Longboat Key is a ten-mile barrier island split between Manatee County to the north and Sarasota County to the south, and it represents the Gulf Coast luxury market at its most complete. With a median home price of $1.185 million and an average sale price of $1.64 million, with 234 condominiums currently on the market ranging from $43,500 to $13 million, Longboat Key has both the price point breadth and the amenity ecosystem to serve the full spectrum of luxury buyers.
The island’s defining feature is the Longboat Key Club — a 410-acre resort with 45 holes of championship golf, 20 Har-Tru tennis courts, a 291-slip full-service marina, a full spa, a fitness center, and six dining venues ranging from casual to fine dining. For buyers who specifically want resort amenity access from their home rather than from a hotel, Longboat Key delivers what few barrier islands can match: a self-contained luxury lifestyle accessible from a primary or vacation residence.
Barrett Henry covers the Longboat Key market as part of his broader Manatee County practice. This guide covers the key market segments, neighborhoods, amenities, and considerations that define the Longboat Key buying decision.
Longboat Key Real Estate Market Overview (2026)
The Longboat Key market in early 2026 shows the luxury market characteristics common to this price range: properties are sitting longer on the market (average 89 days), sellers are more flexible on price than during the 2022 peak, and cash buyers dominate the transaction profile. With 234 condominiums and a range of single-family properties on the market, buyers have real options and meaningful negotiating leverage.
The condominium market here is heavily affected by Florida’s 2022 structural inspection legislation. Condos in buildings three stories or taller that are over 30 years old are required to undergo milestone inspections and complete reserve studies. For Longboat Key, where many of the most desirable condo buildings were constructed in the 1970s and 1980s, this legislation has created a complex situation: some buildings are well-funded and have completed their inspections without surprises; others have delivered assessment notices to owners as reserve shortfalls become clear.
Buyers of any Longboat Key condominium should specifically request the most recent milestone inspection report, reserve study, reserve fund balance, and any pending or recently levied special assessments before making an offer. This is not optional due diligence — it is the document set that determines whether the condo association’s financial health supports the purchase price you are considering.
The single-family market on Longboat Key is dominated by Gulf-front, bayfront, and canal-front properties, plus some interior lots. Single-family pricing reflects the scarcity of land on a barrier island — there is no meaningful new single-family construction on the island, and the supply is essentially fixed. This makes Longboat Key’s single-family market fundamentally different from the new-construction-driven markets of Lakewood Ranch and Parrish.
Longboat Key Neighborhoods and Condo Communities
The Promenade is a gated luxury Gulf-front community with 112 residences on 6.5 acres. Built in 1985, floor plans range from 1,585 to 4,172 square feet. The Promenade offers the Gulf of Mexico from your door — it is one of the most desirable Gulf-front condominium addresses on the island for buyers who want direct beach access combined with resort-quality shared amenities.
The Pierre is another prestige address — 66 luxurious units built in 1990 with floor plans from 2,400 to 3,600 square feet. The Pierre’s larger floor plans cater to buyers who want condo living without the space compromise that many island condominiums require.
Inn on the Beach offers condominiums in the $1 million to $1.4 million range in an oceanfront location — a somewhat more accessible entry to Gulf-front living than the premier Gulf-front communities at higher price points.
The Resort at Longboat Key Club is a 410-to-440-acre resort offering 222 condominium suites with Gulf of Mexico and Sarasota Bay views. This is the most complete resort-residential experience on the island — owners have access to the full Longboat Key Club amenity package including the golf courses, tennis facility, marina, spa, and dining, while the property’s management program allows owners to participate in hotel-style rental income when not in residence.
At the more affordable end of the condo market, units in older non-Gulf-front buildings provide access to the island at price points starting in the mid-hundreds of thousands — though these properties require the most careful evaluation of the building’s structural inspection status and HOA reserve funding given their age.
The Longboat Key Club: Golf, Tennis, Marina, and Resort Life
The Longboat Key Club is the anchor amenity for the island’s real estate market and the reason many buyers choose Longboat Key over other Gulf Coast options. The 45-hole championship golf complex — comprising the Harbourside and Islandside courses — provides one of the most complete resort golf experiences in Florida without leaving the island. The 20 Har-Tru tennis courts form one of the largest resort tennis facilities in the southeast, and the pickleball courts have been expanded in recent years to reflect the sport’s explosive growth.
The 291-slip marina accommodates vessels up to 90 feet and provides dockage, fuel, pump-out, and full marine services — making Longboat Key one of the few Gulf Coast barrier islands where serious boaters can dock their vessels from their residential address. Bay access from the marina connects to the Sarasota Bay intracoastal system and the Gulf beyond through New Pass at the island’s north end.
For buyers who are not members of the Club, the question of membership cost and availability is an important part of the acquisition evaluation. Club membership is distinct from property ownership and carries its own initiation fees and annual dues. Buyers who specifically want Club access should confirm membership availability before committing to a purchase, as membership capacity is limited.
Restaurants on Longboat Key
Longboat Key has a dining scene befitting a luxury resort island — fine dining, polished casual waterfront, and genuine independent concepts that go well beyond what you typically find on a small barrier island.
Chart House delivers Gulf and Sarasota Bay terrace dining with a menu anchored by Macadamia Crusted Mahi, Slow-Roasted Prime Rib, and award-winning seafood presentations. This is consistently one of the best fine dining experiences available without leaving the island. Shore Longboat Key is the sophisticated contemporary option — Lobster Risotto, Wagyu Beef Burger, and a modern coastal cuisine that has made it a go-to for residents who want fine dining without the Chart House formality.
Dry Dock Waterfront Grill offers “polished casual” dining overlooking Sarasota Bay — Coconut Shrimp, Grouper Sandwich, and fresh seafood in a setting that captures the essence of casual Florida waterfront dining. Mar Vista Dockside Restaurant and Pub features locally sourced ingredients, a private dock for boat arrivals, and an outdoor deck with tropical landscaping and bay views. Ventura’s Italian Kitchen and Wine Bar brings family-owned Italian — homemade dishes, hand-tossed pizzas, and waterfront al fresco dining — to the island mix.
The Longboat Key Club’s six dining venues add another layer, ranging from casual poolside and golf course dining to more formal options within the resort. For residents, the combination of Club dining and the island’s independent restaurant scene means most meals can be taken on Longboat Key without requiring a trip to mainland Sarasota or Bradenton.
Parks and Beaches on Longboat Key
Longboat Key has 10 miles of award-winning Gulf of Mexico beaches accessible via 12 public access points along Gulf of Mexico Drive. The beaches here are significantly less crowded than Anna Maria Island’s beaches during peak season — a reflection of the island’s lower residential density, fewer daytrippers, and the absence of the public beach infrastructure (lifeguards, concessions, parking) that draws the broadest spectrum of beach visitors.
Bayfront Park at 4052 Gulf of Mexico Drive offers tennis and pickleball courts, basketball courts, Sarasota Bay views, and recreational facilities — the primary community park serving residents who want active recreation beyond the Club. Quick Point Nature Preserve features wooden boardwalks through mangroves, tidal ponds, and salt marshes with designated fishing areas — one of the most distinctive natural environments accessible on the island. Joan M. Durante Park at 5500 Gulf of Mexico Drive is a coastal hammock forest reclaimed from development, featuring native plants and a walking environment that provides a genuine Florida natural experience.
Longboat Key’s beaches are largely undeveloped — most access points have portable facilities only. Dogs are not permitted on the beaches. This limited infrastructure is by design and contributes to the island’s quiet, uncrowded character that residents specifically value.
Flood Risk and Insurance on Longboat Key
All residents on Longboat Key are in Level A of Manatee County’s hurricane evacuation zone — the highest-priority evacuation category for life-threatening storm surge risk. Most structures east of Gulf of Mexico Drive are in FEMA flood Zone AE, with a Base Flood Elevation of 10 feet above sea level required for new structures. Coastal high-hazard area design criteria require wind load resistance of 150 mph.
Standard homeowner’s insurance policies do not cover flood or storm surge damage. Flood insurance through NFIP or the private flood market is required for mortgaged properties and is strongly advisable for cash buyers. Windstorm coverage — particularly important for Gulf Coast properties — may be handled through Citizens Property Insurance or a private carrier under a separate policy from the standard homeowner’s insurance. Hurricane deductibles typically increase to 2 percent of insured value during a hurricane watch or warning period.
Longboat Key participates in FEMA’s Community Rating System, which provides flood insurance premium discounts to property owners based on the town’s flood mitigation measures. As of late 2025, the town was still navigating insurance and FEMA reimbursements from the 2024 hurricane season. See our Florida flood zones guide for full context on coastal zone designations and insurance requirements for barrier island properties.
Schools on Longboat Key
Longboat Key sits on the border of Manatee and Sarasota Counties, and school district assignment depends on the specific property’s location on the island. Properties in the Manatee County portion are served by the Manatee County School District (B grade, 2025). Properties in the Sarasota County portion are served by the Sarasota County School District. Buyers with school-age children should verify the specific school zone assignment for any property under consideration and confirm school quality for the assigned schools.
In practice, Longboat Key’s primary-residence population skews significantly toward empty nesters, retirees, and seasonal residents — school district quality is less often a primary driver of the purchase decision here than in family-oriented markets like Lakewood Ranch or Parrish. For the relatively small number of families with school-age children who choose Longboat Key as a primary residence, both the Manatee and Sarasota County school systems offer solid options.
Longboat Key vs. Anna Maria Island: Choosing Between the Two
Buyers evaluating Gulf Coast barrier island options in the area consistently face the comparison between Longboat Key and Anna Maria Island. The two islands share the same Gulf Coast, but serve meaningfully different buyer profiles.
Anna Maria Island is more casual, more family-oriented, more community-focused, and more active in its short-term rental market. It has a lower median price range and more investor activity. The Pine Avenue village character, the accessible public beach infrastructure, and the island’s social fabric appeal to buyers who want genuine beach community living.
Longboat Key is more private, more formal, more resort-oriented, and more focused on the amenity ecosystem of the Longboat Key Club. The buyer profile is predominantly retirees, empty nesters, and luxury second-home buyers. The island’s uncrowded beaches, its private marina and golf facility, and its more exclusive character are specifically valued by buyers who are willing to pay for what the island offers.
Neither is better than the other — they serve different needs. The right choice depends entirely on what you value most in a Gulf Coast residence: Anna Maria Island for community and casual energy; Longboat Key for privacy and resort completeness.
Frequently Asked Questions About Longboat Key FL
What is the median home price on Longboat Key?
$1.185 million median (January 2026), with an average sale price of $1.64 million. Condominiums range from $43,500 to over $13 million with 234 currently active on the market. Average days on market is 89 days.
Is Longboat Key in Manatee County?
Partially — Longboat Key straddles the Manatee/Sarasota county line. The northern portion of the island is in Manatee County; the southern portion is in Sarasota County. Property tax rates, school district assignments, and some regulatory jurisdictions differ based on the specific property’s county location.
What is the Longboat Key Club?
The Longboat Key Club is a 410-acre resort and private club featuring 45 holes of championship golf, 20 Har-Tru tennis courts, a 291-slip full-service marina, spa, fitness center, and six dining venues. Membership is separate from property ownership and carries initiation fees and annual dues. It is the anchor amenity that defines the island’s luxury lifestyle proposition.
Is Longboat Key in a flood zone?
Yes. All residents are in Level A of the hurricane evacuation zone — the highest-priority category. Most structures east of Gulf of Mexico Drive are in FEMA flood Zone AE with a 10-foot Base Flood Elevation requirement. Flood insurance through NFIP or private market is required for mortgaged properties and strongly advisable for cash buyers.
What condo buildings should I know about on Longboat Key?
The Promenade (112 Gulf-front units, 1,585-4,172 sq ft), The Pierre (66 units, 2,400-3,600 sq ft), Inn on the Beach ($1M-$1.4M oceanfront), and The Resort at Longboat Key Club (222 suites with full Club access) are the notable communities. For any Longboat Key condo purchase, requesting the milestone inspection report, reserve study, and HOA financials is essential due diligence under Florida’s 2022 structural inspection legislation.
How does Longboat Key compare to Anna Maria Island?
Longboat Key is more private, formal, and resort-oriented. Anna Maria Island is more casual, community-focused, and active in the STR market. Longboat Key has the Club’s 45-hole golf, 291-slip marina, and 20 tennis courts. Anna Maria Island has the Pine Avenue village character, Manatee Beach public infrastructure, and Holmes Beach’s dining scene. Choose based on which lifestyle matches your actual priorities.
What are the best restaurants on Longboat Key?
Chart House (fine dining, Gulf and bay terrace), Shore Longboat Key (contemporary luxury), Dry Dock Waterfront Grill (polished casual, Sarasota Bay views), Mar Vista Dockside (locally sourced, boat arrival dock), and Ventura’s Italian Kitchen and Wine Bar (family-owned Italian, al fresco waterfront). The Longboat Key Club’s six dining venues add additional options for Club members.
Dining on Longboat Key: The Restaurant Scene
Longboat Key’s dining scene reflects its price point — upscale, water-oriented, and serious about food in a way that casual beach towns are not. The established restaurants that define the island dining experience:
Chart House: Gulf of Mexico and Sarasota Bay terrace views with an award-winning menu anchored by the Macadamia Crusted Mahi and Slow-Roasted Prime Rib. Chart House is the special-occasion restaurant that residents use for celebrations and that visitors make reservations for before they arrive.
Shore Longboat Key: Sophisticated upscale contemporary cuisine with Gulf views — Lobster Risotto, Wagyu Beef Burger, and a culinary ambition that matches the island’s luxury property market. Shore is where the serious food-focused buyer will find Longboat Key’s dining credibility.
Dry Dock Waterfront Grill: “Polished casual” overlooking Sarasota Bay, with signature Coconut Shrimp and Grouper Sandwich drawing consistently positive reviews. Dry Dock is the waterfront lunch and casual dinner destination that handles volume without sacrificing quality.
Mar Vista Dockside Restaurant & Pub: The local institution — a mix of seafood classics and inventive dishes with locally sourced ingredients, served on an outdoor deck with tropical landscaping and bay views. Mar Vista accepts boats at its dock, making it one of the few true dockside-arrival dining experiences on the key.
Ventura’s Italian Kitchen & Wine Bar: Family-owned, with homemade Italian and hand-tossed pizzas in a waterfront al fresco setting. Ventura’s fills the neighborhood restaurant role — the place you walk to on a Tuesday night when you don’t want a special occasion, just a good meal.
Longboat Key’s Parks and Nature
Longboat Key’s parks provide a counterpoint to the resort and condo environment — natural and recreational spaces that give residents and visitors access to the island’s quieter character:
Bayfront Park (4052 Gulf of Mexico Drive): The island’s primary active recreation facility, with tennis courts, pickleball courts, and basketball courts overlooking Sarasota Bay. The combination of water views and competitive courts makes Bayfront Park the gathering point for the island’s active-adult athletic community.
Quick Point Nature Preserve: Wooden boardwalks winding through mangroves, tidal ponds, and salt marshes at the southern tip of the key, with designated fishing areas. Quick Point is the island’s nature destination for residents who want the quiet marsh ecology rather than the Gulf beach experience.
Joan M. Durante Park (5500 Gulf of Mexico Drive): A coastal hammock forest reclaimed from development, planted with native species, providing shaded walking and a visual break from the built environment that is increasingly rare on developed barrier islands.
Bicentennial Park: Dog-friendly park — relevant for the significant portion of Longboat Key residents who bring dogs to the island, since the Gulf beaches themselves do not allow dogs.
Notable Condo Buildings on Longboat Key
The condominium market is the primary real estate story on Longboat Key — understanding the individual buildings helps buyers target properties that match their lifestyle and budget:
The Promenade: A luxury gated Gulf-front community built in 1985, with 112 residences across 6.5 acres of Gulf of Mexico frontage. Floor plans range from 1,585 to 4,172 square feet — one of the island’s larger-unit Gulf-front buildings. The combination of scale, established age, and Gulf frontage positions The Promenade as one of the key’s most sought-after addresses.
The Pierre: Built in 1990, with 66 luxurious units ranging from 2,400 to 3,600 square feet. At these sizes, The Pierre units function more like private residences than typical condominium units — the 2,400-square-foot floor means a buyer gets a genuinely spacious home in a building with elevator access and shared amenities.
The Resort at Longboat Key Club: A 410-to-440-acre resort with 222 condominium suites and the Longboat Key Club’s full amenity suite — 45 holes of championship golf, a 291-slip marina, 20 Har-Tru tennis courts, spa, fitness center, and 6 dining venues from casual to fine dining. Buyers purchasing here are buying into one of the most complete resort-community platforms on Florida’s Gulf Coast.
Insurance and Hurricane Exposure: What Buyers Must Know
Longboat Key is an exposed barrier island in the path of Gulf of Mexico tropical systems — a fact that the island’s luxury market has historically priced in partially but not completely. Buyers in the $1 million-and-above range should understand the insurance structure before closing:
Evacuation Zone: The entire Town of Longboat Key is in Level A — the highest-priority evacuation zone in Manatee and Sarasota Counties. This means that when a major hurricane threatens the Gulf Coast, Longboat Key residents are among the first asked to evacuate. Most full-time residents have an established evacuation plan; seasonal residents should develop one before they need it.
Flood zones: Most structures on the island east of Gulf of Mexico Drive are in Zone AE, which maps the base flood elevation at approximately 10 feet above sea level. New construction must be built to meet this elevation requirement and must also meet 150-mile-per-hour wind load design criteria for the coastal high-hazard area designation.
Hurricane deductible: During any hurricane watch or warning, windstorm deductibles escalate to 2 percent of the insured value of the structure. On a $1.5 million condo, that is a $30,000 out-of-pocket deductible before insurance covers wind damage. Buyers need to plan for this exposure as part of the total cost of island ownership.
Insurance structure: Standard homeowners insurance policies do not cover flood damage — a separate NFIP or private flood policy is required. Wind coverage often comes through Citizens Property Insurance Corporation or a specialty coastal carrier. The Town of Longboat Key participates in the FEMA Community Rating System (CRS), which provides flood insurance premium discounts to compliant property owners. Buyers should work with an independent insurance agent who specializes in Florida coastal properties to understand the full insurance cost before closing on any Longboat Key property.
{ “@context”: “https://schema.org”, “@type”: “FAQPage”, “mainEntity”: [ { “@type”: “Question”, “name”: “What is the median home price on Longboat Key?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “$1.185 million median (January 2026) with an average sale price of $1.64 million. Condominiums range from $43,500 to over $13 million. Average days on market is 89 days.” } }, { “@type”: “Question”, “name”: “What is the Longboat Key Club?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “A 410-acre resort and private club featuring 45 holes of championship golf, 20 Har-Tru tennis courts, a 291-slip marina, spa, fitness center, and six dining venues. Membership is separate from property ownership and requires initiation fees and annual dues.” } }, { “@type”: “Question”, “name”: “Is Longboat Key in a flood zone?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “Yes. All residents are in Level A of the hurricane evacuation zone — highest priority. Most structures east of Gulf of Mexico Drive are in FEMA flood Zone AE with a 10-foot Base Flood Elevation requirement. Flood insurance is required for all mortgaged properties.” } }, { “@type”: “Question”, “name”: “Is Longboat Key in Manatee County?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “Partially — the northern portion is in Manatee County, the southern portion in Sarasota County. Property tax rates, school district assignments, and some regulatory jurisdictions differ based on the specific property’s county location.” } }, { “@type”: “Question”, “name”: “How does Longboat Key compare to Anna Maria Island?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “Longboat Key is more private, formal, and resort-oriented with the Club’s golf, marina, and tennis. Anna Maria Island is more casual, community-focused, and active in the STR market. Choose based on which lifestyle matches your actual priorities.” } }, { “@type”: “Question”, “name”: “What condo buildings are notable on Longboat Key?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “The Promenade (112 Gulf-front units), The Pierre (66 luxury units), Inn on the Beach ($1M-$1.4M oceanfront), and The Resort at Longboat Key Club (222 suites with full Club access). Always request the milestone inspection report, reserve study, and HOA financials for any condo purchase.” } }, { “@type”: “Question”, “name”: “What are the best restaurants on Longboat Key?”, “acceptedAnswer”: { “@type”: “Answer”, “text”: “Chart House (fine dining, Gulf and bay views), Shore Longboat Key (contemporary luxury), Dry Dock Waterfront Grill (polished casual, bay views), Mar Vista Dockside (locally sourced, boat dock), and Ventura’s Italian Kitchen (family-owned, al fresco waterfront).” } } ] }