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Regatta Landing Windstar Naples Florida Condos for Sale

Naples Florida Real Estate

Windstar Naples Real Estate

Homes For Sale2$1.1M - $7.5M
Condos For Sale11$449K - $2M
Sold ( Past 6 Months )34$395K - $4M
Last updated at 9:25am 04/01/2026

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$1,350,000
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Regatta Landing at Windstar

2472 Breakwater Way 11102, Naples, FL 34112

Condos - 2,348 ft² / 3,152 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2021
Regatta Landing Windstar Naples Condos for Sale: Skip the waitlist and step directly into the Windstar lifestyle. This exceptional residence offers the rare opportunity for immediate Social Membership at Windstar on Naples Bay, granting access to one of Naples’ most sought-after private communities without delay. Even more extraordinary, a private 30-foot boat slip with a 12,000-pound electric lift is included, complete with water and electric, delivering direct Gulf access with no bridges. From dock to open water in minutes, your boating lifestyle begins the moment you arrive. Welcome to 2472 Breakwater Lane, Unit 11-102, a sophisticated coastal retreat built in 2021, offering 2,348 square feet of beautifully designed living space and 3,152 total square feet, including a private two-car garage. Designed for luxury buyers who value refined finishes and effortless indoor-outdoor living, this residence blends architectural elegance with the relaxed rhythm of Naples waterfront living. From the moment you enter, soaring 12-foot ceilings and expansive hurricane impact-resistant doors and windows flood the home with natural light, creating an airy and grand ambiance. The open floor plan flows seamlessly, ideal for entertaining guests after a day on the water or hosting intimate evenings during season. Quartz countertops shimmer throughout the home, offering a clean, contemporary aesthetic that pairs beautifully with the coastal palette and high-end finishes. Step onto the screened lanai and take in peaceful, serene water views that create a calming backdrop to daily life. Morning coffee feels more tranquil, and evening sunsets reflect softly across the water, delivering the true essence of Naples waterfront living. The spacious two-bedroom plus den layout offers exceptional flexibility. The den functions beautifully as a private office, media room, or reading retreat, and with minimal modification could easily be converted into a third bedroom to accommodate additional guests or evolving lifestyle needs. The primary suite is a true sanctuary, thoughtfully designed with two separate walk-in closets featuring custom built-in cabinetry for elegant organization. The spa-inspired bath elevates the experience with dual vanities, a luxurious soaking tub, and a massive, expansive walk-in shower that creates a private retreat feel. It is a space designed for both relaxation and indulgence after a day on the water or enjoying the club amenities. Located within the gates of Windstar on Naples Bay, residents enjoy a private marina, championship golf, tennis, fitness, dining, and a private beach club on Keewaydin Island, all just minutes from the world-class dining, shopping, and cultural charm of downtown Naples and its pristine Gulf beaches. For the discerning buyer seeking luxury, boating convenience, serene water views, and immediate access to an elite club lifestyle, this residence offers a rare opportunity to live exceptionally.



$1,249,000
Decrease*
$46K
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Regatta Landing at Windstar

2472 Breakwater Way 11101, Naples, FL 34112

Condos - 2,348 ft² / 3,028 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2021
Regatta Landing Windstar Naples Condos for Sale: Beautiful first-floor end unit with no neighboring building next door. Built in 2021, this highly desirable open floor plan features 2 bedrooms + den (with Murphy bed), 2 full baths, loads of upgrades, and an attached 2-car garage, along with storm impact windows and doors, crown molding, and 2,348 sq. ft. of living area with over 3,000 sq. ft. total. The thoughtfully designed layout flows effortlessly from the spacious great room into the expansive open kitchen, beautifully appointed with an oversized island, custom white wood cabinetry, stainless steel appliances, induction cooktop, double wall oven, wine cooler, and quartz countertops. Large-format tile flooring runs throughout the main living areas, enhancing the home’s bright and airy ambiance. The luxurious primary suite offers a comfortable sitting or desk area, two custom walk-in closets with built-ins, and a spa-inspired bath featuring dual vanities, a walk-in shower, and a relaxing soaking tub. Regatta Landing, located directly on Haldeman Creek, offers owners the opportunity to purchase 20–30 ft. boat slips, most with lifts, when available, providing direct deep-water access to Naples Bay and the Gulf—enhancing the ultimate boating lifestyle. Residents also enjoy a sparkling private community pool and spa, along with a social grill room perfectly positioned on the waterway—ideal for embracing the Southwest Florida lifestyle. Windstar offers exceptional amenities including a Tom Fazio–designed golf course, newly redesigned clubhouse with sweeping views of Naples Bay, 72-slip deep-water marina with direct Gulf access in under ten minutes, clay tennis courts, bocce ball, state-of-the-art fitness center, and private Windstar boat shuttle to Keewaydin Island’s white sandy beach featuring a shaded pavilion, restrooms, charcoal grill, and exceptional shelling & fishing!



$1,624,750
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Regatta Landing at Windstar

2488 Breakwater Way 201, Naples, FL 34112

Condos - 3,563 ft² / 4,453 ft² - 2 Car Garage

3+Den / 3 Baths

Built 2020
Regatta Landing Windstar Naples Condos Under Contract: Welcome to Elevated Coastal Living at its finest in Regatta Landing at Windstar on Naples Bay Step into an exceptional waterfront lifestyle in this rarely available and absolutely stunning coach home offering 3,563 square feet under air (and 4,453 total) of refined, light-filled living space designed for both luxurious comfort and effortless entertaining. Built in 2020 and loaded with upgrades, this residence lives like a single-family home with the ease of condo living. From the moment you enter your private elevator into the expansive open floor plan, you’re greeted by soaring ceilings, sweeping peaceful views, and designer finishes throughout. The gourmet kitchen is a showstopper that is sprawling in scale with a massive center island with Quartz countertops, induction cooktop, dual wall ovens, and a walk-in pantry that’s practically a room of its own. Entertain in style with a wet bar, coffee bar, and two wine coolers—all perfectly designed to impress guests or unwind in luxury. This home offers Three spacious Bedrooms plus a Den and Three Full Bathrooms, with one guest suite generous enough to serve as a second primary bedroom complete with its own en-suite bath, enormous walk-in closet, and ample square footage for long-term visitors or multigenerational living. The screened back lanai offers a peaceful escape with serene water views, lush tropical landscaping, and electric hurricane shutters for peace of mind. Hurricane-impact resistant windows and doors throughout further enhance safety and security. Step outside to your private balcony, enjoy morning coffee with the birds, or toast to golden hour sunsets. Tucked behind the gates of Regatta Landing, the newest community in prestigious Windstar on Naples Bay, you’ll enjoy exclusive access to a resort-style cabana pool with a summer kitchen overlooking the water—a perfect retreat just steps from your front door. Windstar on Naples Bay is one of Naples’ best-kept secrets offering residents a private boat shuttle to the Keewaydin Island Beach Club, with trips running multiple times daily and sunset cruises in the evening. Windstar’s unmatched amenities include a Tom Fazio-designed golf course, tennis and pickleball courts, a clubhouse with fine dining, a fitness center, and a deepwater marina. Ideally located just minutes from downtown Naples and the sugar sand beaches, you’ll also love being right at the gateway to the Bayshore Arts District an eclectic and rapidly growing hub of creativity and culture. Walk or bike to waterfront dining, breweries, live music, art galleries, the botanical gardens, and more. If you’re looking for a home that blends spacious luxury, waterfront serenity, and a vibrant lifestyle this one checks every box.



$1,795,000
Sold Price:
$1,700,000
Sold Date:
01/08/2026
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Regatta Landing at Windstar

2472 Breakwater Way 11-202, Naples, FL 34112

Condos - 3,403 ft² / 4,437 ft² - 2 Car Garage

4 Bed / 3 Baths

Built 2021
Regatta Landing Windstar Naples Condos: Your Naples Dream Home is ready- 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 professionally decorated and 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 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 making it perfect for entertaining in effortless style. Elegant finishes like shiplap detailing add charm and warmth, while the oversized attached two-car garage, with extra storage area, and hurricane impact doors and windows provide both comfort and security.Beyond the residence lies a lifestyle that is truly unmatched. Windstar on Naples Bay is a guard-gated, private country club community offering a world of amenities: a Tom Fazio–designed 18-hole championship golf course, tennis, and a soon-to-be-completed state-of-the-art fitness center overlooking the water (2026). The bayside clubhouse offers fine dining with sweeping views, while a private boat shuttle whisks you away to Windstar’s exclusive retreat on Keewaydin Island, where a pristine beach awaits. For boaters, Windstar boasts a private deepwater marina with 72 slips, private Marina Clubhouse and a full-time harbormaster. All of this is just five minutes from downtown Naples, where world-class dining, shopping, and beaches await, and right next to the Bayshore Arts District, one of the city’s most vibrant neighborhoods. This is more than a home....it’s a gateway to the ultimate Naples lifestyle.



$1,345,500
Sold Price:
$1,200,000
Sold Date:
10/21/2025
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Regatta Landing at Windstar

2431 Breakwater Way 10101, Naples, FL 34112

Condos - 2,681 ft² / 2,681 ft² - 2 Car Garage

3 Bed / 2 Baths / 1 Half

Built 2016
Regatta Landing Windstar Naples Condos: No Wait. No Compromise. IMMEDIATE FULL GOLF MEMBERSHIP AVAILABLE with This Property — Start Playing from Day One. Bypass Windstar’s current 6-year waitlist and secure your spot in one of Naples’ most exclusive golf and waterfront communities. Located in the sought-after Regatta Landing at Windstar on Naples Bay, this upscale coach home offers a rare opportunity to enjoy a luxury lifestyle—with full golf privileges from the moment you move in. Offering nearly 2,700 square feet of thoughtfully designed living space, this ground-floor residence combines high-end finishes with everyday comfort. The interior features beautifully updated 12x24 porcelain tile flooring, lending a modern, clean look that runs throughout the main living areas. Tall ceilings, expansive windows, and an open layout create a bright and welcoming atmosphere. The chef’s kitchen is designed to impress—with a large center island, premium stainless steel appliances, and custom cabinetry, it serves as the heart of the home for both entertaining and daily living. The primary suite is an elegant escape, featuring a cozy sitting area, dual custom walk-in closets, and an expansive spa-like bathroom complete with a deep soaking tub, large walk-in shower, and dual vanities with high-end finishes. Two additional bedrooms and two-and-a-half bathrooms provide privacy and flexibility for family or guests. Step out onto the private lanai overlooking tranquil preserve views—it’s fully screen-enclosed and can be upgraded with impact-resistant sliders for year-round enjoyment. A private two-car attached garage adds convenience and security. Windstar on Naples Bay is a lifestyle destination all its own—offering a deep-water marina with 72 private slips, a newly renovated clubhouse with dining overlooking the bay, tennis courts, a full fitness center, and exclusive boat access to Keewaydin Island’s private beach club. Just minutes from downtown Naples and the cultural charm of the Bayshore Arts District, everything you need is within reach. Golf. Water. Beach. No waiting. Immediate full golf membership opportunities like this are exceptionally rare. This is more than a home—this is your front-row seat to the Windstar lifestyle.




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*Just Listed: new properties that came on the market within the last 30 days.
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*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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