Winterpark Naples Real Estate : 19 Condos for Sale

Winterpark Naples Condos for Sale: 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!

Winterpark Naples 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.

Winterpark Naples Condos for Sale: 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 Naples Condos for Sale: 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.

Winterpark Naples Condos for Sale: 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

Winterpark Naples Condos for Sale: 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.

Winterpark Naples Condos for Sale: 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!

Winterpark Naples Condos for Sale: 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!

Winterpark Naples Condos for Sale: 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!

Winterpark Naples Condos for Sale: Welcome to 3676 Arctic Circle, a furnished turnkey condo located in Winter Park. Located only ten minutes from Fifth Avenue shopping and dining, and fifteen minutes from Naples beaches, this location and price cannot be beat. This two-bedroom, two-bathroom home features an updated kitchen and primary bathroom, tile throughout with wood-looking tile in the living area and bedrooms, a large laundry room, and impact-resistant windows. Impact-resistant windows make for a worry-free hurricane season and also help keep the condo cool. This condo does not back up to another building; it instead views a grassy area, giving the feeling of privacy and peace. Winter Park provides many amenities, including tennis courts, pickleball courts, a large community pool, and scheduled activities for residents. The HOA fees include water, interior/exterior pest control, cable, internet, and more. Whether you are looking for a new primary residence or vacation home, this condo checks all the boxes.

Winterpark Naples Condos for Sale: Wonderful furnished, 2 bedroom/ 2 bath, end unit, 1st floor condo in Winterpark. Impact windows and doors, new plumbing throughout, new AC, mostly new appliances. Fully furnished, turn key. Secluded condo location with landscape view in front and back and a screened porch off of the kitchen. Easy to rent seasonally or annually. Close to beach, downtown, I75, shopping, restaurants and entertainment. Winterpark has tennis, pools, recreation facilities, events and a real community. End unit with only one neighbor next door. New washer and dryer inside condo in large laundry room and pantry. Winterpark has some of the lowest fees in Naples.

Winterpark Naples Condos for Sale: A Slice of Sunshine in Winterpark! Live like royalty without the royal price tag in this beautifully updated turnkey-furnished 2-bedroom, 2-bath condo in the heart of Naples. Located in the popular Winterpark community, this first-floor corner unit is all about ease, elegance, and effortless Florida living. Step inside and feel the vacation vibes—sleek tile flooring, a breezy open layout, and a light-filled living area perfect for entertaining or relaxing after a beach day. Cook up something delicious in the stylish kitchen featuring stainless appliances and a cozy breakfast bar. The split-bedroom floor plan offers privacy, and the primary suite is a tranquil retreat with an updated bath and walk-in shower. Even better? Impact-resistant windows and doors, no stairs, assigned parking, and a location just minutes from 5th Avenue, white-sand beaches, and vibrant shopping and dining. Enjoy resort-style amenities: a sparkling pool, tennis, pickleball, bocce, shuffleboard, and a social clubhouse. HOA includes water, lawn care, pest control, and more—just lock and go! Welcome to your castle on Ice Castle Way.

Winterpark Naples Condos for Sale: Welcome to Winterpark in Naples, a highly sought-after community just minutes from downtown and the Gulf of Mexico. This spacious 2-bedroom, 2-bath condo offers vaulted ceilings, an open floor plan, and a split-bedroom design for added privacy. New roof 2 years old! The primary suite features a walk-in closet and private bath with walk-in shower, while the guest bedroom and second full bath provide comfort for visitors. The kitchen includes modern appliances, a breakfast bar, and plenty of storage, opening seamlessly to the dining and living areas with sliding doors to a private patio perfect for relaxing outdoors. Additional highlights include in-unit laundry, assigned parking, and concrete block construction. Winterpark is known for its resort-style amenities including one of the largest community pools in Naples, tennis courts, and a clubhouse, all surrounded by lush landscaping. With low-maintenance living, affordable association fees, and a prime location near shopping, dining, golf, and Naples’ beautiful beaches, this condo offers the perfect blend of comfort, convenience, and the Florida lifestyle.

Winterpark Naples Condos for Sale: Welcome to your dream condo close to Beautiful Downtown Naples and Downtown Naples' Beach! This stunning 2 bedroom, 2 bath condominium with Open Floor Plan and Split Bedrooms offers a remodeled kitchen with upgraded Granite Countertops, sleek newer modern Appliances and ample storage space with plenty of drawers and open to a large Great Room for Entertaining! Both Bathrooms have been tastefully updated with new vanities topped off with Beautiful Upgraded Countertops providing a spa like retreat! The condo also features a large convenient outdoor storage for bicycles or beach toys which is perfect for enjoying Florida's sunny lifestyle. The community is complete with a Clubhouse, Resort-Style Pool, and a lovely walking trail ideal for relaxing, and tennis and pickleball courts for the active enthusiast! 1 pet is permitted!

Winterpark Naples Condos for Sale: This spacious over 1200 sq foot Winterpark condo boasts 2 bedroom, 2 bath over looking a beautiful greenspace. With a resort style pool, bocce ball, pickleball, tennis, walking trails and organized activities you will feel right at home. Newer AC and roof. Condo fee includes water/sewer, exterior insurance and maintenance, cable, landscape grounds, and the amenities The complex allows rentals both short term and annual with some restrictions. Buyer and buyers agent to verify all information.

Winterpark Naples Condos for Sale: Escape to Your Naples Oasis. A Turnkey Treasure in WINTERPARK. Get ready to fall in love with this stunning, immaculately maintained 2 bedroom, 2 bathroom, first-floor condominium in the vibrant WINTERPARK community, a true gem in the heart of Naples, Florida! This turnkey furnished beauty is your ticket to effortless coastal living, blending modern updates with resort-style amenities that will make every day feel like a vacation. Step inside and be wowed by the bright, airy open layout, where sleek tile and laminate flooring flows seamlessly throughout. Freshly painted walls, new plantation blinds, and modern ceiling fans create a chic, coastal vibe, while updated copper piping, new bathroom faucets, new closet doors, and crisp baseboard trim add a touch of sophistication and peace of mind. The spacious living area opens to an inviting open patio, perfect for sipping morning coffee or evening cocktails under the Florida sun. Plus, a screened-in front lanai offers a cozy spot to unwind, and a separate laundry room and exterior storage closet to keep everything tidy and convenient. The Location is terrific! Just a quick 10-minute drive to downtown Naples and its world-famous sandy beaches. You’re also steps away from Publix, Starbucks, and local dining hotspots. But the real magic happens in WINTERPARK'S Resort-Style amenities. Dive into one of the largest community pools in Naples, challenge friends to pickleball, tennis or bocce, or join in the fun with planned community activities. There’s never a dull moment here! This 1,234 sq ft condominium is a dream for full-time residents, seasonal snowbirds, or savvy investors, with deeded parking and a strong rental program. Also available for seasonal or year round rental.

Winterpark Naples Condos for Sale: Don’t miss this opportunity in Naples! This fully furnished, turnkey two-bedroom, two-bath condo is an investor’s dream. Enjoy it as your own retreat, and when you’re away, rent it seasonally to generate income. Ideally located just minutes from Naples’ famed 5th Avenue and pristine Gulf beaches, this condo combines lifestyle and investment potential. Already secured with tenants for the upcoming season, it’s ready to start working for you from day one.

Winterpark Naples Condos for Sale: Discover an exceptional opportunity to own one of only 8 unique corner units in this celebrated Naples community. The moment you step inside, your eyes are drawn upward to the breathtaking cathedral ceilings, creating an immediate sense of grandeur and space. Updated Flooring, elegant floors flow throughout, providing a perfect , polished canvas for your final touches. This 2 Bedroom / 2 Bath condo offers the perfect blend of resort-style living and prime location. You have the freedom to add your personal flair and complete the minor updates needed to create your spectacular dream home. Live the vibrant Naples Lifestyle, with Downtown Naples, Beautiful Beaches, Tin City and Celebration park all just minutes away. The community itself is a destination, boasting a resort-style pool, clubhouse, pickleball and tennis courts. This is more than a home; it's an investment in a highly sought-after , luxurious Florida Lifestyle at a low cost.

Winterpark Naples Condos for Sale: Welcome to Winterpark in Naples, one of the most desirable communities just minutes from downtown and the white-sand beaches! This spacious condo offers comfort, convenience, and resort-style living. Residents enjoy one of the largest resort-style pools in Naples, pickleball and tennis courts, clubhouse, bike and jogging paths, shuffleboard, and beautifully landscaped grounds. The community also features BBQ picnic areas, library, guest room, fitness center, and more! Inside, you’ll find a bright and open floor plan with impact-resistant windows, volume ceilings, and modern finishes. Located close to shopping, dining, entertainment, and world-class beaches, Winterpark is the perfect blend of relaxed Florida living and active community life. Don’t miss the opportunity to own in this well-maintained community with low fees and abundant amenities

Winterpark Naples Condos Under Contract: 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!

Winterpark Naples Condos Under Contract: LOCATION, LOCATION, LOCATION — This Is the One! This rarely available 2nd-floor END unit offers one of the best locations in the Winterpark community! Ideally situated close enough to walk to all the fantastic amenities, yet privately tucked away on Arctic Circle with no drive-through traffic. Enjoy an expansive wide green space directly behind the building, providing extra privacy and beautiful views. Inside, you’ll find a move-in ready condo with thoughtfully updated bathrooms, stylish flooring, and tasteful furnishings—where every detail has been well cared for. Winterpark is one of Naples’ most sought-after communities thanks to its unbeatable proximity to 5th Avenue South & 3rd Street South shopping and dining, Bayfront, Tin City, and Naples’ renowned sugar-sand beaches plus a wide variety of top-rated restaurants! If you’re dreaming of a resort-style lifestyle, Winterpark delivers with one of the largest resort-style pools in Naples, an updated clubhouse with regular social activities, tennis and pickleball courts, bocce, and miles of biking and jogging paths. The perfect condo, in the perfect location, at an amazing price point—don’t miss this opportunity!

Winterpark Naples Condos Under Contract: Welcome to your slice of paradise in the sought-after Winterpark community! This beautifully maintained 2nd-floor condominium offers serene views of the resort-style pool and is ideally situated in a premier location within the community—tucked away from busy streets for added peace and privacy. Boasting over 1,200 square feet of living space, this spacious unit features a thoughtfully designed open floor plan with two bedrooms, two bathrooms, and a dedicated laundry room. The entire unit has been replumbed and is free of polybutylene piping, offering peace of mind and long-term reliability. Inside, you'll find elegant tile flooring throughout—NO carpet—creating a clean, modern aesthetic that's easy to maintain. Impact-resistant windows provide enhanced safety, energy efficiency, and quiet comfort. The layout is perfect for both seasonal getaways and year-round living, with generous natural light and a welcoming ambiance. Offered turnkey, this residence is move-in ready and fully furnished for effortless living. Located just minutes from downtown Naples and the pristine Gulf beaches, you'll enjoy convenient access to world-class dining, shopping, and entertainment. Whether you're seeking a vacation retreat or a full-time residence, this condo delivers the perfect blend of comfort, style, and Florida charm.

Winterpark Naples Condos Under Contract: ***WINTERPARK***QUAINT CONDO***2BEDS/2BATHS***FULLY FURNISHED***DOGS ALLOWED*** Welcome to this charming 2-bedroom, 2-bathroom condo located in the beautiful city of Naples, FL. This cozy home is perfect for those seeking a comfortable and convenient living space. The unit comes fully furnished, allowing you to move in hassle-free and start enjoying your new home right away. The community offers a refreshing pool, providing a great opportunity to relax and cool off during those warm Florida days. Tennis enthusiasts will be delighted to find a tennis court within the community, allowing you to stay active and enjoy some friendly competition. With its prime location in Naples, you'll have easy access to all the amenities and attractions this vibrant city has to offer. Whether you're looking to explore the stunning beaches, indulge in delicious dining options, or shop at the nearby boutiques, this house is perfectly situated to fulfill all your desires.

Winterpark Naples Condos: 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.