Eleven miles of barrier-island luxury between the Gulf of Mexico and Sarasota Bay — Bay Isles, Country Club Shores, Sleepy Lagoon, and the storied Gulf-front towers. A resident broker's guide to Longboat Key by Danielle Gladding, Queens Harbour homeowner and Florida Broker since 1987.
I walk these streets most mornings.
This guide covers the island end to end. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.
That first line is not a marketing line. Danielle Gladding lives in Queens Harbour inside Bay Isles on Longboat Key and walks the neighborhood most mornings. I am Danielle. I arrived in Sarasota in 1976, and my husband Nick and I chose this island deliberately. For the record, because it matters on a page about this town: Nick is a retired land use and environmental attorney and holds the District 3 seat on the Longboat Key Town Commission.
If you are reading this, you are probably making a similar choice. Maybe you are coming from Chicago, New York, Boston, Atlanta, Dallas or Nashville. Maybe you have spent months scrolling listing sites and comparing photos. You know you want Longboat Key. What you need to know is which Longboat Key, because there are sixteen residential neighborhoods inside Bay Isles alone, and many more along the rest of the island.
This page is written to give you a real picture. Not a brochure. The neighborhoods, the buildings, the water, the dining and the arts, and the candid tradeoffs. When you are ready for a private conversation, both of our numbers are at the bottom of this page.
The fast picture for buyers who like to start with the facts.
Longboat Key is not one market. It is a collection of gated communities, canal streets, Gulf-front towers and quiet north-end pockets, and each behaves differently on price, inventory and timing. Here is the clear-eyed layout.
This is where Nick and I live. Bay Isles is a gated community on the bay side of the south end, with sixteen residential neighborhoods behind its gates — among them Queens Harbour, Harbour Oaks, The Bayou, Corey's Landing, Winding Oaks and Sabal Cove. Inside the gates you will find waterfront single-family homes, villas and mid-rise condominiums, along with the Resort at Longboat Key Club's tennis gardens and the Moorings Marina.
The fact buyers most often get wrong: the Bay Isles Beach Club on the Gulf conveys with every home inside the gates, by deed. A Longboat Key Club golf membership does not. It is a separate membership with a separate buy-in. Buyers who have owned in Florida before get this wrong as often as first-timers.
What I tell every buyer: Bay Isles is sixteen markets, not one. Pricing inside Queens Harbour does not track pricing inside Harbour Oaks, and a villa in one neighborhood and a waterfront estate in another are different purchases with different associations. The work is matching the neighborhood to the way you will actually live.
Country Club Shores sits on the bay side of the south end: single-family homes, most of them on canals with access to Sarasota Bay and on to the Gulf through New Pass. Original homes sit beside substantial renovations and new construction. For buyers who want a boat at the dock and a single-family home rather than a condominium, it is one of the first places to look. Check the canal depth and the dock itself against your boat before anything else.
Smaller pockets on the bay side, mostly waterfront lots, with a mix of original mid-century homes and substantial renovations.
A narrow finger of land with canal-front homes and water access, and a street scale that feels more like a boating village than a resort. It comes up in conversation more often than its size would suggest.
Longboat Key's Gulf-front condominium buildings date from the 1970s onward — the Water Club, the Beachplace, L'Ambiance, Promenade, Tangerine Bay, Players Club and others. Each building has its own amenity package, its own pet and rental rules, and its own assessment history. Two units in two neighboring buildings can be valued very differently, and the view has little to do with it. The building's reserves, renovation history and board do.
Since 2022, Florida condominium law has materially changed the assessment picture for older Gulf-front buildings. The Town of Longboat Key applies a 30-year milestone inspection threshold, and our guide to Longboat Key milestone inspections and reserves walks through what that means for a buyer. Some buildings have managed reserves and renovations well. Others face special assessments. I walk every condominium buyer through the building's financials, reserve study and inspection status before they sign a contract. There is no version of buying a Longboat Key condominium where that conversation should be skipped.
The north end of Longboat Key has an older Florida feel, closer to Anna Maria Island, with historic cottages, newer construction and beachfront condominiums mixed together. The streets are quieter, the landscaping is less formal, and the north end sits on the Manatee County side of the line.
People do not buy on Longboat Key for square footage. They buy for what the days actually feel like.
Boating is the defining lifestyle of this island. Sarasota Bay is the backyard, and New Pass and Longboat Pass put the Gulf of Mexico minutes away. The Moorings Marina sits inside Bay Isles, Marina Jack in downtown Sarasota takes larger vessels, and private docks line the canal neighborhoods. Fishing, sailing, paddleboarding and a sunset on the boat are not weekend activities here. They are Tuesdays. Our boating and dockage guide covers slips, depths and access.
The Resort at Longboat Key Club operates two courses on the island: Harbourside, inside Bay Isles, and Islandside, on the Gulf side. Both are part of the Club's membership, which is separate from home ownership and carries its own buy-in. University Park Country Club, The Founders Club and Concession Golf Club are a short drive away on the mainland.
The Longboat Key Club is the social and athletic center of the south end: the tennis gardens, pickleball, the spa, the fitness center and the dining rooms. For many buyers the Club is a deciding factor, which is exactly why the membership question belongs at the start of a search rather than the end. See our guide to the Longboat Key Club condominiums behind the gates.
White-sand Gulf beach runs most of the island's length. Bay Isles owners have deeded access to the Bay Isles Beach Club, and other communities have their own arrangements. Public beach access points exist along Gulf of Mexico Drive, but day to day, the beach here is a quiet one.
A multi-use path runs along Gulf of Mexico Drive for much of the island, and the pace of traffic makes walking and cycling part of ordinary life rather than an outing. I walk Bay Isles most mornings.
One of the great misunderstandings about Longboat Key is that buyers think they are choosing between island life and city life. They are not. The island sits twelve to eighteen minutes from St. Armands Circle and downtown Sarasota.
For the full list, see where to eat on Longboat Key.
About twelve minutes south, St. Armands and Lido Key offer another full dining and shopping district — the St. Armands location of the Columbia Restaurant, Cha Cha Coconuts, Lynches Pub & Grub and many more, set around the Circle's boutiques and evening foot traffic.
About eighteen minutes south, downtown Sarasota puts the bayfront, Main Street and a serious restaurant scene within reach. Alison Kanter and I work the whole market together, so if you are weighing downtown living against island living, we can show you both sides of that choice.
Sarasota calls itself Florida's Cultural Coast, and it earns the name. From a Longboat Key home you are a short drive from:
I have been guiding buyers in this market since 1981, and the reasons cluster into clear patterns. If two or three of these resonate, you are probably looking in the right place.
Some buyers weigh Longboat Key against Lakewood Ranch, the master-planned community on the mainland east of Interstate 75. They are very different propositions, and I want to be straight with you about the difference.
Longboat Key is a barrier island organized around the water: the beach, the bay, docks, walkability and a short drive to downtown Sarasota's arts. Most of its homes are waterfront or water-view condominiums and single-family homes.
Lakewood Ranch is a large master-planned community built largely since the 1990s, with new construction, larger lots, golf and country clubs, trails, polo and its own Main Street. It sits roughly 30 to 40 minutes from the Gulf beaches.
Danielle Gladding & Co. Realty works both markets, and the useful conversation is about which property type, which commute and which daily rhythm fit your life. That is worth settling before you make an expensive choice.
Showing houses is not the same as helping someone make the right decision. Here is how the process actually works.
Before I show you a single property, we talk about what your days are going to look like. Full-time or seasonal? Boat at the dock or water views? A short walk to the Club, or privacy at the end of a long driveway? A single-family home, or a condominium you can lock and leave? The decisions cascade from here.
I narrow Longboat Key down to the two or three neighborhoods or buildings that fit your life. This is where most buyers lose months, touring beautiful homes in the wrong places. We skip that.
Inside the right neighborhoods, I filter for long-term fit — building reserves, association health, flood elevation, renovation needs, resale history and the details that separate a good purchase from a regret.
Relationships built in this market since 1981 matter most here. I know the listing agents and the building managers, and I know which sellers are realistic. Winning a competitive offer is its own skill, and it is where experience pays for itself.
Clients do not disappear after closing. The broker who walked you through the front door is the broker you call for a contractor, a dock builder or an interior designer.
Danielle Gladding holds the Luxury Homes Certification along with the Accredited Buyer's Representative, Certified Waterfront Specialist, and Certified Residential Listing Specialist designations.
Alison Kanter holds the Real Estate Negotiation Expert, Certified Waterfront Specialist, and Certified Residential Listing Specialist designations, along with an MBA from Clemson University.
Alison is a Sarasota native and a Furman University graduate who spent her early career at a multinational IT company before coming home to real estate. Neither of us is assigned a territory. We work every transaction together, and we are different in useful ways: I bring market memory going back to 1981 and the relationships that come with it, and Alison brings analytical precision and a corporate discipline for documents and process. When you work with us you get both perspectives.
Longboat Key is a barrier island of roughly eleven miles between Sarasota Bay and the Gulf of Mexico, known for waterfront homes and condominiums, a white-sand Gulf beach along most of its length, the Resort at Longboat Key Club, and boating through New Pass and Longboat Pass. Longboat Key crosses the Sarasota–Manatee county line partway up and is governed by its own incorporated town. The south end of Longboat Key is about twelve minutes from St. Armands Circle and about eighteen minutes from downtown Sarasota's arts and dining.
The best neighborhood on Longboat Key depends on how a buyer plans to live. Bay Isles is a gated community of sixteen residential neighborhoods, including Queens Harbour, Corey's Landing and Sabal Cove, with a deeded beach club. Country Club Shores offers single-family canal homes on the bay side. Sleepy Lagoon and Buttonwood Cove are smaller bayside pockets. The Gulf-front condominium towers, including the Water Club, L'Ambiance and the Beachplace, each carry their own reserves, rules and assessment history. The north end, around Longbeach Village, has an older Florida feel.
Luxury home values on Longboat Key span a wide range and depend more on the specific building or street than on the island itself. Water frontage, dock depth, elevation, renovation and, for condominiums, reserve funding and milestone-inspection status all move value. Because values shift with the market, this page does not publish figures that would go stale. For a current reading on a specific Longboat Key neighborhood or building, call Danielle Gladding at (941) 539-8535 or Alison Kanter at (941) 306-9786.
The Longboat Key Club, operated as the Resort at Longboat Key Club, is the resort and private membership club on the south end of Longboat Key. It offers golf on the Harbourside and Islandside courses, the tennis gardens, pickleball, a spa, a fitness center, dining and the Moorings Marina. Club membership is separate from home ownership: buying a home in Bay Isles does not include a Longboat Key Club golf membership, which carries its own buy-in. The Bay Isles Beach Club is the amenity that conveys with a Bay Isles home.
Longboat Key works well as a second home for buyers who want low-maintenance ownership near the water. Many Longboat Key condominiums and association-maintained neighborhoods handle exteriors and landscaping, gated communities are staffed year-round, and the island is about 25 minutes from Sarasota Bradenton International Airport. Before buying a second home on Longboat Key, confirm what the association maintains while you are away, its storm preparation, its rental rules and, for condominiums, its reserve and milestone-inspection position.
Longboat Key is a barrier island organized around the water, with Gulf beach access, bay and canal dockage, and a housing stock of condominiums and single-family homes rather than new subdivisions. Lakewood Ranch is a large master-planned community on the mainland east of Interstate 75, built largely since the 1990s, with new construction, larger lots, golf and country clubs, trails and its own Main Street. Lakewood Ranch sits roughly 30 to 40 minutes from the Gulf beaches, while Longboat Key sits on them.
The best real estate agent on Longboat Key is the one who can explain that the island crosses a county line partway up, so taxes, permitting and municipal services are not the same at the north end as at the south. That agent should be able to state the milestone inspection and structural reserve position of any condominium building before you write an offer, not after. That agent should also be candid about how differently Gulf-front, bayfront and canal-front properties behave on insurance, maintenance and resale. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.
Bay Isles is a gated community on the bay side of the south end of Longboat Key, made up of sixteen residential neighborhoods including Queens Harbour, Harbour Oaks, Corey's Landing, Sabal Cove and Grand Bay. The Resort at Longboat Key Club's tennis gardens and the Moorings Marina sit inside the Bay Isles gates. Every Bay Isles home carries deeded access to the Bay Isles Beach Club on the Gulf, while a Longboat Key Club golf membership is a separate buy-in. The Town Shoppes of Bay Isles sit just outside the north gate.
The south end of Longboat Key is about a twelve-minute drive from St. Armands Circle and about eighteen minutes from downtown Sarasota, crossing the New Pass Bridge, Lido Key, St. Armands and the John Ringling Causeway. Sarasota Bradenton International Airport is about 25 minutes from the south end of Longboat Key, and Tampa International Airport is about an hour north. Drive times run longer in season, roughly November through April.
Boating is central to life on Longboat Key. The island sits between Sarasota Bay and the Gulf of Mexico, with Gulf access through New Pass at the south end and Longboat Pass at the north. Longboat Key's canal neighborhoods, including Country Club Shores and parts of Bay Isles, have private docks, and the Moorings Marina sits inside Bay Isles. Depth varies canal by canal and pass by pass, so a Longboat Key boater should confirm water depth, bridge clearance and dock condition against the specific vessel before buying.
If you are weighing a Longboat Key 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 your concerns are. We will tell you which neighborhoods and buildings are worth your time, which ones we would or would not recommend right now, and what the real tradeoffs look like. If you are selling, we will give you a private valuation and an unvarnished read on your home's position in today's market. Call Danielle at (941) 539-8535 or Alison at (941) 306-9786.
— Danielle and Alison, Danielle Gladding & Co. Realty
I walk these streets most mornings.
This guide covers the island end to end. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.
That first line is not a marketing line. Danielle Gladding lives in Queens Harbour inside Bay Isles on Longboat Key and walks the neighborhood most mornings. I am Danielle. I arrived in Sarasota in 1976, and my husband Nick and I chose this island deliberately. For the record, because it matters on a page about this town: Nick is a retired land use and environmental attorney and holds the District 3 seat on the Longboat Key Town Commission.
If you are reading this, you are probably making a similar choice. Maybe you are coming from Chicago, New York, Boston, Atlanta, Dallas or Nashville. Maybe you have spent months scrolling listing sites and comparing photos. You know you want Longboat Key. What you need to know is which Longboat Key, because there are sixteen residential neighborhoods inside Bay Isles alone, and many more along the rest of the island.
This page is written to give you a real picture. Not a brochure. The neighborhoods, the buildings, the water, the dining and the arts, and the candid tradeoffs. When you are ready for a private conversation, both of our numbers are at the bottom of this page.
The fast picture for buyers who like to start with the facts.
Longboat Key is not one market. It is a collection of gated communities, canal streets, Gulf-front towers and quiet north-end pockets, and each behaves differently on price, inventory and timing. Here is the clear-eyed layout.
This is where Nick and I live. Bay Isles is a gated community on the bay side of the south end, with sixteen residential neighborhoods behind its gates — among them Queens Harbour, Harbour Oaks, The Bayou, Corey's Landing, Winding Oaks and Sabal Cove. Inside the gates you will find waterfront single-family homes, villas and mid-rise condominiums, along with the Resort at Longboat Key Club's tennis gardens and the Moorings Marina.
The fact buyers most often get wrong: the Bay Isles Beach Club on the Gulf conveys with every home inside the gates, by deed. A Longboat Key Club golf membership does not. It is a separate membership with a separate buy-in. Buyers who have owned in Florida before get this wrong as often as first-timers.
What I tell every buyer: Bay Isles is sixteen markets, not one. Pricing inside Queens Harbour does not track pricing inside Harbour Oaks, and a villa in one neighborhood and a waterfront estate in another are different purchases with different associations. The work is matching the neighborhood to the way you will actually live.
Country Club Shores sits on the bay side of the south end: single-family homes, most of them on canals with access to Sarasota Bay and on to the Gulf through New Pass. Original homes sit beside substantial renovations and new construction. For buyers who want a boat at the dock and a single-family home rather than a condominium, it is one of the first places to look. Check the canal depth and the dock itself against your boat before anything else.
Smaller pockets on the bay side, mostly waterfront lots, with a mix of original mid-century homes and substantial renovations.
A narrow finger of land with canal-front homes and water access, and a street scale that feels more like a boating village than a resort. It comes up in conversation more often than its size would suggest.
Longboat Key's Gulf-front condominium buildings date from the 1970s onward — the Water Club, the Beachplace, L'Ambiance, Promenade, Tangerine Bay, Players Club and others. Each building has its own amenity package, its own pet and rental rules, and its own assessment history. Two units in two neighboring buildings can be valued very differently, and the view has little to do with it. The building's reserves, renovation history and board do.
Since 2022, Florida condominium law has materially changed the assessment picture for older Gulf-front buildings. The Town of Longboat Key applies a 30-year milestone inspection threshold, and our guide to Longboat Key milestone inspections and reserves walks through what that means for a buyer. Some buildings have managed reserves and renovations well. Others face special assessments. I walk every condominium buyer through the building's financials, reserve study and inspection status before they sign a contract. There is no version of buying a Longboat Key condominium where that conversation should be skipped.
The north end of Longboat Key has an older Florida feel, closer to Anna Maria Island, with historic cottages, newer construction and beachfront condominiums mixed together. The streets are quieter, the landscaping is less formal, and the north end sits on the Manatee County side of the line.
People do not buy on Longboat Key for square footage. They buy for what the days actually feel like.
Boating is the defining lifestyle of this island. Sarasota Bay is the backyard, and New Pass and Longboat Pass put the Gulf of Mexico minutes away. The Moorings Marina sits inside Bay Isles, Marina Jack in downtown Sarasota takes larger vessels, and private docks line the canal neighborhoods. Fishing, sailing, paddleboarding and a sunset on the boat are not weekend activities here. They are Tuesdays. Our boating and dockage guide covers slips, depths and access.
The Resort at Longboat Key Club operates two courses on the island: Harbourside, inside Bay Isles, and Islandside, on the Gulf side. Both are part of the Club's membership, which is separate from home ownership and carries its own buy-in. University Park Country Club, The Founders Club and Concession Golf Club are a short drive away on the mainland.
The Longboat Key Club is the social and athletic center of the south end: the tennis gardens, pickleball, the spa, the fitness center and the dining rooms. For many buyers the Club is a deciding factor, which is exactly why the membership question belongs at the start of a search rather than the end. See our guide to the Longboat Key Club condominiums behind the gates.
White-sand Gulf beach runs most of the island's length. Bay Isles owners have deeded access to the Bay Isles Beach Club, and other communities have their own arrangements. Public beach access points exist along Gulf of Mexico Drive, but day to day, the beach here is a quiet one.
A multi-use path runs along Gulf of Mexico Drive for much of the island, and the pace of traffic makes walking and cycling part of ordinary life rather than an outing. I walk Bay Isles most mornings.
One of the great misunderstandings about Longboat Key is that buyers think they are choosing between island life and city life. They are not. The island sits twelve to eighteen minutes from St. Armands Circle and downtown Sarasota.
For the full list, see where to eat on Longboat Key.
About twelve minutes south, St. Armands and Lido Key offer another full dining and shopping district — the St. Armands location of the Columbia Restaurant, Cha Cha Coconuts, Lynches Pub & Grub and many more, set around the Circle's boutiques and evening foot traffic.
About eighteen minutes south, downtown Sarasota puts the bayfront, Main Street and a serious restaurant scene within reach. Alison Kanter and I work the whole market together, so if you are weighing downtown living against island living, we can show you both sides of that choice.
Sarasota calls itself Florida's Cultural Coast, and it earns the name. From a Longboat Key home you are a short drive from:
I have been guiding buyers in this market since 1981, and the reasons cluster into clear patterns. If two or three of these resonate, you are probably looking in the right place.
Some buyers weigh Longboat Key against Lakewood Ranch, the master-planned community on the mainland east of Interstate 75. They are very different propositions, and I want to be straight with you about the difference.
Longboat Key is a barrier island organized around the water: the beach, the bay, docks, walkability and a short drive to downtown Sarasota's arts. Most of its homes are waterfront or water-view condominiums and single-family homes.
Lakewood Ranch is a large master-planned community built largely since the 1990s, with new construction, larger lots, golf and country clubs, trails, polo and its own Main Street. It sits roughly 30 to 40 minutes from the Gulf beaches.
Danielle Gladding & Co. Realty works both markets, and the useful conversation is about which property type, which commute and which daily rhythm fit your life. That is worth settling before you make an expensive choice.
Showing houses is not the same as helping someone make the right decision. Here is how the process actually works.
Before I show you a single property, we talk about what your days are going to look like. Full-time or seasonal? Boat at the dock or water views? A short walk to the Club, or privacy at the end of a long driveway? A single-family home, or a condominium you can lock and leave? The decisions cascade from here.
I narrow Longboat Key down to the two or three neighborhoods or buildings that fit your life. This is where most buyers lose months, touring beautiful homes in the wrong places. We skip that.
Inside the right neighborhoods, I filter for long-term fit — building reserves, association health, flood elevation, renovation needs, resale history and the details that separate a good purchase from a regret.
Relationships built in this market since 1981 matter most here. I know the listing agents and the building managers, and I know which sellers are realistic. Winning a competitive offer is its own skill, and it is where experience pays for itself.
Clients do not disappear after closing. The broker who walked you through the front door is the broker you call for a contractor, a dock builder or an interior designer.
Danielle Gladding holds the Luxury Homes Certification along with the Accredited Buyer's Representative, Certified Waterfront Specialist, and Certified Residential Listing Specialist designations.
Alison Kanter holds the Real Estate Negotiation Expert, Certified Waterfront Specialist, and Certified Residential Listing Specialist designations, along with an MBA from Clemson University.
Alison is a Sarasota native and a Furman University graduate who spent her early career at a multinational IT company before coming home to real estate. Neither of us is assigned a territory. We work every transaction together, and we are different in useful ways: I bring market memory going back to 1981 and the relationships that come with it, and Alison brings analytical precision and a corporate discipline for documents and process. When you work with us you get both perspectives.
Longboat Key is a barrier island of roughly eleven miles between Sarasota Bay and the Gulf of Mexico, known for waterfront homes and condominiums, a white-sand Gulf beach along most of its length, the Resort at Longboat Key Club, and boating through New Pass and Longboat Pass. Longboat Key crosses the Sarasota–Manatee county line partway up and is governed by its own incorporated town. The south end of Longboat Key is about twelve minutes from St. Armands Circle and about eighteen minutes from downtown Sarasota's arts and dining.
The best neighborhood on Longboat Key depends on how a buyer plans to live. Bay Isles is a gated community of sixteen residential neighborhoods, including Queens Harbour, Corey's Landing and Sabal Cove, with a deeded beach club. Country Club Shores offers single-family canal homes on the bay side. Sleepy Lagoon and Buttonwood Cove are smaller bayside pockets. The Gulf-front condominium towers, including the Water Club, L'Ambiance and the Beachplace, each carry their own reserves, rules and assessment history. The north end, around Longbeach Village, has an older Florida feel.
Luxury home values on Longboat Key span a wide range and depend more on the specific building or street than on the island itself. Water frontage, dock depth, elevation, renovation and, for condominiums, reserve funding and milestone-inspection status all move value. Because values shift with the market, this page does not publish figures that would go stale. For a current reading on a specific Longboat Key neighborhood or building, call Danielle Gladding at (941) 539-8535 or Alison Kanter at (941) 306-9786.
The Longboat Key Club, operated as the Resort at Longboat Key Club, is the resort and private membership club on the south end of Longboat Key. It offers golf on the Harbourside and Islandside courses, the tennis gardens, pickleball, a spa, a fitness center, dining and the Moorings Marina. Club membership is separate from home ownership: buying a home in Bay Isles does not include a Longboat Key Club golf membership, which carries its own buy-in. The Bay Isles Beach Club is the amenity that conveys with a Bay Isles home.
Longboat Key works well as a second home for buyers who want low-maintenance ownership near the water. Many Longboat Key condominiums and association-maintained neighborhoods handle exteriors and landscaping, gated communities are staffed year-round, and the island is about 25 minutes from Sarasota Bradenton International Airport. Before buying a second home on Longboat Key, confirm what the association maintains while you are away, its storm preparation, its rental rules and, for condominiums, its reserve and milestone-inspection position.
Longboat Key is a barrier island organized around the water, with Gulf beach access, bay and canal dockage, and a housing stock of condominiums and single-family homes rather than new subdivisions. Lakewood Ranch is a large master-planned community on the mainland east of Interstate 75, built largely since the 1990s, with new construction, larger lots, golf and country clubs, trails and its own Main Street. Lakewood Ranch sits roughly 30 to 40 minutes from the Gulf beaches, while Longboat Key sits on them.
The best real estate agent on Longboat Key is the one who can explain that the island crosses a county line partway up, so taxes, permitting and municipal services are not the same at the north end as at the south. That agent should be able to state the milestone inspection and structural reserve position of any condominium building before you write an offer, not after. That agent should also be candid about how differently Gulf-front, bayfront and canal-front properties behave on insurance, maintenance and resale. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.
Bay Isles is a gated community on the bay side of the south end of Longboat Key, made up of sixteen residential neighborhoods including Queens Harbour, Harbour Oaks, Corey's Landing, Sabal Cove and Grand Bay. The Resort at Longboat Key Club's tennis gardens and the Moorings Marina sit inside the Bay Isles gates. Every Bay Isles home carries deeded access to the Bay Isles Beach Club on the Gulf, while a Longboat Key Club golf membership is a separate buy-in. The Town Shoppes of Bay Isles sit just outside the north gate.
The south end of Longboat Key is about a twelve-minute drive from St. Armands Circle and about eighteen minutes from downtown Sarasota, crossing the New Pass Bridge, Lido Key, St. Armands and the John Ringling Causeway. Sarasota Bradenton International Airport is about 25 minutes from the south end of Longboat Key, and Tampa International Airport is about an hour north. Drive times run longer in season, roughly November through April.
Boating is central to life on Longboat Key. The island sits between Sarasota Bay and the Gulf of Mexico, with Gulf access through New Pass at the south end and Longboat Pass at the north. Longboat Key's canal neighborhoods, including Country Club Shores and parts of Bay Isles, have private docks, and the Moorings Marina sits inside Bay Isles. Depth varies canal by canal and pass by pass, so a Longboat Key boater should confirm water depth, bridge clearance and dock condition against the specific vessel before buying.
If you are weighing a Longboat Key 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 your concerns are. We will tell you which neighborhoods and buildings are worth your time, which ones we would or would not recommend right now, and what the real tradeoffs look like. If you are selling, we will give you a private valuation and an unvarnished read on your home's position in today's market. Call Danielle at (941) 539-8535 or Alison at (941) 306-9786.
— Danielle and Alison, Danielle Gladding & Co. Realty
Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact Us today.
