Browse All Four Winds Properties for Sale

2 Beds ⋅ 2 Baths ⋅ 226016825 MLS ⋅ Four Winds BLDG.

Step into this move-in-ready, well maintained, fully updated condo and experience the best of Naples waterfront living. This 2-bedroom, 2-bath home sits directly on a canal with partial Naples Bay views, overlooking the Tin City area—and offering stunning sunsets each evening from the comfort of your own space. With 5th Avenue South, 3rd Street, and multiple Gulf beach access points just 5–10 minutes away, you’ll enjoy unmatched proximity to Naples’ top boutiques, restaurants and pristine beaches. A deeded 26' boat dock is included, providing direct access to the bay. Cruise to Tin City or Bayfront for dinner, fish the nearby mangroves or open Gulf, or head to famous Keewaydin Island—just a short ride by boat. The condo features a long list of recent upgrades: brand-new hurricane-impact windows with a transferable warranty, a new roof and electrical service, updated kitchen and bathrooms, a new soaking tub, new flooring, and a 2-year-old AC system and appliances. The community pool is being fully renovated, and the assessment has already been covered. This is a rare opportunity to own a beautifully updated waterfront home in a prime Naples location—without the long commute from the outskirts. Whether you’re seeking a vacation getaway or a full-time residence, this condo offers convenience, comfort, and nightly sunsets that make every day feel like a getaway.

1100 Little Neck CT Unit F52, Naples

Courtesy of Premiere Plus Realty Company.

$649,000

3 Beds ⋅ 2 Baths ⋅ 226016242 MLS ⋅ Four Winds BLDG.

Welcome to your Waterfront Escape with BOAT LIFT - this beautifully maintained first-floor, 3-bedroom, 2-bathroom furnished condo offers the perfect blend of comfort, convenience, and coastal living. Step inside to find a bright, open layout with tasteful furnishings throughout, making this home truly move-in ready. This spacious living and dining areas flow seamlessly to a screened lanai, where you can relax and enjoy tranquil canal views and gentle breezes. The kitchen is well-dashed appointed, with ample cabinetry and counter space, ideal for both everyday living and entertaining. The primary suite features a private bath and generous closet space, while two additional bedrooms provide flexibility for guests, a home office, or family living. What truly sets this property apart is the included deeded 25ft boat dock with lift, offering direct canal access - perfect for boating enthusiasts looking to get on the water with ease. Additional highlights include convenient first-floor access, elegantly furnished for immediate enjoyment or rental potential, laundry in residence, assigned parking, and peaceful waterfront setting. Whether you're seeking a fulltime residence, seasonal retreat or investment opportunity, this condo delivers the ultimate Florida lifestyle -just minutes from open water and dining and shopping on 5th Ave, 3rd Street, and Bayshore Drive. Boat, relax, and live the waterfront Dream!

1200 Blue Point AVE Unit A2, Naples

Courtesy of Compass Florida LLC. 239-530-8555

$845,000

2 Beds ⋅ 2 Baths ⋅ 226012677 MLS ⋅ Four Winds BLDG.

Experience effortless, maintenance-free living in this beautifully updated 2-bedroom, 2-bath residence with sitting room/den, ideally located in the highly sought-after Royal Harbor area. Situated in the desirable Four Winds community, this property offers unmatched convenience just a short walk, bike ride, quick trip to downtown Naples’ iconic Fifth Avenue, known for its upscale dining, boutique shopping, and pristine Gulf beaches. This rarely available third-floor corner end unit with elevators boasts breathtaking panoramic western views over Naples Bay, delivering spectacular sunsets from nearly every room. Completely updated with exceptional attention to style and detail, the home exudes a light, airy coastal elegance. Step inside to a spacious open concept living area where walls of windows frame the stunning waterfront backdrop. The thoughtfully designed layout flows seamlessly from the living room to the den featuring a cozy fireplace and into the dining area with a custom built-in bar, perfect for entertaining. The chef’s kitchen is a standout, showcasing stainless steel appliances, shaker-style cabinetry, a custom wood hood, open shelving, white quartz countertops, and a designer backsplash. Unwind on the enclosed lanai while taking in sweeping sunset views over the bay. The serene primary suite also enjoys water views, a generous walk-in closet, and a beautifully appointed en-suite bath with dual vanities and a walk-in shower. The guest bedroom offers equally impressive views, while the second full bath has been fully updated with a walk-in shower. Additional highlights include: New impact-resistant windows and front door, in-unit laundry and ample guest parking. A boater's dream with updated docks on this 5 acre beautiful landscaped property. Included in the your common property includes equal ownership of a private caretaker's cottage. Four Winds offers a host of brand new amenities with all assessments paid, including a new pool, stone tile surround, waterfront party deck, refreshed landscaping, and a brand-new clubhouse, all overlooking Naples bay (anticipated completion Summer 2026), along with tennis and pickleball courts. Perfectly positioned with easy access to downtown Naples, I-75, and both Naples and Fort Myers airports, this 55+ community also presents an excellent investment opportunity as a highly desirable rental property. An on-site optional 26-foot private boat dock slip #15 available as a separate purchase at $25,000, providing direct and convenient access to the Gulf. With the nearby new construction condos at Avra Metropolitan ranging in price from $2-7M as well as The Halcyon with canal frontage in the $3-7M price range this is truly a great value for a fully renovated home directly on Naples Bay.

1140 LITTLE NECK CT Unit D37, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$450,000

3 Beds ⋅ 2 Baths ⋅ 225078444 MLS ⋅ Four Winds BLDG.

Discover your ideal retreat with this exceptional three-bedroom, two-bath waterfront condominium, offering direct deep-water access to the stunning Gulf of Mexico. Boat slips available for lease. On picturesque Naples Bay, this property features breathtaking views and a serene atmosphere that epitomizes coastal living. As you enter inside, you'll be greeted by an open and airy living space that invites natural light and panoramic water views. The open floor plan flows seamlessly into the cozy living and dining areas, and lanai making it ideal for entertaining family and friends. The main suite is a true oasis, complete with an en-suite bath and walk in closet. This condominium is part of a vibrant community, boasting fantastic amenities including a sparkling community pool, a welcoming clubhouse and convenient tennis courts. Whether you seek relaxation, recreation or potential rental income, this complex has something for everyone. Priced significantly below market value for a quick sale, this property presents a unique opportunity to own a piece of paradise. Don’t miss out on this exceptional waterfront haven, so schedule a viewing today and experience the charm of Naples living!

1200 Blue Point AVE Unit A1, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Downing Frye Realty Inc..

$375,000

2 Beds ⋅ 2 Baths ⋅ 225065989 MLS ⋅ Four Winds BLDG.

BEST PRICED WATERFRONT CONDO IN THE SANDPIPER AREA! Boaters will appreciate the 27-foot deeded boat dock complete with water and power, providing direct, bridge-free access to the Gulf of Mexico. This top-floor, end-unit residence at Four Winds on Naples Bay offers 2 bedrooms and 2 bathrooms in a prime location set across 5 beautifully maintained acres, all within walking distance to downtown Naples. The condo has been thoughtfully updated with granite countertops, stainless steel appliances, a new HVAC system, a new roof, and storm-impact sliders, creating a move-in-ready coastal retreat. Residents enjoy a waterfront lifestyle with amenities that include a bayside pool overlooking Naples Bay, pickleball and tennis courts, a social chickee hut, and a brand-new pool house currently under construction. Located just minutes from downtown Naples, world-class dining, shopping, and pristine Gulf beaches, this property also allows immediate rental opportunities, making it an excellent option for both personal enjoyment and investment.

1125 Little Neck CT Unit G63, Naples

Courtesy of John R Wood Properties. 239-331-1259

Selling Office: John R Wood Properties.

$565,000

3 Beds ⋅ 2 Baths ⋅ 224055153 MLS ⋅ Four Winds BLDG.

Highly desired waterfront residence in Oyster Bay features spectacular sunset views overlooking Naples Bay. Fully furnished and move-in ready, it offers 3 bedrooms, 2 bathrooms, in-unit laundry, and a deeded boat dock fitting up to a 27ft boat with direct access to Naples Bay and the Gulf of Mexico. Located on the 2nd floor right off the elevator. Beautifully updated with no damage from hurricane Ian! The kitchen features granite countertops, ample cabinetry and a breakfast bar. Open and spacious living area! Enjoy stunning water views from your master bedroom, which includes an oversized walk-in closet and an upgraded en-suite with dual sinks and a walk-in shower. A modern barn door separates the 2 guest bedrooms from the main living areas. Four Win?ds is a 55+ community with fantastic amenities such as tennis/pickleball courts, a heated community pool, cabana area, shuffleboard, BBQ area, and newly upgraded boat docks. Ideally located minutes from downtown Naples, beaches, shops, fine dining, and marinas! Secure parking and storage area included.

1200 BLUE POINT AVE Unit A5, Naples

Courtesy of EXP Realty LLC.

Selling Office: Armada Real Estate, Inc..

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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.

Four Winds Real Estate & Homes