Browse All Southpointe Yacht Club Properties for Sale

Rare waterfront estate on exclusive Southpointe Island at Windstar on Naples Bay. Tucked behind double gates within an intimate enclave of only ten estate residences, this exceptional property offers privacy, direct Gulf access, and an unparalleled Naples lifestyle just minutes from downtown and world-renowned beaches. Positioned on nearly half an acre, this home features a private 40-ft dock in the backyard with the option to purchase an additional 50-ft protected slip in Windstar’s private marina—an extraordinary offering seldom available in Naples Bay communities. Spanning over 6,100 sq ft of refined interior living space, this 5-bedroom + den, 4 full and 2 half bath residence showcases spectacular 20+ ft contoured ceilings, abundant natural light, and meticulous attention to detail throughout. The chef’s kitchen is designed for both function and style, featuring custom cabinetry imported from Japan, quartzite countertops, a gas cooktop island, premium appliances, and seamless flow to the expansive outdoor living areas. The luxurious owner’s suite offers tranquil water and preserve views, a private balcony, and a spa-inspired bath with jetted soaking tub and walk-in steam shower. An elevator provides convenient access to the second level. Impact-resistant WinDoor windows and doors and a newer roof provide peace of mind. Outdoor living is exceptional, with nearly 5,000 sq ft of covered and open-air space including multiple balconies, a custom saltwater pool and spa with cascading water features, summer kitchen, and spacious lanai—ideal for entertaining or quiet waterfront relaxation. Residents of Windstar on Naples Bay enjoy access to a full suite of private club amenities, including championship golf, tennis, an active clubhouse, private beach access via shuttle, and a full-service marina with harbormaster. Membership opportunities subject to club approval and availability. A rare opportunity to own an estate-level waterfront home combining boating, privacy, and proximity at an exceptional value on Naples Bay.

1450 Gulfstar DR S, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$3,900,000

4 Beds ⋅ 3 Baths ⋅ 224070135 MLS

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!

1390 Gulfstar DR S, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$5,450,000

4 Beds ⋅ 5.5 Baths ⋅ 224045146 MLS

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.

1515 Gulfstar DR S, Naples

Courtesy of Gulf Coast International Prop.

Selling Office: John R Wood Properties.

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

Southpointe Yacht Club Real Estate & Homes