Longboat Key Homes for Sale & Communities

Beachfront living with a sporty streak: alongside the Gulf-side pool and fitness center, residents get both tennis and pickleball, and the private stretch of sand out front does most of the selling. A realistic on-ramp to Gulf-front ownership on the island.

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A small Gulf-front building for buyers who want the beach without the crowd. Steps to the sand, a pool right on the Gulf, and a tidy set of shared spaces, quiet coastal ownership with the classics covered.

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Low-rise, low-key, and right on the Gulf. Private beach out the door and a heated pool, wrapped in an Old Florida feel the newer towers cannot manufacture, built for buyers chasing calm over grandeur.

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Sand-at-your-door beachfront with genuine rental legs. The pool sits on the Gulf, there are courts for tennis and pickleball, and the casual resort feel makes it an easy pick for seasonal owners and income-minded buyers alike.

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North-end Gulf-front living in a two-story format, so it never reads as a high-rise. Owners get their own heated pool and courts, plus the run of the Cedars Tennis Resort just across the road.

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An amenity-heavy beachfront community built for people who actually use them: eight tennis courts, two heated pools, a fitness center, and a steady social calendar. Direct Gulf access with plenty going on.

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A gated beachfront community of roughly 220 residences on the south end, with a twist: owners can place a unit in the on-site resort rental program and share in the revenue while away. Pool, fitness, beach, and optional Longboat Key Club membership round it out.

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A traditional Gulf-front high-rise for buyers who want the tower experience without an ultra-luxury price. Private beach, a heated pool on the sand, fitness with a sauna, tennis, and the wide water views the height buys you.

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Ten residences behind a gate, directly on the Gulf mid-island, scarcity by design. Homes run estate-scale (roughly 3,500 to 4,800 sq ft), sharing a pool and spa and a clubhouse outfitted with an owners' lounge, catering kitchen, fitness, and sauna.

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A boutique six-story building of just 22 residences on the sand mid-island, and one of the more flexible ones out here, small pets are welcome and monthly rentals are allowed. Two-bedroom homes open to Gulf-view balconies above a heated pool and a remodeled beachfront social room.

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Two towers, 88 residences, and a simple pitch: face west for Gulf sunsets or east for bay-and-golf sunrises. A beachfront pool and spa and a fitness center with sauna and steam keep it comfortable year-round.

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Thirty-six townhouse-style condos on the north-end beach, with two-story layouts, screened lanais, and paver paths that put you on the sand in under a minute. A Gulf-side heated pool and a clubhouse keep it low-key and walkable.

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A waterfront community of 134 residences across four mid-rise buildings, built for people who want a real amenity deck: private beach, a big heated pool and spa, four Har-Tru courts, a putting green, and a clubhouse with fitness.

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Classic two-tower Gulf-front living on the south end. The pool sits on the beach, there is tennis and pickleball, and a clubhouse and fitness center cover the rest, straightforward beachfront without the luxury markup.

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Ninety residences in a Gulf-front tower with an unusually convenient footprint: golf across the street and the island's main shopping plaza a short walk away. Most homes are two-bedroom split plans with floor-to-ceiling glass above a Gulf-side pool and spa.

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Eight units, right on the beach, with a pool-and-Gulf view from every one. An on-site manager runs daily, weekly, and monthly rentals, which makes it a favorite for owners who want the place to earn between stays.

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About as simple as beachfront ownership gets: eight units, some of the smallest footprints on the island, and private sand a few steps from every door. No resort machinery, no crowd, just the Gulf.

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A gated community of 28 condos at the far north end, with a large heated pool and a private path to the sand. Its flexible pet and rental rules make it easier to own on your own terms than most of the island.

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A 36-unit condo-hotel directly on the beach, where nearly every unit has a full kitchen and a water-facing balcony. An on-site office books nightly stays, making it one of the island's most flexible income properties.

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Eight Gulf-front residences, each a roomy three-bedroom with a screened balcony, two covered spaces, and water views. Small, quiet, and central, a getaway that does not ask much of you.

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A small Gulf-side resort community on the north end, sold turnkey-furnished in efficiency, one-, and two-bedroom layouts. A heated pool sits beside the private beach, joined by a putting green and shuffleboard, and nightly rentals with an on-site office make it an easy income buy.

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Three gated mid-rise buildings directly on the Gulf toward the south end, with just over 60 condos so it never feels dense. Private beach, a heated pool, kayak storage, and under-building parking, and, true to the name, the sunsets earn their keep.

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Fifteen residences right on the sand, from studios to two-bedrooms, sharing a heated beachside pool and an on-site rental office. Easy to own, easy to rent, a low-lift way into beachfront.

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Direct Gulf-front with a pool on the beach and not much else in the way, which is the point. For buyers who want walk-out sand and Gulf views without paying for services they will not use.

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Two elegant towers on the south-end beach with staffed, full-service living: 24-hour concierge, a heated pool and spa, fitness, and a social room with a catering kitchen. Beachfront for buyers who want the building to do the work.

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A classic Gulf-front building that keeps it uncomplicated: tennis and pickleball, a pool, a clubhouse, an outdoor kitchen, and covered parking. The straightforward Longboat beach lifestyle, done right.

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Eight residences mid-island, each a three-bedroom of roughly 3,260 sq ft with wraparound terraces and an enclosed two-car garage. You step out to a private beach with the island's shops and dining minutes away, intimate, but not isolated.

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Gulf-front with a genuine beach-club feel: a heated pool and spa on the sand, social spaces that lean toward a library-and-lounge vibe, a fitness room, sauna, and covered parking. Direct beach access with the amenities that matter and none of the high-rise scale.

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A smaller Gulf-front building for buyers who want intimacy over amenities-for-show. Heated pool, a clubhouse, a sauna, a grilling area, and a private walkway to the beach, the essentials, well kept.

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Gulf-front and resort-easy: a heated pool, beach access, grills, and tropical grounds built for casual stay-and-play rather than formal tower living. A relaxed way to own on the water.

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Exclusivity through smallness: Veinte keeps the neighbor count low and the water views big, with direct beach access, a Gulf-facing pool, on-site fitness, a court for tennis and pickleball, and a secure gated entry. For buyers who want quiet luxury with a light footprint.

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Gulf-front living for the racquet crowd: two Har-Tru courts that double for pickleball, a resort clubhouse with fitness and sauna, and a pool with a hot tub. Beach plus sport in one established address.

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Gulf-front luxury behind the Longboat Key Club gates, built around privacy: single-residence elevator entries, no walls shared between homes, and terraces wide enough to live on. The service level is the point, concierge, round-the-clock security, and a full amenity deck at a large scale.

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Estate-sized condominiums on the south-end beach with only two homes per floor, so every residence is a wrap-around end unit with its own elevator landing and a direct line to the private sand. Scarcity does the pricing here.

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Ownership with a five-star hotel attached: the residences sit within the St. Regis resort, so owners tap its restaurants, spa, pools, and saltwater lagoon while keeping a private clubhouse and beach club to themselves. Butler and concierge service come standard.

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An ultra-luxury Gulf-front address on a handful of beachfront acres near the south end, where the homes run estate-scale with private elevators and enclosed garages. Guard-gated and concierge-served, with density kept deliberately low.

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A rarefied Gulf-front community where a small number of homes share landscaped beachfront acreage. Residences are large, many with private elevators, sitting above their own garages, privacy and scale in equal measure.

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One of the newest boutique buildings on the Gulf, with full-width residences that pull in both Gulf and bay views. Wellness runs through the design, from filtered air and water to a spa, fitness center, and yoga studio.

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New, modern, and unapologetically high-end: Aria brings contemporary architecture and wide water views to the Gulf-front market for buyers who want current design over established prestige.

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A gated boutique building of just eleven residences with private-elevator entries and coastal-contemporary lines. The amenities sit right on the sand, a small, design-forward footprint for buyers who want new over nostalgic.

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A gated, two-tower beachfront community that trades on service and reputation: concierge, a guard gate, a beachfront clubhouse, a resort pool, and a fitness-and-spa package. It holds value about as well as anything on the island.

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A gated Gulf-front high-rise on the south end with mature grounds and a genuine tower lifestyle, from two-bedroom residences up to full penthouses. Established and dependable rather than brand-new.

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A large gated beachfront community that has historically allowed more lease flexibility than most Longboat luxury, and trades more often as a result. Full resort amenities with a friendlier price of entry.

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One of the island's most complete beachfront communities, spread across dozens of south-end acres minutes from St. Armands Circle. The amenity list runs deep, and the scale keeps pricing more attainable than the trophy towers.

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Two twelve-story towers on hundreds of feet of private beach, built for a social, active kind of ownership. A clubhouse, fitness center, pool, and Har-Tru courts anchor the community.

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A south-end Gulf-front building inside the Longboat Key Club environment, prized for lower density and generous floor plans. Guest suites make hosting easy, and the amenity set is quietly complete.

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A gated enclave in the Longboat Key Club area with layered, manned security and a beachfront amenity campus. It suits buyers who want privacy first and a full amenity set second.

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A Gulf-front community of furnished condos and one of the few places on Longboat that permits short vacation rentals, with an on-site rental office and full-time manager to run them. Beach, pool, courts, and cash flow in one address.

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An intimate Gulf-front community set right on a private beach mid-island, and one of the rare Longboat addresses that permits short-term rentals, so owners can hold a beach residence that also earns.

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A gated community on the sand at the southern tip, built around a distinctive oval tower on acreage, private beach and tiki huts on one side, a protected marina on the other. Boating and beach in a single, unusual package.

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A Gulf-front high-rise on the beach, not to be confused with the bayside Longboat Harbour boating community, offering direct beach access, a fitness center, and a clubhouse in a straightforward tower package.

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A true Gulf-to-Bay community: a clubhouse, pool, fitness center, and courts on one side, a bayside dock on the other. The rare dual-waterfront layout is the draw for buyers who refuse to choose between beach and boat.

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A sprawling Gulf-to-Bay community with the amenity depth to match: private beach, multiple pools, Har-Tru courts, a fitness center, clubhouse, and a fishing pier, all on low-density grounds. Resort energy without the resort density.

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Gulf-to-Bay with a casual streak: private beach access, a pool, and a bay-side fishing pier, wrapped in a relaxed setting. For buyers who want direct sand and an unfussy coastal pace.

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Gulf-to-Bay living with the boater in mind: community boat slips, private beach access, a pool, clubhouse, and fitness room. The marina side and the social side both pull their weight here.

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A Gulf-to-Bay community that gives you bay views up front and the private beach just across the road. Personal boat slips, tennis, pickleball, a clubhouse, and a pool make it a natural for buyers who want both boating and beach.

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A genuine Gulf-to-Bay community in the middle of the island. Bay-side homes get Sarasota Bay views, a day dock, boat slips, and a kayak launch; Gulf-side homes are steps from the private beach, and everyone shares the pool, courts, and clubhouse.

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Mid-island Gulf-to-Bay with a mid-rise on each side. Residents get private beach access, a heated pool, courts for tennis and pickleball, a clubhouse, and a bayside day dock with a fishing pier, both waterfronts, one community.

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A mid-island community of about 80 condos, duplexes, and villas that quietly does it all: two heated pools, a big clubhouse, and an owner's marina with leasable docks on the bay, plus a private beach with a pavilion directly across the road. Boating, beach, and social life at a sane price point.

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An amenity-rich, outdoors-first community with a private-beach twist: access runs through the Whitney Beach Conservancy, giving it a protected, uncrowded feel. Tennis, pickleball, shuffleboard, a resort pool, BBQ areas, and kayak launching keep residents busy.

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Gulf-to-Bay flexibility with a residential (not resort-hotel) feel: deeded beach access across the road, two pools, a fitness center with sauna, courts, a clubhouse, kayak storage, and walking trails. Built for buyers who want boating and beach in one address.

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A bayfront community organized around the water: community boat slips, a waterfront pool, and a fitness room overlooking Sarasota Bay. Residential and boating-focused on the south end.

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Estate-sized condominiums on Sarasota Bay at the north end, wrapped around a private protected harbor with deep-water slips for vessels up to about 70 feet. Serious dockage, with a bayfront pool, tennis, and fitness to match.

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An intimate bayfront community on the north end where every residence comes with a deeded slip in the deep-water marina, and the layouts are built to keep bay views in the main living space. For owners whose boat is part of the floor plan.

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A bayside boating community with its own docks and a private boat ramp, plus a heated pool, clubhouse, and tennis. Deeded beach access sits just across the road, boating first, beach a minute later.

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One of the island's established bay-side boating addresses: a large community of condominiums with slips for many boats and a bayfront clubhouse that actually gets used. Tennis, pickleball, and fitness fill out an active social scene.

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A boutique bayfront community of just nine units for buyers who want the water without the crowd. Boat slips and a dock, a community pool, and a court, small, quiet, and boating-ready.

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A tucked-away waterfront community of nine residences at the northern tip, with a waterside pool, a tennis court, and small docks for kayaks and boats. The beach waits at the end of the street and the north-end restaurants are a short walk.

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A gated tower community within Bay Isles, set between the Harbourside golf course and Sarasota Bay, 272 residences across six buildings, all wrapped in full-service, gated luxury with sweeping bay views.

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A gated bayfront community inside Bay Isles mixing townhomes and condos, and carrying one of the deepest amenity benches behind the gates. Pools, courts, a clubhouse, a kayak launch, and a bayfront walking path make it easy to never leave.

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Maintenance-free single-family homes inside the Bay Isles gates, looking out on Sarasota Bay, community lakes, or the golf course, some with private docks. Easy ownership with a full Beach Club membership attached.

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A gated pocket of custom single-family homes inside Bay Isles, each one different, set behind heavy landscaping beside a quiet lagoon. Ownership includes the Bay Isles Beach Club and optional Longboat Key Club membership.

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Custom single-family homes behind the Bay Isles gates, with sites on the Bay Isles Waterway, along the golf course, or over the lakes. Deeded Beach Club access and optional Longboat Key Club membership come with the address.

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A gated Bay Isles neighborhood of homes and maintenance-free villas with a pool, tennis, and a mix of bay and golf-course settings. It keeps a real neighborhood feel while sitting inside a full-service gate.

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A gated Bay Isles condominium community on the south end, built as three mid-rises with just four homes per floor and views of the bay, the harbor, or the golf course. Low density behind the gates.

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A gated enclave of freestanding, maintenance-free homes inside Bay Isles, spread over two quiet cul-de-sacs, with golf-course views in the smaller north section. Beach Club access comes with ownership.

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The canal-and-bayfront side of Bay Isles, built for boaters who want a secure, gated setting with real water access. Homes here range widely in scale and price, from villas to bayfront estates.

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Forty-two Spanish-style villas inside Bay Isles bordering the Harbourside golf course, with a community pool and spa and the Moorings marina within walking distance. The unusual part: owners hold the land under their villas, so several have added private pools.

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A boutique Bay Isles enclave of bayfront villas, each with a deep-water dock for boats up to about 30 feet. Pool, tennis, maintenance-free living, and Beach Club access, boating built into the address.

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A small, low-density Bay Isles enclave defined by golf-course views and a gated, upscale-residential calm. A community pool and Bay Isles Beach Club membership round it out.

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Gated Bay Isles villas, many backing directly onto the Harbourside golf course, with a community pool and maintenance-free living. A natural pick for golf-view buyers who want to be behind the Bay Isles gate.

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A small Bay Isles enclave positioned for daily convenience, steps from shopping, the library, tennis, and the Moorings marina. Gated living with everything close.

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A Bay Isles community built around greenery: a pool, a private park, and walking trails set in a lush residential setting. For buyers who want the gate and the quiet, with nature at the door.

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A south-end canal neighborhood where the water is the whole point: most homes sit on deep-water canals with private docks, and deeded beach access plus an optional Longboat Key Club membership sit just across the street. A boater's address first, a house second.

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A north-end bayside enclave of 82 homes built along some of the island's widest deep-water canals, with bridge-free runs to Sarasota Bay and the Intracoastal, and deeded beach access across Gulf of Mexico Drive. Serious boating with the sand still in reach.

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A north-end neighborhood that runs from bayside canals all the way to the Gulf beach, with everything from custom waterfront estates to old-Florida cottages. Many homes have private docks; some Gulf-side homes simply have the beach out back.

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A gated cluster of custom waterfront estates on a private peninsula, where every home has a water view and downtown Sarasota is minutes away. Privacy and proximity in the same breath, and priced accordingly.

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Arguably the most exclusive address on Longboat: a private enclave of eight estate homes set directly on the beach, with the Islandside golf course across the street. Ultra-rare, and it prices like it.

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A private island of about 38 acres in the Intracoastal off the north tip, reachable only by boat, holding a handful of elevated homes on large lots with private docks. Genuine seclusion, minutes from Longboat's marinas and restaurants.

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A gated, low-density pocket known for some of the largest home lots on Longboat Key. For buyers who want waterfront land and real privacy rather than a community amenity package.

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A north-end waterfront neighborhood where most homes line deep-water canals with no fixed bridges between you and the Intracoastal and bay. The housing stock runs from established island homes to full rebuilds.

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A small waterfront neighborhood with a hidden-gem reputation and rarely much for sale. The appeal is simple: a quieter setting and canal-style living for buyers willing to wait for the right house.

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A small bay-side canal enclave built on oversized lots with private deep-water docks, and no gates or shared amenities to speak of. The draw is exactly that: privacy, elbow room, and serious dockage.

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A secluded north-end neighborhood along Millar Bay, reached by a winding, mangrove-lined road, where custom homes sit on generous tropical lots with deep-water docks and bay views. Tennis and pickleball are close by. Privacy is the product.

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A gated enclave of just eight homes on the north end, each with a deeded deep-water dock and a bridge-free path to the Intracoastal and Gulf. A community pool and deeded beach access complete a boater's dream at small scale.

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Twelve custom homes behind a gate among lush landscaping at the island's northern tip, sharing community docks, a pool, and a court. Longbeach Village and the Gulf beach are both an easy walk.

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The island's original settlement at the north tip, roughly 290 homes ranging from old-Florida cottages to renovated coastal houses, with no HOA and no gates. Bayfront restaurants and a genuine village feel are the whole appeal.

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A quiet residential neighborhood with a boating bent and an easy, everyday island pace. For buyers who value privacy and livability over amenities and gates.

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Sports-first living inside the Cedars Tennis Resort on the north end: Har-Tru tennis and pickleball, a Junior Olympic pool, fitness, and a clubhouse. Built for buyers who want an active, racquet-centric lifestyle.

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A boutique north-end enclave with maintenance-free lawns and a neighborhood pool, plus beach access and the north-end's restaurants and shops close at hand. Low-friction ownership in a quiet corner.

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A tiny, pet-friendly building of twelve condos tucked into the island, with little in the way of amenities and the beach a short walk across the road. Simple island living, with Publix, the library, and the Bayfront Park courts nearby.

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A relaxed residential condo community with two heated pools, a clubhouse, and on-site management, easy, low-maintenance ownership without paying for a mega-tower's overhead. For buyers who want community feel over resort scale.

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A 55+ community on the bay side built around a private deep-water marina, with a genuinely busy social calendar and a rare blend of bay, beach, and neighbor-to-neighbor living. Deeded beach access sits across the road.

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