Cherry Oaks Homes with Pickleball Amenities

Cherry Oaks Homes with Pickleball Amenities

Welcome to Cherry Oaks, a hidden gem nestled in the heart of Naples, Florida, within Collier County. This charming subdivision offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a vibrant community atmosphere.

As you explore Cherry Oaks, you'll be captivated by the lush landscapes and meticulously designed homes that reflect the essence of Florida living. Each residence is thoughtfully crafted to provide comfort and style, ensuring that you feel right at home from the moment you step inside.

One of the standout features of Cherry Oaks is its commitment to an active lifestyle, highlighted by the community's exceptional pickleball amenities. Whether you’re a seasoned player or a curious beginner, the pickleball courts are a fantastic way to stay fit, socialize, and enjoy the beautiful Florida sunshine. Imagine spending your afternoons perfecting your serve or engaging in friendly matches with neighbors, all while surrounded by the serene beauty of Cherry Oaks.

In addition to pickleball, the community fosters a welcoming environment with numerous parks, walking trails, and recreational areas, encouraging residents to embrace the outdoors. Located just a short drive from Naples' pristine beaches, world-class dining, and shopping, Cherry Oaks provides the perfect balance of relaxation and convenience.

Discover the charm of Cherry Oaks, where your dream home awaits, and an active lifestyle is just a step away. Come experience the delightful blend of community spirit and Florida luxury that makes Cherry Oaks a truly special place to call home.

Newest Cherry Oaks Homes with Pickleball Amenities

9031 Cherry Oaks TRL Unit 101, Naples
$560,000
3 Beds ⋅ 2 Baths ⋅ 226038680 MLS ⋅ Cherry Oaks BLDG.
Welcome to this beautifully appointed 3-bedroom + den, 2-bath coach home in the highly desirable Cherry Oaks Village. Perfectly positioned to capture stunning golf course and tranquil water views, this residence offers an exceptional blend of comfort, style, and location. Enjoy breathtaking western exposure from the expansive lanai, where you'll take in unforgettable sunset views each evening. The home also benefits from additional southern exposure along the side, enhanced by its prime positioning next to the community pool--allowing for abundant natural light without obstruction from neighboring buildings. The close proximity to the satellite pool adds an extra layer of convenience, making it feel like your own private retreat. Inside, the home features engineered hardwood flooring in all bedrooms and the den, complemented by tile throughout the main living areas for a clean and cohesive look. For added peace of mind and comfort, the property is equipped with dual automatic screens, including both durable metal shutters and sun shades--providing protection, privacy, and ease of use. This is a rare opportunity to enjoy scenic views, exceptional natural light, and an unbeatable location within one of the community's most sought-after neighborhoods. The award-winning, resort style community of Fiddler's Creek is enhanced by a club and spa, fitness center, swimming pools, two golf courses, tennis courts, pickleball courts, a bocce court, fine and casual dining, social activities, and miles of biking and walking paths. Optional beach club and marina memberships are available. Experience the epitome of luxury living, where every detail is thoughtfully curated to complement your lifestyle.

9031 Cherry Oaks TRL Unit 101, Naples
8951 Cherry Oaks TRL Unit 101, Naples
$549,000
3 Beds ⋅ 2 Baths ⋅ 226038364 MLS ⋅ Cherry Oaks BLDG.
Sunset first. Everything else second. There's something about a western exposure over water that never gets old. From the screened lanai, the view stretches across the lake to the golf course beyond, with the setting sun providing a different show every evening. And unlike a view you only appreciate from one room, this one becomes part of how you live. Welcome to Cherry Oaks at Fiddler's Creek. This first-floor coach home gives you single-family living without the upkeep: 2,408 square feet, a three-bedroom-plus-den floor plan, two full baths, and a two-car garage attached right to the residence. Bring your suitcase and start enjoying Naples. Inside, the layout is open, bright, and comfortable. Oversized sliders pull the lake view straight into the living area, and finishing touches like plantation shutters, crown molding, and designer lighting give every room a polished feel. The kitchen is built for everyday living and entertaining, with granite countertops, soft-close cabinetry, a gas cooktop, tile backsplash, GE Profile stainless steel appliances, and a casual dining area. The primary suite is a retreat of its own, two walk-in closets with custom built-ins, dual vanities, a separate makeup vanity, soaking tub, and oversized walk-in shower. Two guest bedrooms provide comfortable accommodations for family and friends, while the den offers a dedicated space for a home office, reading room, or media room. The beautifully renovated guest bathroom brings an unexpected touch of luxury with Brazilian Cristallo quartzite, a walk-in shower, shiplap detailing, and updated lighting. The improvements extend well beyond the finishes. Storm Smart impact windows, updated lanai sliders, no-see-um screening, a whole-home HVAC replacement, and a tankless water heater are among the investments already made. The lanai received new porcelain tile in 2025, and both guest bedrooms have updated flooring. Even the garage has been thoughtfully finished with epoxy flooring, cabinetry, and slat-wall storage. Beyond your front door, Fiddler's Creek offers a lifestyle that's difficult to duplicate. Recent community enhancements include a refreshed resort-style pool with waterfalls and slides, an upgraded Gator Grille, and 10 new pickleball courts. The renovated clubhouse features a fitness center, six Har-Tru tennis courts, a hot tub, sauna, and steam room. Golf is never required, but it's there when you want it. An optional membership opens up the championship course, the new golf clubhouse, the marina, and a private beach club, and there's currently no wait to join. The sunset views draw you in. The space, condition, furnishings, and Fiddler's Creek lifestyle make it easy to stay.

8951 Cherry Oaks TRL Unit 101, Naples
9097 Cherry Oaks TRL Unit 202, Naples
$699,999
3 Beds ⋅ 3 Baths ⋅ 226036140 MLS ⋅ Cherry Oaks BLDG.
Imagine trading Northeast winters for Christmas through Easter in your own Naples country-club retreat. INSTANT - NO WAIT LIST for JW BEACH MEMBERSHIP OPTION Only with this condo! Welcome to Fiddler’s Creek, where life extends far beyond the gates. Spanning nearly 4,000 acres of tropical landscapes, nature preserves, lakes and championship golf scenery, this private resort community offers an extraordinary combination of country-club living, recreation and coastal adventure. Why settle for an ordinary gated neighborhood when your Florida days can include so much more? At the heart of Fiddler’s Creek is a spectacular 54,000-square-foot Club & Spa with resort-style pools and cascading waterfalls, fitness and spa facilities, tennis, pickleball, bocce, and two exceptional dining choices, Gator Grille and Caxambas. Golf enthusiasts can explore separately available membership at The Golf Club; optional Tarpon Club membership opens up beach and marina experiences. Morning matches, afternoon swims, dinners with friends and boating adventures can all become part of your winter routine. And when it's time to come home, Mr. and Mrs. Clean welcome you to discover this immaculate coastal “cream puff” in Cherry Oaks, TURNKEY FURNISHED** and MOVE IN READY. Featuring one of the LARGEST CONDOMINIUM FLOOR PLANS IN FIDDLER’S CREEK, this spacious second-floor end residence offers an impressive 3,010 SQ. FT. OF LIVING SPACE, 3 bedrooms plus den, 3 full baths and an attached 2-car garage. Enjoy the spaciousness of a single-family home with room for holiday gatherings, entertaining friends, hosting overnight guests and making wonderful family memories. Beautifully coordinated coastal interiors, plantation shutters, natural-gas cooking and NEW 2026 waterproof luxury vinyl plank flooring create an inviting atmosphere. An expansive screened lanai captures western sunsets, tropical privacy and glimpses toward the golf course and lake. Designated space allows for a potential future private elevator. Two pets permitted within community weight restrictions. LOWEST Condo Fees in all of Fiddlers Creek entire community for this floor plan. An exceptionally rare opportunity makes this vacation residence even more compelling: the optional transfer of the seller's JW Marriott Marco Island/Rookery Social & Beach Membership. Imagine days on the beach and sunset cocktails overlooking the Gulf, with resort dining and social privileges. SKIP ONE WAITLIST. GET ACCESS TO ANOTHER. The transfer offers a way to bypass the Social Membership waitlist and become eligible to join the separate Rookery Golf Membership waitlist. Golf membership is not included. Bring your suitcase, welcome family and friends, and spend your season enjoying the country-club lifestyle instead of preparing a second home. Whether escaping winter, gathering for the holidays or living here year-round, your Naples retreat is ready for you.

9097 Cherry Oaks TRL Unit 202, Naples
9154 Cherry Oaks LN Unit 101, Naples
$569,000
3 Beds ⋅ 2 Baths ⋅ 226016081 MLS ⋅ Cherry Oaks BLDG.
Enjoy tranquil golf course views from this well-maintained, beautifully furnished first-floor end residence in the desirable Cherry Oaks village of Fiddler’s Creek, ideally on The Lane, a quiet, private enclave with no through traffic and a serene lake in front, offering exceptional privacy and a peaceful setting. With sought-after southwestern exposure, this spacious home is filled with plentiful natural light, enhancing its warm and inviting ambiance throughout. Thoughtfully designed with popular Blossom floor plan, this coach home features three spacious bedrooms plus a den, two full baths and a two-car garage, all complemented by a light, open-concept layout. Porcelain tile flooring set on a diagonal flows through the main living areas, while plantation shutters, recessed lighting and ceiling fans add style and comfort. Expansive sliding glass doors anchor the living space, seamlessly blending indoor and outdoor living while framing picturesque views of the beautiful Rookery golf course, creating a setting to relax or entertain on the private screened lanai. The open kitchen serves as a central gathering space, appointed with upgraded stainless steel appliances, including a French door refrigerator with a freezer drawer, quartz countertops, natural gas cooking, a spacious island with pendant lighting, tile backsplash, breakfast bar and a pantry with custom wood shelving, offering functionality and refined design. The private primary suite is a tranquil retreat featuring plantation shutters, direct lanai access and two walk-in closets with wood shelving, while the en-suite bath includes dual vanities, a soaking tub, frameless glass walk-in shower and private water closet. Two additional guest bedrooms provide comfortable accommodations with ample closet space and easy access to a full bath. A separate laundry room with a full-size washer and dryer and utility sink adds convenience. Additional features include storm shutters, a tankless gas water heater and a two-car garage with epoxy flooring and built-in cabinetry. Residents enjoy lush landscaping and the impressive 54,000-square-foot clubhouse with fine and casual poolside dining, resort-style pools with waterfalls and slides, state-of-the-art fitness center with trainers and classes, spa services, sauna and steam room, active tennis and pickleball with 10 pickleball courts, bocce and a vibrant social and event calendar, along with miles of scenic, tree-lined sidewalks for recreation, running and bicycling, while optional golf, beach and marina memberships complete this exceptional Naples lifestyle. The two championship golf courses within the community add to the beauty. Exceptional location convenient to 5th Ave and 3rd Street in Old Naples, the boutiques and beaches of Marco Island, and everything we love about life in Southwest Florida. Schedule your tour of this outstanding coach home and exceptional community today, you will not be disappointed.

9154 Cherry Oaks LN Unit 101, Naples
9041 Cherry Oaks TRL Unit 201, Naples
$875,000
3 Beds ⋅ 3 Baths ⋅ 226015860 MLS ⋅ Cherry Oaks BLDG.
Spectacular renovation at an elegant top floor end unit with endless golf and lake views. Upgrades include impact windows and doors, new solid wood cabinets in kitchen with lighted counter, new stainless steel appliances, wine cooler in central island (8x5 feet), soft close doors everywhere, pull out coffee station and toaster oven, almost new and upgraded elevator (3 years) new tile throughout (even in the lanai), new cabinets in kitchen and master bathroom, new fixtures in bathrooms, instahot, A/C only 2 years old, smooth wall finish in living area and new paint throughout. Lives like a single family house. Gas cooking! Fiddler's Creek Club & Spa membership transfer is available for 1-time fee of $5,000. Walking distance to the community pool and to the Fiddler's Creek award-winning Club and Spa. Amenities include Fiddler's Creek 54,000 sq ft Club and Spa with resort style swimming pools, sauna, fitness center, poolside bar and grille, fine dining restaurant, 2 championship golf courses, Tarpon Club Marina with dry and wet storage and private Beach membership.

9041 Cherry Oaks TRL Unit 201, Naples
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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.

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