Winterpark Naples Real Estate : 18 Condos for Sale

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: 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 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: 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: Seller is open to considering concessions toward the buyer’s closing costs, creating an exceptional opportunity to step into this beautifully renovated Naples retreat with added financial flexibility. Welcome home to your private oasis in the heart of Naples. This stunning 2-bedroom, 2-bath condo has been thoughtfully remodeled from top to bottom, offering a bright, airy feel that immediately impresses. Soaring vaulted ceilings and abundant natural light enhance the sense of space, while the extensive upgrades make the home feel truly brand new. The all-new kitchen and bathrooms are showstoppers, featuring modern cabinetry, elegant quartz countertops, and brand-new appliances—including a washer and dryer for everyday convenience. Both bathrooms boast newly installed showers and a beautifully refinished tub/shower combination. Behind the scenes, peace of mind comes standard with upgraded PEX plumbing supply lines and a new water heater. Throughout the home, you’ll find luxury vinyl plank flooring, fresh designer paint, updated baseboards and trim, stylish new lighting, and a contemporary ceiling fan—every detail curated for a polished, move-in-ready experience. Both bedrooms are generously sized with ample closet space, and the oversized laundry room offers valuable extra storage rarely found in condos. Ideally located in the highly desirable Winterpark community, this pet-friendly neighborhood puts you within walking distance of Publix, Starbucks, popular restaurants, and everyday conveniences. Residents enjoy resort-style amenities including a large heated pool, pickleball, tennis, bocce, and scenic paved walking and biking paths. Best of all, you’re just minutes from Naples’ world-famous white-sand beaches and the upscale shopping and dining of 5th Avenue South. This is is the Naples lifestyle you’ve been waiting for. Don’t miss your opportunity to make it yours.

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: 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: Winterpark Condo

Winterpark Naples Condos for Sale: Conveniently located within minutes from Fifth Avenue South, Naples beaches, Bakers Park, boat/water-toys ramp, shopping, dining, and everyday essentials. Publix and a fire station are within walking distance, with additional medical facilities and government services nearby. Situated in a non-flood zone, the home enjoys enhanced privacy with a landscaped green area and mature trees adjacent to the property, along with an open Davis Boulevard streetscape view rather than a parking lot. Set within a well-established, quiet, low-rise condominium community in the desirable Winterpark area of Naples, this residence offers a refined blend of comfort, ease, and low-maintenance living. Light-filled interiors feature a neutral palette, cathedral ceilings, tasteful updates, and a functional layout designed for both full-time and seasonal enjoyment. The kitchen flows seamlessly into the main living area, while bedrooms provide calm, private retreats. Interior highlights include wood blinds, porcelain flooring in the primary bedroom and walk-in closet with generous shelving, and carpet, bathroom finishes, and kitchen countertops updated within recent years. An enclosed outdoor living area enhances the home’s indoor-outdoor lifestyle, offering a private space to relax, dine, or enjoy the Florida climate year-round. The community’s professionally maintained grounds, low-rise architecture, and residential character make this property particularly well-suited for buyers seeking a full-time residence, seasonal escape, or effortless lock-and-leave lifestyle. Association-managed exterior elements and a resort-style community pool support ease of ownership and long-term enjoyment. Cable and water are included.

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: 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: 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: Most of the updating has already been done for you! Have a vinyl flooring of your choice laid over the 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 kitchen with upgraded Granite Countertops, stainless steel appliances and opens to a large Great Room! 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: 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 for Sale: 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 Under Contract: 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 Under Contract: Well-maintained second-floor apartment located in the desirable Winterpark community in Naples. This 2 bedroom, 2 bathroom unit offers a bright and functional layout with an open living and dining area, perfect for everyday living or seasonal use. The unit features spacious bedrooms & ample closet space.Winterpark is a well-established community with mature landscaping and convenient amenities. Excellent location close to shopping, dining, beaches, downtown Naples, and major roads. Ideal as a primary residence, second home, or investment property.

Winterpark Naples Condos Under Contract: 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 Under Contract: Nestled at the end of a cul-de-sac, this first-floor end-unit condo offers a level of privacy and accessibility that’s hard to find in Naples at this price. With no road noise from Davis Boulevard and no building directly in front or to the side, this residence feels peaceful and secluded yet remains close to everything. The lush grassy side and back yards feel like your own private oasis, and with the walking path just steps from your back door, a nice stroll takes you right to the resort-style amenities. This two-bedroom, two-bath unit has been thoughtfully updated, allowing you to skip the renovations and start enjoying the Naples lifestyle immediately. Its freshly painted interior features impact windows and doors, tile flooring throughout, stainless appliances, white cabinetry and stone counter tops, and modern tile-surround step-in showers. AC system and roof were replaced in 2022. Owners are permitted to have one household pet. Winterpark offers its residents one of Naples’ largest community pools, tennis and pickleball courts, and a community room. Centrally located, the beaches and downtown shops and restaurants are just minutes away and conveniences like Publix, Starbucks and Home Depot are right around the corner.

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: 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.