Located within the gated Queens Harbour enclave in Bay Isles, this direct bayfront residence offers a well-designed courtyard-style floor plan with water views, flexible living spaces, and a private dock--set on a quiet cul-de-sac in one of Longboat Key's most established communities. Spanning approximately 3,470 square feet of living space across two levels, the home features four bedrooms, four full baths, and one half bath, with a layout that prioritizes privacy and functionality. The first floor hosts three en-suite guest bedrooms, a dedicated office, and the main living areas, while the entire second floor is reserved for the primary suite, creating a true owner's retreat. The main level welcomes you with an open living and dining arrangement highlighted by cathedral ceilings, tile flooring, and walls of sliding glass doors that open to the bayfront patio. This seamless indoor-outdoor connection frames tranquil water views, ideal for relaxing or entertaining. The formal dining space also enjoys bayfront exposure and flows naturally into the kitchen. The kitchen is thoughtfully positioned for daily living and gatherings, offering solid wood cabinetry, stone countertops, a center island, breakfast bar seating, pantry storage, and a full suite of stainless-steel appliances. Adjacent family and living spaces enhance the home's livability while maintaining clear sightlines to the water. Two of the first-floor guest bedrooms include en-suite baths, while a third guest suite--a private cabana across the pool courtyard--offers flexibility for visiting family or multi-generational living. The office is also located on the first level, providing the ideal amount of separation. Upstairs, the primary suite occupies the entire second floor, offering privacy and elevated views. This retreat features a spacious bedroom, walk-in closet, and a well-appointed en-suite bath with dual sinks, soaking tub, separate shower, and private water closet. Outdoor amenities include a private pool courtyard, open dock with direct bay frontage, providing access for boating and paddle sports. A new tile roof was installed in 2023, and the property includes a two-car garage. Queens Harbour residents enjoy a maintenance-free lifestyle with 24-hour guard-gated security, community heated pool and spa. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front pavilions, grilling areas, and pristine beaches just minutes away. Perfectly positioned behind the gates of Bay Isles, this residence is close to Harbourside Golf & Marina, the Longboat Key Club, and island dining. St. Armands Circle, Lido Beach, and downtown Sarasota are all within easy reach, providing access to shopping, waterfront restaurants, cultural venues, and year-round events. A well-located bayfront opportunity offering space, privacy, and a flexible floor plan in one of Longboat Key's most desirable communities.
Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
01
Exterior & Building
Stories
2
Garage Spaces
2.0
Water Source
Public
Utilities
Cable Available, Electricity Connected
Pool
Deck, Heated, In Ground, Outside Bath Access
Roof
Tile
Lot Features
Cul-De-Sac, Flood Zone, In County, Landscaped, Near Golf Course, Near Marina
Parking
Driveway, Garage Door Opener
Heat Type
Central, Electric, Zoned
Air Conditioning
Central Air, Zoned
Sewer
Public Sewer
Substructure
Stem Wall
HOA Amenities
Fence Restrictions, Gated, Maintenance, Pool, Recreation Facilities, Security, Vehicle Restrictions
Security Features
Gated Community, Secured Garage/Parking
Other Exterior Features
Courtyard, French Doors, Lighting, Private Entrance, Private Yard, Sliding Doors
01
Lot & Area
Status
For Sale
Living Area
3,470 Sq.Ft.
Total Area
4,686 Sq.Ft.
Lot Size
0.3 Acres
MLS® ID
A4681540
Type
Residential
Year Built
2000
Neighborhood
Longboat Key
Architecture Styles
Courtyard, Custom
Water Frontage
Bay/Harbor
View Description
Pool,Water
01
Finance
Sales Price
$2,895,000
Real Estate Taxes
$24,368/yr
HOA Fees
$1,113/mo
Zoning
PD
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Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.
Gorgeous white sand beaches run for 12 miles along Longboat Key’s enchanting coastline.
Longboat Key, FL -- At a Glance
Population
7,512
Median Age
71.5 years
ZIP Code
34228
Avg. Individual Income
$138,251
Listing Agent
Roger Pettingell
Rental Policy
30-day minimum (no STR)
Longboat Key Zone Guide -- South vs. North
Zone
Vibe
Property Type
Key Communities
Price Range
South Key
Resort, Golf Club, exclusive gated
St. Regis Residences, Country Club Shores
The St. Regis Longboat Key, Bay Isles, Country Club Shores
[INSERT: current South Key range]
Mid-Key
Panoramic Gulf views, high-rise
Luxury condos and co-ops
Water Club, Promenade, Grand Bay, L'Ambiance
[INSERT: current Mid-Key range]
North Key
Old Florida charm, low-rise, private
Private estates, low-rise condos
The Village, Whitney Beach area, Queen's Harbor
[INSERT: current North Key range]
Price ranges updated from active MLS. Verify current figures with Roger Pettingell. MLS data
Looking for a Longboat Key Realtor?
Roger Pettingell has more Longboat Key closed sales than any other individual agent in Sarasota. He knows every zone, every building, and every canal on this island.
Who is the best real estate agent on Longboat Key?
Roger Pettingell is consistently ranked the top-producing individual agent on Longboat Key, with over $200 million in closed sales volume and decades of experience representing buyers and sellers across every zone of the island. He has sold more homes on Longboat Key than any other agent and knows the specific attributes of each community -- from the South Key gated estates near the St. Regis to the high-rise condos along Mid-Key and the Old Florida private estates on the North End. For buyers, he provides off-market access. For sellers, he brings the buyer network that moves luxury property at full price.
Is Longboat Key a good place to buy real estate?
Longboat Key is one of the most consistently desirable barrier islands in Florida for luxury real estate investment. Its 30-day minimum rental policy protects property values and neighborhood character, making it ideal for end-users, snowbirds, and buyers who prioritize equity appreciation over short-term rental income. The island's limited land supply, Gulf-front positioning, and access to Sarasota's arts and cultural amenities create sustained demand. The St. Regis resort presence on the south end has further elevated the island's profile for ultra-luxury buyers.
What is the difference between North and South Longboat Key?
South Longboat Key (the gated "The Gates" area) is characterized by resort-adjacent exclusivity -- the St. Regis Longboat Key, Country Club Shores, and Bay Isles are concentrated here, offering golf club access and the highest price per square foot on the island. Mid-Key features panoramic Gulf-view high-rises including Water Club, Grand Bay, and L'Ambiance. North Longboat Key (The Village) has an Old Florida atmosphere with low-rise estates and private residences, attracting buyers who prefer a quieter, less resort-driven lifestyle at slightly lower price points than the south end.
What are the rental rules on Longboat Key?
Longboat Key enforces a 30-day minimum rental policy, which prohibits short-term rentals (Airbnb, VRBO, or weekly rentals) throughout the island. This ordinance is one of the defining factors that separates Longboat Key from Siesta Key, which allows weekly and daily rentals. The 30-day minimum makes Longboat Key more attractive to buyers focused on a quiet residential experience and long-term appreciation rather than rental cash flow.
Where is Longboat Key located?
Longboat Key is a barrier island located west of Sarasota, Florida, in Sarasota County. It stretches 12 miles along the Gulf of Mexico, connected to the mainland via bridges. The island runs from Sarasota Bay on the east to the Gulf on the west, with Sarasota directly to the south and Manatee County at the north end. ZIP code is 34228. It is approximately 10 minutes from downtown Sarasota by car.
How far is Longboat Key from Siesta Key?
Longboat Key and Siesta Key are separated by approximately 15-20 minutes of driving time (around 12 miles), passing through downtown Sarasota. They are not directly connected -- you travel via the mainland. Despite being neighboring barrier islands in the Sarasota area, they have distinctly different characters: Longboat Key is quieter, more exclusive, and resort-adjacent, while Siesta Key is more tourist-oriented with weekly rental activity and the famous white-quartz sand beach that draws significant seasonal traffic.
Welcome to Longboat Key
Idyllic island community with Gulf and Sarasota Bay views
Longboat Key (34228) is a waterfront community on a barrier island between the Gulf of Mexico and Sarasota Bay. Gorgeous white sand beaches run for 11 miles along the coastline.
However, Longboat Key is not a single neighborhood; it is a diverse collection of lifestyles. Divided by man-made canals and defined by its proximity to either the Gulf (Beach) or the Bay (Boating), choosing the right "Zone" is your first step.
The Longboat Key Lifestyle Map
Before you explore the neighborhoods below, decide which "Zone" fits your vision.
Zone
The Vibe
Real Estate Type
South Key (The Gates)
Resort & Golf Club
The St. Regis / Country Club Shores
Mid-Key
Panoramic Views
High-Rise Condos (Water Club, Promenade)
North Key (The Village)
Old Florida Charm
Low-Rise / Private Estates
Dining, Entertainment & Shopping
Longboat Key is home to a fantastic array of restaurants that combine sublime cuisine with mesmerizing waterfront views.
The Shore: Serves seafood specialties such as Key West shrimp and scallop risotto. The Drydock Waterfront Grill: Overlooking the marina, this is one of the 100 best al fresco dining experiences in the US. Chart House: A refined steakhouse with a terrace perched above the Gulf waters.
Neighborhood Video Tours
Queen's Harbor
Grand Bay
Water Club
Promenade
Beachplace
L'Ambiance
Country Club Shores
Bay Isles Harbor
Ready to Tour Longboat Key?
Roger Pettingell knows every building and every canal. Schedule a private boat or home tour today.
Longboat Key, FL -- At a Glance
Population
7,512
Median Age
71.5 years
ZIP Code
34228
Avg. Individual Income
$138,251
Listing Agent
Roger Pettingell
Rental Policy
30-day minimum (no STR)
Longboat Key Zone Guide -- South vs. North
Zone
Vibe
Property Type
Key Communities
Price Range
South Key
Resort, Golf Club, exclusive gated
St. Regis Residences, Country Club Shores
The St. Regis Longboat Key, Bay Isles, Country Club Shores
[INSERT: current South Key range]
Mid-Key
Panoramic Gulf views, high-rise
Luxury condos and co-ops
Water Club, Promenade, Grand Bay, L'Ambiance
[INSERT: current Mid-Key range]
North Key
Old Florida charm, low-rise, private
Private estates, low-rise condos
The Village, Whitney Beach area, Queen's Harbor
[INSERT: current North Key range]
Price ranges updated from active MLS. Verify current figures with Roger Pettingell. MLS data
Looking for a Longboat Key Realtor?
Roger Pettingell has more Longboat Key closed sales than any other individual agent in Sarasota. He knows every zone, every building, and every canal on this island.
Contact Roger Pettingell
Explore Sarasota's Barrier Islands
Bird Key
Siesta Key
Lido Key Beach
Casey Key
Longboat Key vs. Siesta Key
Living in Sarasota vs. Longboat Key
Best Sarasota Neighborhoods for Retirees
Active Longboat Key Listings
Who is the best real estate agent on Longboat Key?
Roger Pettingell is consistently ranked the top-producing individual agent on Longboat Key, with over $200 million in closed sales volume and decades of experience representing buyers and sellers across every zone of the island. He has sold more homes on Longboat Key than any other agent and knows the specific attributes of each community -- from the South Key gated estates near the St. Regis to the high-rise condos along Mid-Key and the Old Florida private estates on the North End. For buyers, he provides off-market access. For sellers, he brings the buyer network that moves luxury property at full price.
Is Longboat Key a good place to buy real estate?
Longboat Key is one of the most consistently desirable barrier islands in Florida for luxury real estate investment. Its 30-day minimum rental policy protects property values and neighborhood character, making it ideal for end-users, snowbirds, and buyers who prioritize equity appreciation over short-term rental income. The island's limited land supply, Gulf-front positioning, and access to Sarasota's arts and cultural amenities create sustained demand. The St. Regis resort presence on the south end has further elevated the island's profile for ultra-luxury buyers.
What is the difference between North and South Longboat Key?
South Longboat Key (the gated "The Gates" area) is characterized by resort-adjacent exclusivity -- the St. Regis Longboat Key, Country Club Shores, and Bay Isles are concentrated here, offering golf club access and the highest price per square foot on the island. Mid-Key features panoramic Gulf-view high-rises including Water Club, Grand Bay, and L'Ambiance. North Longboat Key (The Village) has an Old Florida atmosphere with low-rise estates and private residences, attracting buyers who prefer a quieter, less resort-driven lifestyle at slightly lower price points than the south end.
What are the rental rules on Longboat Key?
Longboat Key enforces a 30-day minimum rental policy, which prohibits short-term rentals (Airbnb, VRBO, or weekly rentals) throughout the island. This ordinance is one of the defining factors that separates Longboat Key from Siesta Key, which allows weekly and daily rentals. The 30-day minimum makes Longboat Key more attractive to buyers focused on a quiet residential experience and long-term appreciation rather than rental cash flow.
Where is Longboat Key located?
Longboat Key is a barrier island located west of Sarasota, Florida, in Sarasota County. It stretches 12 miles along the Gulf of Mexico, connected to the mainland via bridges. The island runs from Sarasota Bay on the east to the Gulf on the west, with Sarasota directly to the south and Manatee County at the north end. ZIP code is 34228. It is approximately 10 minutes from downtown Sarasota by car.
How far is Longboat Key from Siesta Key?
Longboat Key and Siesta Key are separated by approximately 15-20 minutes of driving time (around 12 miles), passing through downtown Sarasota. They are not directly connected -- you travel via the mainland. Despite being neighboring barrier islands in the Sarasota area, they have distinctly different characters: Longboat Key is quieter, more exclusive, and resort-adjacent, while Siesta Key is more tourist-oriented with weekly rental activity and the famous white-quartz sand beach that draws significant seasonal traffic.
Welcome to Longboat Key
Idyllic island community with Gulf and Sarasota Bay views
Longboat Key (34228) is a waterfront community on a barrier island between the Gulf of Mexico and Sarasota Bay. Gorgeous white sand beaches run for 11 miles along the coastline.
However, Longboat Key is not a single neighborhood; it is a diverse collection of lifestyles. Divided by man-made canals and defined by its proximity to either the Gulf (Beach) or the Bay (Boating), choosing the right "Zone" is your first step.
The Longboat Key Lifestyle Map
Before you explore the neighborhoods below, decide which "Zone" fits your vision.
Zone
The Vibe
Real Estate Type
South Key (The Gates)
Resort & Golf Club
The St. Regis / Country Club Shores
Mid-Key
Panoramic Views
High-Rise Condos (Water Club, Promenade)
North Key (The Village)
Old Florida Charm
Low-Rise / Private Estates
Dining, Entertainment & Shopping
Longboat Key is home to a fantastic array of restaurants that combine sublime cuisine with mesmerizing waterfront views.
The Shore: Serves seafood specialties such as Key West shrimp and scallop risotto.
The Drydock Waterfront Grill: Overlooking the marina, this is one of the 100 best al fresco dining experiences in the US.
Chart House: A refined steakhouse with a terrace perched above the Gulf waters.
Neighborhood Video Tours
Queen's Harbor
Grand Bay
Water Club
Promenade
Beachplace
L'Ambiance
Country Club Shores
Bay Isles Harbor
Ready to Tour Longboat Key?
Roger Pettingell knows every building and every canal. Schedule a private boat or home tour today.
Contact Roger Pettingell
Roger Pettingell is a nationally recognized leader in Sarasota and Manatee Counties’ luxury waterfront real estate market, known for his record-breaking success and white-glove client experience.
Roger Pettingell is a nationally recognized leader in Sarasota and Manatee Counties’ luxury waterfront real estate market, known for his record-breaking success and white-glove client experience.
