Winterpark Naples Real Estate : 20 Condos for Sale

Winterpark Naples Condos for Sale: Welcome to Winterpark, the tropical paradise! This spacious upper-floor 2-bedroom, 2-bath end-unit condo features a front screened balcony, perfect for enjoying your Florida morning coffee or a glass of wine at sunset. Partially furnished (inventory list available). Cathedral ceilings are available only in second-floor units! The open side-wall kitchen design enhances the living space, and the owner’s bathroom features an added barn door for extra privacy. Large laundry room with a private oversized closet and door, extra space on the attic. All appliances are approximately 2 years old. Outside storage included. Newer roof-2022, and CPVC plumbing. Water heater replaced at the end of 2025. Check out this property through our 360° virtual tour! Located just a short walk to the community amenities, no need to cross a busy street. Prime location with quick access to Downtown Naples, the 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 Naples’ beautiful beaches, play tennis or pickleball, enjoy sunset dining at one of the area’s finest restaurants, spend the day shopping, and then relax in the large resort-style pool right in your community. Community amenities include: Resort-style pool, Tennis and Pickleball courts, Clubhouse, Bocce courts. Naples also offers wonderful cultural and entertainment venues, including Gulfshore Opera, Artis – Naples Philarmonic, The Baker Museum, Gulfshore Playhouse, The Naples Players Theater, Naples Botanical Garden, Naples Zoo, and numerous public parks with miles of walking paths. 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 Pelican Bay, Mercato, and much more. Make this home yours today and spend this winter season in sunny Florida!

Winterpark Naples Condos for Sale: Discover comfortable and easy Florida living in this inviting 2-bedroom, 2-bath condo located in the highly desirable Winterpark community. This first-floor residence offers a well-designed floor plan with a welcoming living and dining area, a thoughtfully arranged kitchen, and two comfortably sized bedrooms with excellent closet storage. The primary suite includes an en-suite bath and relaxing views of the community’s green space. Step outside to enjoy Winterpark’s resort-style amenities, including one of the largest community pools in Naples, a clubhouse, pickleball and tennis courts, bocce, and beautifully maintained walking paths. Residents appreciate the convenient East Naples location—just minutes from downtown 5th Avenue, shopping, dining, and Naples’ world-famous beaches. Whether you're seeking a seasonal retreat, full-time residence, or investment property, this Winterpark condo offers wonderful value and a uniquely comfortable Naples lifestyle.

Winterpark Naples Condos for Sale: This Beautifully updated condo is on first floor in the Winterpark community. Unit was completely remodeled in 2021, with tile flooring throughout unit, stainless appliances, new cabinets, new countertops, light fixtures, coffered ceiling in living room, new windows and sliders throughout, custom closets 2022, updated master bath and guest bathroom too! Screened in lanai in front of unit as well as NEW screened in lanai in back of unit added in 2024. Beautiful, landscaped views with lots of room in a tranquil setting. This wonderful diamond in the ruff community has an amazing resort style pool with a clubhouse, and 8 pickleball courts along with bocce and tennis. Minutes to the beaches, restaurants and downtown Naples. You don't want to miss this amazing unit!

Winterpark Naples Condos for Sale: Fully renovated in March 2022 with brand new kitchen, floors and bathrooms. Quartz countertops, glass tile backsplashes, stainless steel appliances, new AC and water heater, luxury vinyl flooring, new hurricane windows and doors. Beautifully furnished/decorated with new furniture and art, this well-appointed home is being sold turnkey. 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, tennis, pickle ball and bocce courts and a lovely walking trail. Conveniently located in the heart of Naples with a short distance to the beach, downtown, 5th Avenue South, Publix and Interstate 75. First floor unit with assigned parking and low association fees.

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: Welcome to this beautifully updated condo in the desirable Winterpark community. Inside, you’ll find a completely renovated kitchen with brand new stainless steel appliances, an electric cooktop, countertops, new cabinetry, and a modern backsplash. The guest bathroom has been fully updated. Additional upgrades include new light fixtures, ceiling fans, fresh interior paint throughout, and even a freshly painted front door. This home comes partially furnished with dining and living room pieces. The master bedroom features a large walk-in closet. The spacious laundry room includes a washer, dryer, and generous storage. When you enter, you'll enjoy your own screened front porch with space for seating, a grill, or bike storage. New owners are also permitted to add a back patio or screened lanai if desired. Winterpark offers exceptional amenities including Pickleball, Tennis, a large resort-style pool, a clubhouse and more. The location is unbeatable with quick access to Naples beaches, Fifth Avenue, and downtown shopping, dining, and entertainment. Schedule your private tour today.

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: Discover the perfect blend of comfort, style, and location in this spacious second-floor corner condo in beautiful Naples. Featuring vaulted ceilings and serene garden views, this light-filled residence offers privacy and tranquility within the lush, peaceful community of Winterpark. This updated 2-bedroom, 2-bath home showcases an open, airy layout with neutral tones that complement any décor. The remodeled kitchen features modern cabinetry, quartz countertops, stainless steel appliances, and a convenient breakfast bar that flows seamlessly into the expansive living and dining areas—ideal for entertaining or relaxing at home. Both bathrooms have also been tastefully renovated. Other updates include a newer A/C and water heater, and a brand-new roof for added peace of mind. Flood insurance is covered by the association. Another advantage is the in-unit laundry room with washer, dryer, and abundant storage. Enjoy Florida living year-round from the screened porch overlooking the garden, the large heated community pool, tennis courts and other playing courts, as well as walking and jogging paths. Other features include private assigned parking and plenty of additional guest parking for even more convenience. Extra private storage accompanies this property to store your bike or anything else you may need. The location is perfect, only a few minutes to Downtown Naples and its world renowned beaches, plus easy access to exceptional dining, shopping and entertainment options. Pet-friendly, rental-friendly and without age restrictions, this condo presents an excellent investment opportunity or seasonal retreat. While other units may be available in the community, this beautifully updated corner residence truly stands out—one you must see in person to fully appreciate.

Winterpark Naples Condos for Sale: WINTERPARK IS A HIDDEN GEM WITH A VERY DESIRABLE LOCATION... ONLY 2-3 MILES TO BAYFRONT, 5TH AVE, DOWNTOWN RESTAURANTS AND SHOPS, AND THE BEACHES... 2 BDRM 2 BATH FIRST FLOOR UNIT WITH LARGE SCREENED IN PATIO LOOKING OUT TO LUSH LANDSCAPING... SNOWFLAKE LANE IS RIGHT NEXT TO THE 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: Nicely appointed 2ND FLOOR UNIT with screened-in deck. Ready to move in. Newer refrigerator and Range in kitchen. A/C is 3 years old. Extensive amenities in the complex including, Tennis Courts, Pickleball, Bocce Ball, Shuffleboard, and a Resort style pool. Walking distance to shopping(Home Depot ,Publix, Walgreen's) and restaurants. Pets are Allowed.

Winterpark Naples Condos for Sale: Enjoy the best of Naples living without the premium price tag! Located just 9 minutes from Downtown Naples and beaches, this second-floor 2 bed/2 bath condo offers an incredibly convenient lifestyle in a prime in-town location, all for under $250K. Whether it’s dinner on 5th Avenue, a beach day, or everyday shopping and errands, everything is close by and easy to reach. Inside, vaulted ceilings and impact-resistant windows and doors create a bright, comfortable space that feels open and secure. The condo has been exceptionally well cared for and is truly easy to move right into. Major building improvements have already been completed, including the full replacement of polybutylene plumbing and aluminum wiring, a newer roof, and a recent professional vent cleaning for improved air quality and peace of mind. Outside, you can enjoy a screened in front porch and a second access point into the kitchen through the impact sliders. The HOA maintains flood insurance that supports Fannie Mae and Freddie Mac financing, and the community and its board are a reflection of strong, proactive management. Amenities are just steps away, including one of the largest community pools in Naples, multiple tennis and pickleball courts, bocce, and an active clubhouse. It’s a setting that makes everyday living feel like a getaway, yet keeps you close to everything that makes Naples so desirable!

Winterpark Naples Condos for Sale: FIXER UPPER - INVESTOR SPECIAL (TLC) ! 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. THIS FIXER UPPER is perfect for investors or DIY buyers seeking to build equity in Prime Location. Solid structure awaiting cosmetic upgrades - Bring your Designer / Contractor - Exceptional Value / Priced to Sell!

Winterpark Naples Condos for Sale: Welcome home to this spacious Winter Park condo featuring 2 bedrooms, 2 bathrooms, and over 1,200 square feet of comfortable living space with serene green space views. Residents enjoy resort-style amenities including a sparkling pool, bocce ball, pickleball, tennis courts, walking trails, and organized social activities. Major updates include a newer A/C and roof. The condo fee includes water, sewer, exterior insurance, exterior maintenance, cable, landscaping, and full access to community amenities. Short-term and annual rentals are permitted with some restrictions, making this a great option for both homeowners and investors. Buyer and buyer’s agent to verify all information.

Winterpark Naples Condos for Sale: Welcome to this beautifully maintained first-floor condo in the highly desirable Winterpark community of Naples. This immaculate 2-bedroom, 2-bath residence is being offered turnkey furnished—simply bring your suitcase and start enjoying the Florida lifestyle. Thoughtfully updated, the unit has been repiped and features impact windows for added peace of mind. The building carries an association flood policy, and the current owners also maintain a separate flood policy on the unit—providing an extra layer of security and confidence for buyers. Hot water heater was replaced in 2023 and AC in 2024. Winterpark is known for its inviting, walkable setting and impressive resort-style pool area, perfect for relaxing or socializing with neighbors. Ideally located just minutes from shopping, dining, downtown Naples, and our beautiful Gulf beaches, this community offers both convenience and charm. Quarterly HOA fees are $1,920 and include the benefits of a well-maintained community and amenities. Whether you’re searching for a winter retreat, full-time residence, or investment opportunity, this move-in-ready condo is a must-see. Don’t miss your chance to own a slice of paradise in Naples!

Winterpark Naples Condos for Sale: Most of the updating has already been taken cared of! Select a vinyl flooring of your choice to lay over existing tile for a totally remodeled look! Close to Beautiful Downtown Naples and the Naples Beach! This 2 bedroom, 2 bath condominium has an Open Floor Plan with Split Bedrooms and offers a totally remodeled/upgraded kitchen with upgraded Granite Countertops and stainless steel appliances. The large Great Room offers a large window area with views of peaceful grounds where you could place an outdoor table with umbrella! Both Bathrooms have been updated with new vanities topped off with Beautiful Upgraded Countertops! 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, tennis, pickle ball courts and a lovely walking trail. 1 pet is permitted!

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 for Sale: CASH BUYER WANTED…MOTIVATIVE SELLER, MAKE AN OFFER ...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 $1,560 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 Under Contract: Tucked away End Unit, no road noise from Davis Blvd. Private feel entrance with lanai that over looks a lovely grass area with beautiful floral blooming trees which is rare and hard to find in this community. No building directly in front or to the side of this unit. Well maintained interior ready for your own touch or for an investor to Seasonally rent. Great rental income in this community due to proximity to downtown and Naples Beaches. Building has Flood Insurance and Poly pipes have been replaced so no issues with getting a loan on the property. All assessments have been paid in full. Original owners, never used as a rental unit. Renovated throughout the years. Winterpark is a large, well-established condominium complex known for its resort-style amenities like a large pool, clubhouse, tennis, and pickleball courts, and its convenient location near beaches, shopping, and dining

Winterpark Naples Condos Under Contract: LOWEST PRICE IN WINTERPARK! 2 bedrooms 2 baths TURNKEY FURNISHED ground floor condo in Winterpark! With 1,246 square feet of air conditioned living area, the living areas are tiled with 18" neutral tone tile. Extra storage closet outside your front door. Winterpark amenities include a spectacular heated, resort-style community pool which is one of the largest swimming pools in Naples. There are bike and jogging trails, beautiful landscaping, 5 tennis courts and 4 pickle ball courts, 2 bocce courts and a clubhouse with a library and lots of social activities if you so desire. You can walk to Kings Lake Square for grocery shopping at Publix and some of the area's tasty and affordable restaurants! This is AN IDEAL year-round or seasonal residence! Please note that the owners never experienced any flood or water intrusion from storms or any thing else, in their nearly 16 years of ownership. Winterpark is just a short drive to renowned Fifth Ave. South with an eye-popping variety of shopping and dining options and Naples beautiful sandy beaches. This condo is an ideal opportunity to own your perfect winter retreat, affordably priced for you to add your personal touches and improvements

Winterpark Naples Condos: 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 Naples Condos: 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!