Sherwood Homes with Pickleball Amenities

Welcome to Sherwood, a vibrant subdivision nestled in the heart of Naples, Florida, in beautiful Collier County. Known for its lush landscapes and tranquil atmosphere, Sherwood offers a perfect blend of comfort and luxury, making it an ideal community for families, retirees, and everyone in between.

One of the standout features of Sherwood is its commitment to active living, highlighted by the availability of homes with pickleball amenities. As one of the fastest-growing sports in the country, pickleball has captured the hearts of many, and residents here have the unique opportunity to engage in this fun and social game right in their own backyards. Imagine stepping out of your beautifully designed home and onto the court, where friendly matches and community events foster connections with neighbors and friends.

The homes in Sherwood are thoughtfully designed, combining modern aesthetics with functional layouts to suit a variety of lifestyles. With spacious interiors, gourmet kitchens, and serene outdoor spaces, these residences provide the perfect backdrop for both relaxation and entertainment. The community also boasts well-maintained amenities, including walking trails and gathering areas, ensuring that residents can enjoy the best of Florida living.

Living in Sherwood means embracing a lifestyle filled with sunshine, camaraderie, and endless recreational opportunities. Whether you’re perfecting your pickleball serve or enjoying a serene evening stroll, this community invites you to experience the charm and warmth of Naples living. Discover your dream home in Sherwood today, where every day feels like a vacation!

Newest Sherwood Homes with Pickleball Amenities

$273,900

2 Beds ⋅ 2 Baths ⋅ 226027799 MLS ⋅ Sherwood BLDG.

Welcome to this charming, two bedroom, two bathroom condo perfectly situated at the end of a private cul-de-sac to offer serene and panoramic Lake views from your private lanai. As you step inside, you’ll be greeted by an abundance of natural light highlighting the spacious open concept living area design for both comfort and style. The kitchen features, sleek countertops, ample cabinetry, and plenty of space for preparing meals or entertaining guests. The living and dining areas, flow, seamlessly, creating and inviting space to relax while enjoying the peaceful beauty of the lake. Both bedrooms are generously sized with large windows that frame stunning water views. The master suite includes a private bath with a separate shower and dual vanities. The second bedroom is perfect for guests, family or as a home office. Additional features include in unit laundry, plenty of storage space and assigned parking space with one garage. Residence can take advantage of the community amenities, including a sparkling pool fitness center walking paths along the lake, as well as Pickleball and tennis courts ideal for outdoor enthusiasts. Best of all this condo is located within 15 minutes of beautiful beaches world class shopping on fifth Avenue and an array of fine dining restaurants, ensuring you’re never far from all the best Naples has to offer. Whether you’re looking for a full-time residence or a weekend retreat, this condo offers the perfect blend of luxury, convenience, and tranquility with breathtaking lake views from nearly every room.

431 Valerie WAY Unit 103, Naples

$348,900

3 Beds ⋅ 2 Baths ⋅ 226026405 MLS ⋅ Sherwood BLDG.

Welcome to Sherwood – Naples Living at Its Best Discover comfort, convenience, and resort-style living in this beautifully maintained 1st-floor end unit coach home in the highly desirable Sherwood community! This 3-bedroom, 2-bath home offers over 1,600 sq. ft. of living space with an open-concept design perfect for everyday living and entertaining. A HOME YOU'LL LOVE The open living and dining areas create a warm and inviting atmosphere. The well-appointed kitchen features abundant cabinetry, granite countertops, upper cabinet lighting, a breakfast area, and plenty of functionality for everyday living. Additional highlights include tile flooring throughout, interior rooms painted within the past two years, a fully updated guest bathroom (2024), a new AC unit (2025), and a new garage door motor (2026). The spacious primary suite offers a walk-in closet, a private en-suite bath with dual vanity cabinet, and a walk-in shower. Two additional bedrooms provide flexibility for family, guests, or a home office. COMFORT & CONVENIENCE Enjoy the ease of first-floor living with an attached garage (no stairs), easy access, and added privacy on your screened lanai—complete with tile flooring. RESORT-STYLE AMENITIES Sherwood residents enjoy access to a wealth of amenities, including 12 acres of picturesque lakes, two pools, a tennis court, four pickleball courts, a fitness room, and a clubhouse with a gathering room and kitchen—perfect for social events and activities. A COMMUNITY THAT HAS IT ALL Sherwood is a pet-friendly community (up to 2 pets) with six neighborhood associations and a master association that maintains our beautiful common areas. Low condo fees include internet, cable, water, garbage, and outdoor pest control for worry-free living. PRIME NAPLES LOCATION Ideally located just off Radio Road, this home is only a short drive to the stunning white sand beaches of Naples and approximately eight miles from Downtown Naples, with close proximity to historic Naples, Tin City, the airport, premier shopping, dining, and easy access to I-75. Whether you're looking for a seasonal retreat or a full-time residence, this move-in ready home offers the perfect blend of comfort, convenience, and the Florida lifestyle. Don't miss your opportunity to own a slice of paradise—schedule a showing today!

517 Robin Hood CIR Unit 101, Naples

$339,900

2 Beds ⋅ 2 Baths ⋅ 226025908 MLS ⋅ Sherwood BLDG.

Motivated Sellers. Gorgeous, newly renovated second floor unit. Vaulted ceilings, open kitchen with views of the preserve from the lanai. Meticulously maintained, custom cabinetry, New impact windows & sliders, modern, light and airy, ready to be enjoyed by the new owners. *Dogs welcome! One or Two Dogs allowed with a 100lb combined weight limit. Have a pick-up truck...? That's ok too! Lots of wonderful amenities come with this beautiful home. Easy access to downtown Naples and I75.

225 Robin Hood CIR Unit 203, Naples

$309,000

2 Beds ⋅ 2 Baths ⋅ 226020731 MLS ⋅ Sherwood BLDG.

Nestled in the charming city of Naples, this beautiful first-floor end unit, Locksley Model, in the vibrant Sherwood community offers both convenience and tranquility. An airy oasis brimming with upgrades, the residence boasts plantation shutters, gleaming hardwood floors, and plush new carpeting, creating an inviting ambiance that welcomes you home. Recently painted, every corner exudes freshness and modern elegance. Enjoy serene moments on the screened lanai, gazing out over a peaceful pond and meticulously maintained landscaping, offering a picturesque backdrop for your daily life. New hurricane impact windows and doors ensure your peace of mind, while the residence stands proudly on high ground with the added benefit of low HOA fees. An active lifestyle awaits with access to brand new pickleball courts, tennis courts, and a lively clubhouse and pool. Perfectly positioned close to the sparkling beaches, vibrant downtown Naples, and an array of shopping and dining experiences, as well as a nearby hospital, this home offers the idyllic blend of luxury and convenience.

225 Robin Hood CIR Unit 101, Naples

$299,000

2 Beds ⋅ 2 Baths ⋅ 226020409 MLS ⋅ Sherwood BLDG.

Welcome to your serene oasis in this beautiful 2-bedroom, 2-bath second-floor condo. As you step inside, you’ll be captivated by the soaring vaulted ceilings that create an expansive great room, perfect for entertaining or relaxing. The stylish tile flows seamlessly from the front door to the inviting lanai, enhancing the open feel of this home. This thoughtfully designed split floor plan offers optimal privacy, with the luxurious owner's suite featuring a spacious walk-in closet and a modern dual-sink bath, while the cozy guest room and bath are tucked away on the opposite side. You'll appreciate the many recent updates, including a brand new water heater, and beautifully updated bathrooms. Enjoy custom closets for all your storage needs and fabulous built-in cabinets throughout. The modern kitchen is a chef's delight, boasting stainless steel appliances. Step onto your screened balcony and take in breathtaking views of the lake with east rear exposure, ideal for soaking up the morning sun. With California shutters adding a touch of elegance, this condo offers 1,115 square feet of comfortable living space, all within a freshly repainted building exterior. Don’t miss your chance to make this lakeside retreat your new home! Cook up a storm in the modern kitchen featuring built-in cabinets and sleek stainless steel appliances. The screened balcony offers a direct view of the lake and faces east, perfect for enjoying morning sunrises. Additional highlights include California shutters and a generous 1,115 square feet of living space. Don’t miss your chance to own this captivating condo in a prime location

241 Robin Hood CIR Unit 202, Naples

$245,000

2 Beds ⋅ 2 Baths ⋅ 226020252 MLS ⋅ Sherwood BLDG.

One or more photo(s) has been virtually staged, AI generated or rendered. Sherwood offers dedicated pickleball courts, tennis, fitness and resort pool. Close to all the good things Naples has to offer. This 2BR / 2BA condo with single-car garage is in tidy original condition. Currently, it is the best-value condo that offers a garage in the immediate MLS area. You will appreciate the convenience of Berkshire Commons shopping & dining to include Publix, Walgreens, First Watch and banking located west on Radio Road. Just across Radio Road you will find Athletica Fitness, Aldi’s and the UPS Store. …and The Sunsets are Free!

432 Valerie WAY Unit 102, Naples

$389,900

2 Beds ⋅ 2 Baths ⋅ 226020153 MLS ⋅ Sherwood BLDG.

MOTIVATED SELLER — PRICE REDUCED! Spacious 2BR + Den Coach Home, Custom Kitchen Remodel, Attached Garage Welcome home to this beautifully updated second-floor coach home in Sherwood, offering approximately 1,656 square feet of bright, open living space with soaring ceilings and abundant natural light — plus the rare convenience of an attached one-car garage and private driveway. The centerpiece is a $50,000+ custom kitchen remodel — quartz countertops, stainless steel appliances, and abundant cabinetry flow into an open-concept layout that's perfect for entertaining or everyday living. Major systems are already handled: a brand-new 2019 roof means one less big-ticket item for you to think about for years to come, alongside newer refrigerator, dishwasher, washer, and water heater — this home is truly move-in ready with the expensive updates already done. A versatile den adds flexible space for a home office, formal dining area, media room, or guest suite — make it your own. Unwind on your private screened lanai overlooking peaceful landscaped views, with one of the community pools just steps away. Enjoy a prime Naples location with low HOA fees, just minutes from shopping, dining, hospitals, top-rated schools, parks, downtown Naples, and the Gulf beaches. Don't miss this move-in-ready opportunity in one of Naples' most convenient communities. Schedule your showing today! **Send in your offers and ask about a 1% lender incentive available through the seller's preferred lender — inquire for details**

509 Robin Hood CIR Unit 202, Naples

$320,000

2 Beds ⋅ 2 Baths ⋅ 226020256 MLS ⋅ Sherwood BLDG.

One or more photo(s) has been virtually staged, AI generated or rendered. Move right into this beautifully updated second-floor villa featuring 2 bedrooms + den, 2 baths, and an attached 1-car garage. The versatile den can easily double as a family room, office, media room, or all-purpose space to fit your lifestyle needs. Freshly repainted inside and showcasing new luxury plank vinyl flooring throughout, this home offers a bright and inviting atmosphere with soaring vaulted ceilings that enhance the open feel. Relax and enjoy the gorgeous views of lush landscaping and preserve area from this peaceful setting. The extended driveway is a rare and highly valuable feature in this community, providing additional convenience for guests and parking. Residents enjoy outstanding amenities including 2 community pools, clubhouse, exercise room, tennis courts, and pickleball. Conveniently located close to downtown Naples, dining, shopping, and beaches, this move-in ready residence offers the perfect blend of comfort, flexibility, and Florida lifestyle living. 3-5% Downpayment assistance available.

357 Robin Hood CIR Unit 202, Naples

$344,900

3 Beds ⋅ 2 Baths ⋅ 226017273 MLS ⋅ Sherwood BLDG.

Turnkey Furnished First-Floor Coach Home with Peaceful Lake Views! Experience the best of Southwest Florida living in this turnkey furnished, beautifully maintained 3-bedroom, 2-bath first-floor coach home in the highly sought-after Sherwood community of Naples. Featuring tranquil lake views, an attached garage, and the convenience of one-level living with no stairs, this residence offers the perfect combination of comfort, style, and location. Filled with natural light, the open-concept floor plan creates an inviting atmosphere for both everyday living and entertaining. Tile flooring flows throughout the main living areas, while the spacious kitchen is thoughtfully designed with stainless steel appliances, abundant cabinetry, upper and lower cabinet lighting, and generous counter space that seamlessly connects to the dining and living areas. Wake up to peaceful water views in the spacious primary suite, complete with a walk-in closet and a private ensuite bath. Two additional bedrooms provide versatile space for family, guests, or a home office. Step outside to your screened lanai and enjoy morning coffee or evening cocktails while overlooking the serene lake and taking in Naples' breathtaking sunsets. Set within an impeccably maintained 88-acre community, Sherwood offers an exceptional resort-style lifestyle. Residents enjoy two heated pools, tennis courts, four pickleball courts, a fitness center, clubhouse, and 12 acres of scenic lakes surrounded by lush tropical landscaping. The pet-friendly community welcomes up to two pets, while low condominium fees include cable, high-speed internet, and water, providing outstanding value—NO CDD. Ideally located just off Radio Road, you'll be only minutes from Naples' world-famous Gulf beaches, historic downtown Naples, Fifth Avenue South, Tin City, premier shopping, dining, golf, and entertainment. New Whole Foods will be located off Davis and Santa Barbara. Convenient access to I-75 and Naples Airport makes travel effortless. Whether you're searching for a full-time residence or a seasonal retreat, this move-in-ready coach home offers everything you've been looking for - an unbeatable location, beautiful lake views, exceptional amenities, and the carefree Florida lifestyle you've been dreaming of. Don't miss this opportunity to own your piece of paradise in one of Naples' most desirable communities!

320 Robin Hood CIR Unit 101, Naples

Start Your Search

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.