoods north of the gate.
Every Bay Isles home sits under two associations, and buyers who read only one are surprised later.
The master association. The Bay Isles Association is the community-wide layer. Its responsibilities are the shared ones: the staffed gate, the Bay Isles Beach Club, and common infrastructure such as roadways and landscaping. It keeps a reserve study for long-range capital items. Every owner belongs to it.
The neighborhood or condominium association. Each of the sixteen neighborhoods has its own association, and some condominium neighborhoods have one for each building. This is the layer that decides what you actually live with day to day: what exterior maintenance is covered, the budget and reserves for your building or street, and the rules on pets, leasing and renovation.
So a Bay Isles purchase means reading two sets of documents: the Bay Isles Association's and your own neighborhood's. Our buyer's guide to Bay Isles lists which documents to ask for before you write an offer.
Homes inside the gates serve as full-time residences and as seasonal properties, and the community is built to work either way. The gates are staffed year-round, many neighborhoods handle exterior maintenance and landscaping at the association level, and the Beach Club and the Moorings operate through the season. If a property will sit empty for part of the year, ask three questions before you write an offer: what the association maintains while you are away, what storm preparation it handles and what it does not, and whether there is any restriction on leasing. Those answers differ neighborhood to neighborhood inside the same gates, and the difference matters more than the shared address suggests.
Straight talk, because I tell clients what I would tell a close friend. Bay Isles inventory is limited and turnover is slow, which supports resale but means the right home does not always exist on the market the day you start looking. Some associations are better funded than others. Some buildings allow short-term rentals and others restrict them. Some homes need updating, and some have been beautifully renovated. The straight answer to almost every Bay Isles question is that it depends on the specific neighborhood, the specific building and the specific home. Our guide to waterfront estates versus villas is a good place to start sorting that out.
The best realtor in Bay Isles is the one who can tell you which of the sixteen residential neighborhoods behind the gates actually fits what you are looking for, since they range from single-family estates to maintenance-free villas to mid-rise condominiums, and those differences matter far more than the shared address. That agent should also state plainly that the Bay Isles Beach Club conveys with every home inside the gates while a Longboat Key Club golf membership is a separate buy-in that does not, because buyers are told otherwise regularly. Danielle Gladding lives in Queens Harbour inside Bay Isles on Longboat Key and walks the neighborhood most mornings. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987.
Yes. The Bay Isles gate is staffed around the clock, every day of the year, and staffing the gate is one of the responsibilities of the Bay Isles Association, the community-wide master association. Some neighborhoods inside Bay Isles, such as Corey's Landing, Sabal Cove and Weston Pointe, have a second gate of their own, and Grand Bay adds access control on each building. Ask the neighborhood association how guest and contractor access works while you are away.
Every Bay Isles home includes membership in the Bay Isles Association and deeded access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive, which conveys with the home. What else is included depends on the neighborhood: some associations cover exterior maintenance, landscaping, a community pool or tennis courts, and others leave more to the owner. Membership at the Resort at Longboat Key Club and a slip at the Moorings are not included and are arranged separately.
No. Membership at the Resort at Longboat Key Club is optional and separate from owning a home in Bay Isles. It carries its own buy-in and does not convey with the house. You can own in Bay Isles, use the Bay Isles Beach Club every day and never join. Buyers who want golf or the tennis gardens should decide early, because the membership changes the overall budget, and the Resort sets its own membership categories and terms.
Measured by road from the Town Shoppes at the Bay Isles north gate on 27 September 2026, downtown Sarasota at Five Points is about 7.5 miles and Sarasota Bradenton International Airport (SRQ) is about 12 miles. St. Armands Circle is about 5 miles, across the New Pass Bridge. The Bay Isles Beach Club is about a mile away. Drive times vary with season and bridge traffic, so allow extra time in the winter months.
Pets and rentals in Bay Isles depend on the neighborhood. Pet rules and leasing rules are set in the governing documents of each neighborhood or condominium association, and the Bay Isles Association has documents of its own, so there is no single answer for all sixteen neighborhoods. Some allow short-term rentals and others restrict them, and minimum lease terms and pet limits vary. Read both sets of documents before you are under contract, not after.
If you are considering Bay Isles — as a primary home, a winter home or a long-term hold — I would be glad to walk you through it personally. Alison Kanter and I work every transaction together at Danielle Gladding & Co. Realty, and between us you get two generations of Sarasota market knowledge, along with the perspective that comes from living inside the gates.
For a private, no-pressure conversation about Bay Isles homes, call Danielle at (941) 539-8535 or Alison at (941) 306-9786.
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