Bay Isles Harbor is a double-gated enclave of 67 architect-designed homes on four quiet streets of wide canals at the south end of Bay Isles, Longboat Key. An active boating community with Gulf access and bay views from every home — guided by resident broker Danielle Gladding and Alison Kanter
Behind the Bay Isles gate, there is a second gate.
That is not a figure of speech. At the south end of Bay Isles sits Bay Isles Harbor, and reaching it means passing through the community's main guarded entry, then through a second private gate into Harbor itself. A gate within the gate. Ask anyone who knows Longboat Key and they will point to this address as the most private inside Bay Isles. The rest of the picture explains why: 67 architect-designed homes on four quiet streets of wide canals, bridge-free access out to Sarasota Bay and on to the Gulf, bay views and lush landscaping from every residence.
We are Danielle Gladding and Alison Kanter, a Sarasota mother-daughter team. Danielle has been a Realtor since 1981 and a Broker since 1987 — forty-five years selling this market, fifty years living in it. She and her husband Nick live inside Bay Isles, in Queens Harbour on the north side. Bay Isles Harbor sits at the south end. Opposite ends of the same community, behind the same gate. Neighbors.
What follows is the working picture of Bay Isles Harbor: the streets, the canals, the park, the water, what conveys with the home and what does not, and how the enclave fits inside the larger Bay Isles community. When you are ready for a private conversation, our number is at the bottom.
The fast picture, for buyers who like to start with the facts.
● Location: A double-gated enclave at the south end of Bay Isles, the master-planned gated community on the south end of Longboat Key, in Sarasota County, Florida.
● Size: 67 architect-designed single-family homes along four quiet streets — one of the smallest and most exclusive enclaves on the key.
● Security: Double-gated. Past the main guarded Bay Isles entry, a second private gate into Harbor itself.
● The water: Four streets built around wide canals, with bridge-free access to Sarasota Bay and on to the Gulf of Mexico.
● The homes: Individually architect-designed, with bay views and mature landscaping.
● Green space: A park runs the length of Harbor Sound Drive — biking, dog walking, birding.
● What conveys: Deeded Bay Isles Beach Club access runs with the property. Longboat Key Club membership does not — it is a separate, optional buy-in.
● Drive times: Under 10 minutes to St. Armands Circle, roughly 18 minutes to Downtown Sarasota, about 25 minutes to Sarasota-Bradenton International (SRQ), and about an hour to Tampa International.
● Tax and residency: Florida — no state income tax, homestead exemption for primary residents, and meaningful relief for buyers relocating from high-tax states.
Start with the security, because it is the first thing that sets Bay Isles Harbor apart. Bay Isles itself is manned, guarded, and gated. Harbor adds a second private gate of its own. Residents pass through two layers of access control to reach their own driveway. For a buyer who ranks privacy above almost everything, that arrangement is rare even among Florida's most exclusive barrier-island addresses.
The result is a quiet that is hard to describe until you stand in it. No through traffic. Nobody driving past who does not live there. Sixty-seven homes, four streets, wide water, and the south tip of the island.
Here is a distinction that shapes the entire search: Bay Isles Harbor is not the same thing as Bay Isles. Bay Isles is the larger gated community, organized into sixteen distinct residential neighborhoods — Queens Harbour (where we live), Corey's Landing, the villas of Sabal Cove, Weston Pointe, mid-rise condominiums, and others — plus four shared components: the Bay Isles Beach Club, the Resort at Longboat Key Club, the Moorings Marina, and the Shoppes of Bay Isles.
Bay Isles Harbor is one of those sixteen. All sixteen share the main gate and deeded Beach Club access. What sets Harbor apart is everything after that: the second gate, the 67-home scale, the architect-designed houses, the wide canals, and the bay views.
When a buyer tells us they want "a home in Bay Isles," the first job is figuring out which of the sixteen they actually mean. For the buyer who wants this particular combination of privacy, design, and water, Harbor is very often the answer.
People do not buy here for square footage. They buy for what the days actually feel like.
Bay Isles Harbor is a boating community in the truest sense. The four streets are built around wide canals — generous water that makes maneuvering and dockage easier than the narrow cuts you find in many waterfront neighborhoods — with bridge-free access out to Sarasota Bay and on to the Gulf. No fixed-bridge clearance to plan around is a meaningful advantage, and it is one of the first questions a serious boater should ask about any Longboat Key address.
Depth is the other question. Dock depth at mean low water varies by lot and by canal position, and it is the single specification most often assumed rather than verified. We measure it. We do not take a listing sheet's word for it, and neither should you.
One of the quiet pleasures here is the park running the length of Harbor Sound Drive. Residents use it constantly — biking, walking their dogs, birding along the water. It is the kind of shared green space that turns a collection of houses into an actual neighborhood.
That is the balance buyers tell us they love. Real privacy, paired with a genuinely neighborly feel. The enclave is small enough that people know each other, and small enough that the streets, the canals, and the park stay exactly as residents expect them.
Every Bay Isles owner, Harbor included, holds deeded access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive — a private, gated stretch of Gulf beach reserved for Bay Isles residents. Tiki huts. A large covered pavilion. Barbecue stands, volleyball nets on the sand, an ice machine, and storage bins assigned by lottery twice a year. It is a residents-only beach in practice, not a marketing phrase.
The deeded access runs with the property, so it comes with the house. The annual membership cost is scaled to the value of your home, which means two neighbors on the same street can carry different numbers. Ask for the actual figure on the specific property, not the community average.
This is the distinction buyers most often get wrong, and it costs real money to get wrong at the contract stage.
The Longboat Key Club sits next door and is the social and athletic anchor of the island's south end: two golf courses, a long-respected tennis program, expanding pickleball, a spa, a fitness center, a deepwater marina, and several dining venues. It is a genuine draw, and for many of our clients it is a deciding factor.
Buying a home in Bay Isles Harbor does not include a Longboat Key Club membership. At this time, membership is a separate, optional buy-in — you apply, you are approved, you pay an initiation fee, and you carry annual dues, all independent of the purchase price of the house. It is not deeded, it does not automatically transfer from seller to buyer, and it is not the same arrangement as the Beach Club.
Sellers sometimes describe their membership as though it comes with the house. Occasionally an agent repeats it. Club policies also change, which is why we confirm current membership categories, initiation, dues, transfer terms, and any waitlist directly with the Club before a client writes an offer — rather than relying on what a listing says or what worked for the last buyer.
The quiet does not mean isolation. St. Armands Circle is under ten minutes south, with a full universe of dining and boutique shopping. Downtown Sarasota — the cultural capital of Florida's west coast — is roughly twenty minutes away, home to The Ringling, Sarasota Opera, Sarasota Orchestra, Asolo Repertory Theatre, the Van Wezel, and Selby Gardens. Alison specializes in Downtown Sarasota, Bird Key, and St. Armands, so if your search ever leans toward combining island life with downtown access, that is precisely her territory.
After more than forty years guiding buyers through Sarasota's premier addresses, the reasons cluster into clear patterns.
● An architect-designed single-family home with bay views — not a production build, not a condominium.
● Two layers of gated security: the main guarded Bay Isles entry and Harbor's own private gate.
● An active boating lifestyle on wide canals with bridge-free Gulf access.
● Real privacy paired with a small, neighborly community of only 67 homes.
● The Harbor Sound Drive park, and a walkable, dog-friendly enclave.
● Deeded Bay Isles Beach Club access that conveys with the property, plus the option — not the obligation — of a Longboat Key Club membership next door.
● Multi-generational potential: a primary residence now, a gathering place for grandchildren, a legacy asset later.
● Tax-favorable Florida residency, which matters most to buyers relocating from Illinois, New York, Massachusetts, and other high-tax states.
● Durable long-term value — a 67-home enclave behind two gates, on a barrier island where land does not expand.
THE DUE DILIGENCE WE WALK EVERY BAY ISLES HARBOR BUYER THROUGH Buying an architect-designed home inside a double-gated enclave means layered governance: the master Bay Isles Association, the Beach Club association and its dues, and the Bay Isles Harbor Association, which is overseen by a Board of Directors handling the day-to-day management of the enclave. Each layer affects your monthly carry and your resale. Then there is the question of what you are actually buying. Deeded Beach Club access conveys. A Longboat Key Club membership does not — that is a separate application, a separate initiation, and separate annual dues, and we confirm the current terms with the Club rather than with the listing. Beyond the associations, the items that matter most on a waterfront lot are dock permitting, dock depth at mean low water, flood elevation, and how the specific home sits on its canal and its route to the Gulf. We walk every buyer through all of it — association and reserve health, deeded access, pending capital projects, and the water itself — before they sign. With only 67 homes, the worst outcome is overpaying for the wrong lot when the right one was a street away. |
Most agents will show you houses. That is not the same as helping you make the right decision. Here is how our process actually runs.
1. The lifestyle conversation. Before we show you a single property, we talk about what your days are going to look like. Full-time or seasonal? A boat at the dock, or water views from the lanai? Do you want the Club, or do you want the beach and the quiet? The answers confirm whether Harbor is genuinely your fit, or whether another of the sixteen Bay Isles neighborhoods suits you better.
2. The lot-by-lot match. Inside Harbor's four streets, the lots are not interchangeable. Canal width, dock depth, southern exposure, and how a home sits on the water change both the value and the daily experience. Two houses on the same street can be very different purchases. A listing photo will not tell you which is which — walking these streets for four decades does.
3. The property filter. We filter for long-term fit: association and reserve health, flood elevation, dock permitting, renovation-versus-rebuild economics, Club membership terms if you want them, and resale strength. On a waterfront architect-designed home, these details separate a good purchase from a regret.
4. The negotiation and close. Forty-five years of relationships matter most here. We know the listing agents, we know the association managers behind this gate, and we know which sellers are realistic and which are not. The negotiation is where our experience pays for itself.
5. The handoff. Our clients do not disappear after closing. The same team that walked you through the front door is the team you call for a contractor, a dock builder, an interior designer, or an introduction to a neighbor. When your broker lives inside the same gate, that is more than a figure of speech.
We work as a team, and we are different in exactly the right ways. Danielle brings forty-five years of Sarasota market memory, instinct, and relationships — and she lives inside Bay Isles, which makes Harbor as much her home turf as any address on the island. Alison brings analytical precision, corporate discipline, and tech-forward process, along with deep expertise in Downtown Sarasota, Bird Key, and the St. Armands–Lido island chain. Together we cover every premier waterfront address on Florida's west coast. You are not getting one perspective. You are getting two, and they balance each other completely.
If you are weighing a Bay Isles Harbor purchase, the most useful next step is a confidential, no-pressure conversation. Not a pitch. A conversation.
Tell us what you are trying to accomplish, what your timeline looks like, and what is worrying you. We will tell you whether Harbor is your fit or whether another neighborhood inside Bay Isles suits you better, which of the 67 homes are worth your time, what the Club membership would actually cost you on top of the house, and — just as important — when something is likely to come available before it reaches the market. If you are selling, we will give you a private valuation: twenty minutes, on the phone or in person, and a clear read on your home's position in today's market.
That is what it means to have a resident broker. The straight answer, from your neighbor.
— Danielle & Alison | Danielle Gladding & Co. Realty
DanielleGladdingCo.com · Broker Since 1987 · Bay Isles Resident, Queens Harbour
Format each question as an H3 in Presence. Each answer opens with a complete, citable first sentence.
Bay Isles Harbor is a small, double-gated enclave of 67 architect-designed homes at the south end of Bay Isles, a guarded gated community on Longboat Key, Florida. Set along four quiet streets of wide canals with bridge-free access to Sarasota Bay and the Gulf of Mexico, it is an active boating community where homes enjoy bay views and mature landscaping. Owners hold deeded access to the Bay Isles Beach Club, and the Longboat Key Club sits adjacent.
Yes — Bay Isles Harbor is double-gated. Residents pass through the main guarded Bay Isles entry gate and then a second private gate into Harbor itself, creating two layers of access control. That arrangement gives the enclave a level of privacy and security rare even among Florida's most exclusive barrier-island communities.
Bay Isles Harbor contains 67 architect-designed homes arranged along four quiet streets, making it one of the smallest and most exclusive enclaves on Longboat Key. Because the community is small and owners tend to hold for the long term, properties here rarely reach the open market and often sell quietly when they do.
No — Bay Isles Harbor is one of sixteen residential neighborhoods within the larger Bay Isles community. Bay Isles also includes Queens Harbour, Corey's Landing, Weston Pointe, the villas of Sabal Cove, and mid-rise condominiums, along with four shared components: the Bay Isles Beach Club, the Resort at Longboat Key Club, the Moorings Marina, and the Shoppes of Bay Isles. Bay Isles Harbor refers specifically to the double-gated enclave of 67 architect-designed waterfront homes at the southern end.
No — buying a home in Bay Isles Harbor does not include a Longboat Key Club membership. At this time, Club membership is a separate, optional buy-in: buyers apply, pay an initiation fee, and carry annual dues independent of the purchase price of the home. This is different from the Bay Isles Beach Club, where access is deeded and conveys with the property. Because Club policies and membership categories change, we confirm current terms directly with the Club before a client writes an offer.
Deeded access to the private Bay Isles Beach Club on the Gulf conveys with every Bay Isles home, including those in Bay Isles Harbor. The Beach Club at 2111 Gulf of Mexico Drive is a gated, residents-only stretch of beach with tiki huts, a large covered pavilion, barbecue stands, volleyball nets, an ice machine, and storage bins assigned by lottery twice a year; its annual membership cost is scaled to the value of the home. Within Harbor itself, residents also enjoy a park running the length of Harbor Sound Drive. Longboat Key Club golf, tennis, marina, spa, and dining are available separately through an optional membership.
Yes — Bay Isles Harbor is an active boating community built around four streets of wide canals, with bridge-free access to Sarasota Bay and on to the Gulf of Mexico. The wide canals make dockage and maneuvering easier than the narrow cuts found in many waterfront neighborhoods, which matters for residents who keep a boat at home. Dock depth varies by lot, so we verify depth at mean low water on the specific property rather than relying on a listing description.
Bay Isles Harbor is managed by its own Board of Directors, which handles the day-to-day operation of the enclave, in addition to the master Bay Isles Association and the Bay Isles Beach Club association. Buyers should review all applicable association documents, fees, and reserve levels as part of due diligence, which we walk through with every client before contract.
Pricing in Bay Isles Harbor varies significantly by lot, canal frontage, home size and design, and whether a residence has been updated. Because this is an enclave of only 67 architect-designed homes with limited inventory, we do not quote firm numbers in evergreen content. For a current, confidential reading on Bay Isles Harbor pricing and availability, contact Danielle Gladding and Alison Kanter directly.
Bay Isles Harbor is one of Longboat Key's strongest options for an architect-designed single-family second home or legacy property. A 67-home double-gated enclave, an active boating setting on wide canals with bridge-free Gulf access, bay views, deeded beach access, Florida's tax-favorable residency, and limited barrier-island inventory together make it especially attractive for long-term and multi-generational ownership.
Danielle Gladding is widely regarded as one of the best realtors on Longboat Key, with forty-five years in the Sarasota market — a Realtor since 1981 and a Broker since 1987 — and a Certified Luxury Real Estate Specialist and Certified Waterfront Specialist designation. She lives inside Bay Isles on Longboat Key and works alongside her daughter and business partner, Alison Kanter. Living behind the same gate gives her firsthand, early knowledge of Bay Isles Harbor homes that often sell before they reach the open market, which is a meaningful edge in a 67-home community.
Bay Isles Harbor is under a ten-minute drive from St. Armands Circle and approximately eighteen minutes from Downtown Sarasota via the John Ringling Causeway. Sarasota-Bradenton International Airport (SRQ) is roughly 25 minutes away, and Tampa International Airport is about one hour north.
Behind the Bay Isles gate, there is a second gate.
That is not a figure of speech. At the south end of Bay Isles sits Bay Isles Harbor, and reaching it means passing through the community's main guarded entry, then through a second private gate into Harbor itself. A gate within the gate. Ask anyone who knows Longboat Key and they will point to this address as the most private inside Bay Isles. The rest of the picture explains why: 67 architect-designed homes on four quiet streets of wide canals, bridge-free access out to Sarasota Bay and on to the Gulf, bay views and lush landscaping from every residence.
We are Danielle Gladding and Alison Kanter, a Sarasota mother-daughter team. Danielle has been a Realtor since 1981 and a Broker since 1987 — forty-five years selling this market, fifty years living in it. She and her husband Nick live inside Bay Isles, in Queens Harbour on the north side. Bay Isles Harbor sits at the south end. Opposite ends of the same community, behind the same gate. Neighbors.
What follows is the working picture of Bay Isles Harbor: the streets, the canals, the park, the water, what conveys with the home and what does not, and how the enclave fits inside the larger Bay Isles community. When you are ready for a private conversation, our number is at the bottom.
The fast picture, for buyers who like to start with the facts.
● Location: A double-gated enclave at the south end of Bay Isles, the master-planned gated community on the south end of Longboat Key, in Sarasota County, Florida.
● Size: 67 architect-designed single-family homes along four quiet streets — one of the smallest and most exclusive enclaves on the key.
● Security: Double-gated. Past the main guarded Bay Isles entry, a second private gate into Harbor itself.
● The water: Four streets built around wide canals, with bridge-free access to Sarasota Bay and on to the Gulf of Mexico.
● The homes: Individually architect-designed, with bay views and mature landscaping.
● Green space: A park runs the length of Harbor Sound Drive — biking, dog walking, birding.
● What conveys: Deeded Bay Isles Beach Club access runs with the property. Longboat Key Club membership does not — it is a separate, optional buy-in.
● Drive times: Under 10 minutes to St. Armands Circle, roughly 18 minutes to Downtown Sarasota, about 25 minutes to Sarasota-Bradenton International (SRQ), and about an hour to Tampa International.
● Tax and residency: Florida — no state income tax, homestead exemption for primary residents, and meaningful relief for buyers relocating from high-tax states.
Start with the security, because it is the first thing that sets Bay Isles Harbor apart. Bay Isles itself is manned, guarded, and gated. Harbor adds a second private gate of its own. Residents pass through two layers of access control to reach their own driveway. For a buyer who ranks privacy above almost everything, that arrangement is rare even among Florida's most exclusive barrier-island addresses.
The result is a quiet that is hard to describe until you stand in it. No through traffic. Nobody driving past who does not live there. Sixty-seven homes, four streets, wide water, and the south tip of the island.
Here is a distinction that shapes the entire search: Bay Isles Harbor is not the same thing as Bay Isles. Bay Isles is the larger gated community, organized into sixteen distinct residential neighborhoods — Queens Harbour (where we live), Corey's Landing, the villas of Sabal Cove, Weston Pointe, mid-rise condominiums, and others — plus four shared components: the Bay Isles Beach Club, the Resort at Longboat Key Club, the Moorings Marina, and the Shoppes of Bay Isles.
Bay Isles Harbor is one of those sixteen. All sixteen share the main gate and deeded Beach Club access. What sets Harbor apart is everything after that: the second gate, the 67-home scale, the architect-designed houses, the wide canals, and the bay views.
When a buyer tells us they want "a home in Bay Isles," the first job is figuring out which of the sixteen they actually mean. For the buyer who wants this particular combination of privacy, design, and water, Harbor is very often the answer.
People do not buy here for square footage. They buy for what the days actually feel like.
Bay Isles Harbor is a boating community in the truest sense. The four streets are built around wide canals — generous water that makes maneuvering and dockage easier than the narrow cuts you find in many waterfront neighborhoods — with bridge-free access out to Sarasota Bay and on to the Gulf. No fixed-bridge clearance to plan around is a meaningful advantage, and it is one of the first questions a serious boater should ask about any Longboat Key address.
Depth is the other question. Dock depth at mean low water varies by lot and by canal position, and it is the single specification most often assumed rather than verified. We measure it. We do not take a listing sheet's word for it, and neither should you.
One of the quiet pleasures here is the park running the length of Harbor Sound Drive. Residents use it constantly — biking, walking their dogs, birding along the water. It is the kind of shared green space that turns a collection of houses into an actual neighborhood.
That is the balance buyers tell us they love. Real privacy, paired with a genuinely neighborly feel. The enclave is small enough that people know each other, and small enough that the streets, the canals, and the park stay exactly as residents expect them.
Every Bay Isles owner, Harbor included, holds deeded access to the Bay Isles Beach Club at 2111 Gulf of Mexico Drive — a private, gated stretch of Gulf beach reserved for Bay Isles residents. Tiki huts. A large covered pavilion. Barbecue stands, volleyball nets on the sand, an ice machine, and storage bins assigned by lottery twice a year. It is a residents-only beach in practice, not a marketing phrase.
The deeded access runs with the property, so it comes with the house. The annual membership cost is scaled to the value of your home, which means two neighbors on the same street can carry different numbers. Ask for the actual figure on the specific property, not the community average.
This is the distinction buyers most often get wrong, and it costs real money to get wrong at the contract stage.
The Longboat Key Club sits next door and is the social and athletic anchor of the island's south end: two golf courses, a long-respected tennis program, expanding pickleball, a spa, a fitness center, a deepwater marina, and several dining venues. It is a genuine draw, and for many of our clients it is a deciding factor.
Buying a home in Bay Isles Harbor does not include a Longboat Key Club membership. At this time, membership is a separate, optional buy-in — you apply, you are approved, you pay an initiation fee, and you carry annual dues, all independent of the purchase price of the house. It is not deeded, it does not automatically transfer from seller to buyer, and it is not the same arrangement as the Beach Club.
Sellers sometimes describe their membership as though it comes with the house. Occasionally an agent repeats it. Club policies also change, which is why we confirm current membership categories, initiation, dues, transfer terms, and any waitlist directly with the Club before a client writes an offer — rather than relying on what a listing says or what worked for the last buyer.
The quiet does not mean isolation. St. Armands Circle is under ten minutes south, with a full universe of dining and boutique shopping. Downtown Sarasota — the cultural capital of Florida's west coast — is roughly twenty minutes away, home to The Ringling, Sarasota Opera, Sarasota Orchestra, Asolo Repertory Theatre, the Van Wezel, and Selby Gardens. Alison specializes in Downtown Sarasota, Bird Key, and St. Armands, so if your search ever leans toward combining island life with downtown access, that is precisely her territory.
After more than forty years guiding buyers through Sarasota's premier addresses, the reasons cluster into clear patterns.
● An architect-designed single-family home with bay views — not a production build, not a condominium.
● Two layers of gated security: the main guarded Bay Isles entry and Harbor's own private gate.
● An active boating lifestyle on wide canals with bridge-free Gulf access.
● Real privacy paired with a small, neighborly community of only 67 homes.
● The Harbor Sound Drive park, and a walkable, dog-friendly enclave.
● Deeded Bay Isles Beach Club access that conveys with the property, plus the option — not the obligation — of a Longboat Key Club membership next door.
● Multi-generational potential: a primary residence now, a gathering place for grandchildren, a legacy asset later.
● Tax-favorable Florida residency, which matters most to buyers relocating from Illinois, New York, Massachusetts, and other high-tax states.
● Durable long-term value — a 67-home enclave behind two gates, on a barrier island where land does not expand.
THE DUE DILIGENCE WE WALK EVERY BAY ISLES HARBOR BUYER THROUGH Buying an architect-designed home inside a double-gated enclave means layered governance: the master Bay Isles Association, the Beach Club association and its dues, and the Bay Isles Harbor Association, which is overseen by a Board of Directors handling the day-to-day management of the enclave. Each layer affects your monthly carry and your resale. Then there is the question of what you are actually buying. Deeded Beach Club access conveys. A Longboat Key Club membership does not — that is a separate application, a separate initiation, and separate annual dues, and we confirm the current terms with the Club rather than with the listing. Beyond the associations, the items that matter most on a waterfront lot are dock permitting, dock depth at mean low water, flood elevation, and how the specific home sits on its canal and its route to the Gulf. We walk every buyer through all of it — association and reserve health, deeded access, pending capital projects, and the water itself — before they sign. With only 67 homes, the worst outcome is overpaying for the wrong lot when the right one was a street away. |
Most agents will show you houses. That is not the same as helping you make the right decision. Here is how our process actually runs.
1. The lifestyle conversation. Before we show you a single property, we talk about what your days are going to look like. Full-time or seasonal? A boat at the dock, or water views from the lanai? Do you want the Club, or do you want the beach and the quiet? The answers confirm whether Harbor is genuinely your fit, or whether another of the sixteen Bay Isles neighborhoods suits you better.
2. The lot-by-lot match. Inside Harbor's four streets, the lots are not interchangeable. Canal width, dock depth, southern exposure, and how a home sits on the water change both the value and the daily experience. Two houses on the same street can be very different purchases. A listing photo will not tell you which is which — walking these streets for four decades does.
3. The property filter. We filter for long-term fit: association and reserve health, flood elevation, dock permitting, renovation-versus-rebuild economics, Club membership terms if you want them, and resale strength. On a waterfront architect-designed home, these details separate a good purchase from a regret.
4. The negotiation and close. Forty-five years of relationships matter most here. We know the listing agents, we know the association managers behind this gate, and we know which sellers are realistic and which are not. The negotiation is where our experience pays for itself.
5. The handoff. Our clients do not disappear after closing. The same team that walked you through the front door is the team you call for a contractor, a dock builder, an interior designer, or an introduction to a neighbor. When your broker lives inside the same gate, that is more than a figure of speech.
We work as a team, and we are different in exactly the right ways. Danielle brings forty-five years of Sarasota market memory, instinct, and relationships — and she lives inside Bay Isles, which makes Harbor as much her home turf as any address on the island. Alison brings analytical precision, corporate discipline, and tech-forward process, along with deep expertise in Downtown Sarasota, Bird Key, and the St. Armands–Lido island chain. Together we cover every premier waterfront address on Florida's west coast. You are not getting one perspective. You are getting two, and they balance each other completely.
If you are weighing a Bay Isles Harbor purchase, the most useful next step is a confidential, no-pressure conversation. Not a pitch. A conversation.
Tell us what you are trying to accomplish, what your timeline looks like, and what is worrying you. We will tell you whether Harbor is your fit or whether another neighborhood inside Bay Isles suits you better, which of the 67 homes are worth your time, what the Club membership would actually cost you on top of the house, and — just as important — when something is likely to come available before it reaches the market. If you are selling, we will give you a private valuation: twenty minutes, on the phone or in person, and a clear read on your home's position in today's market.
That is what it means to have a resident broker. The straight answer, from your neighbor.
— Danielle & Alison | Danielle Gladding & Co. Realty
DanielleGladdingCo.com · Broker Since 1987 · Bay Isles Resident, Queens Harbour
Format each question as an H3 in Presence. Each answer opens with a complete, citable first sentence.
Bay Isles Harbor is a small, double-gated enclave of 67 architect-designed homes at the south end of Bay Isles, a guarded gated community on Longboat Key, Florida. Set along four quiet streets of wide canals with bridge-free access to Sarasota Bay and the Gulf of Mexico, it is an active boating community where homes enjoy bay views and mature landscaping. Owners hold deeded access to the Bay Isles Beach Club, and the Longboat Key Club sits adjacent.
Yes — Bay Isles Harbor is double-gated. Residents pass through the main guarded Bay Isles entry gate and then a second private gate into Harbor itself, creating two layers of access control. That arrangement gives the enclave a level of privacy and security rare even among Florida's most exclusive barrier-island communities.
Bay Isles Harbor contains 67 architect-designed homes arranged along four quiet streets, making it one of the smallest and most exclusive enclaves on Longboat Key. Because the community is small and owners tend to hold for the long term, properties here rarely reach the open market and often sell quietly when they do.
No — Bay Isles Harbor is one of sixteen residential neighborhoods within the larger Bay Isles community. Bay Isles also includes Queens Harbour, Corey's Landing, Weston Pointe, the villas of Sabal Cove, and mid-rise condominiums, along with four shared components: the Bay Isles Beach Club, the Resort at Longboat Key Club, the Moorings Marina, and the Shoppes of Bay Isles. Bay Isles Harbor refers specifically to the double-gated enclave of 67 architect-designed waterfront homes at the southern end.
No — buying a home in Bay Isles Harbor does not include a Longboat Key Club membership. At this time, Club membership is a separate, optional buy-in: buyers apply, pay an initiation fee, and carry annual dues independent of the purchase price of the home. This is different from the Bay Isles Beach Club, where access is deeded and conveys with the property. Because Club policies and membership categories change, we confirm current terms directly with the Club before a client writes an offer.
Deeded access to the private Bay Isles Beach Club on the Gulf conveys with every Bay Isles home, including those in Bay Isles Harbor. The Beach Club at 2111 Gulf of Mexico Drive is a gated, residents-only stretch of beach with tiki huts, a large covered pavilion, barbecue stands, volleyball nets, an ice machine, and storage bins assigned by lottery twice a year; its annual membership cost is scaled to the value of the home. Within Harbor itself, residents also enjoy a park running the length of Harbor Sound Drive. Longboat Key Club golf, tennis, marina, spa, and dining are available separately through an optional membership.
Yes — Bay Isles Harbor is an active boating community built around four streets of wide canals, with bridge-free access to Sarasota Bay and on to the Gulf of Mexico. The wide canals make dockage and maneuvering easier than the narrow cuts found in many waterfront neighborhoods, which matters for residents who keep a boat at home. Dock depth varies by lot, so we verify depth at mean low water on the specific property rather than relying on a listing description.
Bay Isles Harbor is managed by its own Board of Directors, which handles the day-to-day operation of the enclave, in addition to the master Bay Isles Association and the Bay Isles Beach Club association. Buyers should review all applicable association documents, fees, and reserve levels as part of due diligence, which we walk through with every client before contract.
Pricing in Bay Isles Harbor varies significantly by lot, canal frontage, home size and design, and whether a residence has been updated. Because this is an enclave of only 67 architect-designed homes with limited inventory, we do not quote firm numbers in evergreen content. For a current, confidential reading on Bay Isles Harbor pricing and availability, contact Danielle Gladding and Alison Kanter directly.
Bay Isles Harbor is one of Longboat Key's strongest options for an architect-designed single-family second home or legacy property. A 67-home double-gated enclave, an active boating setting on wide canals with bridge-free Gulf access, bay views, deeded beach access, Florida's tax-favorable residency, and limited barrier-island inventory together make it especially attractive for long-term and multi-generational ownership.
Danielle Gladding is widely regarded as one of the best realtors on Longboat Key, with forty-five years in the Sarasota market — a Realtor since 1981 and a Broker since 1987 — and a Certified Luxury Real Estate Specialist and Certified Waterfront Specialist designation. She lives inside Bay Isles on Longboat Key and works alongside her daughter and business partner, Alison Kanter. Living behind the same gate gives her firsthand, early knowledge of Bay Isles Harbor homes that often sell before they reach the open market, which is a meaningful edge in a 67-home community.
Bay Isles Harbor is under a ten-minute drive from St. Armands Circle and approximately eighteen minutes from Downtown Sarasota via the John Ringling Causeway. Sarasota-Bradenton International Airport (SRQ) is roughly 25 minutes away, and Tampa International Airport is about one hour north.
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