Winterpark Naples Real Estate - 19 Condos For Sale

Charming 2 Bed, 2 Bath in Desirable Winterpark – Prime Naples Location Nestled in the heart of sunny Naples, this beautifully updated 2-bedroom, 2-bathroom condo in Winter park offers the perfect blend of comfort, style, and convenience. The open-concept layout is ideal for entertaining, while the spacious screened-in lanai provides a peaceful space to relax and unwind. Located just a short drive to 5th Avenue, Naples Beach, Publix, and a variety of restaurants and shops, this highly sought-after community.

Well appointed 2 bedroom, 2 bath condo. This unit is tastefully decorated. Primary bedroom offers King size bed, bathroom with walk in shower. The 2nd bedroom has a twin beds. The guest bathroom has been tastefully remodeled. The Kitchen has granite countertops, newer refrigerator, microwave and dishwasher. There are 3 televisions throughout the unit. The location could not get any better. This home is close to downtown and within walking distance to shopping and dining. The Resort style Pool, Tennis courts , Pickleball and Bocce are yours to enjoy. The amenities are absolutely wonderful. Make this your Florida retreat!

Winterpark Condominiums are conveniently located close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. The kitchen is a dream, newly updated. The living-dining area is extremely spacious and the unit is an always preferred split bedroom floorplan. There is a laundry room in the condo with an extra laundry closet for storage or rental purposes. This unit has been recently tastefully renovated featuring new kitchen cabinetry, gorgeous quartz stone counters, luxurious backsplash, all new tile flooring throughout, beautifully renovated primary bathroom, impact windows, newer HVAC & water heater. This unit will have no lender issues as the Condo Association holds Flood Insurance for the building. The amenities include resort-style community pool, tennis & pickle ball courts, bocce and the community clubhouse with regular activities just steps away. This community has one of the largest community pools in Naples Florida, along with 5 Tennis courts, 4 Pickleball courts, and 2 Bocce ball courts. After you spend your day with all of these activities, it's just 3 miles to the world famous Naples Beaches and 5TH Avenue for amazing restaurants, shopping and entertainment.

Welcome to Winterpark, one of Naples’ most popular communities just minutes from downtown. This beautifully updated 2-bedroom, 2-bath corner condo has been fully remodeled from top to bottom. The brand-new kitchen features all new appliances, cabinets and counter tops, both bathrooms have been updated, the plumbing, HVAC and water heater has been redone, and there’s fresh new flooring throughout. It’s completely move-in ready and makes a great winter getaway or year round condo in a fantastic location 5 minutes to the beach and Olde Naples. Winterpark is known for its resort-style amenities, including one of the largest pools in Naples, brand new pickleball and tennis courts, and an active social scene. With wide open green spaces and a true Florida feel, it’s a classic community that continues to stand out. Come see it for yourself. This one won’t last.

Tropical Paradise - Winterpark IX! This 2-bedroom, 2-bathroom condo is ideal as a Florida tropical vacation home, a full-time residence or investment property. Offered Furnished. Ground-floor unit- no stairs and no hassle. Only a few buildings in Winterpark community feature a screened lanai; perfect for enjoying your Florida morning coffee or a glass of wine at sunset. New roof-2024, A/C-2020, Water Heater-2016, new piping, Impact Resistant windows and doors. Check out this property on our 360° Virtual Tour! Located just a short walk to the community amenities - no need to cross a busy street, unlike owners in some other buildings. A rare opportunity to purchase in one of the most desirable buildings. Up to 12 leases are allowed per year, making it an excellent investment property, or a vacation home. Prime location with quick access to Naples Downtown, white-sand Naples beaches, shopping, dining, and local attractions. Simple and cozy - this is how we live on the Gulf in Naples. Take a short trip to swim and sunbathe on one of the Naples beaches, play tennis or pickleball, dine and watch the sunset at one of the finest restaurants, or enjoy a fun day of shopping and then relax in the large resort-style pool right in the community. The amenities include a spacious resort-style pool, tennis and pickleball courts, a clubhouse, and bocce. Naples also welcomes everyone to enjoy its cultural and entertainment venues, including the Gulfshore Opera, Artis, The Baker Museum, Gulfshore Playhouse, The Naples Players Theater, Naples Botanical Garden, Naples Zoo, and numerous public parks with miles of walking paths, and even the Sun-N-Fun Lagoon water park. Don’t miss Fifth Avenue South and Third Street South in Olde Naples, as well as The Village Shops on Venetian Bay in Park Shore, Waterside Shops in the Pelican Bay area, Mercato, and much more. Make this home yours today, spend this winter season in sunny Florida!

Excellent unit, less than 5 minutes from Naples' pristine beaches, pier, restaurants, and more. This bright and spacious second-floor condo unit is perfect for a small family or as a vacation rental. Very well-maintained, you will not be disappointed. Reasonable HOA fees and amazing amenities, including a pool, multiple tennis courts, and many more, in this great community. Furniture is negotiable

Welcome to this beautifully maintained 2-bedroom, 2-bath second-floor end unit in the highly sought-after western section of the Winterpark community of Naples, FL. This light-filled home enjoys a desirable southern exposure, allowing sunshine to pour through the spacious rear windows and brighten the open living area all day long. Inside, you’ll appreciate the tasteful tile flooring, upgraded countertops, and well-chosen, subtle design updates that give the space a fresh, inviting feel. The screened front lanai offers the perfect spot for your morning coffee or a relaxing evening enjoying Naples’ tropical breezes. Winterpark is known for its resort-style amenities, including one of the largest community pools in Southwest Florida, tennis and pickleball courts, and an active social scene that makes it easy to connect with neighbors. Located just minutes from 5th Avenue South, pristine Gulf beaches, shopping, and dining, this condo offers comfort, convenience, and the best of Naples living. Whether you’re seeking a seasonal retreat or a full-time residence, this move-in-ready home is ready for you to enjoy.

Newly renovated 2 bedroom, 2 bathroom Condo Available! Just 4 miles to beautiful downtown Naples, 5th Avenue! Complete renovation includes a beautiful new kitchen with updated cabinetry, countertops and appliances. New flooring, lighting, plumbing fixtures, and new hot water heater and furnace. Enjoy pickleball, tennis, Boccee Ball, Walking, Bike Paths, and a resort style community pool, great for socializing!

THIS WINTERPARK VIII ASSOC CONDO HAS LOWEST HOA FEES IN WINTERPARK + INCLUDES FLOOD INSURANCE!!! Perfectly positioned with easy access to downtown Naples and area beaches, this 2B/2BA unit is ideal for buyers looking to downsize or escape the harsh winters up north. The completely remodeled open floor plan features a custom-built wall unit in living room with lots of storage, (2023) HVAC unit, vaulted ceiling, smart thermostat and modern updates with an inspiring crisp/clean grey & white interior color palette throughout to compliment the wood-like plank tile flooring. Kitchen boasts sleek white + charcoal Euro-style cabinets, glass tile backsplash, dramatic quartz waterfall counter w/ bar seating and stainless-steel appliances. Both baths have been modernized as well. The primary ensuite also features Euro-style sleek cabinetry, 3" thick counters, dual sinks & showerheads. Guest bath has stunning white vanity with glass countertop, decorative tile, jetted tub w/ rain showerhead and bluetooth fan. In addition, this bright and sunny second floor unit offers a screened outdoor patio to relax and unwind with a book or favorite beverage. Pet friendly and great resort-style amenities including large community pool, bocce, shuffleboard, pickleball and tennis courts. Truly a coastal get-a-way you'll love coming home to.

WINTERPARK IS A HIDDEN GEM WITH A VERY DESIRABLE LOCATION... 2 BDRM 2 BATH FIRST FLOOR UNIT WITH LARGE SCREENED IN PATIO LOOKING OUT TO LUSH LANDSCAPING... 2-3 MILES TO BAYFRONT, 5TH AVE, DOWNTOWN RESTAURANTS AND SHOPS, AND THE BEACHES... ... WALK TO RESORT STYLE POOL (ONE OF THE LARGEST IN NAPLES) / FIVE TENNIS COURTS, FOUR PICKLEBALL COURTS, BOCCE... FULLY FURNISHED TURNKEY... NEW HW TANK, CEILING POLY PIPES RECENTLY CHANGED IN LAUNDRY ROOM, AND NEWER MSTR BATH... THIS IS A VERY FRIENDLY ACTIVE COMMUNITY WITH GREAT RENTAL POTENTIAL... ENJOY YOUR WINTERS IN THE SUNSHINE!

Charming 2-Bedroom, 2-Bathroom First-Floor Condo in Naples, FL A beautifully maintained 2-bedroom, 2-bathroom first-floor condo, in the heart of Naples, FL. Features all-tile flooring throughout, impact-resistant windows for added peace of mind, and updated kitchen and bathrooms. Enjoy granite countertops and sleek stainless steel appliances. Offers spacious living, open floor plan. Amenities: resort-style pool. Recreation: pickleball, shuffleboard, tennis, and bocce courts. Location: Located in a desirable Naples neighborhood, this condo is just minutes away from beautiful beaches, shopping, dining, and all the attractions that make Naples a premier destination. Whether you’re here for the season or looking for a rental investment, this location provides the best of Florida living. Affordable HOA: The HOA fee is $1,557 paid per quarter, breaks down to about $520.00 on a monthly basis; offering great value for the exceptional amenities and well-maintained grounds. A lockable storage area, guest parking spots available. Don’t miss out on the opportunity to make this charming condo your new home!

Stop searching for an affordable condo in Naples—this one has already been beautifully updated and is truly move-in ready! This 2-bedroom, 2-bath end-unit on the 2nd floor offers both privacy and natural light, along with a desirable open layout. Enjoy vaulted ceilings, impact windows, and updated flooring that give the home a bright, modern feel. The primary suite features a spacious walk-in closet, and the entire condo can be offered turnkey as furnishings are negotiable, so you can skip the renovations and start enjoying Naples living right away. With low fees that include everything but FPL, ownership here is simple and affordable. Located just minutes from the Gulf beaches, 5th Avenue South, and downtown Naples, this property is ideal as a first home, seasonal retreat, or investment opportunity. Homes like this don’t last long at this price—schedule your showing today!