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.
WINDSTAR Naples FL
WINDSTAR
320Acres
64Homes
4Plans
Naples Collier County
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.

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
Community News • Stay Informed

WINDSTAR Latest News and Information

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Local Weather
Thursday 22nd of October 2026

WINDSTAR Weather Forecast

✓
Community Features

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
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Local Market
Thursday 22nd of October 2026

Naples Median Price Trend

Southwest Coast Realty

Interested in WINDSTAR?

Buying or Selling in WINDSTAR

Send us a message or call directly to learn more about this community and available real estate opportunities.

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Call Direct
239-229-9926
WINDSTAR

More Information

Your information will only be used to respond to your real estate inquiry.
4 Floor Plans

WINDSTAR Floor Plans

Historical Floor Plans: WINDSTAR is sold out of new construction. These are floor plans that were offered by the builder during 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

Latest News & Updates

9 Articles
Showing 1–3 of 9
WINDSTAR Naples Florida real estate news
Blog
October 21, 2026
Collier County Florida September 2026 Real Estate Market Update in 4K
Naples, FL Real Estate Market News By Ken O'Brian
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WINDSTAR Naples Florida real estate news
Blog
October 21, 2026
Lee County Florida Real Estate Market Update September 2026 in 4K
Naples, FL Real Estate Market News By Ken O'Brian
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WINDSTAR Naples Florida real estate news
Blog
October 5, 2026
Walking 5th Ave South in Naples Florida in 4K
Naples, FL Real Estate Market News By Ken O'Brian
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WINDSTAR Naples Florida real estate news
Blog
October 5, 2026
Lee County Florida Real Estate Market Report August 2026
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Blog
October 5, 2026
Collier County Florida Real Estate Market Update August 2026
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Blog
January 13, 2025
Collier County Florida November 2024 Real Estate Market Report
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Blog
January 13, 2025
Lee County Florida November 2024 Real Estate Market Update
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Blog
November 29, 2024
Lee County Florida October 2024 Real Estate Statistics in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Blog
November 29, 2024
Collier County Florida October 2024 Real Estate Statistics in 4K
Naples, FL Real Estate Market News By Ken O'Brian
Read More
WINDSTAR Archives

Archived Community Posts

7 Articles
Showing 1–3 of 7
WINDSTAR Naples Florida real estate news
Archived Blog
August 16, 2022
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...
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
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WINDSTAR Naples Florida real estate news
Archived Blog
May 13, 2022
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.
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Archived Blog
July 11, 2020
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...
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
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WINDSTAR Naples Florida real estate news
Archived Blog
April 25, 2020
windstar naples florida new condos on 4-24-2020
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Archived Blog
March 16, 2020
2020-03-15 Regatta Landing at Windstar New Home Community - Naples , Florida New condo inventory
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
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WINDSTAR Naples Florida real estate news
Archived Blog
March 10, 2020
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...
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
Read More
WINDSTAR Naples Florida real estate news
Archived Blog
January 5, 2018
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: ...
Regatta Landing At Windstar Naples, FL 34102 By Ken O'Brian
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