About

WINDSTAR
Naples, FL

🏓 Pickleball

Regatta Landing at Windstar in Naples Florida is a gated coach home community featuring 64 upscale coach home condominiums.

Located within the 320-acre Windstar on Naples Bay master-planned community, Regatta Landing offers 3 bedroom and 3 bedroom plus loft designs, all with two-car garages, and with boat dockage available for sale, direct ocean access is mere minutes away.

Regatta Landing is located just off Bayshore Road in Naples.

We are not affiliated with the HOA or management of WINDSTAR, and we do not handle rentals within the community.
Our role is as a real estate brokerage, assisting buyers and sellers with their real estate needs within WINDSTAR.

Be sure to read the Southwest Florida monthly real estate market report to gain insights on the local market.

Go to Real Estate Market Report
WINDSTAR Naples FL
WINDSTAR
320Acres
64Homes
4Plans
Naples Collier County
Resale Homes
View WINDSTAR Active Listings
Community Street Names
Breakwater Way and Windward Ct.
Naples Attractions
Historic Palm Cottage, 5th Ave South, 3rd Street, Naples Train Museum, Barefoot Beach Preserve, Tin City, Naples Winter Wine Festival, Naples Botanical Garden, Corkscrew Swamp Sanctuary, Naples Pier and Beaches, Lowdermilk Beach, Revs Institute, Big Cypress, Greenway, The Bird Rookery Swamp, Rookery Bay Environmental Learning Center, and Air Boat Rides.


Market Report Video
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Community News-Stay Informed

WINDSTAR Latest News and Information

Friday 28th of August 2026
WINDSTAR Weather Forecast
WINDSTAR Amenities & Info
Fitness room
Gated
Community pool
Dining
Boating
Golf is optional
18 hole championship golf course
Clubhouse
Beach shuttle
Gulf access
Pickleball
Marina
HOA fees $100-$200 per month
No age restrictions
Boat docks available
Sold Out of new construction
WINDSTAR Site Map
WINDSTAR site map Open Site Map
Friday 28th of August 2026
Naples
Median Price Trend

Interested in WINDSTAR?

Buying or Selling in WINDSTAR
Feel free to send a message or call anytime.

Call Direct
239-229-9926
WINDSTAR

More Information

WINDSTAR

Photo Gallery

Regatta Landing At Windstar-New Home Rebate-Call Now!
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4 Floor Plans
WINDSTAR Floor Plans

WINDSTAR is sold out of new construction. These are the floor plans that were offered by the builder at the time of construction.

Showing 1–3 of 4
Grenada floor plan at WINDSTAR, Naples, Florida
Grenada Sold Out
1st Floor Unit
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 2,348 sqft
  • ✓ 2 car garage
Aruba floor plan at WINDSTAR, Naples, Florida
Aruba Sold Out
1st Floor Unit
  • ✓ 2 bed
  • ✓ 2 bath
  • ✓ 2,633 sqft
  • ✓ 2 car garage
Martinique floor plan at WINDSTAR, Naples, Florida
Martinique Sold Out
2nd Floor Unit
  • ✓ 3 bed
  • ✓ 3 bath
  • ✓ 3,403 sqft
  • ✓ 2 car garage
Cayman floor plan at WINDSTAR, Naples, Florida
Cayman Sold Out
2nd Floor Unit
  • ✓ 3 bed
  • ✓ 3 bath
  • ✓ 3,854 sqft
  • ✓ 2 car garage
WINDSTAR

Blog

Showing 1–3 of 11
WINDSTAR Naples Florida COLLIER COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET REPORT...
Blog
2025 January 13
COLLIER COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET REPORT...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDSTAR Naples Florida LEE COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET UPDATE...
Blog
2025 January 13
LEE COUNTY FLORIDA NOVEMBER 2024 REAL ESTATE MARKET UPDATE...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDSTAR Naples Florida LEE COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Blog
2024 November 29
LEE COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDSTAR Naples Florida COLLIER COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Blog
2024 November 29
COLLIER COUNTY FLORIDA OCTOBER 2024 REAL ESTATE STATISTICS IN 4K...
Categories: Naples, FL Real Estate Market News
By Ken O'Brian
Read More
WINDSTAR Naples Florida GOOD NEWS FOR BUYERS, RESALE HOME INVENTORY AND NEW HOME INVENTORY CONTINUES TO RISE IN SOUTHWEST FLORIDA.  THE BUILDERS
Archived Blog
2022 August 16
GOOD NEWS FOR BUYERS, RESALE HOME INVENTORY AND NEW HOME INVENTORY CONTINUES TO RISE IN SOUTHWEST FLORIDA. THE BUILDERS ARE REDUCING PRICES AND GIVING BUYER INCENTIVES. SELLERS ON MLS ARE CUTTING PR...
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
WINDSTAR Naples Florida MLS INVENTORY IN SW FLORIDA IS UP OVER 80% IN THE LAST 11 WEEKS!  SURE LOOKS LIKE MUCH BETTER PRICES ARE COMING.  CONTAC
Archived Blog
2022 May 13
MLS INVENTORY IN SW FLORIDA IS UP OVER 80% IN THE LAST 11 WEEKS! SURE LOOKS LIKE MUCH BETTER PRICES ARE COMING. CONTACT ME NOW TO GET MORE INFO....
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
WINDSTAR Naples Florida VERY OPEN FLOOR PLANS:
DOWNSTAIRS---2,348 SQ. FT. LOW $600’S FINISHED
 
UPSTAIRS –-----3,403 SQ. FT. (WITH ELEVAT
Archived Blog
2020 July 11
VERY OPEN FLOOR PLANS: DOWNSTAIRS---2,348 SQ. FT. LOW $600’S FINISHED UPSTAIRS –-----3,403 SQ. FT. (WITH ELEVATOR) LOW $700S FINISHED—1 LEFT HOA IS $599 CURRENTLY, WILL GO UP TO APPR...
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
WINDSTAR Naples Florida WINDSTAR NAPLES FLORIDA NEW CONDOS ON 4-24-2020...
Archived Blog
2020 April 25
WINDSTAR NAPLES FLORIDA NEW CONDOS ON 4-24-2020...
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
WINDSTAR Naples Florida 2020-03-15 REGATTA LANDING AT WINDSTAR NEW HOME COMMUNITY - NAPLES , FLORIDA NEW CONDO INVENTORY...
Archived Blog
2020 March 16
2020-03-15 REGATTA LANDING AT WINDSTAR NEW HOME COMMUNITY - NAPLES , FLORIDA NEW CONDO INVENTORY...
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
WINDSTAR Naples Florida WINDSTAR / REGATTA LANDING
*PRIVATE BEACH ON KEEWAYDIN ISLAND

NEW COACH HOMES (VERY  OPEN FLOOR PLANS, AND SPACIOUS)
Archived Blog
2020 March 10
WINDSTAR / REGATTA LANDING *PRIVATE BEACH ON KEEWAYDIN ISLAND NEW COACH HOMES (VERY OPEN FLOOR PLANS, AND SPACIOUS) DOWNSTAIRS---2,348 SQ. FT. LOW $600’S FINISHED UPSTAIRS –-----3,403 S...
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
WINDSTAR Naples Florida QUICK MOVE IN HOMES:: MARTINIQUE A

PRICED AT $917,990

    HOMESITE: #1521
    2534 WINDWARD COURT #15-201
    NA
Archived Blog
2018 January 05
QUICK MOVE IN HOMES:: MARTINIQUE A PRICED AT $917,990 HOMESITE: #1521 2534 WINDWARD COURT #15-201 NAPLES, FL 34112 MLS: #216042461 SQ FT: 3,563 BEDS: 4 BATHS: ...
Categories: Regatta Landing At Windstar Naples, FL 34102
By Ken O'Brian
Read More
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