• UNDER CONTRACT
    $1,895,000

    Regatta Landing Windstar

    2472 Breakwater Way # 202, Naples, FL 34112
    • Condos - 3,403 ft²
    • 4 Bed
    • 3 Baths
    • Build 2021

    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.

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    • UNDER CONTRACT
    $1,875,000

    Clipper Cove Windstar

    3844 Clipper Cove Dr, Naples, FL 34112
    • Homes - 3,295 ft²
    • 5 Bed
    • 3 Baths / 2 Half
    • Build 1998

    Welcome to 3844 Clipper Cove Drive in the desirable Clipper Clove enclave of Windstar on Naples Bay. This 4-5 Bedroom, 3 full plus 2 half bath, 2-story home has been thoughtfully redesigned and renovated ideal for today's Naples lifestyle. Enter into a welcoming foyer to an open-concept living area with soaring 2-story ceilings, gorgeous wide plank light oak floors, expansive view and incredible natural light. Spacious living room with fireplace and built-in wet bar with wine refrigerator, ice maker and open shelving is ideal for entertaining. Wall of glass which pockets all the way seamlessly blends indoor/outdoor living so desired in Naples opens out to outdoor living oasis with gorgeous pool, spa plus a pool bath with southwestern vistas of the 10th fairway affording all afternoon sun and sunsets. Gorgeous dining area with custom built-ins. A true chef's eat-in kitchen features Viking appliances, quartz countertops and corresponding backsplash and timeless shaker cabinetry. Office with an adjoining powder room could also serve as additional guest quarters. Master suite oasis with spacious bedroom, walk-in closet with custom built-ins and a spa-like bath including walk-in shower, freestanding soaking tub and double vanity. Ascend to the second floor to an open loft-like club room perfect for media room. A second master suite with step-out balcony is perfect for private morning coffee or for sunset viewing. 2 additional guest bedrooms with shared hall bath complete this floor. Truly exceptional and a rarity to find this level of high-design and finish in a home in Windstar. 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 and Royal Harbor, billiards room, 6 Har-Tru tennis courts, bocce courts and a state of the art fitness center slated for 2025. 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.

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    • Sold
    $1,999,000
    $1,800,000

    Harrington Sound Windstar

    4677 Lighthouse Ln, Naples, FL 34112
    • Homes - 3,290 ft²
    • 4+Den
    • 3 Baths / 1 Half
    • Build 1995

    Spacious Estate Home with Stunning Lake & Golf Course Views offering Exceptional Outdoor Living Situated on a beautifully landscaped half-acre lot in Harrington Sound at Windstar on Naples Bay, this custom-designed, single-level estate home offers nearly 3,300 sq. ft. of living space and an exceptional outdoor retreat. One of the many highlights of this property is the expansive 2,600 sq. ft. screened-in pool and spa area, designed for year-round enjoyment. Featuring a large covered lanai with a summer kitchen, this inviting space is perfect for entertaining while taking in the expansive lake and golf course views overlooking Windstar’s 4th fairway. The heated pool and spa ensure comfort in every season. Inside, the home offers four bedrooms plus a den and 3.5 bathrooms, along with practical updates including electric storm shutters, a five-year-old roof, and a whole-house Generac generator (installed in 2020). A three-car garage provides ample storage. Additionally, an optional social membership to the exclusive Windstar Country Club, located directly on Naples Bay, is available with the purchase of this home—providing access to world-class amenities, waterfront dining, and a lively social scene. Windstar offers incredible amenities including: Tom Fazio designed golf course, newly redesigned clubhouse with spectacular views of Naples Bay, 72 slip deep-water marina with direct Gulf access in less than ten minutes, clay tennis courts, bocce ball, fitness, Keewaydin Island Beach Club with boat shuttle and private membership.

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    • Sold
    $1,899,000
    $1,800,000

    Regatta Landing Windstar

    2542 Windward Ct # 201, Naples, FL 34112
    • Condos - 3,563 ft²
    • 3+Den
    • 3 Baths
    • Build 2021

    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.)

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  • $1,695,000

    Regatta Landing Windstar

    2481 Breakwater Way # 6201, Naples, FL 34112
    • Condos - 3,854 ft²
    • 3+Den
    • 3 Baths / 1 Half
    • Build 2020

    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 your private elevator, lead to the great room, kitchen and dining areas, all filled with an abundance of natural light. Enjoy endless sunsets and sweeping lake and golf course views from the western exposure sliding glass doors leading to the oversized lanai. The well appointed chef’s kitchen features quartz countertops, modern stainless appliances, a curved island, wine/beverage cooler PLUS a hidden walk-in pantry. The spacious great room is complemented by a corner island bar with a second wine/beverage cooler, perfect for entertaining. The expansive primary suite reveals a private sitting area with lanai access and expansive golf and water views all of its own. The spa-like primary bath features dual vanities, a large walk-in shower, his and hers walk-in closets and coffee bar. Two additional en-suite guest rooms, PLUS an office/den and powder room complement this generous floor plan. An oversized two-car garage with extra ground floor storage are much desired bonuses. Regatta Landing features a private gated entrance for quick and easy access into the community, a private community pool, a gathering area and boat docks for purchase/lease if available. Just minutes from the downtown energy of Old Naples and the pristine Gulf beaches, Regatta Landing and the Windstar community offer an unprecedented Naples lifestyle.

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  • $1,695,000
    $1,595,000

    Clipper Cove Windstar

    3872 Clipper Cove Dr, Naples, FL 34112
    • Homes - 2,727 ft²
    • 3+Den
    • 2 Baths / 1 Half
    • Build 1999

    Welcome to 3872 Clipper Cove Drive in the desirable Clipper Clove enclave of Windstar on Naples Bay. This 3-4 Bedroom, 2 full plus 1 half bath 2-story home has been thoughtfully updated, ideal for today's Naples lifestyle. Enter into a welcoming foyer to an open-concept living area with soaring 2-story ceilings giving this home a light and airy vibe. Spacious living room with fireplace and bar area ideal for entertaining. Wall of glass opens out to an outdoor living oasis with a gorgeous pool and grassy area ideal for dog lovers. Expansive southwestern vistas of the 10th fairway affording all afternoon sun and sunsets. Gorgeous dining area with custom built-ins. A true chef's eat-in kitchen. Office with an adjoining powder room could also serve as additional guest quarters. Master suite oasis with spacious bedroom, walk-in closet with custom built-ins and a spa-like bath including walk-in shower, soaking tub and double vanity. Ascend to the second floor to an open loft-like club room with custom built-ins is perfect for a media room. Guest bedroom plus a cozy sleeping loft with built-in trundle beds and hall bathroom complete this floor. 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 and Royal Harbor, 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.

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    • Sold
    $1,675,000
    $1,575,000

    Clipper Cove Windstar

    3868 Clipper Cove Dr, Naples, FL 34112
    • Homes - 2,799 ft²
    • 4 Bed
    • 4 Baths
    • Build 1998

    SKIP THE WAIT - IMMEDIATE FULL GOLF MEMBERSHIP available at WINDSTAR ON NAPLES BAY! The buyer of 3868 Clipper Cove Drive will be able to take advantage of a RARE OPPORTUNITY TO BYPASS AN OTHERWISE 7 YEAR WAITING list as the owners will transfer their membership granting the buyers the option for full and immediate golf membership. 3868 Clipper Cove Drive, a single-family home with views of the 10th fairway has an open floorplan with great living and entertaining space and plenty of room for family and guests. It features 3-4 bedrooms, a loft overlooking the great room and 4 full bathrooms. Relax in the outdoor area which offers a heated inground pool, pool side lounging and dining space as well as a lanai. Windstar, a waterfront gated community, features a Tom Fazio designed 18 hole golf course, tennis, and bocce courts. The newly renovated clubhouse has stunning views of Naples Bay and Port Royal as well as amazing sunsets. The club house has multiple indoor and outdoor dining areas, wine room, meeting space, and a billiards room. There are also Har-Tru tennis courts, bocce courts and slated for 2025 - a state-of-the-art fitness center. A unique amenity is Windstar’s private Keewaydin Island beach club accessed by Windstar’s private boat shuttle which also provides sunset cruises through Port Royal and out to the Gulf. Another attraction is a full service 72-slip deep water marina. Windstar enjoys an ideal location just a short drive to downtown's 5th Avenue known worldwide for its fine dining, shopping, and beaches. The Windstar property is situated in the vibrant Bayshore Arts District, and near to the Naples Botanical Garden and Naples Pickleball Center. Golf, tennis, bocce, private Keewaydin Island beach club, sunset cruises, fantastic newly renovated club house … available in time for the season…no wait list!!

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    • Sold
    $1,695,000
    $1,535,000

    Ketch Cay Windstar

    1737 York Island Dr, Naples, FL 34112
    • Homes - 2,336 ft²
    • 3 Bed
    • 2 Baths
    • Build 1995

    Welcome to 1737 York Island Drive, a rare opportunity on a quiet cul-de-sac in the desirable Ketch Cay community of Windstar on Naples Bay. This stunning home boasts over 2400 square feet and has been remastered and renovated inside and out. The living space was redesigned to create an open-concept floor plan including a spacious living room, dining area and kitchen seamlessly blending the indoor/outdoor Naples lifestyle. A true chef's kitchen replete with custom cabinetry and island, stainless steel appliances and granite countertops is ideal for entertaining. Living and dining areas open out to your screened-in lanai with serene western views over the 6th hole and mangroves to truly enjoy the sunsets and breezes off Naples Bay just beyond the mangroves. A side paver patio is ideal for outdoor grilling. Enter your Master Suite oasis through double doors to a spacious bedroom with green views and lanai access. 3 closets including a walk-in featuring custom built-ins. Spa-like Master Bath features European-style walk-in shower, elegant freestanding soaking tub, double vanity and separate water closet. Split floor plan offers 2 guest bedrooms plus a shared full bath and a spacious den ideal for media room, home office or additional guest quarters. Three separate outdoor living spaces to truly enjoy the best of sunrise to sunset from the pool to the lanai to the patio. 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 club house with multiple dining areas with stunning views of Naples Bay, Port Royal and Royal Harbor, billiards room, 6 Har-Tru tennis courts, 3 bocce courts and a new state of the art 15,000 square foot fitness center slated for mid-2026 completion. Bypass the lengthy wait list as this property includes a transferable highly-coveted social membership if desired! 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 boasts modern features and amenities including hardwood floors, hurricane windows and doors, updated systems, plumbing and electrical. If you are looking to buy the quintessential, resort style home to fully enjoy the 2024-2025 season in Naples look no further!

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    • Sold
    $1,699,000
    $1,525,000

    Clipper Cove Windstar

    3812 Clipper Cove Dr, Naples, FL 34112
    • Homes - 3,294 ft²
    • 4+Den
    • 3 Baths / 1 Half
    • Build 1997

    Immediate Full Golf Membership Available & Stunning Fairway Views! Purchasing this exceptional home grants buyers instant eligibility for an optional full golf membership at Windstar Country Club-bypassing the typical 6-7 year waiting period! This stunning 4 bedroom + den, 3.5-bathroom + loft pool home offers breathtaking views of Windstar’s 10th fairway and has been meticulously upgraded with premium enhancements, including: • A brand-new outdoor summer kitchen with a built-in grill • A completely renovated master bathroom & custom master closet • New wine fridge and bar—perfect for entertaining • New kitchen appliances for a sleek, modern touch • New flooring throughout the main living area, adding elegance and warmth • New impact doors for enhanced security and efficiency • New roof installed in 2022 With soaring ceilings and nearly 3,300 sq. ft. of living space, this impressive single-family home also features an air conditioned two-car garage, lush tropical landscaping, and numerous additional upgrades over the past few years. This is a rare opportunity to own a luxury home in Naples' premier gated golf community—with access to an immediate full golf membership! Windstar offers incredible amenities including: Tom Fazio designed golf course, newly redesigned clubhouse with spectacular views of Naples Bay, 72 slip deep-water marina with direct Gulf access in less than ten minutes, clay tennis courts, bocce ball, fitness, Keewaydin Island Beach Club with boat shuttle and private membership.

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    • Sold
    $1,575,000
    $1,425,000

    Ketch Cay Windstar

    1725 York Island Dr, Naples, FL 34112
    • Homes - 2,418 ft²
    • 4 Bed
    • 4 Baths
    • Build 1999

    Remastered Ketch Cay Home, featuring an open floor plan, four-bedroom, four-bath layout, is nestled among tall palms, bougainvillea, hibiscuses, a shady lady (black olive) tree, and a majestic 50’ oak tree. Upon ascending the steps and opening the tall, thick, double French doors, a sense of tranquility and harmony with nature envelops you. Inside, the imported French White Oak flooring adds a touch of elegance to the 2,460 sq ft interior, installed specifically for this unique home. The light, airy, and relaxed ambiance of the home is complemented by views of the golf course, mangrove tree groves, and flowering hibiscus, enhanced by high ceilings throughout. Renovated between 2017 and 2024, upgrades include a new tile roof, an open-plan layout, an additional bath, two new porches, a new pool with travertine tile, updated electrical wiring and plumbing, Kitchen Aid appliances, and a 125-gallon water tank with a lifetime warranty. The 2021 air conditioning system is programmable for daytime comfort and nighttime cooling, while the pool waterfall adds a soothing touch, which can be easily turned off. The pool area features space for an outdoor barbecue, a mini kitchen with electric plugs and water access, and a convenient connecting shower. The back porch is equipped with new small-mesh screening, tile flooring, and two fans, along with Miami side screening for added privacy. Located in Windstar, a sought-after community for boaters and golfers, residents have access to a Tom Fazio championship golf course, top-rated Har-Tru tennis facilities, a fitness center, kayaking, boat and marina facilities, and a private ferry to Keewaydin Island. The community also boasts an elegant New clubhouse, fine dining options, and stunning views of Naples Bay. Situated in the heart of Naples, near 5th Ave, restaurants, shopping, entertainment, and pristine beaches, this home offers the perfect blend of luxury and convenience. Your search ends here—this is the one.

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  • $1,395,000
    $1,375,000

    Regatta Landing Windstar

    2431 Breakwater Way # 101, Naples, FL 34112
    • Condos - 2,681 ft²
    • 3 Bed
    • 2 Baths / 1 Half
    • Build 2016

    IMMEDIATE WINDSTAR FULL GOLF MEMBERSHIP AVAILABLE WITH THIS PROPERTY! A Rare Opportunity Awaits in Windstar! Welcome to Regatta Landing in the highly coveted Windstar on Naples Bay gated community. This exceptional first-floor coach home is a true masterpiece of luxury, offering 2,681 square feet of living space with extraordinarily high-end bespoke finishes throughout. With an attached two-car Garage, Three expansive Bedrooms and Three beautifully designed Bathrooms, this home exudes elegance and comfort at every turn. What sets this property apart is its extremely rare opportunity to secure immediate full golf membership to Windstar on Naples Bay, allowing you to skip the current six-year waitlist and start enjoying the club’s Tom Fazio-designed 18-hole golf course and world-class amenities from day one. Step inside to discover an expansive open floor plan, thoughtfully designed for both living and entertaining, bathed in natural light. The heart of the home is the chef’s kitchen, a true showstopper featuring an oversized island, top-of-the-line appliances, and flawless craftsmanship. The primary suite is a private retreat, boasting a spacious sitting area, his-and-hers custom closets, and a spa-like bathroom with a soaking tub, separate shower, and dual sinks. Enjoy serene and peaceful views from the lanai, which can be customized to your liking with screens or enclosed with hurricane-impact resistant sliders creating an additional living space. Windstar on Naples Bay offers an unparalleled lifestyle with an impressive array of world-class amenities. Golf enthusiasts will fall in love with the 18-hole Tom Fazio-designed golf course, where stunning fairways meet lush landscapes. The community’s newly renovated clubhouse serves as a sophisticated hub for dining, socializing, and enjoying breathtaking views of Naples Bay. Windstar residents also enjoy exclusive access to Windstar's private beach located on Keewaydin Island, accessible via Windstar’s private shuttle, The Keewaydin Queen. This service offers multiple daily trips, including sunset cruises to the island, where members can relax on the pristine sands with amenities provided. In the evenings, the shuttle transforms into a convenient water taxi, offering direct access to Naples’ finest waterfront restaurants. Adding to the community’s distinction is its status as the only neighborhood in Naples with a deep-water 72-slip private marina. Boating enthusiasts can take advantage of the full-time harbormaster and the private marina clubhouse, making it the perfect haven for those who love life on the water. Perfectly positioned in the vibrant Bayshore Arts District, this home is surrounded by cultural gems, art galleries, and unique dining experiences. Even better, you’re just five minutes from downtown Naples, where world-class restaurants, boutique shopping, and the sugar-sand beaches await.

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  • $1,350,000

    Somerset At Windstar Windstar

    2165 Paget Cir # 1, Naples, FL 34112
    • Homes - 1,908 ft²
    • 3 Bed
    • 2 Baths
    • Build 1989

    THIS IS THE MOST MAGNIFICENT VIEW IN WINDSTAR! AND....The home affords the opportunity for buyer to skip the wait on a SOCIAL MEMBERSHIP, which is currently on a waitlist. MAKE ME YOUR OWN is what we hear from this unbelievable property on the circle in Somerset. It is offered for sale "AS IS". Seller has cared for this home, as an original owner in the neighborhood and hopes to sell to someone who loves the views and location, that it has to offer, as much as she has. This is a 3 bedroom house, currently used as two bedrooms/den, with A SOARING CEILING MAKES IT AN OPEN, SPACIOUS FLOOR PLAN. The lanai is waiting to be extended and looks over water in all directions to a perfect short distance view of the golfing. It allows privacy but the ability to enjoy the play. The location on the circle's curve creates a more pie-shaped lot providing a perfect space for a larger outdoor entertaining spot.(Of course this must be checked by a survey.) For those who prefer it, the beautiful community pool and spa are directly across the street! It couldn't be better! It is obvious that Windstar Club is coveted with it's waitlisted GOLF AND SOCIAL memberships. Everyone wants a place in Somerset at Windstar! The championship golf course is designed by Tom Fazio and worth waiting for. The Social Membership is full of activities and events at the brand new Clubhouse with it's incredible Naples Bay views and perfect opportunities to meet all of the new Windstar residents. Windstar is exclusive with a private beach at Keewaydin with shuttle service daily as well as sunset cruises, AND a 72- slip marina to lease or purchase boat slips offering direct access to the Gulf. Bayshore with Botanical Gardens and all of the new restaurants makes it a perfect place to spend time and enjoy also a wonderful investment opportunity. Remember it is just 6 or 7 minutes from Old Naples with shopping and restaurants galore. People call it paradise.....you will call it home!

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