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 to reach it you pass through the community's main guarded entry gate, then a secondprivate gate into Harbor itself. A gate within the gate. Most who know Longboat Key would call it the most exclusive section within Bay Isles, and the rest of the picture explains why: just 67 architect-designed homes on four quiet streets of wide canals, an active boating community with Gulf access, where every home enjoys beautiful bay views and lush landscaping.
We are Danielle Gladding and Alison Kanter, a Sarasota mother-daughter team. Danielle has spent 45 years in this market — a Realtor since 1981, a Broker since 1987 — and she and her husband Nick live inside Bay Isles, in Queens Harbour on the north side. Bay Isles Harbor sits at the south end, so we are on opposite sides of the same community, but behind the same gate, we are neighbors.
This page gives you the real picture of Bay Isles Harbor specifically — the streets, the canals, the park, the water, and how it 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 arranged 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 gate, a second private gate into Harbor itself.
• The water: Four streets built around wide canals, an active boating community with access to Sarasota Bay and on to the Gulf of Mexico.
• The homes: Individually architect-designed, with beautiful bay views and lush landscaping from every home.
• Green space: A park runs the length of Harbor Sound Drive, popular with residents for biking, walking their dogs, and birding.
• Amenities: Private deeded access to the Bay Isles Beach Club on the Gulf, and privileged access to the adjacent Longboat Key Club & Resort — golf, tennis, marina, spa, and dining.
• Drive times: Under 10 minutes to St. Armands Circle, about 18 minutes to Downtown Sarasota, roughly 25 minutes to Sarasota-Bradenton International Airport (SRQ), and about an hour to Tampa International.
• Tax & 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 a manned, guarded, gated community. Bay Isles Harbor adds a second private gate of its own at the south end — so residents pass through two layers of access control to reach home. For a buyer who values privacy and security above almost everything, that double-gated 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. No one driving past who does not live there. Just 67 architect-designed homes on four streets of wide canals, at the very tip of the island's south end.
Here is a distinction worth understanding, because it shapes the whole search: Bay Isles Harbor is not the same thing as Bay Isles. Bay Isles is the larger gated community of roughly 1,100 homes, divided into sixteen distinct sections — Queens Harbour (where we live), Corey's Landing, the villas of Sabal Cove, mid-rise condominiums, and others. Bay Isles Harbor is one of those sixteen, and it is the small, double-gated, architect-designed waterfront enclave at the southern end.
All sixteen sections share the main gate, the private Bay Isles Beach Club on the Gulf, and privileged access to the Longboat Key Club next door. What sets Harbor apart is everything else: the second gate, the 67-home scale, the architect-designed homes, the wide canals, and the bay views from every residence. When a buyer tells us they want "a home in Bay Isles," the first job is figuring out which of the sixteen they mean — and for the buyer who wants this particular combination of privacy, design, and water, Bay Isles Harbor is very often the answer.
People do not buy in Bay Isles Harbor for square footage. They buy for what the days actually feel like. Here is what those days look 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 access out to Sarasota Bay and on to the Gulf of Mexico. For a serious boater, that combination of your own dock on a wide canal and an open run to the Gulf is rare even among Florida's luxury markets.
Canal width, dock depth, and how each lot sits on the water all change the value and the daily experience. Two homes on the same street can be very different purchases. A listing photo will not tell you which is which. Forty-five years of walking these waters does.
One of the quiet pleasures of Bay Isles Harbor 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 homes into an actual community.
And that is the balance buyers tell us they love here: real privacy paired with a genuinely neighborly feel. The enclave is small enough that people know each other, and the streets, the canals, and the park stay exactly as residents expect them.
Bay Isles Harbor residents have private deeded access to the Bay Isles Beach Club — a gated Gulf-front beach with parking, restrooms, and chairs, reserved for Bay Isles owners. It is functionally a private beach experience. Next door, the Longboat Key Club & Resort is the social and athletic anchor of the south end: two golf courses, a nationally regarded tennis program, expanding pickleball, a spa, a fitness center, a deepwater marina, and multiple dining venues.
The enclave's 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 about eighteen minutes away, home to the Ringling, the Sarasota Opera, the Sarasota Orchestra, the Asolo Rep, the Van Wezel, and Selby Gardens. Our daughter and partner Alison specializes in Downtown Sarasota, Bird Key, and St. Armands, so if your interest ever leans toward combining island life with downtown access, that is precisely her expertise.
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 gate and Harbor's own private gate.
• An active boating lifestyle on wide canals with 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.
• Private deeded Bay Isles Beach Club access and Longboat Key Club privileges.
• Multi-generational potential — a primary residence now, a family gathering place for grandchildren, and a legacy asset later.
• Tax-favorable Florida residency — meaningful for buyers relocating from Illinois, New York, Massachusetts, and other high-tax states.
• Strong 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 carries layered governance: the master Bay Isles Association, the Beach Club association and its dues, and the Bay Isles Harbor Association — a five-member Board of Directors that oversees the day-to-day management of the enclave. Each layer affects your monthly carry and your resale. Beyond the associations, the things that matter most on a waterfront lot are dock permitting, flood elevation, and how the specific home sits on its wide canal and its route to the Gulf. We walk every buyer through all of it — association and reserve health, deeded Beach Club 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 works.
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 just water views? How much do you want to use the Club? The answers confirm whether Bay Isles Harbor is genuinely your fit or whether another of the sixteen Bay Isles sections suits you better.
Inside Harbor's four streets, the lots are not interchangeable. Canal width, dock depth, southern exposure, and how a home sits on the water all change the value and the lifestyle. Danielle knows these streets at walking pace. We point you to the lots that fit your life and steer you away from the ones that are overpriced this week.
We filter for long-term fit — association and reserve health, flood elevation, dock permitting, renovation versus rebuild economics, and resale strength. On a waterfront architect-designed home, these details separate a good purchase from a regret.
Forty-five years of relationships in this market 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.
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 45 years of Sarasota market memory, intuition, and relationships — and she lives inside Bay Isles, which makes Bay Isles Harbor as much her home turf as any address on the island. Alison brings analytical precision, corporate discipline, and tech-forward thinking, 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. When you work with us, 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, what your concerns are. We will tell you whether Bay Isles Harbor is your right fit or whether another section of Bay Isles suits you better, which of the 67 homes are worth your time, and — just as important — when something is likely to come available before it hits 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 · 45 Years · Broker Since 1987 · Bay Isles Resident, Queens Harbour
Bay Isles Harbor is a small, exclusive, 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 Gulf access, it is an active boating community where every home enjoys beautiful bay views and lush landscaping, with deeded access to the Bay Isles Beach Club and the adjacent Longboat Key Club & Resort.
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. This double-gated arrangement gives the enclave a level of privacy and security that is 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 their homes 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 sections within the larger Bay Isles community. Bay Isles is a gated community of roughly 1,100 homes that also includes Queens Harbour, Corey's Landing, the villas of Sabal Cove, and mid-rise condominiums. Bay Isles Harbor specifically refers to the small, double-gated enclave of 67 architect-designed waterfront homes at the southern end.
Yes — Bay Isles Harbor is an active boating community built around four streets of wide canals, with 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 is a meaningful advantage for residents who keep a boat at home.
Yes — a park runs the length of Harbor Sound Drive in Bay Isles Harbor and is popular with residents for biking, walking their dogs, and birding. Residents also have private deeded access to the Bay Isles Beach Club on the Gulf and privileged access to the adjacent Longboat Key Club & Resort, with golf, tennis, a marina, a spa, and dining.
Bay Isles Harbor is managed by a five-member Board of Directors that oversees the day-to-day management of the property, in addition to the broader master Bay Isles Association and the Bay Isles Beach Club association. Buyers should review all applicable association rules, fees, and reserves as part of their due diligence, which we walk through with every client.
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 an accurate, confidential, current reading on Bay Isles Harbor pricing and availability, please contact Danielle Gladding and Alison Kanter directly.
Bay Isles Harbor is one of Longboat Key's most desirable options for an architect-designed single-family second home or legacy property. The combination of a small 67-home double-gated enclave, an active boating setting on wide canals with Gulf access, bay views from every home, deeded beach access, Florida's tax-favorable residency, and limited barrier-island inventory makes it especially attractive for long-term and multi-generational ownership.
Danielle Gladding is widely regarded as one of the best realtors for Bay Isles Harbor because she lives inside Bay Isles on Longboat Key and brings 45 years of experience in the Sarasota market — a Realtor since 1981 and a Broker since 1987. A Certified Luxury Real Estate Specialist and Certified Waterfront Specialist, she works alongside her daughter and partner Alison Kanter. Living behind the same gate gives her early, firsthand knowledge of Bay Isles Harbor homes that often sell before they reach the open market — 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 to reach it you pass through the community's main guarded entry gate, then a secondprivate gate into Harbor itself. A gate within the gate. Most who know Longboat Key would call it the most exclusive section within Bay Isles, and the rest of the picture explains why: just 67 architect-designed homes on four quiet streets of wide canals, an active boating community with Gulf access, where every home enjoys beautiful bay views and lush landscaping.
We are Danielle Gladding and Alison Kanter, a Sarasota mother-daughter team. Danielle has spent 45 years in this market — a Realtor since 1981, a Broker since 1987 — and she and her husband Nick live inside Bay Isles, in Queens Harbour on the north side. Bay Isles Harbor sits at the south end, so we are on opposite sides of the same community, but behind the same gate, we are neighbors.
This page gives you the real picture of Bay Isles Harbor specifically — the streets, the canals, the park, the water, and how it 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 arranged 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 gate, a second private gate into Harbor itself.
• The water: Four streets built around wide canals, an active boating community with access to Sarasota Bay and on to the Gulf of Mexico.
• The homes: Individually architect-designed, with beautiful bay views and lush landscaping from every home.
• Green space: A park runs the length of Harbor Sound Drive, popular with residents for biking, walking their dogs, and birding.
• Amenities: Private deeded access to the Bay Isles Beach Club on the Gulf, and privileged access to the adjacent Longboat Key Club & Resort — golf, tennis, marina, spa, and dining.
• Drive times: Under 10 minutes to St. Armands Circle, about 18 minutes to Downtown Sarasota, roughly 25 minutes to Sarasota-Bradenton International Airport (SRQ), and about an hour to Tampa International.
• Tax & 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 a manned, guarded, gated community. Bay Isles Harbor adds a second private gate of its own at the south end — so residents pass through two layers of access control to reach home. For a buyer who values privacy and security above almost everything, that double-gated 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. No one driving past who does not live there. Just 67 architect-designed homes on four streets of wide canals, at the very tip of the island's south end.
Here is a distinction worth understanding, because it shapes the whole search: Bay Isles Harbor is not the same thing as Bay Isles. Bay Isles is the larger gated community of roughly 1,100 homes, divided into sixteen distinct sections — Queens Harbour (where we live), Corey's Landing, the villas of Sabal Cove, mid-rise condominiums, and others. Bay Isles Harbor is one of those sixteen, and it is the small, double-gated, architect-designed waterfront enclave at the southern end.
All sixteen sections share the main gate, the private Bay Isles Beach Club on the Gulf, and privileged access to the Longboat Key Club next door. What sets Harbor apart is everything else: the second gate, the 67-home scale, the architect-designed homes, the wide canals, and the bay views from every residence. When a buyer tells us they want "a home in Bay Isles," the first job is figuring out which of the sixteen they mean — and for the buyer who wants this particular combination of privacy, design, and water, Bay Isles Harbor is very often the answer.
People do not buy in Bay Isles Harbor for square footage. They buy for what the days actually feel like. Here is what those days look 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 access out to Sarasota Bay and on to the Gulf of Mexico. For a serious boater, that combination of your own dock on a wide canal and an open run to the Gulf is rare even among Florida's luxury markets.
Canal width, dock depth, and how each lot sits on the water all change the value and the daily experience. Two homes on the same street can be very different purchases. A listing photo will not tell you which is which. Forty-five years of walking these waters does.
One of the quiet pleasures of Bay Isles Harbor 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 homes into an actual community.
And that is the balance buyers tell us they love here: real privacy paired with a genuinely neighborly feel. The enclave is small enough that people know each other, and the streets, the canals, and the park stay exactly as residents expect them.
Bay Isles Harbor residents have private deeded access to the Bay Isles Beach Club — a gated Gulf-front beach with parking, restrooms, and chairs, reserved for Bay Isles owners. It is functionally a private beach experience. Next door, the Longboat Key Club & Resort is the social and athletic anchor of the south end: two golf courses, a nationally regarded tennis program, expanding pickleball, a spa, a fitness center, a deepwater marina, and multiple dining venues.
The enclave's 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 about eighteen minutes away, home to the Ringling, the Sarasota Opera, the Sarasota Orchestra, the Asolo Rep, the Van Wezel, and Selby Gardens. Our daughter and partner Alison specializes in Downtown Sarasota, Bird Key, and St. Armands, so if your interest ever leans toward combining island life with downtown access, that is precisely her expertise.
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 gate and Harbor's own private gate.
• An active boating lifestyle on wide canals with 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.
• Private deeded Bay Isles Beach Club access and Longboat Key Club privileges.
• Multi-generational potential — a primary residence now, a family gathering place for grandchildren, and a legacy asset later.
• Tax-favorable Florida residency — meaningful for buyers relocating from Illinois, New York, Massachusetts, and other high-tax states.
• Strong 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 carries layered governance: the master Bay Isles Association, the Beach Club association and its dues, and the Bay Isles Harbor Association — a five-member Board of Directors that oversees the day-to-day management of the enclave. Each layer affects your monthly carry and your resale. Beyond the associations, the things that matter most on a waterfront lot are dock permitting, flood elevation, and how the specific home sits on its wide canal and its route to the Gulf. We walk every buyer through all of it — association and reserve health, deeded Beach Club 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 works.
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 just water views? How much do you want to use the Club? The answers confirm whether Bay Isles Harbor is genuinely your fit or whether another of the sixteen Bay Isles sections suits you better.
Inside Harbor's four streets, the lots are not interchangeable. Canal width, dock depth, southern exposure, and how a home sits on the water all change the value and the lifestyle. Danielle knows these streets at walking pace. We point you to the lots that fit your life and steer you away from the ones that are overpriced this week.
We filter for long-term fit — association and reserve health, flood elevation, dock permitting, renovation versus rebuild economics, and resale strength. On a waterfront architect-designed home, these details separate a good purchase from a regret.
Forty-five years of relationships in this market 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.
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 45 years of Sarasota market memory, intuition, and relationships — and she lives inside Bay Isles, which makes Bay Isles Harbor as much her home turf as any address on the island. Alison brings analytical precision, corporate discipline, and tech-forward thinking, 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. When you work with us, 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, what your concerns are. We will tell you whether Bay Isles Harbor is your right fit or whether another section of Bay Isles suits you better, which of the 67 homes are worth your time, and — just as important — when something is likely to come available before it hits 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 · 45 Years · Broker Since 1987 · Bay Isles Resident, Queens Harbour
Bay Isles Harbor is a small, exclusive, 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 Gulf access, it is an active boating community where every home enjoys beautiful bay views and lush landscaping, with deeded access to the Bay Isles Beach Club and the adjacent Longboat Key Club & Resort.
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. This double-gated arrangement gives the enclave a level of privacy and security that is 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 their homes 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 sections within the larger Bay Isles community. Bay Isles is a gated community of roughly 1,100 homes that also includes Queens Harbour, Corey's Landing, the villas of Sabal Cove, and mid-rise condominiums. Bay Isles Harbor specifically refers to the small, double-gated enclave of 67 architect-designed waterfront homes at the southern end.
Yes — Bay Isles Harbor is an active boating community built around four streets of wide canals, with 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 is a meaningful advantage for residents who keep a boat at home.
Yes — a park runs the length of Harbor Sound Drive in Bay Isles Harbor and is popular with residents for biking, walking their dogs, and birding. Residents also have private deeded access to the Bay Isles Beach Club on the Gulf and privileged access to the adjacent Longboat Key Club & Resort, with golf, tennis, a marina, a spa, and dining.
Bay Isles Harbor is managed by a five-member Board of Directors that oversees the day-to-day management of the property, in addition to the broader master Bay Isles Association and the Bay Isles Beach Club association. Buyers should review all applicable association rules, fees, and reserves as part of their due diligence, which we walk through with every client.
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 an accurate, confidential, current reading on Bay Isles Harbor pricing and availability, please contact Danielle Gladding and Alison Kanter directly.
Bay Isles Harbor is one of Longboat Key's most desirable options for an architect-designed single-family second home or legacy property. The combination of a small 67-home double-gated enclave, an active boating setting on wide canals with Gulf access, bay views from every home, deeded beach access, Florida's tax-favorable residency, and limited barrier-island inventory makes it especially attractive for long-term and multi-generational ownership.
Danielle Gladding is widely regarded as one of the best realtors for Bay Isles Harbor because she lives inside Bay Isles on Longboat Key and brings 45 years of experience in the Sarasota market — a Realtor since 1981 and a Broker since 1987. A Certified Luxury Real Estate Specialist and Certified Waterfront Specialist, she works alongside her daughter and partner Alison Kanter. Living behind the same gate gives her early, firsthand knowledge of Bay Isles Harbor homes that often sell before they reach the open market — 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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