Connect With Us


Login using...

Windstar on Naples Bay

windstar on naples bay

Windstar on Naples Bay is a 320-acre gated community with 15 distinctive neighborhoods in a location on Naples Bay close to Olde Naples.  The community has 554 residences including condos, coach homes, villas, single-family homes and waterfront estates.  The community offers golf, social and sports memberships to accommodate a variety of lifestyle options.    Read more about Windstar on Naples Bay.

Windstar Naples Bay Condos And Homes For Sale

Refine your search to less than 500 properties to save.
Click on the map to draw your polygon search.
Click on the map to draw your radius search.
Search only mappable listings within the map's bounds.

3284 Lookout Ln, NAPLES

3 Beds, 4 Baths, 3,275 SqFt
H.14372 Key West inspired home nestled in a quiet Windstar neighborhood. This 3 or 4 bedroom + den, 3.5 bath home wraps around a spacious newly screened courtyard with outdoor kitchen, pebble finish pool/spa, pondside setting plus golf course views. Perfect for lounging or entertaining. Custom paver path winds through your botanical oasis of lush landscape to a shaded pergola/patio adjacent to the lanai. Enjoy west-facing views from the a/c
John R. Wood PropertiesNaples Area Board of Realtors Logo

MLS® #219018420


2439 Breakwater Way 9202, NAPLES

3 Beds, 4 Baths, 3,856 SqFt
C.16984 WELCOME TO REGATTA LANDING” This Waterfront 2nd floor coach home is ready for you, with boat dock for up to a 30ft boat included, w/direct access to Naples Bay. Featuring 3,856 sq. ft. of luxurious living area, w/private elevator. The Coastal Contemporary Flair of This Cayman floor-plan (3 BR + den /Study, 3 full baths, a half bath) offers a great room w/soaring volume ceilings, hardwood flooring, custom light fixtures & plantation
John R Wood PropertiesNaples Area Board of Realtors Logo

MLS® #220001903


1701 Gulfstar Dr S 102, NAPLES

2 Beds, 3 Baths, 2,437 SqFt
Wonderfully updated condo with a view of the harbor right outside your door. Open the doors to the screened lanai to feel the breeze from the water and smell the salty air. Custom woodwork in living and dining areas add a touch of elegance. The neighborhood clubhouse overlooks the community pool and spa where you can socialize with your friends and swim year round.. The buildings have all been freshly painted with new roofs and landscaping. And
Coldwell Banker Residential RENaples Area Board of Realtors Logo

MLS® #220000713


1717 Gulfstar Dr S 201, NAPLES

3 Beds, 3 Baths, 2,437 SqFt
Fantastic open floor plan and rarely available 1st floor 3 Bedroom 3 full Bath coach home located in Yacht Harbour Cove at Windstar on Naples Bay! This well maintained home includes quality furnishings, beautifully remodeled bathrooms, spacious open kitchen with walk-in pantry, plantation shutters, chilled wine room, His & Her walk-in closets with custom built-ins, 490 sq. ft. screened terrace, 2 car garage with extra storage, brick paver
Downing Frye Realty Inc.Naples Area Board of Realtors Logo

MLS® #220007605


1754 York Island Dr, NAPLES

4 Beds, 3 Baths, 2,462 SqFt
Beautiful courtyard pool home with fabulous privacy and stunning golf course and lake views in Ketch Cay at Windstar on Naples Bay, located only minutes to 5th Avenue. This four-bedroom, three-full-bath home boasts tremendous upgrades throughout including imported marble flooring, Plantation shutters, crown molding, ceiling speakers in all rooms, a spacious kitchen and great room, a private master suite, spectacular lake and golf course views
Premier Sotheby's International RealtyNaples Area Board of Realtors Logo

MLS® #219061015


4966 Bollard Ct, NAPLES

3 Beds, 3 Baths, 2,451 SqFt
H.14349 One-of-a-kind Courtyard Home in WINDSTAR featuring a private pool and spa AND waterfront lake views, golf course, and sunset views. Once you enter the courtyard through lush landscaping, you are swept away with the beauty, privacy, and calm serenity of soft waterfalls streaming gently into the pool and relaxing gentle breezes surrounding you. Enjoy star-filled nights and beautiful sunsets from your highly desirable SW exposure lanai
John R. Wood PropertiesNaples Area Board of Realtors Logo

MLS® #219017205


2439 Breakwater Way 9102, NAPLES

2 Beds, 3 Baths, 2,633 SqFt
Immaculate Coastal coach home located in Regatta Landing, the newest community within Windstar on Naples Bay! This spacious 1st floor coach home offers over 2,600 sq. ft. of living area with a long list of quality upgrades and owner improvements including stainless KitchenAid appliances with double wall ovens, quartz counters, under cabinet lighting, frameless shower doors, crown molding, plantation shutters, beautiful French Oak hardwood floors
Downing Frye Realty Inc.Naples Area Board of Realtors Logo

MLS® #220001250


2513 Breakwater Way 2102, NAPLES

2 Beds, 3 Baths, 2,633 SqFt
First-floor coach home ready immediately in Regatta Landing in Windstar on Naples Bay. Like new with multiple upgrades, this popular Aruba open floor plan is perfect for a sophisticated casual lifestyle. Entertain in the gourmet kitchen with maple cabinets, double ovens, wine cooler, Santa Cecilia granite countertops, and large island with bar stool seating. The spacious Master bedroom has an adjacent bonus room that can be used as a study or
Premier Sotheby's International RealtyNaples Area Board of Realtors Logo

MLS® #219081739


2132 Paget Cir 1.47, NAPLES

3 Beds, 3 Baths, 2,611 SqFt
V.2794 - Step in to this beautifully renovated villa. This 2 story villa offers 3+den, 2.5 baths, beautiful pool/spa area, fireplace, vaulted ceilings, crown molding, gorgeous wood flooring and plantation shutters throughout. Kitchen offers gorgeous granite counter tops, white cabinets, SS appliances and large island kitchen. Large dining and living combined area allows for great family gatherings or entertaining friends. Master bedroom, den
John R. Wood PropertiesNaples Area Board of Realtors Logo

MLS® #219002533


2488 Breakwater Way 13-101, NAPLES

2 Beds, 2 Baths, 2,348 SqFt
This is a hidden gem and unique value opportunity. Just a couple miles from 5th Ave and beaches. Located within a double gated enclave of 64 luxury residences. New construction. Those who know Regatta Landing at Windstar agree it's Naples' best kept secret. This property offers everything that makes Naples desirable. Proximity to downtown, golf, boating, beach access, resort pool, and waterfront dining over Naples Bay. Golfers can join
Compass Florida NaplesNaples Area Board of Realtors Logo

MLS® #219058485


4403 Yacht Harbor Dr, NAPLES

3 Beds, 2 Baths, 2,125 SqFt
Fabulous 3 bed/2 bath residence in glorious Windstar on Naples Bay overlooking the 4th fairway of the challenging Fazio designed golf course. You'll love entertaining your guests around your private, exceptionally large heated updated pool that makes this home all about Florida living. Other total renovations include master and guest baths; new storm resistance pool cage; new resurfaced pool deck; new pool heater and pump; plantation shutters
Sun RealtyNaples Area Board of Realtors Logo

MLS® #219071635


2109 Paget Cir 1.3, NAPLES

3 Beds, 2 Baths, 1,908 SqFt
MOTIVATED SELLER! Beautifully Remodeled Luxury Home – 3 Bedroom, 2 full Baths and 2 car garage. Large lake view, light and charming with spectacular landscaping. Located in Windstar, one of Naples' most awarded communities, Tom Fazio 18 hole golf course, 6 Har-Tru tennis courts, state of the art fitness center with personal trainers. Limited memberships still available! Also includes a beautiful private pool and clubhouse for neighborhood use
Premier Sotheby's International RealtyNaples Area Board of Realtors Logo

MLS® #219078270

More About Windstar on Naples Bay

Windstar Amenities

  • Tom Fazio designed 18-hole championship golf course
  • Six har-tru tennis courts
  • Waterfront clubhouse
  • Fitness and wellness center
  • Casual and fine dining
  • 72-slip marina
  • Private beach club on Keewaydin Island accessed via boat shuttle

Windstar Location

Windstar is located on Naples Bay off Bayshore Road, south of US-41.  This location is southwest of downtown and offers an outstanding location for access the open waters of the Gulf of Mexico.

Blog Posts About Windstar

Four Coach Home Models Selling at Regatta Landing

A selection of model homes is now selling at Regatta Landing in Windstar on Naples Bay. This premiere community offers large coach homes with attached garages, within one of the area’s premiere boating and golf course communities.The four coach home models for sale are part of a total of just 64 coach homes available within Regatta Landing. Designated for active adults, the amenity-rich community offers the luxury of maintenance-free living, surrounded by the enjoyment of an exceptional l... Read More

Windstar Upgrading Clubhouse

This month the clubhouse at Windstar on Naples Bay in Naples will begin a $1.4 million interior remodel, and the club is expected to close for the summer.  The members of Windstar in Naples have approved this redesign in addition to an already approved $1.4 million golf course project which will include a greens rebuild for 22 putting greens.  Gulfshore Business Magazine named Windstar as the Best Private Country Club in Southwest Florida in 2013 and 2014.The Clubhouse upgrades will inclu... Read More

Seller Resources

Data last updated: January 28th, 2020 at 7:46am EST and updating occurs daily

Naples Area Board of Realtors Logo The data relating to real estate for sale on this Website come in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than Premiere Plus Realty Co. 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.