Windstar Naples Florida - 7 Homes, 16 Condos, 20 Sold

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.

A Rare Find with over 600+ feet of waterfront and quick direct access out Gordon Pass to the Gulf. Your private 65’ dock with 15,000 lb lift, and plenty of room to expand, sits just outside your expansive outdoor living area with pool and barbeque kitchen. Inside, this 5400+ sq ft home has 4 bedrooms, 5 full and 1 half bath, plus a “crows nest” den overlooking the marina. Two of the bedrooms, with two baths and a sitting room with kitchenette occupy a secluded second floor wing which adds to its privacy and quiet. All of this in the gated community of Windstar, a unique club which gives you both a deepwater harbor as well as a Tom Fazio designed golf course just minutes to Olde Naples famous 5th Avenue and Beaches. Other Club amenities include a dining room overlooking Naples Bay, tennis and fitness programs, as well as other social activities. Windstar also offers a shuttle boat to Keewaydin Island with its unspoiled beach. Just outside the gates you’ll also find Bayshore Drive with its unique array of restaurants and watering spots. Plenty to do within reach or just relax and enjoy this beautiful one-of-a-kind home.

Attention Boaters, nature lovers, 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 Home, It's Better by the Bay! A unique opportunity to avoid the estimated 7 year wait list and purchase a Windstar on Naples Bay Full Golf Membership shortly after closing! The moment you pull into the majestic driveway you will say ‘Welcome Home’. This is an updated, upgraded, and refreshed Estate Home in the Harrington Sound neighborhood of Windstar. Designed for daily living and entertaining across its many indoor and outdoor living spaces, this home is anchored by one of the most spectacular views in all of Windstar. The custom infinity edge pool ‘waterfalls’ into a beautiful lake with a preserve area on the opposite shore which will never be developed. With soaring ceilings, hickory floors, custom millwork and cabinetry, an open floor plan, and incredible lake and nature views, this home provides a tranquil coastal modern feel. On the south end of this home is the very large primary suite which opens to the custom pool and spa and tremendous views. It has a large sitting area, dual walk-in closets with custom cabinetry, and a luxurious primary bath. Also on the south end of this Estate home is a den with abundant space and a ½ bath. A formal dining and living room provides plenty of space for large celebrations and gatherings. The great room is the center of the home with an updated kitchen with designer appliances, a wet bar with wine cooler, a morning room and informal dining area, and a family room with a gas fireplace. On the north end of the home is a guest bedroom with oversized closets and an ensuite bath, and a lakeside guest bedroom with oversized closets and ensuite bath. The outdoor living spaces offer over 1,500 square feet of living area, with 500 square feet under roof for outdoor dining and living, almost 950 square feet of screened lanai/pool area, and a 250 square foot lakeside ‘tranquility’ patio. This home has many special features - a propane tank that powers the easy-on gas fireplace and the whole house generator; an oversized garage; professional landscaping; and more. 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). “Welcome Home - It’s Better by The Bay!”

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!”

Discover your dream home in the prestigious Windstar community! This stunning 2 story residence features 4 spacious bedrooms plus a versatile den, office, and 5.5 luxurious bathrooms, providing ample space for family and guests. Step inside to a welcoming 2 story entry foyer with an expansive view of the Home, the outdoor area and Golf Course. This light and bright Home offers a main floor encompassing a generous Great room that flows seamlessly into the formal Dining room, Parlor and Chef’s Kitchen, complete with elegant Granite countertops, top-of-the-line Stainless steel appliances, an island, a breakfast counter, Casual dining area and an abundance of cabinetry and storage, including a convenient walk-in pantry. The Family room is adorned with a cozy dual Fireplace, perfect for relaxation or entertaining. The Primary suite with luxurious ensuite bathroom has sliders to access the outdoor area. This home is a split bedroom floorplan with guest bedroom with ensuite bathroom off the main foyer allowing for maximum privacy. Upstairs you will be delighted with the massive Loft with an outdoor screened in Terrace that spans the entire room with space to Entertain. There are 2 additional spacious Bedrooms, one with access to the terrace, and 2 full Bathrooms. Outside, the gorgeous Pool beckons you to unwind on the oversized screened Lanai with outdoor Kitchen, all while enjoying breathtaking views of the lush Golf course and Lake with unobstructed Sunsets—a perfect backdrop for Entertaining or Serene evenings under the Stars. The home also boasts a generous 3-car Garage equipped with an Electric charging station, catering to your modern Lifestyle. As a resident of Windstar, you’ll enjoy Exclusive Amenities, including complimentary boat shuttles to KeeWaydin Private Beach, allowing for effortless access to the beautiful Waterways and stunning Sunsets. Don’t miss the opportunity to call this magnificent home yours! Schedule your private tour today and experience the ultimate in luxury living!

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 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!

***Motivated Seller! Price just reduced $100k to give the buyer $50,000 off for an elevator plus another $50,000 for any other changes.*** Welcome to Yacht Harbour Cove, part of Naples only gated, golf, tennis & boating communities within Windstar on Naples Bay. This 2 level furnished coach home is situated on the yacht basin of the Southpointe Yacht Club & Marina giving you the ability to rent or purchase a boat slip in the protected, tucked away bay leading directly to the Gulf of Mexico & the most gorgeous beaches Naples has to offer. This light, bright home with soaring ceilings throughout has an open flow and features 2 Primary Suites with walk-in closets & dual vanities. The 3rd bedroom has a bathroom that also connects to the den, which could be a 4th bedroom making it a potential Jack & Jill style layout...OR keep the den as a 2nd living room, gym, art studio or office space. Just off the kitchen & living room there is a full-span screened-in terrace that stretches across to the main suite with it's own private patio entrance. This home lives & feels very spacious with just under 3,000 interior square feet and each of the bedrooms has great privacy as they are all separated from each other. This upper level unit has an oversized garage for 2 cars including all the extra toys & does have an elevator shaft in place. This prime location is just minutes away from Naples by car or boat & you can take the Intercoastal Waterway south to Keewaydin, Isles of Capri or Marco Island for even more beaching & boating options. Experience the best of Naples living with the close-by Celebration Park, Bayshore Arts District & all within 10 minutes of downtown's famous 5th Avenue shopping & fine dining.

Welcome to Regatta Landing, a luxurious coach home neighborhood in the gates of Windstar offering upscale, open-concept residences & some of the finest amenities Naples has to offer. From boating, golf, tennis & a first class newly renovated club house, plus a beach shuttle to Windstar’s private beach, this home truly checks all the boxes. Attention to detail was key in this home’s design & elegant upgrades. This dual level, 3 Bedroom, 3 bath smart home has exquisite styling & upgraded finishes throughout. A chef’s delight, this island kitchen includes tons of counter space, storage, Monogram S/S appliances, an induction cooktop, wine chiller, custom walk-in pantry & island dining for 4. Across the living room, you will find the fully equipped corner bar perfect for entertaining. The expansive primary suite is just off the kitchen & includes all the finest spa indulgences every owner deserves including heated towel bars, walk-in wardrobes & private patio access. Across the home, the second bedroom ensuite could be used as a 2nd primary due to its comparable size & the third bedroom comes with a walk-in closet & its own private veranda. Additionally the home office is located just off the main living area via French door entry. From the oversized 2 car garage, it’s easy to send groceries up on the elevator, or enter through the main front door to a gorgeous, sleek glass railing staircase complimented with souring 16 foot ceilings and a suspended crystal light fixture. The home features all quartz counters & backsplashes plus all lighting, fans & window shades have Lutron switch panels & remotes. Wood-look porcelain tile spans the main living rooms including the balcony porches and there is plush carpeting in every bedroom. Windstar on the Bay is truly one of Naples best kept secrets with its marina options, boating proximity to open water & our local beaches, plus being so close to downtown Naples for a fraction of the price. Just outside the gates, you can also enjoy the beautiful Naples Botanical Gardens, Naples Art District studios, Celebration Food Park & many other unique dining experiences...so lots to do right nearby. Are you ready to enjoy Naples best hidden gem community? (Owner has now moved his items out of the home.)

Welcome to the exclusive, privately gated enclave of Regatta Landing, located within the premier boating and golfing community of Windstar on the Bay. This beautifully finished, second floor unit boasts over 3800 SF, lives like a single family home and is being offered turnkey furnished. A grand entry with a dramatic staircase, OR private elevator, lead to the great room, kitchen and dining areas, all filled with an abundance of natural light. Enjoy endless sunsets, lake and golf course views from the western exposure windows and oversized lanai. The well appointed chef’s kitchen features quartz countertops, modern stainless appliances, an island bar PLUS a hidden walk-in pantry. The expansive primary suite reveals a private sitting area with lanai access and golf & water views of its own. The spa-like primary bath features dual vanities, a large walk-in shower, two walk in closets and coffee bar. Two additional en-suite guest rooms, PLUS an office and powder room compliment this generous floor plan. An oversized two-car garage with extra ground floor storage are much desired bonuses. Just minutes from downtown energy and pristine Gulf beaches, Regatta Landing and the Windstar communities offer an unprecedented Naples lifestyle.

$200K PRICE IMPROVEMENT allows you to create your Dream Home-check out our VIRTUAL RENOVATION & STAGING (Kitchen-Living Room-Dining Room) to create Open-Concept living along with our VIRTUAL REMODEL & STAGING of the Entertaining Wing and Great Room! Appraised at $1.875 M with NEW FLAT TILE ROOF September '24! A RARE OPPORTUNITY to purchase a corner lot single-story property in Windstar. Situated on a spacious 1/3-acre, this amazing home backs up to the 10th green and offers BREATHTAKING views of the 11th fairway on the Tom Fazio-designed golf course. French doors open into the ENTERTAINING WING of the home. This versatile 600 sq ft space is ready for your imagination. Create memories with parties (large & small), game nights, sports viewing, movie premiers and more (Check out our VIRTUAL REMODEL & STAGING)! IMPACT-RESISTANT panorama windows and sliders open to a HUGE paved lanai with a grand stairway descending to a CUSTOM SELF-CLEANING POOL. Picture-window screens all along the pool cage offer unobstructed views. New Flat Tile Roof comes with a 5-YEAR WARRANTY and Skylights-affordable insurance for YEARS to come! The large eat-in kitchen with bay window offers quartz countertops and 2023 stainless-steel appliances, including a French-door refrigerator, microwave and induction stove with air fryer/convection self-cleaning oven. Large living room and family dining room allow you to convert this space into an open-concept floor plan (see our VIRTUAL RENOVATION & STAGING)!. Primary bedroom boasts immense walk-in closets, large shower, and soaking tub. Second bedroom with attached bathroom plus additional bedroom/den with 3rd bathroom. Electric Hurricane Fabric Storm Shutters provide quick and convenient protection for the covered lanai area. Whole house KINETCO Water Filtration System, Home-Tech Home Warranty and OVERSIZED GARAGE! What’s more, this property includes a highly-coveted SOCIAL MEMBERSHIP. Bypass the almost 2-year waitlist! Exclusive access to the newly renovated clubhouse and all clubhouse activities, restaurants, wine room, clay tennis courts, bocce courts, group fitness classes, as well as a jam-packed calendar of social events. Life-style bonus-take your guests on the Keewaydin boat shuttle. Travel through beautiful Naples Bay to Windstar's private coastal paradise on Keewaydin Island or enjoy a picturesque sunset cruise (runs October thru June). Windstar is the area’s only gated golf community with its own private deep-water marina, providing direct access to Naples Bay and the Gulf. The Southpointe Marina has 72 slips and can accommodate yachts up to 70 feet. Windstar's Bayshore Arts District location is home to the Botanical Garden, hip eateries & a quick drive to downtown Naples-fine dining, shopping, galleries & beaches. Get ready for YOUR PARADISE!