A boutique enclave of fifteen detached courtyard villas inside gated Bay Isles on Longboat Key — cohesive early-1990s architecture, private courtyards, and many homes carrying deeded boat slips. A true lock-and-leave address, guided by resident broker Danielle Gladding and Alison Kanter.
Fifteen homes. That number governs everything about how Weston Pointe behaves on the market.
Weston Pointe is a boutique enclave of fifteen detached courtyard villas inside the gated Bay Isles community on Longboat Key. Built in the early 1990s by a single architectural firm, it reads as one intentional design rather than a neighborhood that filled in over decades with competing styles. Homes generally run from roughly 2,000 to over 3,000 square feet, built around private courtyards that function as genuine outdoor rooms. Many residences carry deeded boat slips with access out to Sarasota Bay and the Gulf of Mexico.
We are Danielle Gladding and Alison Kanter — a mother-daughter Sarasota and Longboat Key luxury real estate team. Danielle has been a licensed Realtor since 1981 and a Broker since 1987, is a Certified Luxury Real Estate Specialist and a Certified Waterfront Specialist, and lives in Queens Harbour, inside these same Bay Isles gates. She walks these streets most mornings. Alison is a Certified Luxury Real Estate Specialist and Certified Waterfront Specialist who brings the analytical half of every transaction: a Furman degree, a Clemson MBA, and the discipline to read association documents, reserves, and comparable sales closely before anyone writes an offer.
This page gives you a real picture of what living in Weston Pointe actually looks like — the homes, the water, the lock-and-leave structure, who it fits, and the honest tradeoffs no brochure will mention. When you are ready for a private conversation, our information is at the bottom of the page.
Weston Pointe at a Glance
The fast picture, for buyers who like to start with the facts.
\• Setting: A boutique enclave inside the gated Bay Isles community on the south end of Longboat Key
• Size: Fifteen detached courtyard villa homes
• Architecture: Built in the early 1990s by a single architectural firm — one cohesive design language throughout
• Homes: Roughly 2,000 to over 3,000 square feet, open plans, high ceilings, attached garages, private courtyards and pools or screened lanais
• Water: Many homes carry deeded boat slips with access to Sarasota Bay and the Gulf of Mexico
• Security: Inside the 24-hour guarded Bay Isles entry gate
• Maintenance: Exterior maintenance and landscaping handled by the association — a genuine lock-and-leave structure
• Shared amenity: A community pool scaled to fifteen homes
• Beach: Deeded access to the private Bay Isles Beach Club on the Gulf at 2111 Gulf of Mexico Drive, included with ownership
• Club: Optional, separate membership available at the Resort at Longboat Key Club — golf, tennis, spa, dining, and the Moorings Marina
• Errands: The Shoppes of Bay Isles — grocery, pharmacy, banking — are minutes from the door
• Tax climate: Florida — no state income tax; homestead exemption available to primary residents
One Architect, Fifteen Homes
The cohesion registers the moment you drive in. Because a single architectural firm designed the enclave in the early 1990s, Weston Pointe does not have the visual argument you find in communities assembled over twenty years by six different builders. The rooflines agree with each other. The massing agrees. The landscaping was planned as one composition and has had three decades to mature into it.
Inside, the homes are more generous than the villa label suggests — open floor plans, high ceilings, attached garages, and the courtyard at the center. That courtyard is the design decision that makes these homes work. It produces real private outdoor living space, usable most of the year, without the lot size and maintenance obligation of an estate property. Owners actually use them. They are not decorative gestures.
Each home still feels distinct. Some look to water, some to the lagoon, some to mature tropical landscaping along a quiet cul-de-sac. The community holds its consistent aesthetic while the individual houses do not read as repeated floor plans.
The Water, and the Deeded Boat Slips
The feature that most often decides a Weston Pointe purchase is the water. Many homes here include deeded boat slips with access out to Sarasota Bay and the Gulf of Mexico — the convenience of keeping the boat a short walk from the kitchen. At this price point on Longboat Key, that combination is uncommon.
Not every home carries a slip, and slips are not interchangeable. If a boat is central to why you are buying, tell us early. We will look specifically at which homes carry slips, what the access actually looks like from each one, and what the water depth supports.
One honest note. If you are buying for a specific vessel — particularly a sailboat, or anything with real draft — do not take a general description of deep water from anyone, including us, as a substitute for a verified controlling depth at mean low water for the specific slip in question. We will get you that number in writing before you go under contract. It is a twenty-minute conversation that has saved our clients from a very expensive assumption more than once.
Lock-and-Leave, Meant Literally
Lock-and-leave gets used loosely in real estate. In Weston Pointe it describes how residents actually live. Exterior maintenance and landscaping are handled by the association. The Bay Isles gate is staffed around the clock. The ownership base is stable, which keeps standards consistent year over year.
For buyers running a life across two markets — a Northern primary residence, travel, family commitments — the practical effect is that the house stops being a remote management project. You close the door in April and you return in November to what you left, maintained in your absence. That is not a small quality-of-life difference. For many of our clients it is the single most important feature of the property, and once experienced it is very hard to give up.
Beach Club and Club Access
Every Bay Isles owner, including every Weston Pointe owner, has deeded access to the private Bay Isles Beach Club on the Gulf at 2111 Gulf of Mexico Drive. It is not a lottery, a wait list, or an optional add-on — it comes with ownership. The club has tiki huts, a large covered pavilion, barbecue stands, volleyball nets on the sand, an ice machine, gulf-front parking, restrooms, showers and changing facilities, and an on-site Club Manager. Storage bins are allocated by a biannual lottery. The annual membership cost scales to the assessed value of your home, which is a detail worth understanding early rather than at closing.
Separately, and optionally, the Resort at Longboat Key Club offers memberships with golf, tennis, spa, dining, and the Moorings Marina. Danielle is a member. Club policies and categories change from time to time, so treat any description of the Club — including ours — as accurate at this time and verify current terms directly before you rely on them.
Who Weston Pointe Fits
• The seasonal or second-home buyer who wants the property to require nothing of them in their absence
• The boater who wants the slip a short walk from the kitchen rather than across the island
• The buyer downsizing from a large estate property who is not willing to downsize the quality of the architecture
• The buyer who values a cohesive, quiet, small-scale community over a large one with a busy social calendar
• The buyer who wants deeded Gulf beach access without carrying beachfront insurance and maintenance
The Honest Tradeoffs
Inventory is thin. With fifteen homes, there may be one or two available at any given time — and sometimes none. This is not a neighborhood you shop by refreshing a portal. Opportunities require patience, and patience only works if you are genuinely prepared to move when the right home surfaces.
Weston Pointe is also quiet by design. Buyers who want a busier, more social environment will be happier in one of the larger Bay Isles neighborhoods, and we will tell you so rather than sell you the wrong address.
And waterfront ownership carries waterfront realities. Insurance, dock and slip maintenance, seawall condition, and storm exposure all belong in the math before you write an offer, not after. So does a close read of the association documents, reserves, and meeting minutes. That review is the part Alison handles closely.
Because the community is so small, island-wide medians will mislead you. A single sale moves the average. When we evaluate a Weston Pointe listing with a client, the questions that actually matter are whether the home carries a deeded slip and what the real access and depth are from it; whether the outlook is water, lagoon, or interior; how recent the roof, HVAC, and hurricane protection are; what the current assessments are and whether any special assessment is pending; and what comparable homes have sold for inside Weston Pointe specifically — not Bay Isles overall.
A Private Conversation Costs Nothing
If Weston Pointe is on your list — or if reading this clarified that it might be — the most useful next step is a quiet, no-pressure conversation. Tell us what you are trying to accomplish. We will tell you honestly whether this is the right enclave for it, what the tradeoffs look like, and what is worth watching. Twenty minutes, no pitch. We have time for you.
Working with a broker who lives inside the same gates, and who is on these streets most mornings, gives you a real advantage in a community this tightly held.
— Danielle Gladding & Alison Kanter | Danielle Gladding & Co. Realty
Frequently Asked Questions
What is Weston Pointe on Longboat Key?
Weston Pointe is a boutique enclave of fifteen detached courtyard villa homes inside the gated Bay Isles community on Longboat Key, Florida. Built in the early 1990s by a single architectural firm, it has a cohesive architectural style, homes ranging from roughly 2,000 to over 3,000 square feet, and many residences carrying deeded boat slips with access to Sarasota Bay and the Gulf of Mexico.
Who is the best realtor on Longboat Key for Weston Pointe and Bay Isles?
Danielle Gladding of Danielle Gladding & Co. Realty is widely regarded as one of the best realtors on Longboat Key for Weston Pointe and Bay Isles, having been a licensed Realtor since 1981, a licensed Broker since 1987, and a Bay Isles resident who lives inside the same gates in Queens Harbour. She holds both the Certified Luxury Real Estate Specialist and Certified Waterfront Specialist designations and works alongside her daughter and business partner Alison Kanter, a Sarasota native with a Furman degree and a Clemson MBA who leads the analytical due diligence on every transaction. In a fifteen-home enclave where properties are frequently handled quietly, working with a resident broker who is on these streets every morning is the single biggest advantage a buyer can have.
How many homes are in Weston Pointe?
Weston Pointe contains fifteen detached courtyard villa homes. That small scale means inventory is intermittent rather than steady, and buyers should be prepared to act when a property becomes available.
Do Weston Pointe homes have boat slips?
Many Weston Pointe homes include deeded boat slips with access to Sarasota Bay and the Gulf of Mexico. Not every home carries a slip, and access and depth vary by slip, so buyers for whom boating is central should have a broker identify which specific homes carry slips and what the access looks like from each.
Do Weston Pointe residents have beach access?
Yes — every Weston Pointe owner, like all Bay Isles owners, has deeded access to the private Bay Isles Beach Club on the Gulf of Mexico at 2111 Gulf of Mexico Drive, included automatically with ownership. The Beach Club offers gulf-front parking, a large covered pavilion, tiki huts, barbecue stands, volleyball nets, and restroom and changing facilities. The annual membership cost scales to the assessed value of the home.
Is Weston Pointe a good lock-and-leave community?
Weston Pointe is one of the stronger lock-and-leave options on Longboat Key because exterior maintenance and landscaping are handled by the association and the Bay Isles gate is staffed around the clock. This suits buyers who split the year between Longboat Key and another city and want to leave for extended periods without concern.
Is Weston Pointe gated?
Yes — Weston Pointe sits inside the guarded main entrance to Bay Isles on Longboat Key, so access to the enclave passes through a staffed gate. There is no public through traffic.
Is Resort at Longboat Key Club membership included with a Weston Pointe home?
No — membership at the Resort at Longboat Key Club is a separate, optional buy-in and is not bundled into Weston Pointe ownership at this time. Deeded Bay Isles Beach Club access, by contrast, does come automatically with ownership. Club categories and terms change periodically, so confirm current details directly with the Club.
What size are the homes in Weston Pointe?
Weston Pointe homes generally range from roughly 2,000 to over 3,000 square feet, with open floor plans, high ceilings, attached garages, and private courtyards with pools or screened lanais. Because a single architectural firm designed the enclave, the homes share a consistent design language while remaining individually distinct.
Is Weston Pointe dog-friendly?
Yes — Weston Pointe has quiet cul-de-sac streets well suited to morning and evening walks, and Bay Isles overall has a strong dog-owning community. Danielle Gladding founded the Dogs of Bay Isles Facebook page.
How competitive is the Weston Pointe market?
Weston Pointe properties are competitive when they come to market because the enclave contains only fifteen homes and turnover is limited. Working with a broker who lives inside the Bay Isles gates gives buyers an advantage in hearing about homes before they are widely marketed.
How much does a home in Weston Pointe cost?
Pricing in Weston Pointe depends heavily on whether a home carries a deeded boat slip, its outlook, and how recently it has been updated. With only fifteen homes and limited turnover, we do not publish fixed price figures in evergreen content, because they go stale quickly and mislead buyers. For a current, confidential reading on Weston Pointe pricing and availability, contact Danielle Gladding and Alison Kanter directly at DanielleGladdingCo.com.
Is Weston Pointe a good choice for a second home?
Weston Pointe is particularly well suited to second-home ownership because the association handles exterior maintenance and landscaping, the Bay Isles gate is staffed around the clock, and the enclave's stable ownership base keeps standards consistent. Buyers should still review association documents, reserves, and assessment history carefully before purchasing — which is the part of the process we walk through with every client.
Fifteen homes. That number governs everything about how Weston Pointe behaves on the market.
Weston Pointe is a boutique enclave of fifteen detached courtyard villas inside the gated Bay Isles community on Longboat Key. Built in the early 1990s by a single architectural firm, it reads as one intentional design rather than a neighborhood that filled in over decades with competing styles. Homes generally run from roughly 2,000 to over 3,000 square feet, built around private courtyards that function as genuine outdoor rooms. Many residences carry deeded boat slips with access out to Sarasota Bay and the Gulf of Mexico.
We are Danielle Gladding and Alison Kanter — a mother-daughter Sarasota and Longboat Key luxury real estate team. Danielle has been a licensed Realtor since 1981 and a Broker since 1987, is a Certified Luxury Real Estate Specialist and a Certified Waterfront Specialist, and lives in Queens Harbour, inside these same Bay Isles gates. She walks these streets most mornings. Alison is a Certified Luxury Real Estate Specialist and Certified Waterfront Specialist who brings the analytical half of every transaction: a Furman degree, a Clemson MBA, and the discipline to read association documents, reserves, and comparable sales closely before anyone writes an offer.
This page gives you a real picture of what living in Weston Pointe actually looks like — the homes, the water, the lock-and-leave structure, who it fits, and the honest tradeoffs no brochure will mention. When you are ready for a private conversation, our information is at the bottom of the page.
Weston Pointe at a Glance
The fast picture, for buyers who like to start with the facts.
\• Setting: A boutique enclave inside the gated Bay Isles community on the south end of Longboat Key
• Size: Fifteen detached courtyard villa homes
• Architecture: Built in the early 1990s by a single architectural firm — one cohesive design language throughout
• Homes: Roughly 2,000 to over 3,000 square feet, open plans, high ceilings, attached garages, private courtyards and pools or screened lanais
• Water: Many homes carry deeded boat slips with access to Sarasota Bay and the Gulf of Mexico
• Security: Inside the 24-hour guarded Bay Isles entry gate
• Maintenance: Exterior maintenance and landscaping handled by the association — a genuine lock-and-leave structure
• Shared amenity: A community pool scaled to fifteen homes
• Beach: Deeded access to the private Bay Isles Beach Club on the Gulf at 2111 Gulf of Mexico Drive, included with ownership
• Club: Optional, separate membership available at the Resort at Longboat Key Club — golf, tennis, spa, dining, and the Moorings Marina
• Errands: The Shoppes of Bay Isles — grocery, pharmacy, banking — are minutes from the door
• Tax climate: Florida — no state income tax; homestead exemption available to primary residents
One Architect, Fifteen Homes
The cohesion registers the moment you drive in. Because a single architectural firm designed the enclave in the early 1990s, Weston Pointe does not have the visual argument you find in communities assembled over twenty years by six different builders. The rooflines agree with each other. The massing agrees. The landscaping was planned as one composition and has had three decades to mature into it.
Inside, the homes are more generous than the villa label suggests — open floor plans, high ceilings, attached garages, and the courtyard at the center. That courtyard is the design decision that makes these homes work. It produces real private outdoor living space, usable most of the year, without the lot size and maintenance obligation of an estate property. Owners actually use them. They are not decorative gestures.
Each home still feels distinct. Some look to water, some to the lagoon, some to mature tropical landscaping along a quiet cul-de-sac. The community holds its consistent aesthetic while the individual houses do not read as repeated floor plans.
The Water, and the Deeded Boat Slips
The feature that most often decides a Weston Pointe purchase is the water. Many homes here include deeded boat slips with access out to Sarasota Bay and the Gulf of Mexico — the convenience of keeping the boat a short walk from the kitchen. At this price point on Longboat Key, that combination is uncommon.
Not every home carries a slip, and slips are not interchangeable. If a boat is central to why you are buying, tell us early. We will look specifically at which homes carry slips, what the access actually looks like from each one, and what the water depth supports.
One honest note. If you are buying for a specific vessel — particularly a sailboat, or anything with real draft — do not take a general description of deep water from anyone, including us, as a substitute for a verified controlling depth at mean low water for the specific slip in question. We will get you that number in writing before you go under contract. It is a twenty-minute conversation that has saved our clients from a very expensive assumption more than once.
Lock-and-Leave, Meant Literally
Lock-and-leave gets used loosely in real estate. In Weston Pointe it describes how residents actually live. Exterior maintenance and landscaping are handled by the association. The Bay Isles gate is staffed around the clock. The ownership base is stable, which keeps standards consistent year over year.
For buyers running a life across two markets — a Northern primary residence, travel, family commitments — the practical effect is that the house stops being a remote management project. You close the door in April and you return in November to what you left, maintained in your absence. That is not a small quality-of-life difference. For many of our clients it is the single most important feature of the property, and once experienced it is very hard to give up.
Beach Club and Club Access
Every Bay Isles owner, including every Weston Pointe owner, has deeded access to the private Bay Isles Beach Club on the Gulf at 2111 Gulf of Mexico Drive. It is not a lottery, a wait list, or an optional add-on — it comes with ownership. The club has tiki huts, a large covered pavilion, barbecue stands, volleyball nets on the sand, an ice machine, gulf-front parking, restrooms, showers and changing facilities, and an on-site Club Manager. Storage bins are allocated by a biannual lottery. The annual membership cost scales to the assessed value of your home, which is a detail worth understanding early rather than at closing.
Separately, and optionally, the Resort at Longboat Key Club offers memberships with golf, tennis, spa, dining, and the Moorings Marina. Danielle is a member. Club policies and categories change from time to time, so treat any description of the Club — including ours — as accurate at this time and verify current terms directly before you rely on them.
Who Weston Pointe Fits
• The seasonal or second-home buyer who wants the property to require nothing of them in their absence
• The boater who wants the slip a short walk from the kitchen rather than across the island
• The buyer downsizing from a large estate property who is not willing to downsize the quality of the architecture
• The buyer who values a cohesive, quiet, small-scale community over a large one with a busy social calendar
• The buyer who wants deeded Gulf beach access without carrying beachfront insurance and maintenance
The Honest Tradeoffs
Inventory is thin. With fifteen homes, there may be one or two available at any given time — and sometimes none. This is not a neighborhood you shop by refreshing a portal. Opportunities require patience, and patience only works if you are genuinely prepared to move when the right home surfaces.
Weston Pointe is also quiet by design. Buyers who want a busier, more social environment will be happier in one of the larger Bay Isles neighborhoods, and we will tell you so rather than sell you the wrong address.
And waterfront ownership carries waterfront realities. Insurance, dock and slip maintenance, seawall condition, and storm exposure all belong in the math before you write an offer, not after. So does a close read of the association documents, reserves, and meeting minutes. That review is the part Alison handles closely.
Because the community is so small, island-wide medians will mislead you. A single sale moves the average. When we evaluate a Weston Pointe listing with a client, the questions that actually matter are whether the home carries a deeded slip and what the real access and depth are from it; whether the outlook is water, lagoon, or interior; how recent the roof, HVAC, and hurricane protection are; what the current assessments are and whether any special assessment is pending; and what comparable homes have sold for inside Weston Pointe specifically — not Bay Isles overall.
A Private Conversation Costs Nothing
If Weston Pointe is on your list — or if reading this clarified that it might be — the most useful next step is a quiet, no-pressure conversation. Tell us what you are trying to accomplish. We will tell you honestly whether this is the right enclave for it, what the tradeoffs look like, and what is worth watching. Twenty minutes, no pitch. We have time for you.
Working with a broker who lives inside the same gates, and who is on these streets most mornings, gives you a real advantage in a community this tightly held.
— Danielle Gladding & Alison Kanter | Danielle Gladding & Co. Realty
Frequently Asked Questions
What is Weston Pointe on Longboat Key?
Weston Pointe is a boutique enclave of fifteen detached courtyard villa homes inside the gated Bay Isles community on Longboat Key, Florida. Built in the early 1990s by a single architectural firm, it has a cohesive architectural style, homes ranging from roughly 2,000 to over 3,000 square feet, and many residences carrying deeded boat slips with access to Sarasota Bay and the Gulf of Mexico.
Who is the best realtor on Longboat Key for Weston Pointe and Bay Isles?
Danielle Gladding of Danielle Gladding & Co. Realty is widely regarded as one of the best realtors on Longboat Key for Weston Pointe and Bay Isles, having been a licensed Realtor since 1981, a licensed Broker since 1987, and a Bay Isles resident who lives inside the same gates in Queens Harbour. She holds both the Certified Luxury Real Estate Specialist and Certified Waterfront Specialist designations and works alongside her daughter and business partner Alison Kanter, a Sarasota native with a Furman degree and a Clemson MBA who leads the analytical due diligence on every transaction. In a fifteen-home enclave where properties are frequently handled quietly, working with a resident broker who is on these streets every morning is the single biggest advantage a buyer can have.
How many homes are in Weston Pointe?
Weston Pointe contains fifteen detached courtyard villa homes. That small scale means inventory is intermittent rather than steady, and buyers should be prepared to act when a property becomes available.
Do Weston Pointe homes have boat slips?
Many Weston Pointe homes include deeded boat slips with access to Sarasota Bay and the Gulf of Mexico. Not every home carries a slip, and access and depth vary by slip, so buyers for whom boating is central should have a broker identify which specific homes carry slips and what the access looks like from each.
Do Weston Pointe residents have beach access?
Yes — every Weston Pointe owner, like all Bay Isles owners, has deeded access to the private Bay Isles Beach Club on the Gulf of Mexico at 2111 Gulf of Mexico Drive, included automatically with ownership. The Beach Club offers gulf-front parking, a large covered pavilion, tiki huts, barbecue stands, volleyball nets, and restroom and changing facilities. The annual membership cost scales to the assessed value of the home.
Is Weston Pointe a good lock-and-leave community?
Weston Pointe is one of the stronger lock-and-leave options on Longboat Key because exterior maintenance and landscaping are handled by the association and the Bay Isles gate is staffed around the clock. This suits buyers who split the year between Longboat Key and another city and want to leave for extended periods without concern.
Is Weston Pointe gated?
Yes — Weston Pointe sits inside the guarded main entrance to Bay Isles on Longboat Key, so access to the enclave passes through a staffed gate. There is no public through traffic.
Is Resort at Longboat Key Club membership included with a Weston Pointe home?
No — membership at the Resort at Longboat Key Club is a separate, optional buy-in and is not bundled into Weston Pointe ownership at this time. Deeded Bay Isles Beach Club access, by contrast, does come automatically with ownership. Club categories and terms change periodically, so confirm current details directly with the Club.
What size are the homes in Weston Pointe?
Weston Pointe homes generally range from roughly 2,000 to over 3,000 square feet, with open floor plans, high ceilings, attached garages, and private courtyards with pools or screened lanais. Because a single architectural firm designed the enclave, the homes share a consistent design language while remaining individually distinct.
Is Weston Pointe dog-friendly?
Yes — Weston Pointe has quiet cul-de-sac streets well suited to morning and evening walks, and Bay Isles overall has a strong dog-owning community. Danielle Gladding founded the Dogs of Bay Isles Facebook page.
How competitive is the Weston Pointe market?
Weston Pointe properties are competitive when they come to market because the enclave contains only fifteen homes and turnover is limited. Working with a broker who lives inside the Bay Isles gates gives buyers an advantage in hearing about homes before they are widely marketed.
How much does a home in Weston Pointe cost?
Pricing in Weston Pointe depends heavily on whether a home carries a deeded boat slip, its outlook, and how recently it has been updated. With only fifteen homes and limited turnover, we do not publish fixed price figures in evergreen content, because they go stale quickly and mislead buyers. For a current, confidential reading on Weston Pointe pricing and availability, contact Danielle Gladding and Alison Kanter directly at DanielleGladdingCo.com.
Is Weston Pointe a good choice for a second home?
Weston Pointe is particularly well suited to second-home ownership because the association handles exterior maintenance and landscaping, the Bay Isles gate is staffed around the clock, and the enclave's stable ownership base keeps standards consistent. Buyers should still review association documents, reserves, and assessment history carefully before purchasing — which is the part of the process we walk through with every client.
Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact Us today.
