Sherwood Homes under $500,000

Welcome to Sherwood, a charming subdivision nestled in the heart of Florida, where community spirit meets modern living. This delightful neighborhood is known for its lush landscapes, friendly neighbors, and a variety of amenities that make it an ideal place to call home. With a perfect blend of tranquility and accessibility, Sherwood offers residents the best of both worlds.

One of the most appealing aspects of Sherwood is its diverse selection of homes, particularly those priced under $500,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a range of options that cater to your needs and lifestyle. From cozy single-family homes with inviting front porches to contemporary townhouses with modern finishes, Sherwood has something for everyone.

The community is designed with families in mind, boasting well-maintained parks, playgrounds, and walking trails that invite outdoor activities and social gatherings. Residents enjoy a strong sense of community, with regular events and activities that foster connections among neighbors. Additionally, Sherwood's convenient location provides easy access to shopping, dining, and entertainment options, ensuring that everything you need is just a stone's throw away.

Living in Sherwood means embracing a lifestyle that balances comfort, convenience, and community. With homes available under $500,000, now is the perfect time to explore what this delightful subdivision has to offer. Discover your dream home in Sherwood, where every day feels like a vacation in sunny Florida!

Newest Sherwood Homes under $500,000

$307,000

3 Beds ⋅ 2 Baths ⋅ 2026043254 MLS ⋅ Sherwood BLDG.

Enjoy living the southwest Florida lifestyle in this spacious and inviting 1st floor end unit condo boasting tranquil lake views. This charming 3 bedroom 2 bath condo is nestled in the beautifully landscaped community of Sherwood in Naples. Enjoy peaceful pond views with a sparkling fountain, mature trees, and tropical landscaping from your private covered lanai—perfect for morning coffee or evening relaxation while taking in the incredible views the enclosed patio provides in any season. Leave the windows open or closed on the patio as the screens will allow the breezes to flow. Step inside to an open-concept living area featuring 1,225 square feet of living space under air conditioning with new impact windows and doors. The home features crown molding in every room, warm wood-look flooring, a new AC system in 2025, a spacious living room with views of the lake and real wood plantation shutters that allow for lots of soft natural light. The stylish eat-in kitchen boasts rich wood cabinetry, a double stainless-steel sink, and stainless appliances, smooth-top range, and a breakfast bar. The master bedroom suite offers a generous layout with ample storage and an ensuite bathroom with walk-in shower and a spacious walk in closet. There are two additional bedrooms providing flexible space that could be used as guest bedrooms or a home office or hobby room. A second full bathroom features a tub & shower combination. Additional highlights include a private garage and an assigned parking space right outside the front door. The property sits in Flood Zone X— meaning no flood insurance is required. The community setting offers a peaceful serene atmosphere with sidewalks, lush greenery, two swimming pools, a clubhouse, tennis and pickle ball courts, exercise room and all just minutes to Naples’ finest beaches, shopping, dining, and entertainment. This well-maintained move in-ready condo is ideal as a full-time residence, seasonal getaway, or investment property.

289 Robin Hood CIR Unit 101, Naples

$299,500

3 Beds ⋅ 2 Baths ⋅ 226035508 MLS ⋅ Sherwood BLDG.

Experience ultimate convenience, style and peace of mind in this highly desirable first-floor corner unit featuring tranquil lake views. As a corner residence, this 3-bedroom, 2-bathroom home offers enhanced privacy and an abundance of natural light throughout its thoughtful floor plan.The heart of the home highlights a well-appointed kitchen equipped with elegant granite countertops, sleek stainless steel appliances and a newer washer and dryer. Built for complete peace of mind and maximum insurance savings, the property features a new roof (2024), full impact-resistant windows and sliding glass doors and automatic hurricane shutters. Step outside to enjoy serene water views from a residence that seamlessly combines modern updates with secure, low-maintenance living.

257 Robin Hood CIR Unit 101, Naples

$359,000

3 Beds ⋅ 2 Baths ⋅ 226022376 MLS ⋅ Sherwood BLDG.

Welcome to this bright and spacious 3-bedroom, 2-bathroom end-unit condo. Perfectly positioned overlooking a secluded lake with a tranquil fountain view. The open and airy floor plan features vaulted ceilings, abundant natural light, and a screened lanai where you can relax and enjoy the peaceful waterfront scenery. Offered partially furnished, this home is ideal as a full-time residence, seasonal retreat, or investment opportunity. Major improvements provide peace of mind, including a new A/C system installed in 2023, a new roof completed in 2019, a brand-new water heater, and new impact-resistant doors and windows throughout. A private one-car garage adds convenience and additional storage. Residents of Sherwood enjoy an array of amenities, including two community pools, tennis and pickleball courts, a clubhouse with a full kitchen for social gatherings and events, fitness equipment, and a library.

305 Robin Hood CIR Unit 204, Naples

$440,000

3 Beds ⋅ 2 Baths ⋅ 226034495 MLS ⋅ Sherwood BLDG.

Welcome to easy Naples living in this beautifully renovated 3-bedroom, 2-bath condo in the desirable Sherwood community. Tucked away on a quiet street, this meticulously maintained residence enjoys a tranquil lake view with amazing sunsets, added privacy and a bright, open-concept interior, designed for comfortable everyday living. Completely renovated in 2024, the home features extensive, thoughtfully selected upgrades throughout. The redesigned open-concept kitchen showcases new white cabinetry, quartz countertops, an extended high-bar area and center island, new stainless-steel appliances, granite sink, modern faucet, and elegant champagne globe pendant lighting. High-quality (12mm) engineered flooring with premium Proflex Maxximum SIM90 sound-reducing and moisture-barrier underlayment extending throughout the living areas and stairs. Both bathrooms have been completely renovated with ceramic tile, walk-in showers, white cabinetry, quartz countertops, wide mirrors, and modern LED lighting. Additional enhancements include 6” crown molding, LED lighting throughout, remote-controlled ceiling fans, a tiled lanai, and professionally organized closets with custom shelving and hanging systems. All bedrooms are generously sized, while the attached one-car garage provides convenient parking and additional storage. Further improvements include a new LG stackable washer and dryer with laundry sink, Rheem Gladiator 55-gallon WiFi-enabled water heater with leak detection and automatic shutoff, YoLink smart whole-home leak detection system, fresh white interior paint, and an updated garage with epoxy flooring. Building roof replaced in 2018, with wind-mitigation reports available. Offered partially furnished and meticulously cared for, this condo is ready to enjoy! Sherwood residents enjoy two community pools, a fitness center, tennis and 4 pickleball courts. Conveniently located near I-75, downtown Naples, shopping, dining, Gulf beaches, Paradise Coast Sports Complex, and Great Wolf Lodge, this property combines tranquility with easy access to everything Naples has to offer. With its long-lake view, privacy, extensive renovation, and desirable Naples location, this is a wonderful opportunity for a full-time residence or seasonal retreat.

250 Robin Hood CIR Unit 201, Naples

$335,000

2 Beds ⋅ 2 Baths ⋅ 226032895 MLS ⋅ Sherwood BLDG.

LAKE VIEWS — SPACIOUS FLOOR PLAN — ATTACHED GARAGE — CONVENIENT NAPLES LOCATION! Welcome home! This beautifully updated second-floor residence in Sherwood offers 2 bedrooms plus a versatile den, 2 full bathrooms, an attached 1-car garage, and a spacious floor plan! Step inside to a bright and inviting interior designed for comfortable Florida living. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating an open and welcoming space for everyday living and entertaining. The flexible den adds valuable additional space and can easily serve as a home office, media room, family room, or multipurpose retreat. One of the highlights of the home is its peaceful LAKE VIEW, complemented by lush landscaping that creates a relaxing backdrop to enjoy throughout the day. The generous layout, thoughtful updates, and ATTACHED 1-CAR GARAGE add both comfort and convenience. Residents of Sherwood enjoy a wonderful selection of community amenities, including COMMUNITY POOLS, a clubhouse, exercise room, TENNIS COURTS, and PICKLEBALL. Ideally located in Naples, this move-in-ready residence provides convenient access to downtown Naples, beautiful Gulf beaches, shopping, dining, and everyday conveniences. With its desirable lake setting, spacious interior, garage, and central location, this lovely home offers an exceptional opportunity to enjoy the Southwest Florida lifestyle.

475 Robin Hood CIR Unit 202, Naples

$360,000

3 Beds ⋅ 2.5 Baths ⋅ 2026036256 MLS

SHORT SALE - THIRD-PARTY APPROVAL REQUIRED. Welcome to the best value in Sherwood, nestled on the border of Lehigh Acres and Fort Myers. As you enter this charming neighborhood, you'll be greeted by wide streets and a welcoming family-friendly atmosphere. With two convenient entrances/exits, this community offers both accessibility and tranquility. Step inside this stunning home and be welcomed by a foyer that leads to the formal living room, perfect for entertaining or relaxing. The beautifully remodeled kitchen is a chef's dream, featuring granite countertops, double ovens, and two spacious pantries. The inviting family room opens seamlessly to the pool and large screened patio through sliding glass doors, creating an ideal indoor-outdoor living space. A convenient half-bath is located downstairs for guests. Upstairs, you'll find oversized bedrooms with generous walk-in closets and a versatile bonus room, offering endless possibilities for a playroom, office, or media room. The upstairs laundry room adds extra convenience, keeping chores close to where you need them. Enjoy serene lake views from your backyard oasis, complete with a pool and ample space for your family to relax or entertain. This home is move-in ready with a brand-new roof and insulation, two new HVAC units, and a new hot water heater. Don't miss this incredible opportunity to own a spacious, upgraded pool home in the sought-after Sherwood community.

8197 Silver Birch WAY, Lehigh Acres

$310,000

2 Beds ⋅ 2 Baths ⋅ 226030507 MLS ⋅ Sherwood BLDG.

Enjoy peaceful lakefront living and exceptional privacy in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Sherwood community of Naples. Ideally positioned on a quiet street, the residence showcases a tranquil long-lake view that can be enjoyed from the spacious living area and screened lanai. The light-filled interior offers an open, comfortable floor plan with tile flooring throughout the main living areas. The kitchen features granite countertops, warm wood cabinetry, stainless steel appliances, a convenient breakfast bar, and an easy flow into the dining and living spaces—perfect for everyday living and entertaining. Both bedrooms are generously sized, including a private primary suite, while the flexible dining area provides additional space for gathering or relaxing. A one-car garage adds valuable storage and convenience, and the condo is being sold partially furnished, making it easy to begin enjoying the Southwest Florida lifestyle right away. Sherwood offers resort-style amenities including two community pools, a fitness center, tennis, and pickleball. Conveniently located with easy access to I-75, downtown Naples, exceptional dining and shopping, beautiful Gulf beaches, the Paradise Coast Sports Complex, and Great Wolf Lodge. Meticulously maintained, private, and offering one of the most appealing long-lake views in the community, this property is ideal as a full-time residence, seasonal retreat, or Naples getaway.

145 Robin Hood CIR Unit 104, Naples

$335,900

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

MOTIVATED SELLER- PRICE REDUCTION!! 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

$334,900

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

$459,777

5 Beds ⋅ 3 Baths ⋅ 226025402 MLS

Spacious 5 bedroom, 3.5 bathroom lakefront home in the desirable Sherwood community! This beautifully maintained two story residence is over 2,650 square feet of living space with an open floor plan, first floor primary suite, spacious secondary bedrooms, and a large screened lanai overlooking tranquil water views. Enjoy the brick paver driveway, extended two car garage, tropical landscaping, and an ideal location close to shopping, dining, schools, and Fort Myers. Whether you’re looking for room to grow or the perfect home for entertaining, this property checks every box. Don’t miss this incredible opportunity!

8285 Silver Birch WAY, Lehigh Acres

$389,900

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

MOTIVATED SELLER — PRICE REDUCED! SPACIOUS 2BR + DEN COACH HOME — CUSTOM KITCHEN REMODEL — NEW REFRIGERATOR & MICROWAVE — 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 an attached one-car garage and private driveway. The centerpiece is a $50,000+ custom kitchen remodel featuring quartz countertops, stainless steel appliances, and abundant cabinetry. A newly installed refrigerator with an icemaker and a new over-the-range microwave complement this inviting kitchen, which flows seamlessly into the main living areas for easy entertaining and everyday living. Additional updates include a roof replaced in 2019, a newer dishwasher, washer, and water heater. Ceilings throughout the condo are scheduled to be painted, and a new ceiling fan is planned for the garage. A versatile den offers flexible space for a home office, formal dining area, or media room—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 convenient Naples location close to shopping, dining, hospitals, schools, and parks, with easy access to downtown Naples and the Gulf beaches. Don’t miss the opportunity to make this updated coach home your own. Schedule your showing today and bring your offer!

509 Robin Hood CIR Unit 202, Naples

$299,900

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

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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.

Sherwood Homes under $500,000

Newest Sherwood Homes under $500,000

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