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Naples Florida Windstar Homes for Sale

Naples Florida Real Estate

Windstar Naples Real Estate

Homes For Sale7$989K - $8.4M
Condos For Sale16$495K - $1.7M
Sold23$449K - $6M
Last updated at 9:45pm 01/27/2025

$3,999,999
Decrease*
$700K
Apply for Financing

MLS# 224070135

1390 Gulfstar Dr S, Naples, FL 34112

Homes - 3,300 ft² / 3,800 ft² - 2 Car Garage

4+Den / 3 Baths / Pool / Spa

Built 1995

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!

PROPERTY DETAILS:

Community Name: Windstar
Community Type: Boating, Gated, Golf Course, Tennis
Subdivision: Southpointe Yacht Club
Amenities: Bocce Court, Clubhouse, Fitness Center, Golf Course, Marina, Pickleball, Restaurant, Tennis Court(s)
Building Design: Ranch, Single Family
Building Desc: 1 Story/Ranch
Living Area: 3,300 ft²
Total Area: 3,800 ft²
View: Bay, Canal, Mangroves, Water Feature
Waterfront Desc: Navigable
Boat Access: Boat Lift, Dock Deeded, Dock Included
Unit Floor: 1
Total Floors: 1
Parking: Attached
Garage Spaces: 2
Construction: Concrete Block, Stucco
Exterior Features: Dock Deeded, Dock Included, Screened Lanai/Porch, Built In Grill
Roof: Tile
Private Pool: Below Ground, Electric Heat
Private Spa: Heated Electric
Floor Description: Carpet, Tile
Interior Features: Built-In Cabinets, French Doors, Laundry Tub, Pantry, Wired for Sound, Walk-In Closet(s)
Pets: Yes
Units in Building: 1
On Site Since: 08/27/2024
Irrigation: Central
Water: Central
Equipment: Auto Garage Door, Central Vacuum, Cooktop - Electric, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Icemaker, Security System, Smoke Detector, Washer
Floor Plan Type: Other
Furnished Desc: Partially
Maintenance: Master Assn. Fee Included, Security, Street Lights, Street Maintenance
Min Days of Lease: 30
Leases Per Year: 3
Rear Exposure: S
Restrictions: Deeded, No Commercial, No RV
Acres: 0.5
Lot Desc: Cul-De-Sac
Lot Left: 220
Lot Right: 225
Lot Back: 100
Lot Frontage: 100
HOA Fees: $3,500 Quarterly
Master HOA Fee: $1,033 Quarterly
Total Annual Recurring Fees: $18,132
Taxes: $28,390
Tax Year: 2023
Golf Type: Golf Equity
Gulf Access Type: No Bridge(s)/Water Direct

THIS PROPERTY IS COURTESY OF:

John R Wood Properties

IMAGES:

LOCATION:

AREA SPECIALIST:


Helen Mikhailova
2025 Five Star Real Estate Agent

Certified Luxury Home Marketing Specialist
Helen Mikhailova

AREA Specialist, REALTOR®
Broker Associate
GRI - Graduate Realtor Institute
CLHMS - Certified Luxury Home Marketing Specialist
Million Dollar GUILD
SRS - Seller Representative Specialist
Five Star Real Estate Agent 2020-2022 Award

Luxury of Naples Group at Premiere Plus Realty

Phone: (239) 217-6283

Websitehttps://www.realtyofnaples.com

Bio: Helen Mikhailova is a highly accomplished Real Estate Broker with a Graduate Real Estate Institute (GRI) designation, a Luxury Home Marketing Specialist certification, and a newly earned Residential Interior Designer Certification. Fluent in English, Ukrainian, and Russian, Helen's multilingual abilities, business acumen, and global travel experience make her an exceptional choice for clients from diverse backgrounds.
Since 2005, Helen has called Naples home and has been helping clients navigate the real estate market since 2011. Her 14+ years of experience in real estate have equipped her with the expertise and insight to guide clients through every stage of the buying or selling process.
With a Master’s Degree in Mathematics, Helen brings a unique analytical perspective to real estate, ensuring clients receive informed, data-driven guidance. Her dedication to excellence has earned her recognition as a 5-star Agent from 2020 to 2023, and again in 2025, a testament to her commitment to client satisfaction and outstanding results.
"I love working with people and seeing their joy when a deal closes. Real estate allows me to connect with individuals, build meaningful relationships, and help them achieve their goals. Every day is different, exciting, and rewarding—it’s why I love what I do."
Helen’s deep knowledge of Naples and its unique communities comes from nearly two decades of living in the area. Her extensive travels enable her to confidently compare Naples to some of the world’s finest destinations. "Naples is one of the most sophisticated, attractive, and relaxing towns I’ve ever experienced. I am proud to call it my home and to help others do the same."
Helen specializes in creating stress-free, enjoyable real estate experiences for her clients. Whether working with locals or newcomers to sunny Florida, she excels at making the process seamless and satisfying.
"Through clear communication and a personalized approach, I help my clients turn their vision of living in beautiful, sunny Naples into reality."

CONTACT / REQUEST APPOINTMENT:


In order to better assist our clients, we need to know as much as possible relating to: you, your situation, your needs, what you are looking for, and how we can best assist you. Please be as detailed as possible, for if you are vague, we may miss something - thus, not providing the best service possible. Your satisfaction is our top priority. By providing your phone number, you consent to receive communications, including but not limited to text messages and phone calls, from Luxury Of Naples Group regarding your inquiries, appointments, updates, or other services. Message and data rates may apply. You can opt-out at any time by replying STOP to any text message or contacting us. Thank you and we look forward to earning your business.








Broker Reciprocity LogoThis property is courtesy of John R Wood Properties.

*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*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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