Windstar Naples Real Estate - 5 Homes, 12 Condos For Sale

Discover the ultimate in privacy, luxury, and coastal living with this stunning waterfront estate, located on an exclusive gated island with only 10 estate homes. Nestled on nearly half an acre, this direct Gulf access property offers a rare combination of tranquility and convenience with a premier location just 5 minutes from downtown Naples and the world renowned beaches. Designed for the discerning buyer, this exceptional home features 5 bedrooms plus a den/office, 6 bathrooms, and 6,104 square feet of elegantly appointed living space. High-end finishes abound, including a chef’s kitchen with sleek, custom cabinetry imported from Japan, quartzite countertops, a center island with a gas cooktop, and top-of-the-line appliances. Impact-resistant doors and windows provide peace of mind, while a private elevator ensures ease of access to the second level. The 4,851 square feet of outdoor living space is truly breathtaking, offering multiple balconies with serene waterfront views, a massive covered lanai with a custom saltwater pool and spa, and cascading waterfall features. Entertain in style with a summer kitchen, pool bath, and ample space for gatherings. Your private 40-foot composite boat dock in the backyard is perfect for all your boating needs. This property offers the option to purchase an additional 50-foot boat slip located in Windstar on Naples Bay’s private marina. A premier destination for boating enthusiasts, offering unmatched convenience, luxury, and access to the Gulf of Mexico. This deep water marina features 72 slips, each equipped with electric and water connections to ensure every need is met for vessels of various sizes. At the heart of this waterfront oasis is a private clubhouse, staffed by a full-time harbormaster dedicated to providing exceptional service and overseeing marina operations. Windstar on Naples Bay is a one-of-a-kind community nestled along the serene waters of Naples Bay, this prestigious neighborhood offers everything you need to enjoy the best of Southwest Florida. At the heart of Windstar is its Tom Fazio-designed championship golf course, a beautifully maintained 18-hole course offering breathtaking views, challenging play, and world-class facilities. The community also offers a private beach on Keewaydin Island, accessible exclusively to residents via a daily shuttle. Additional amenities include tennis, a vibrant clubhouse with dining options, social events, activities and a soon-to-be built state of the art fitness facility. Just outside the gates of Windstar on Naples Bay, the Bayshore Arts District awaits—a thriving and eclectic neighborhood bursting with creativity, culture, and culinary delights. Known as one of Naples’ most exciting areas, the Bayshore Arts District offers a unique blend of art galleries, local boutiques, live entertainment, and waterfront attractions, all within minutes of Windstar. This estate offers the ultimate blend of luxury, privacy, and convenience.

Calling all Boaters, Nature Enthusiasts, and Privacy Seekers! Experience the true beauty of SW Florida’s coastal wonders! Don't miss this opportunity to live on the exclusive Island at Southpointe in Windstar. This beautiful home is one of only 10 estates on this private gated island on Naples Bay with quick direct boating access to the Gulf. This half acre lot and home has spectacular views of Naples Bay being the 3rd house from the island's tip. The 2000+ sq.ft. lanai w/ a large pool & spa offers multiple areas for serene and private enjoyment of the lush mangrove and Bay views. 4 bedrooms and a separate office ensure space and privacy for you, your family, and friends. A private boat dock with a 6,000 lb lift sits behind the home for a smaller vessel, jet ski, or kayak. The possibilities are endless to create the sanctuary of your dreams. Slips are available in the Southpointe Marina, only moments away, and can accommodate yachts up to 70 feet. The amenity-rich Windstar on Naples Bay is Naples only gated golf community with its own private deep-water Marina. Windstar offers an exceptional living experience, nestled in the vibrant Bayshore Arts District of Naples. Just a short drive from Downtown, Naples’ renowned 5th Avenue South, and the pristine sugar sand beaches, this community combines cultural richness with coastal elegance. Residents enjoy unparalleled amenities, including a private Tom Fazio-designed 18-hole golf course, a newly completed $14 million Clubhouse renovation, tennis, bocce, and a private beach club on Keewaydin Island with daily shuttle service aboard Windstar's exclusive Keewaydin Queen. Additional perks include sunset cruises, a water taxi to downtown waterfront restaurants, and more. This is a rare opportunity to own a sophisticated coastal estate with an extraordinary location and amenities. Golf and Social memberships are separate and not required. This home sustained NO damage from Hurricanes Helene or Milton! The home's elevation certificate and proof of flood insurance (transferrable) are available upon request. Compare the price of this exquisite property to any comparable sized home or empty .5 acre lot with a sensational view, direct access to the Gulf, and optional amenities here in Naples - you won't find a better value! This is an opportunity to create a showstopper sanctuary like no other currently available!

Welcome to 1520 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. *Beat the 5+ year wait list with an immediate full golf membership option to Windstar Club!* Enter the lobby of this 4-unit boutique building into the elevator which opens directly into your truly exceptional unit boasting expansive panoramic 180 degree views of Naples Bay, Port Royal and Royal Harbor. This home has been thoughtfully redesigned and renovated in 2021 by premier local builder/contractor, BCB Homes. No expense spared with only the finest craftsmanship and building materials, this home has been totally transformed into a modern sanctuary ideal for today's Naples lifestyle. Fabulous open-concept living area takes full advantage of the stunning bay views. A true chef's eat-in kitchen replete with Sub-Zero refrigerator, Wolf induction cooktop, Wolf double ovens, ice maker, custom Ruffino cabinetry and an oversized island flanked with granite counters. Master suite with French oak hardwood herringbone floors, en-suite marble bath plus dual walk-in closets with custom built-ins. 2 additional bedrooms with a connecting bath. Oversized 2-car garage with space for 2 vehicles plus golf cart and great storage. Gorgeous resort-style community pool and spa. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse with multiple dining areas with stunning views of Naples Bay and Port Royal, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for late 2026. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue South and 3rd Street South known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports. Truly exceptional and a rarity to find this level of high-design and finish in a home in Windstar.

Upon arrival at 4535 Lighthouse Lane you will have a warm sense of “Welcome Home - It’s Better by The Bay”! This is an expanded and updated Estate Home in Windstar on Naples Bay. Daily living and entertaining were a major theme during the redesign and creation of this home. The home is truly unique and charming, designed to maximize its golf course location, oversized lot, views, mature landscaping and its many indoor and outdoor living areas' special attributes. It feels cozy while having over 7,000 total square feet of space, including 3,652 under A/C, and a remarkable 2,715 of outdoor living space. This home is made for entertaining and everyday living. Enjoy soaring ceilings, an open floor plan, a coastal modern feel, and indoor and outdoor living areas that magically flow together. The Great Room is the center of the home, with kitchen, dining, and family room opening to the outdoor patios, pool, spa, and fire pit areas. This is ideal for large and small gatherings. On the north end of the home is the primary suite which also opens to the pool and great views. It has a large sitting area, huge closet complex, and an intimate spa-like bathroom. The office off the living room has a custom-built floor- to-ceiling desk and cabinetry. On the south end of the home is the visitor/guest quarters, anchored by a second primary “Cottage” suite with a custom wooden ceiling, sitting area, dressing area, and a spectacular bath. The suite has a private entrance to the outdoor fountain patio. Two additional bedrooms and a bath adjoin the cottage creating a private 'Naples’ experience for relatives or friends. This home has a bounty of special features - custom floor-to-ceiling cabinets throughout, custom closets, designer appliances, home audio system, a unique tranquility fountain and patio overlooking the golf course, built-in gas fire pit, professional landscaping and outdoor lighting, circular driveway with abundant guest parking, new pool and spa (2014), custom-designed lanai screen and deck (2014), 1000 gallon propane tank, generator, new roof and exterior paint (2021), and an oversized garage with new epoxy floor and ceiling loft storage. In the downtown Bayshore Arts District area, “It’s Better by The Bay”. As a Windstar resident take advantage of the Keewaydin Queen’s nautical adventures (Sunset Cruises, Special Events and Private Charters) and enjoy the private beach club at Keewaydin Island. For additional “It’s Better by The Bay” experiences, you can join The Southpointe Yacht Club or The Windstar Club. With this property a Golf Membership at the Windstar Club is negotiable, allowing the buyer to bypass the extensive waiting list and become a member on the day of closing (contingent on the Club’s application process). “Welcome Home - It’s Better by The Bay!”

Experience luxury living at its finest in the prestigious Windstar community! This magnificent two-story home boasts 4 generously sized bedrooms, a flexible den, office space, 5.5 beautifully designed bathrooms, and a sprawling loft/game room, offering plenty of room for family and guests. As you enter, you'll be greeted by a grand two-story foyer with sweeping views of the home, outdoor space, and the lush golf course beyond. The home is bathed in natural light and features a main level that includes a spacious Great Room seamlessly flowing into the formal Dining Room, Parlor, and Chef’s Kitchen. The kitchen is a chef’s dream, with stunning granite countertops, high-end stainless steel appliances, an island, a breakfast counter, a casual dining area, and an abundance of cabinetry and storage, including a convenient walk-in pantry. The Family Room is enhanced by a cozy dual-sided fireplace, ideal for relaxing or entertaining. The luxurious Primary Suite offers an ensuite bathroom with high-end finishes and sliding doors leading out to the outdoor space. This home is thoughtfully designed with a split bedroom layout, with a guest bedroom featuring an ensuite bathroom off the main foyer, ensuring maximum privacy. Upstairs, you'll find a massive Loft with an expansive screened-in terrace that spans the length of the room, perfect for entertaining. There are also two additional spacious bedrooms—one with access to the terrace—and two full bathrooms. Step outside to the stunning pool area, with an oversized screened lanai, Take in breathtaking views of the lush golf course, serene lake, and unobstructed sunsets—an ideal setting for enjoying peaceful evenings under the stars. The home also includes a spacious 3-car garage with an electric charging station to accommodate your modern lifestyle. As a Windstar resident, you’ll enjoy complimentary boat shuttles to the private KeeWaydin Beach, offering easy access to beautiful waterways and spectacular sunsets.

IMMEDIATE GOLF MEMBERSHIP AVAILABLE to Prestigious Windstar on the Naples Bay Country Club, the initiation for golf is now $125,000.00. This is a TRUE opportunity since there is a five-year waitlist for this beautiful Tom Fazio designed golf course. This rare chance to own a residence in the sky which features, 3 bedrooms, plus den, 3 1/2 baths, over 4400 square feet of living space with an amazing kitchen for the gourmet dining. Added amenities include; resort-style pool, seller recently installed electric boat lift for a 30 foot vessel, hot tub, spa, 3 car attached garage, private elevator, and secured building for privacy. The newly renovated Clubhouse (Spring 2024) Windstar on Naples Bay boast of Golf, Tennis, Bocce Courts, Boating, Fine Dining, Exclusive Events, and they have just approved a new state of the art Fitness Center. A Private Complimentary Shuttle is available to take residences to the private Keewaydin Island for day visits, sunset cruises, and Private Events. This WCI community is the only development in the area with both Golf and a first class marina located on Naples Bay.

Welcome Home to 4615 Lighthouse Lane, where it's truly "Better by The Bay"! Situated in the exclusive Harrington Sound neighborhood within the amenity-rich Windstar on Naples Bay community, this unique and charming home is designed to make the most of its expansive double lot. Offering panoramic golf and lake views along with mature landscaping, this home seamlessly blends indoor and outdoor living while ensuring privacy and tranquility. With over 4,100 square feet of living space under A/C and an additional 2,190 square feet of outdoor living area, this residence is both spacious and cozy. It's thoughtfully designed for daily living, hosting friends and family, and entertaining guests of any size. The home features 4 bedrooms, 4 baths, a den, and an oversized 3-car garage. At the heart of the home lies the Great Room, where the kitchen, morning room, and family room open to the outdoor lanai, pool, spa, and a private patio retreat—ideal for enjoying Florida's beautiful weather. Soaring ceilings and recently installed hurricane-impact windows and doors flood the home with natural light. On the south end of the home, the primary suite offers direct access to the pool and breathtaking views. This suite includes a large sitting area, dual walk-in closets, and an updated spa-like bath. The adjacent den features a custom-built desk and floor-to-ceiling cabinetry, providing a perfect space for work or relaxation.VOn the north end, the visitor or guest quarters consist of three generously sized guest bedrooms, each measuring 14 x 14 feet, with two accompanying guest baths. This home is equipped with a range of special features and recent updates. It boasts a majestic circular driveway with ample guest parking, professional landscaping, a whole-house audio system, and a security system. Significant updates include newly installed hurricane impact windows and doors in 2024, an updated master bath in 2023, new HVAC and hot water heaters in 2024 and 2022, a new roof in 2021, and a new pool heater in 2025. The outdoor area is enhanced by custom-designed lanai cabinetry and a pool screen enclosure, complemented by a newly laid travertine pool deck. The modern kitchen and a gas-powered generator further add to the home's appeal. Experience the effortless elegance and comfort of this extraordinary home at 4615 Lighthouse Lane — your oasis of peace and luxury awaits! As a Windstar resident take advantage of the Keewaydin Queen’s nautical adventures (Sunset Cruises, Special Events and Private Charters) and enjoy the Windstar beach at Keewaydin Island. For additional “It’s Better by The Bay” lifestyle experiences and extensive amenities, you can join The Southpointe Yacht Club or The Windstar Club. A tour and visit to either will WOW you! “Welcome Home - It’s Better by The Bay!”

Welcome to 1560 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. Enter the lobby of this 4-unit boutique building to the elevator which opens directly into your 3 Bedroom, 3.5 Bathroom tastefully updated home in over 2600 square feet of living space under AC. Open-concept living area with walls of glass affording stunningly gorgeous western views of golf course, Naples Bay, Port Royal, Royal Harbor and sunsets. Sprawling living room with linear fireplace opens out to screened-in lanai with expansive views seamlessly blending indoor/outdoor living. A true chef's eat-in kitchen replete with shaker cabinetry, contemporary white quartz countertops, GE Monogram appliances, breakfast bar, dining area plus a sitting room with custom millwork accent wall and built-in desk area. Master Suite oasis featuring large bedroom with wall of glass overlooking the bay, dual walk-in closets with custom built-ins plus an en-suite bathroom with walk-in shower, soaking tub, dual vanities and separate water closet. Split floor plan with 2 additional guest suites each with en-suite bathrooms and views of the preserve. Full size laundry room plus a convenient powder room. Oversized 2-car garage. Gorgeous resort-style pool and spa. Deeded boat slip #7 behind the building which can accommodate up to a 30 foot boat and is just a mere 7 minutes out to the Gulf of Mexico. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for 2026 completion. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports. This truly exceptional home has been thoughtfully updated with modern features perfect for today's paradise living. If you are looking to buy the quintessential, resort style low-maintenance home in Naples look no further!

Welcome Home, It's Better by the Bay! Avoid the long wait list and secure your Windstar on Naples Bay Full Golf Membership shortly after closing. This updated and upgraded estate home is nestled in the prestigious Harrington Sound neighborhood of Windstar, offering a perfect blend of elegance and comfort. From the moment you arrive at the majestic driveway, you'll feel the warmth of "Welcome Home." This residence is thoughtfully designed for both daily living and entertaining, featuring expansive indoor and outdoor spaces. The home is anchored by one of the most spectacular views in all of Windstar: a custom infinity edge pool that cascades beautifully into a serene lake, bordered by a preserve area that will remain untouched. With soaring ceilings, exquisite hickory floors, and custom millwork, this home brims with coastal modern charm. The open floor plan seamlessly integrates breathtaking lake and nature views throughout. The south end of the home boasts a magnificent primary suite that opens to the custom pool and spa with stunning vistas. This suite includes a spacious sitting area, dual walk-in closets with custom cabinetry, and a luxurious primary bath. A well-appointed den and a half bath are also located on the south end. The formal dining and living rooms offer abundant space for large gatherings and celebrations. At the heart of the home is the great room, which features an updated kitchen with designer appliances, a wet bar with a wine cooler, a morning room, an informal dining area, and a cozy family room with a gas fireplace. On the north end, you'll find two inviting guest bedrooms, each with oversized closets and ensuite baths, one with direct lake views. The outdoor living areas provide over 1,500 square feet of enjoyment, including 500 square feet under roof for alfresco dining and lounging, nearly 950 square feet of screened lanai/pool area, and a 250 square foot lakeside 'tranquility' patio. This home comes with an array of special features, including a propane tank that powers the convenient gas fireplace and whole-house generator, an oversized garage, and professional landscaping. As a Windstar resident take advantage of the Keewaydin Queen’s nautical adventures (Sunset Cruises, Special Events and Private Charters) and enjoy the private beach club at Keewaydin Island. For additional “It’s Better by The Bay” experiences, you can join The Southpointe Yacht Club or The Windstar Club. With this property a Golf Membership can be purchased immediately after closing, allowing the buyer to bypass the estimated 7-year waiting list and become a member on the day of closing (contingent on the Club’s application process). Experience the serene and stylish lifestyle offered by this exquisite estate home in Windstar—your oasis awaits! “Welcome Home - It’s Better by The Bay!”

Welcome to 1620 Star Point Lane in the highly coveted enclave of Admirals Watch of Windstar on Naples Bay. This unit comes with a deeded boat slip! Enter the lobby of this 4-unit boutique building to the elevator which opens directly into your 3 Bedroom, 3.5 Bathroom totally renovated home in just under 2900 square feet of living space under AC. Open-concept living area with walls of glass affording stunningly gorgeous vast 180 degree western views of golf course, Naples Bay, Port Royal, Royal Harbor and sunsets. Sprawling living room, sitting area, dining area plus a true chef's eat-in kitchen replete with shaker cabinetry, contemporary white quartz countertops, stainless steel appliances including Sub-Zero wine refrigerator, breakfast bar plus another sitting room. Master Suite oasis features large bedroom with wall of glass overlooking golf course and Naples bay, spa-like en-suite bathroom with walk-in shower, freestanding soaking tub, oversized double vanity, separate water closet and a walk-in closet with custom built-ins. Split floor plan with 2 additional guest suites each with juliet balconies with eastern views of both the preserve and 10th fairway. Full size laundry room plus a convenient powder room. Oversized 2-car garage. Gorgeous resort-style pool and spa. Deeded boat slip #3 behind the building which can accommodate up to a 30 foot boat and is just 7 minutes out to the Gulf of Mexico. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with boat shuttle plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for late 2025-early 2026. Preferred location just a short drive via car, bike or golf cart to downtown's 5th Avenue known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports. This truly exceptional home has been thoughtfully renovated with modern features perfect for today's paradise living. If you are looking to buy the quintessential, resort style low-maintenance home to fully enjoy the 2024-2025 season in Naples look no further!

This beautiful custom-built home features recent updates, including a new tile roof and marble-faced fireplace. IN ADDITION, THE SELLER HAS A FULLY TRANSFERABLE GOLF MEMBERSHIP! The spacious chef's kitchen has custom cabinetry, a large walk-in pantry, and newer appliances. Custom 8ft. solid core doors and premium hardware throughout. Plantation shutters and 10ft. sliding glass doors open to the pool courtyard and guest cabana, Custom lighting, skylights, a home office, a central vacuum system, and a heated pool/spa with a waterfall, are just some additional amenities to make your living here a joy. Other notable features include an AqualLink control system, storm shutters, a 2-car garage, brick pavers, and a tropical courtyard. The golf course, lake, and mangrove views from your screened lanai are stunning. Windstar has a Tom Fazio-designed golf course, and clubhouse with spectacular views of Naples Bay and 72 slip deep water marina, affording direct gulf access in less than 10 minutes. The club has clay tennis courts, a fitness center, and the Keewaydin Island Beach Club with a boat shuttle and private membership.

Your Naples Dream Home-Turnkey Furnished Luxury in Naples’ Most Exclusive Boating & Golf Community! Welcome to Regatta Landing—the newest and most sought-after enclave in Windstar on Naples Bay, where luxury living meets unmatched lifestyle perks. Built in 2021, this turnkey furnished residence spans 3,403 square feet under air and 4,437 total square feet, offering an expansive layout with four bedrooms, three full bathrooms, and multiple outdoor living spaces, including balconies and a spacious screened lanai with serene water views. Step inside to discover soaring 14-foot ceilings and an elevated coastal design throughout. The open concept floor plan features a private elevator, gourmet kitchen with oversized island, Monogram appliance package, quartz countertops, walk-in pantry, coffee bar, wet bar, and wine cooler—perfect for entertaining in effortless style. Elegant finishes like shiplap detailing add charm and warmth, while the attached two-car garage with extra storage and hurricane impact doors and windows provide both comfort and security. What truly sets this property apart is its rare offering: the option of ownership of a 38-foot dated slip in the prestigious Windstar Marina. Enjoy instant access to one of Naples’ only deep-water, private marinas, featuring a full-time harbormaster, electric/water hookups, and an exclusive marina clubhouse, all just 5 minutes to the open Gulf. Windstar on Naples Bay is a guard-gated, resort-style community offering a Tom Fazio-designed 18-hole championship golf course, tennis, a brand new state of the art fitness center opening in 2026, fine dining, a bayside clubhouse with panoramic views, and a private boat shuttle to Keewaydin Island. All this just 5 minutes to Downtown Naples, white-sand beaches, and the dynamic Bayshore Arts District, known for its thriving art scene, waterfront eateries, and local culture. Whether you’re a golfer, boater, or simply craving a move-in-ready slice of paradise—this is a rare opportunity to own the best of Naples living.