4500 Gulf Of Mexico Drive 206 Longboat Key, FL 34228
2 Bed
2 Baths
1523 sqft
MLS# A4671822
One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” This residence is now available for public and private showings.
Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire season). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Deborah "Debby" McCaig, Coldwell Banker Realty
$9,000 / mo (USD)
Longboat Key Area Rental
Active
4540 Gulf Of Mexico Drive Ph2 Longboat Key, FL 34228
2 Bed
2 Baths
1325 sqft
MLS# A4706064
RARE LATE-FALL OPPORTUNITY: NOVEMBER & DECEMBER 2026 AVAILABLE FOR A TWO-MONTH MINIMUM STAY AT $10,000, OFFERING A $8,000 SAVINGS. START EVERY DAY ON VACATION WITH A SUNRISE AND END IT WITH A SUNSET. From the first light of sunrise dancing across Sarasota Bay to the breathtaking sunsets over the Gulf of Mexico, this penthouse offers the best of both worlds, and the very essence of Longboat Key living. Bay views grace the eastern side of the residence, while the large kitchen window and entry door offer views west toward the Gulf. Gather each evening along the Gulf-view catwalk to watch spectacular sunsets paint the sky over the water. It's a daily tradition cherished by owners, neighbors, and guests alike, often enjoyed from a beach chair with a favorite beverage in hand. Designed for comfort and relaxation, this two bedrooms and two bath coastal retreat features a newly remodeled open kitchen with island seating, two newly renovated bathrooms, and an inviting open living and dining area. The bright Florida Room is filled with natural light, creating the perfect spot for morning coffee, reading, or simply taking in the peaceful surroundings. Arrive with ease and park directly in your private under-building garage parking space, complete with a dedicated storage closet for all your beach gear. Perched on the top floor, this penthouse residence offers an added sense of tranquility with no unit above. The beautifully updated kitchen is fully equipped for everything from casual breakfasts to gourmet dinners. Pick up fresh ingredients from local farmer's markets or explore the many outstanding dining destinations located just minutes away. Nestled within the 26-acre waterfront community of Windward Bay, guests enjoy access to an impressive collection of resort-style amenities. Highlights include two heated swimming pools, tennis and pickleball courts, two marinas, kayak storage, shuffleboard, a clubhouse with kitchen, library, fitness center, saunas, multiple fire pits, and barbecue areas throughout the grounds. Nature lovers will appreciate the abundance of wildlife, scenic walking paths, and more than a half mile of waterfront trails. Whether your days are spent boating, fishing, kayaking, beachcombing, or simply relaxing in the Florida sunshine, the location places you close to everything. Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and renowned arts and cultural attractions are all nearby. Guests return year after year for the exceptional combination of comfort, location, and coastal charm. In fact, one couple has made this their January through March home away from home for many seasons. More than just a place to stay, this is the kind of vacation retreat where cherished memories are made and lasting traditions begin. Your perfect Longboat Key vacation begins here.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Deborah "Debby" McCaig, Coldwell Banker Realty
$7,000 / mo (USD)
Longboat Key Area Rental
Active
4780 Gulf Of Mexico Dr. Villa 5 Longboat Key, FL 34228
2 Bed
2 Baths
1325 sqft
MLS# A4668115
Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Deborah "Debby" McCaig, Coldwell Banker Realty
STELLAR as distributed by MLS GRID / Listed By: Deborah "Debby" McCaig, Coldwell Banker Realty
Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire season). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”