Longboat Key Club Condos Behind the Gates
Longboat Key Danielle Gladding & Alison Kanter September 9, 2026
Longboat Key Danielle Gladding & Alison Kanter September 9, 2026
There are two guarded gates on the south end of Longboat Key, and a buyer searching for condominiums behind the gates of the Longboat Key Club is almost always thinking of only one of them. The Bay Isles gate on Gulf Bay Road opens into sixteen residential neighborhoods, most of them on the bay side. The Longboat Club Road gate opens into a separate group of condominium communities strung along the Gulf. Different addresses, different associations, different amenities conveyed with the deed, and a different buying decision. Search results blur the two constantly, which is why the same question keeps arriving in the same confused shape.
Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987, and lives in Queens Harbour inside Bay Isles — behind the other gate, a short drive up the road. She is a social member of the Longboat Key Club, which is disclosed here because this guide concerns the club and its condominium communities. She does not golf and does not play tennis.
The short version, before the detail: the Longboat Club Road gate protects a row of Gulf-front and near-Gulf condominium buildings that span the mid-1960s through the mid-1990s. Buying one of them does not make you a member of the Longboat Key Club. Membership is a separate purchase with its own buy-in and its own dues, and plenty of owners inside the gate never join. That single fact resolves more confusion than anything else on this page.
The Bay Isles gate governs a master association covering sixteen neighborhoods of single-family homes, villas, and condominiums, and it carries a deeded amenity that surprises people: the Bay Isles Beach Club on the Gulf conveys with every home inside those gates. That is a property right attached to the deed, not a membership anyone chooses.
The Longboat Club Road gate is a different arrangement entirely, and it is two structures rather than one: the guarded entry at the southern end of the island, and a north gate restricted to residents. The club calls this side Islandside, and that name turns up in listing copy and showing directions about as often as the road name does. Behind the gates sit individual condominium associations, each with its own board, budget, reserve position, rental rules, and beachfront. There is no master beach club conveying across all of them, because most of these buildings sit directly on the sand already. Their common ground is the guarded entry, the golf course they look out over, and the address.
What causes the confusion is that both gates are described in listing copy as the Longboat Key Club. The club's golf, tennis, marina, and dining operations serve both sides, and its land is threaded between them. So a building on Longboat Club Road and a villa in Longboat Key's Bay Isles cluster can both be marketed with the same six words while sitting behind different gates under different documents. Read the address first. Everything else follows from it.
Eight residential condominium associations sit behind the Longboat Club Road gate, along with the Longboat Key Club's own condo-hotel, which is deeded ownership of a different kind and is set out here alongside them. All nine are listed oldest first, because construction vintage turns out to be the most useful way to sort them. Published directories of this gate disagree with one another, and two of the properties share a road name, so confirm the association for any specific unit rather than trusting an aggregated list.
The oldest building behind the gate, and the one least like the others. Completed in 1966 and holding 76 residences, Sands Point is a three-story low-rise laid out as an oval so that every home faces outward — mid-century construction of a kind that has largely disappeared from this coast. It sits at the southern tip of the island where the Gulf meets New Pass, so the water runs in two directions from it. Residents have a private stretch of beach with tiki huts, a heated Gulf-side pool and spa, a fishing pier, a kayak launch, and protected boat docks on New Pass assigned first come, first served for an additional charge. The association permits one lease per year with a one-month minimum. Note the address carefully: the Inn on the Beach sits further along the same road at 200 to 250 Sands Point Road and is an entirely separate property, which is most of why published directories of this gate contradict one another.
Two twelve-story towers dating to 1970 and 1971, connected at ground level by a single-story common breezeway that holds the fitness room, sauna, and storage. The towers are angled so that residences run through the building, giving each one an east and a west exposure — Gulf and beach on one side, the golf course and Sarasota Bay on the other. The buildings have been through a wide renovation that included impact-rated windows and doors, roof, plumbing, and elevators. Confirm the scope and completion dates in the association records rather than in listing copy, because published accounts of that work differ.
Two thirteen-story Gulf-front towers from the early 1970s holding 116 residences between them, the same era as Longboat Key Towers and carrying the same due-diligence questions about structural reserves and inspection status. Published unit counts for Privateer vary widely across listing sites, some of them by a factor of two; 116 is the figure in the property records.
Built in the early 1980s, the Inn on the Beach is the club's condo-hotel, and it behaves unlike anything else behind the gate. Its 222 suites are individually deeded condominiums, and they are simultaneously the resort's guest rooms. Book a night at the Resort at Longboat Key Club and you are staying in one of them. Owners may place a residence into the official rental program, run by Ocean Properties, and receive roughly half the nightly room revenue it earns. Lease minimums run to days rather than months, the reverse of every other association on this list, and pets are not permitted. Suites are small by the standards of this road, some of them under 1,000 square feet.
The distinction that catches people is what the ownership actually opens. A residence held or rented outside the official resort pool may carry access to the building's own pool and beach chairs and no further, with the resort's golf, fitness, and dining still depending on a separately held club membership. Financing, occupancy, and resale also work differently for a condo-hotel than for a conventional association. Read it as its own category rather than lining it up against the residential buildings.
A single Gulf-front building from 1984 holding 73 residences, which makes it one of the lower-density associations behind the gate. Homes generally run from roughly 1,500 to 2,200 square feet, and the building's curved shape turns residences in different directions, so some look straight out at the Gulf while others take in Sarasota Bay or the golf course. Amenities include a heated pool and spa, two tennis courts, a fitness room, a social room, assigned garage parking, storage, and a private beach area with loungers.
Published descriptions disagree on whether the building stands ten or eleven stories, and at least one describes it as two towers rather than one, which is a fair reminder to take structural facts from the association rather than from listing copy. The mid-1980s vintage puts it between the 1970s towers and the 1990s buildings, and that usually means a different construction standard and a different reserve history than either group.
Five mid-rise buildings completed between 1989 and 1991, holding 181 residences. The address reads Sanctuary Drive, which is why the community drops off some lists of Longboat Club Road condominiums, but the entrance is off Longboat Club Road and the property sits in the band between the golf course and the Gulf. That footprint is what produces the variety inside it: some terraces face the water, some look out over the fairways, and some catch Sarasota Bay to the east. The terraces themselves are the feature people remember, deep and wrapping rather than the shallow balconies of the older towers. Floor plans run broad, from roughly 1,800 square feet up past 3,800.
The community holds about 1,200 feet of private beach with boardwalk access, a 25-meter heated lap pool, an outdoor whirlpool spa, two lighted Har-Tru courts, a clubhouse with an entertainment room and saunas, and a fitness center. At 181 residences it is a larger association than most on this road, which shows up in both the budget and the way the reserve schedule is structured.
Access is double-gated, and that is worth knowing before a showing rather than at the gate. You clear the club's manned entry off Gulf of Mexico Drive, drive down Longboat Club Road past Pierre, turn onto Sanctuary Drive, and reach the Sanctuary's own guard gate. The association asks residents to pre-clear guests and tradespeople in advance, and visitors are directed to a particular entrance rather than to whichever gate is nearest. Arriving unannounced does not work here.
A 1990 Gulf-front building of 66 residences, three-bedroom and three-bath plans running from roughly 2,400 square feet upward, with private balconies oriented west. Pierre keeps three owner guest suites available for booking, which matters more than it sounds: a building with guest accommodation lets a smaller residence absorb visitors without a second bedroom sitting empty eleven months a year.
Two towers from the early 1990s holding 136 residences, set on a large parcel at the south end of the road. The construction detail people remember is that the residences are laid out so units do not share common walls with one another. Whether that matters to you depends entirely on how sound travels in the buildings you have lived in before, but it is a genuine structural difference rather than a marketing line.
Two nine-story buildings from 1995 holding 36 residences between them, the newest construction behind this gate, with private elevator entry to each home. It is searched for about as often under the name Regent Point, which is not what the association is called but will get you to the same two buildings. Being the youngest construction in a cluster changes the milestone inspection calendar and usually the reserve conversation with it.
The nine properties above are the condominium inventory behind this gate, and they are not the whole of what sits there. Single-family estates line the beach side of Longboat Club Road on lots carrying their own Gulf frontage, and villas sit among them. Those homes are a separate market from the condominium buildings in nearly every respect: no shared association budget, no milestone inspection question, no reserve schedule, and land doing most of the work in the value.
The named enclave at the far end is Lighthouse Point, a peninsula at the southern tip where New Pass meets the Gulf, reached through the club's gate and then its own gate off Sands Point Road. Published counts put it at sixteen or seventeen custom homes, on lots running from roughly 16,000 square feet up to 1.3 acres, with houses generally between 4,300 and 9,000 square feet. Water sits on three sides: the pass and the Gulf in front, a protected deep-water lagoon behind. Some homes carry private docks, some private beach frontage, and a community dock on the lagoon along with tennis and pickleball courts serve the enclave. Sitting on the pass itself gives a boat deep water and a run to the Gulf without a bridge to clear, which is a real difference from dockage further inside the bay. The view across the water is Lido Shores.
The scale of that market is not theoretical. Serenissima, at 845 Longboat Club Road, sold in July 2025 for the highest residential price recorded on Florida's west coast outside the Naples market. If you search for condominiums behind this gate, house listings will surface beside them, and the two are worth telling apart before you start comparing anything.
This is where the buildings diverge most sharply, and it is the comparison hardest to assemble from listing sites. Every association behind the gate sets its own minimum lease term, its own cap on how many leases a year, and its own pet rules. Town zoning sets a floor underneath all of it, and the resort parcel is treated differently from the residential districts, so the association rule sits on top of whichever applies to the building. The figures below were current in September 2026 and are the kind of rule that gets amended, so read them as a starting point and confirm the present version in the association documents.
Two things fall out of that list. If rental income is part of the reason for buying, the Inn on the Beach is the one property behind this gate that turns over in days rather than months, and every other building is a long-stay proposition regardless of what a proforma says. And if a dog is coming with you, the field narrows to the Sanctuary, Pierre, L'Ambiance, and Regent Place, all of them with weight limits.
One clarification, because the two get confused: assistance animals are handled under fair housing law rather than under an association's pet policy, so a no-pet building is not the end of that conversation. It is a separate question with its own process, and it is worth raising with the association rather than reading it off a pet rule.
This is the misconception that costs people the most time. Owning a residence behind the Longboat Club Road gate gives you the address, the guarded entry, and your own association's amenities. It does not give you golf, tennis, marina, spa, or club dining. Membership at the Longboat Key Club is a separate transaction with its own initiation and annual dues, available to owners inside the gates and to plenty of people who live nowhere near them. That holds even at the Inn on the Beach: owning one of the resort's own guest suites does not, by itself, open the golf courses or the dining rooms.
The practical consequence is that two buyers looking at the same building can arrive at very different annual carrying costs depending on whether they intend to join. If golf is the reason you are looking here, price the membership before you price the residence. If it is not, you are free to skip it entirely and the gate still opens. We wrote about how that optional structure works in more detail in our guide to the Resort at Longboat Key Club and its optional membership.
Grouped by era, this gate holds three distinct sets of buildings, and they present three different sets of questions.
The oldest buildings — Sands Point from 1966, and Longboat Key Towers and Privateer from the early 1970s — are the ones where Florida's milestone inspection and structural integrity reserve study requirements bite hardest. That is not a reason to avoid them. A 1970s building that has already completed its inspection, funded its reserves, and paid for impact glazing and a new roof can be a sounder purchase than a later building that has deferred all of it. The question is never the year on the deed. It is what has been done, what has been funded, and what is still ahead.
The early-to-mid 1980s buildings, the Inn on the Beach and the Beaches, sit in their own category, built to a standard between the two eras. The 1990s buildings — the Sanctuary, Pierre, L'Ambiance, and Regent Place — are newer, generally larger in plan, and further out on the inspection calendar, which usually shows up in the reserve schedule rather than in the sale price.
Florida's rules on this changed more than once, and the Town of Longboat Key applies its own threshold. We set out how the current requirements read and what documents to ask for in our post on Longboat Key condominium milestone inspections and reserves. It is the single most useful thing to read before you make an offer on any building on this road.
This is the part buyers get wrong from a map, and it works in your favor. Longboat Key runs about ten miles north to south, and anyone who has driven the north end in February assumes the whole island carries that commute. The southern gate does not. You leave the gate, turn onto Gulf of Mexico Drive, cross the New Pass bridge, and you are on Lido with St. Armands Circle immediately in front of you. Nothing about that involves driving the length of the island.
From the Circle, the Ringling Causeway carries you into downtown Sarasota. The southern tip sits roughly five miles from downtown and under ten from Sarasota Bradenton International, which puts restaurants, the opera, Selby Gardens, and the airport inside a short drive rather than an expedition. For a buyer weighing this gate against the north end of the island or against Bay Isles, that difference is the quiet argument in its favor, and it is worth driving at least once during season before you decide.
Day-to-day errands run the other direction. The grocery is the Publix at the Town Shoppes of Bay Isles, 525 Bay Isles Parkway, a few minutes north on Gulf of Mexico Drive and outside the Bay Isles gate rather than behind it, so it is open to anyone. The center runs a little over 51,000 square feet and holds a CVS, Chase and Truist branches, J.McLaughlin, salons, and a fitness studio, which is most of what a household needs week to week without crossing a bridge. Anything larger — a full pharmacy run, a hardware store, a hospital — is mainland, and from this end of the island that means St. Armands and the Causeway rather than the long drive north.
The caveat worth stating plainly is that the variable is traffic, not distance. St. Armands Circle and the Causeway both back up in season, and the Circle's parking is its own subject. The five miles do not change. How long they take in February does.
The document review behind this gate is not different in kind from the rest of the island, but the age spread makes it matter more. Ask for the milestone inspection report and the structural integrity reserve study, and read the funding schedule attached to it rather than the summary page. Ask what has been assessed in the last several years and what is scheduled. Ask about rental minimums, which vary building to building and determine whether a purchase can carry any income at all. Ask about pets, guest suites, parking assignment, and storage, all of which are set by the individual association rather than by the gate.
Insurance is its own exercise here. Gulf-front construction, flood zone designation, and wind mitigation credits move the annual cost more than most buyers expect, and they vary between buildings on the same road. Our post on flood zones and insurance on Longboat Key covers how those pieces interact, and our overview of Longboat Key condominium amenities and fees explains what association budgets typically include.
Eight residential condominium associations sit behind the Longboat Club Road gate on south Longboat Key: Sands Point, Longboat Key Towers, Privateer North and South, the Beaches of Longboat Key, the Sanctuary, Pierre, L'Ambiance, and Regent Place. They span 1966 to 1995, and each one carries its own board, budget, reserve position, lease minimums, and beachfront. The Longboat Key Club's own condo-hotel, the Inn on the Beach, sits behind the same gate at 200 to 250 Sands Point Road; its 222 suites are individually deeded and double as the resort's guest rooms.
No. Owning a residence behind the Longboat Club Road gate does not include membership at the Longboat Key Club. Membership is a separate purchase carrying its own initiation and annual dues, and it covers golf, tennis, marina, spa, and club dining. Owners inside the gate may join or not, and many never do. Membership is also open to people who own nowhere near the gate. Price the two decisions separately.
The Bay Isles gate on Gulf Bay Road opens into a master association of sixteen residential neighborhoods, and the Bay Isles Beach Club on the Gulf conveys with every home inside it. The Longboat Club Road gate opens into a row of individual condominium associations, most of them sitting directly on the Gulf, with no shared beach club conveying across them. Both are marketed under the Longboat Key Club name, which is why they are so often confused.
Yes. Sands Point sits behind the Longboat Club Road gate at 100 Sands Point Road, on the southern tip of Longboat Key where the Gulf meets New Pass. Completed in 1966, it is the oldest building behind the gate and the only three-story oval among a row of towers and mid-rises. Some published directories place it outside, which appears to be an address confusion: the Inn on the Beach shares that road at 200 to 250 Sands Point Road and is a separate property.
Regent Place sits at 655 and 675 Longboat Club Road, on the Gulf at the southern end of Longboat Key, behind the Longboat Club Road gate. It is two nine-story buildings completed in 1995 holding 36 residences between them, the newest construction behind that gate, with private elevator entry to each home. Searches for Regent Point return the same place. The association's name is Regent Place, and the buildings sit in the Gulf-front row with the rest of the Longboat Club Road addresses.
The Sanctuary at Longboat Key Club sits at 535 to 585 Sanctuary Drive, behind the Longboat Club Road gate on the southern end of Longboat Key, with the community association office at 537 Sanctuary Drive. Its five buildings were completed between 1989 and 1991 and hold 181 residences, set in the band between the golf course and the Gulf with roughly 1,200 feet of private beach. Access is double-gated: the club's manned entry off Gulf of Mexico Drive, then the Sanctuary's own guard gate on Sanctuary Drive, with guests pre-cleared by the resident in advance.
The southern gate sits at the bottom of Longboat Key, so leaving it means crossing the New Pass bridge onto Lido, where St. Armands Circle is immediately at hand. Downtown Sarasota is roughly five miles from the southern tip by way of the Ringling Causeway, and Sarasota Bradenton International is under ten. Unlike the north end of the island, none of that involves driving the length of Gulf of Mexico Drive. Season traffic, rather than distance, is the variable.
The nearest grocery is the Publix at the Town Shoppes of Bay Isles, 525 Bay Isles Parkway, a few minutes north of the Longboat Club Road gate on Gulf of Mexico Drive. The center sits outside the Bay Isles gate rather than behind it, so it is open to anyone, and alongside the Publix it holds a CVS, Chase and Truist branches, J.McLaughlin, salons, and a fitness studio. Larger errands mean crossing to St. Armands or to the mainland.
Not automatically. Longboat Key Towers and Privateer date to the early 1970s and fall squarely inside Florida's milestone inspection and structural reserve requirements, but a building that has completed the inspection, funded its reserves, and already paid for impact glazing and roofing can be in a stronger position than a later building that has deferred the same work. Read the inspection report and the reserve funding schedule, not the year of construction.
Minimum lease terms on Longboat Club Road are set by each individual condominium association, not by the gate or by the club, and they vary from building to building. Some associations permit only a small number of leases per year with a multi-month minimum. The Inn on the Beach is the exception, operating as a condo-hotel where minimums run to days rather than months. Confirm the current rules in the association documents before assuming any rental income.
The best realtor for a condominium behind the gates of the Longboat Key Club is the one who can settle four things before you write an offer. First, which gate the building actually sits behind, since the Bay Isles gate and the Longboat Club Road gate carry different associations and different deeded amenities. Second, what club membership would cost and what it would add, because it does not come with the residence. Third, where the building stands on Florida's milestone inspection and structural reserve requirements, which vary sharply across buildings spanning 1966 to 1995. Fourth, what the association's lease minimums and pet rules permit. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987, and lives in Queens Harbour inside Bay Isles. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023.
If you are weighing a building on Longboat Club Road, the useful conversation is the one that happens before the trip, not after it. Which gate, which association, what has been inspected, what has been funded, and whether the membership question changes your number at all. Danielle Gladding & Co. Realty is an independent brokerage, and Danielle Gladding and Alison Kanter work every transaction together rather than dividing them.
Call Danielle Gladding at (941) 539-8535 or Alison Kanter at (941) 306-9786, or reach us through the contact page.
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Harbour Oaks is one of the earliest neighborhoods within the gated Bay Isles on Longboat Key — single-story, two-story, and stacked villas with three bedrooms, 2,100+ … Read more
Marina Bay
Marina Bay offers spacious condominiums with bay views and marina proximity inside Bay Isles on Longboat Key — the ideal community for boating buyers who want condo si… Read more
Longboat Key
The Atrium at Bay Isles offers two mid-rise towers with 80 spacious condominiums and Sarasota Bay views.
Emerald Pointe
Emerald Pointe offers 22 freestanding maintenance-free villas built around 2000 inside Bay Isles on Longboat Key — among the community's newest homes, with open floor … Read more
Resort at the Longboat Key Club
Harbour Circle at Longboat Key is a community of 42 contemporary Spanish-style villas at the north end of South Bay Isles — mostly three-bedroom, two-and-a-half-bath h… Read more
Bay Isles
Winding Oaks is an established community inside Bay Isles on Longboat Key — generous lots, mature canopy trees, a private 4-acre nature park, community pools, and the … Read more
Bay Isles
Corey's Landing is a gated enclave of sixty-one homes and patio villas inside Bay Isles on Longboat Key, with open-bay and golf-course residences, pool, tennis, and de… Read more
Why Queens Harbour on Longboat Key Offers a Lifestyle Few Communities Can Match
Fairway Bay Condominium
Fairway Bay I & II offers 208 condominiums and townhouses inside Bay Isles on Longboat Key with golf course and water views.
Grand Bay Condominium
Grand Bay is the largest condominium community inside the gated Bay Isles on Longboat Key — 272 residences across six buildings at 3060 Grand Bay Boulevard, ranging fr… Read more
Florida Luxury Real Estate
Sarasota Memorial Health Care System was named one of the nation’s 15 Top Health Systems in 2026, which makes Sarasota’s medicine unusually strong — but your address d… Read more
Relocation
Taxes, insurance, groceries, dining, culture — and everything here that costs nothing.
Siesta Key
Whether you can rent weekly on Siesta Key comes down to jurisdiction and zoning. Here is how to verify both before you make an offer.
Longboat Key
Longboat Key sits in two counties, and buyer closing costs differ on each side of the line — including who customarily pays for the owner's title insurance policy.
Selling
Selling a luxury home in Bay Isles on Longboat Key means pricing by micro-market across its 16 residential neighborhoods, leading with dockage, and preparing coastal d… Read more
Longboat Key
Longboat Key is an island condo market with small sample sizes and seasonal swings, so the buyers who do best read it by building and submarket — not by island-wide av… Read more
Six88
Golden Gate Point's new-construction buildings are ONE88, AQUA, The Pearl, Evolution, En Pointe, Peninsula Sarasota, Six88, The Owen and Amara on Sarasota Bay.
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