Lakeside Naples Real Estate - 3 Homes, 10 Condos For Sale

Experience the best of Florida living in the Lakeside Community, featuring resort-style amenities and a scenic 40-acre lake. This beautifully updated 3-bedroom, 2-bath, 2-car-garage home is move-in ready and sold turnkey with porcelain tile floors, shiplap ceilings in the living and primary bedroom, quartz countertops, 42" cabinetry, updated appliances, and renovated bathrooms. Solid-core doors and an impact-rated front door add quality and peace of mind. Relax on the enclosed patio with lush vegetation views while enjoying community amenities including tennis, bocce, shuffleboard, billiards, exercise room, sauna, two pools, plus a lake with lighted fountains, fishing pier, kayaking, and a 1.5-mile walking path through mature landscaping. Just minutes from beaches, upscale dining, and in an A-rated school district, this home is ideal for first-time buyers, retirees, or anyone seeking a comfortable, active Florida lifestyle.

Welcome to 2626 Sailors Way, a well-maintained residence ideally located in the heart of North Naples within the gated community of Lakeside of Naples. This lakefront unit offers a functional floor plan with comfortable living spaces and abundant natural light. The interior features an open living and dining area, a well-appointed kitchen with ample cabinetry, and a private screened lanai—perfect for enjoying the Florida lifestyle. The primary suite offers generous closet space and an en-suite bath, while additional bedrooms provide flexibility for guests or a home office. Lakeside of Naples is a gated community offering an array of amenities, including a clubhouse, community pool and spa, tennis and pickleball courts, basketball courts, playground, walking paths, and scenic lakes with fishing areas. The community also features professionally maintained grounds and an on-site management office. Conveniently located near shopping, dining, entertainment, and Naples’ renowned beaches, this property presents an excellent opportunity to enjoy a relaxed and active Southwest Florida lifestyle—whether as a primary residence, seasonal retreat, or investment property.

COMPLETELY RENOVATED LAKESIDE VILLA WITH EXPANSIVE SOUTHERN VIEWS! Experience lakeside living at its finest in this beautifully renovated two-bedroom, two-bath attached villa in the desirable community of Lakeside. Enjoy stunning southern exposure overlooking one of Naples' largest and most picturesque lakes, offering tranquil water views and spectacular sunsets. This move in ready villa is offered furnished and features a modern open layout, vaulted ceilings, stylish modern finishes and abundant natural light. The kitchen showcases all new cabinetry, quartz countertops, and stainless steel appliances, while both baths have been completed redesigned with todays upscale finishes. This neighborhood is a gated community is in an excellent location close to everything Naples has to offer, including beach access, shopping, dining, golf, entertainment. A perfect blend of modern comfort, coastal tranquility, and convenience, this villa is ready for you to enoy from day one. Low quarterly maintenance fees! Single family ownership.

This gated Lakeside Community is in a prime north Naples location. Near the Gulf with some of the best white sand beaches in FL! Minutes from award-winning dining, upscale shopping, top rated golf, outdoor activities, I-75 & more. "A" rated school district. HOA fees are only $976/qtr! You are greeted by a spacious lush green front yard and large oak tree. Inside offers an open floorplan design w/ 1538 sq ft of living area, 3 Bedrooms, 2 full baths, eat-in kitchen, dining area, spacious great room & laundry room. The kitchen was custom designed and brand new with never used brand new whirlpool appliances with warranty! Master BR has walk-in custom made closet & en suite w/ 2 sinks. Enjoy the sunrise or beautifully painted sunset sky from the spacious lanai. The home is completely updated with custom wood cabinets in baths and kitchen, wood look porcelain tile, custom closets in every room of the home, Delta faucets and bath fixtures. THERES NO OTHER HOME FOR SALE IN LAKESIDE AS BEAUTIFULLY DONE AS THIS ONE! The 40-acre lake features 2 lighted fountains, fishing & kayaking! Amenities include a fitness center, sauna, billiards, KT & choice of 2 pools. Play a round of tennis or pickleball. There's also a tot playground, basketball, bocce & shuffleboard. A 1.5 mile walking path meanders through beautiful landscaping.

This lakefront villa offers stunning southern views of a 42-acre lake from the kitchen, living room, dining room, and primary bedroom. It’s bright and airy with vaulted ceilings, fresh paint, and a recently renovated kitchen featuring quartz countertops with stainless steel appliances. The ENTIRE home was been re-piped (Oct 2025) + a new AC has been installed (Oct 2025)! Both bedrooms are oversized, and the updated bathrooms also have sleek quartz finishes. Enjoy the breeze in the screened lanai or keep the glass closed and enjoy the warm sun. The 2-bedroom, 2-bath layout includes a 1-car garage and sits in a gated community just 4 miles from the beach plus it’s walkable to the farmers market, grocery stores, bakeries, and gyms. The community itself is a hidden gem, with two swimming pools, a weight room, five clay tennis courts, a playground, shuffleboard, bocce, and basketball courts. There’s also a 1.5-mile walking path shaded by mature trees and surrounded by lush tropical landscaping. Low HOA fees make it even more appealing.

TOTALLY REMODELED - GORGEOUS - LAKEFRONT - COVERED PARKING - GROUND FLOOR. This Stunning Lakefront Condo in Lakeside is a rare opportunity that has been Completely Remodeled with exquisite detail. Featuring 2 bedrooms and 2 baths, it boasts an open-concept Custom Kitchen designed with the wall removed to create a spacious living area that maximizes breathtaking lake views. The New Kitchen has custom cabinetry with soft close drawers, Whirlpool stainless steel appliances, large deep sink, quartz countertops and a breakfast bar perfect for casual meals and enhanced with recessed lighting and a tray ceiling for added elegance. The Master Shower and Guest Bath have been totally remodeled with new tile, high profile vanities with quartz countertops, upgraded fixtures and beautiful lighting throughout. The condo has new porcelain tile flooring throughout the unit and has additional upgrades including - remote privacy shades, high baseboards for a polished look and a Dry Bar for entertaining, a huge walk-in closet for ample storage, a 2020 Water Heater, New HVAC System, Mounted TV and upgraded lighting & fans. The outdoor space has a beautiful paver deck outside the lanai, ideal for enjoying the lakefront views, a tiled entry with a large storage closet and a screened door for all your cross ventilation needs. Lakeside is a gated community with a 40-acre lake and offers many amenities, including two swimming pools, spa, and a two-story Old Florida clubhouse, complete with sauna, weight room, shower, kitchen facilities, library and game rooms. Lakeside also features five clay tennis courts, tot playground, pickle ball, shuffleboard, bocce and basketball courts. A 1.5 mile walking path meanders through an award-winning lush landscape including two lighted lake fountains. Lakeside is located close to everything - 5 minutes to Mercato, 10 minutes to Vanderbilt Beach & only 20 minutes to downtown Naples. This beautifully remodeled lakefront condo in Lakeside offers a blend of luxury, comfort, and community amenities, making it an ideal choice for those seeking a serene lifestyle with access to recreational activities. With its stunning interior features and prime location, it is both a rare find and a perfect opportunity for prospective homeowners.

Enjoy some of the most incredible lake views and an unbeatable Naples lifestyle in this beautifully located Lakeside condo. Wake up to shimmering water views that fill the living spaces with natural light and create a peaceful, private retreat. A one car attached garage adds everyday convenience and extra storage—an exceptional feature for condo living in Naples. Lakeside is a well established, amenity rich community offering resort style pools, a clubhouse, tennis and pickleball courts, and scenic walking paths winding throughout the neighborhood. Residents enjoy a relaxed, active lifestyle surrounded by mature landscaping and picturesque lakes. Perfectly positioned in the heart of Naples, this home offers an incredible central location just minutes to world-class beaches, Fifth Avenue South, Mercato, dining, shopping, and everyday conveniences. Whether you’re seeking a full-time residence, seasonal escape, or investment opportunity, this condo delivers the ideal blend of views, amenities, and proximity to everything Naples has to offer.

Best-priced single-family home in one of the most desirable zip codes of world-famous Naples, Florida at the time of listing. Situated on a premium corner lot within the highly sought-after Lakeside of Naples, this recently remodeled 2-bedroom, 2-bath residence offers modern updates, privacy, and an exceptional central location. Lakeside of Naples is a privately owned residential community located in the heart of Naples, just off Airport Road, providing quick access to world-class beaches, upscale shopping, and acclaimed dining, while maintaining a peaceful, lake-centered setting. The home features new luxury vinyl flooring, updated light fixtures, and a fully renovated primary bathroom with contemporary finishes. An open-concept living area flows seamlessly into the kitchen with new appliances, making the home truly move-in ready. Step outside to the screened lanai and private patio, surrounded by lush landscaping that offers tranquility and privacy—perfect for relaxing or entertaining. Residents enjoy an exceptional amenity package, including two swimming pools, a spa, and a charming two-story “Old Florida”-style clubhouse featuring a sauna, fitness/weight room, showers, kitchen facilities, library, and game rooms. Additional amenities include five clay tennis courts, pickleball, bocce, basketball courts, shuffleboard, a tot playground, and a 1.5-mile walking path that winds through award-winning landscaping accented by two lighted lake fountains. Ideally located near Naples’ finest beaches, marinas, shopping, dining, and entertainment, this home is just 4 miles to Mercato and 4.5 miles to Vanderbilt Beach. Low HOA fees further enhance the value of this outstanding opportunity.

Steps from the back door of this first floor Coach home, a lake-sized lake features spectacular sunsets almost every day. A few steps away sits a semi-private, sun-drenched swimming pool. All around is a quiet, tree-cooled, socially active, iconic Naples benchmark community noted for its friendly atmosphere and active social schedule. Restaurants, shopping, a major library and various activity centers are a less than mile away. The airport is half an hour up the road, famous 5th Avenue 15 minutes down the road. Just inside the gated entry there is an activity center loaded with sports facilities and a clubhouse for community wide activities. Inside the remarkable two bedroom, two baths, bright, outdoor-oriented home there’s an immediate sense of this is a place to be. On the practical side there’s an attached one-car garage, a separate laundry room, a designated living room, a separate dining room, and importantly, a master sized primary bedroom with a his and her’s master bath. On the other side of the unit, a guest bedroom and nearby full bath welcome visitors or serves as a private area for roommates. The updated kitchen offers storage galore and room for breakfast dining. A pass-through to the formal dining room looks beyond the diners, past the flowering bushes out across the lake with a perfect view of the spectacular Southwest Florida sunsets. This LakeSide fully furnished home has first-time guests simply saying, “Wow," when they come through the front door, and owners returning to the unit will feel that same amazed reaction every time they come home.

Stunning 40-acre lake views provide the breathtaking backdrop for this beautifully finished and upgraded first-floor condo. Light, bright, and open, this spacious residence is filled with sunshine and is ideal for both year-round and seasonal living.Remodeled kitchen with stainless steel appliances, quartz countertops, and tile backsplash.Beyond the tiled lanai, an expanded tiled patio creates a striking visual welcome the moment you enter. Additional upgrades include crown molding, renovated bathrooms, gorgeous 24" all new tile flooring throughout, 5" baseboards, and electric roll-down shutters on the lanai. Lakeside has two community pools, and the charming Old Florida–style clubhouse offers a full array of amenities including pool, fitness and weight room, sauna and showers, kitchen facilities, library, game room, pickleball and tennis courts, shuffleboard, bocce, and basketball. Ideally located just minutes to Mercato, about 10 minutes to Vanderbilt Beach, numerous dining options, and a scenic 1.5-mile walking path. Catch and release fishing are permitted along with kayaking! Covered carport and private storage closet included Building roof replaced in 2018. A true gem!

RARELY AVAILABLE • REMODELED • GORGEOUS LAKEFRONT • GARAGE. This stunning lakefront condo in the highly sought-after LAKESIDE is a rare opportunity and has been remodeled with exquisite detail with over $60,000 of improvements in the last few years. Enjoy serene lake views in a gated community centered around a 40-acre lake and loaded with amenities. Featuring 2 bedrooms and 2 baths, it boasts an open-concept and designed for both style and comfort, this condo showcases extensive upgrades, including: a New 16 SEER2 air conditioning system, Plantation shutters, Tray Ceilings, Ceramic Plank Flooring throughout the main areas, Updated Fans & Lighting, Manual Accordion Hurricane Shutters, New Baseboards and a Beautiful Tiled Lanai. The gorgeous kitchen has Granite countertops and a ceramic backsplash with under cabinet lighting, Custom Cabinetry and Stainless Steel Appliances. The bathrooms have new plumbing fixtures and the primary bathroom has a Waterfall Shower with a trackless door and the guest bath has a Ceramic tile tub with shower surrounds. Lakeside is a gated community with a 40-acre lake and offers many amenities, including two swimming pools, spa, and a two-story Old Florida clubhouse, complete with sauna, weight room, shower, kitchen facilities, library and game rooms. Lakeside also features five clay tennis courts, tot playground, pickle ball, shuffleboard, bocce and basketball courts. A 1.5 mile walking path meanders through an award-winning lush landscape including two lighted lake fountains. This beautifully remodeled lakefront condo in Lakeside offers a blend of luxury, comfort, and community amenities, making it an ideal choice for those seeking a serene lifestyle with access to recreational activities. With its stunning interior features and prime location, it is both a rare find and a perfect opportunity for prospective homeowners and all of this in a prime North Naples location.

Nestled in a peaceful corner of the resort-style community of Lakeside, this charming residence offers a cozy, beach-inspired atmosphere—a perfect blend of relaxation and tranquility. Whether you're unwinding at home or hosting family and friends, this home provides an ideal setting for both everyday living and special occasions. This unique three-bedroom, two-bath split-plan residence blends comfort and style. Spacious living areas, wood tile floors throughout, and a bright, screened lanai create a perfect space to relax and enjoy the surrounding beauty. The thoughtful layout ensures both privacy and convenience, making it an ideal retreat for families or guests. The community features a 41-acre freshwater lake, perfect for boating and fishing, along with walking and jogging paths for outdoor enjoyment. Residents also have access to five clay tennis courts, a tot playground, pickleball, shuffleboard, bocce, and basketball courts. The 2-story clubhouse is fully equipped with exercise equipment, a sauna, card rooms, a library, and billiards, while social spaces like the kitchen and community rooms foster connection and leisure. In a fantastic location, this home is just a short drive from the vibrant outdoor shopping and dining at The Mercato, as well as the waterfront dining and boutiques at Venetian Village. Plus, you're only minutes away from the pristine sands of Vanderbilt Beach, offering the perfect balance of convenience and coastal living. This home truly offers an idyllic lifestyle, combining comfort, privacy, and the convenience of resort-style amenities, all in a prime location. CAR GARAGE + LOW HOA