Cherry Oaks Homes with Pickleball Amenities

Welcome to Cherry Oaks, a vibrant subdivision nestled in the heart of Naples, Florida, within the beautiful Collier County. This charming community is designed for those who appreciate a blend of luxury and leisure, offering an idyllic lifestyle that perfectly captures the essence of Southwest Florida living.

Cherry Oaks is renowned for its stunning homes that come equipped with pickleball amenities, making it a haven for sports enthusiasts and families alike. With the sport’s growing popularity, residents can enjoy easy access to well-maintained courts right within the community. Whether you’re a seasoned player or just starting, the friendly atmosphere encourages residents to engage in friendly matches, fostering a sense of camaraderie among neighbors.

The homes in Cherry Oaks are thoughtfully designed, featuring spacious layouts and modern finishes that cater to a variety of lifestyles. From cozy single-family homes to elegant estates, each residence boasts beautiful landscaping and outdoor spaces ideal for entertaining or simply relaxing in the Florida sun.

Living in Cherry Oaks means more than just enjoying your home; it’s about embracing a lifestyle filled with amenities and activities. The community is conveniently located near Naples' pristine beaches, upscale shopping, and fine dining, ensuring that everything you need is just a short drive away.

Discover the charm of Cherry Oaks, where pickleball courts and beautiful homes create a perfect blend of activity and relaxation. Experience the best of Naples living in this delightful community, and make Cherry Oaks your new home today!

Newest Cherry Oaks Homes with Pickleball Amenities

$599,000

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

$899,000

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 $500. 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

$669,000

3 Beds ⋅ 2 Baths ⋅ 226014907 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

$719,000

3 Beds ⋅ 3 Baths ⋅ 226014126 MLS ⋅ Cherry Oaks BLDG.

RARE JW Marriott Marco Island Rookery Social Membership Available with No Waiting Period. Skip the 500+ member waitlist and enjoy immediate access to beachfront luxury, resort pools, full service spa, valet service, three waterfront restaurants, seasonal golf at Rookery and Hammock Bay from June through October, plus exclusive dining and retail discounts from day one. Welcome to this exceptional top floor end residence in Cherry Oaks at Fiddler's Creek, offering over 3,000 square feet of beautifully updated living space with 3 bedrooms, + den, 3 baths, soaring ceilings, abundant natural light, and a private side entrance. The open concept design centers around a spacious island kitchen with gas cooking, granite countertops, white shaker cabinetry, stainless steel appliances, and generous gathering spaces. ELEVATOR layout in unit for future installation if desired. Enjoy western sunset views overlooking tranquil preserve, golf course, and lake vistas from your private lanai. The second floor location provides peace of mind with no flood concerns and an ideal lock and leave lifestyle. Recent updates, plantation shutters, designer finishes, and meticulous care make this home truly move in ready. Residents enjoy a private neighborhood pool plus access to Fiddler's Creek's 54,000 square foot Club & Spa featuring two restaurants, resort pools, lap pool, fitness center, full service spa, 6 USPTA tennis courts, 10 pickleball courts, bocce, and optional golf. Set within a breathtaking 4,000 acre Audubon sanctuary, this pet friendly residence delivers instant vacation living and exceptional value whether as a year round home, seasonal retreat, or luxury rental investment.

9097 Cherry Oaks TRL Unit 202, Naples

$910,000

3 Beds ⋅ 3 Baths ⋅ 226010269 MLS ⋅ Cherry Oaks BLDG.

Location, location, location! Expansive golf and water view coach home with sunset western exposure in Cherry Oaks and exceptional privacy. Experience refined living in this spacious second-floor end-unit residence, quality-built by reputable Gulf Bay and offered furnished with recently redecorated interiors and like-new, barely used furniture in the desirable community of Fiddler’s Creek. Offering over 3,000 square feet under air with three spacious bedrooms plus a study, three full baths, and an attached private two-car garage, this tranquil, light-filled home lives like a single-family residence and captures breathtaking Rookery golf course and water views with desired western exposure for spectacular nightly sunsets. Ideal adjacent to the community pool, the home offers the rare convenience of enjoying poolside living just steps away, like having your own pool without the maintenance, while the building’s unique positioning provides added privacy on the lanai with no neighboring lanai beside it, allowing for a peaceful outdoor setting. Inside, porcelain tile set on the diagonal flows throughout the main living areas, complementing a thoughtfully designed open layout ideal for everyday comfort and effortless entertaining. The kitchen features granite counters, tumbled marble backsplash, white cabinetry and GE Profile appliances, including a new dishwasher installed in 2025, and opens to the spacious living area filled with abundant natural light from multiple windows and glass sliders framing the beautiful views beyond. The serene primary suite offers windows overlooking the golf course, two walk-in closets, and a spacious bath with dual vanities, soaking tub and separate shower, while two additional guest bedrooms and a private den with French doors provide flexible space for guests, hobbies or a home office. One guest bedroom is exceptionally large and often used as a second primary suite, offering flexibility for extended family or visiting guests. Additional updates include a new clothes washer installed in 2022 and a newer dryer. The expansive screened lanai invites you to relax while taking in sweeping golf and water views framed by glowing sunset skies, creating a setting for calming morning coffee or relaxing evening cocktails. Residents enjoy the exceptional lifestyle of Fiddler’s Creek, featuring resort-style pools, spa services, a fitness center with classes, active tennis and pickleball programs, fine and casual dining, and a full calendar of activities and social events, with optional golf, beach and marina memberships available. The excellent location offers a convenient shopping center just outside the gates with Publix, nail and hair salons, urgent care and a health food café, along with easy access to Marco Island, Old Naples, pristine beaches, parks and the executive airport.

9031 Cherry Oaks TRL Unit 201, Naples

$599,000

3 Beds ⋅ 2 Baths ⋅ 225073887 MLS ⋅ Cherry Oaks BLDG.

This beautifully furnished and exquisitely updated first-floor residence in desirable Cherry Oaks at sought-after Fiddler’s Creek offers a blend of comfort, style and southern exposure with tranquil golf course and water views from the screened lanai. The water feature sits directly in front of the condominium, creating a serene backdrop that enhances the home’s private and peaceful atmosphere. Designed for effortless luxury living, this spacious home features three bedrooms plus a den, two full baths and a two-car garage, providing functionality and elegance in every detail. Inside, the open-concept layout is highlighted by recessed lighting, crown molding, ceiling fans and plantation shutters throughout. The interior is finished with luxury vinyl plank flooring, while the screened lanai features durable porcelain tile. The open kitchen is a showpiece with light cabinetry, under-cabinet lighting, quartz countertops, a porcelain tile backsplash and upgraded Samsung stainless steel appliances with enhanced features, including a five-burner natural gas cooktop, a divided oven that allows two temperature zones, and a refrigerator with a convertible bottom freezer that can function as either a refrigerator or freezer. A breakfast bar and a pantry with custom wood shelving complete this beautifully designed culinary space. The adjacent living room, complete with a three-panel glass slider, opens directly to the lanai, offering seamless indoor-outdoor living and an inviting setting for relaxation and entertaining. The primary bedroom suite is a private retreat featuring dual closets with wood slatted shelving. The renovated ensuite bath offers dual porcelain vanities and a walk-in shower with cut pebble flooring and floor-to-ceiling tile walls. Two guest bedrooms each include well-appointed closets, while the updated guest bath impresses with an accent wall, quartz vanity, and walk-in shower with a glass enclosure and floor-to-ceiling tile walls. A separate laundry room with a full-size washer and dryer and a utility sink adds convenience. Additional highlights include storm shutters, a Rheem HVAC system and a Noritz tankless natural gas water heater. Residents of Fiddler’s Creek enjoy access to a spectacular 54,000-square-foot clubhouse offering casual and fine dining, a resort-style multi-pool swimming complex with waterfalls, slides, and whirlpool, six Har-Tru lighted tennis courts, new pickleball courts, a bocce ball court, and a state-of-the-art fitness center with classes and trainers, along with full spa services. A vibrant year-round social calendar and 24-hour manned gate with roaming security patrol further enhance this resort-style community, providing an unparalleled lifestyle in the heart of Naples. Optional golf course memberships are available at the recently renovated, award-winning Arthur Hills golf course and the new golf clubhouse, with optional beach and marina memberships also offered.

9134 Cherry Oaks LN Unit 102, Naples

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