Winterpark Naples Real Estate : 22 Condos for Sale

Winterpark Naples Condos for Sale: A 1-year home warranty is included with the purchase of this property! 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: 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: THIS WINTERPARK VIII ASSOCIATION CONDO HAS LOWEST HOA FEES IN WINTERPARK + INCLUDES FLOOD INSURANCE. Experience effortless Naples living in this beautifully renovated two-bedroom, two-bath second floor condo, ideally located with convenient access to the vibrant energy of downtown Naples. Thoughtfully updated throughout, this light-filled condominium blends modern sophistication with a relaxed coastal aesthetic. Cathedral ceilings elevate the main living space, enhancing the open, airy feel, while luxury vinyl plank flooring flows seamlessly throughout. The stunning kitchen is a true focal point, featuring distinctive ceiling details, quartzite countertops, and stainless-steel appliances—perfectly designed for both everyday living and entertaining. Enjoy tranquil landscaped views from the screened lanai, creating a private retreat for morning coffee or evening relaxation. Impact-resistant doors and windows provide both peace of mind and energy efficiency. Offered beautifully furnished, this condo provides the perfect opportunity for instant enjoyment. This pet-friendly community includes an impressive array of amenities, including a resort-style pool, clubhouse, scenic walking paths, bocce courts, pickleball, and tennis. A rare opportunity to own a move-in-ready coastal escape in one of Naples’ most convenient locations.

Winterpark Naples Condos for Sale: Discover easy Florida living in this inviting 2-bedroom, 2-bath condo located in the highly desirable Winterpark community. This first-floor corner unit features a bright open floor plan with great views overlooking the peaceful walking path. FURNITURE OPTIONAL. LOCATION LOCATION Enjoy a split-bedroom layout for added privacy, along with a welcoming living and dining area, a thoughtfully arranged kitchen, and washer and dryer in the unit. The primary suite includes an en-suite bath and relaxing green space views. Additional features include an outside storage unit, a screened patio, and a nice-sized open porch out back, perfect for enjoying the Florida lifestyle. Winterpark offers resort-style amenities, including one of the largest community pools in Naples, a clubhouse, pickleball and tennis courts, bocce, and beautifully maintained walking paths. Conveniently located in East Naples, just minutes from downtown 5th Avenue, shopping, dining, and Naples’ world-famous beaches. Whether you’re looking for a seasonal getaway, full-time residence, or investment opportunity, this property offers great value and comfortable Florida living.

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: Move-in ready and beautifully furnished, this 2BR/2BA second-floor condo features an open-concept layout with vaulted ceilings, bamboo flooring in the main living areas, and recessed lighting in the kitchen. Both bathrooms are updated with natural limestone showers and glass enclosures. Enjoy tranquil pond views from the living room and primary bedroom, along with a screened lanai overlooking landscaped grounds. Offered turnkey furnished, this residence is well-suited for seasonal living, investment, or full-time use. Highlights: Hurricane impact windows throughout; vaulted ceilings (2nd-floor units only); pond views from living area and primary bedroom; newer washer/dryer; exterior storage for bikes and beach gear; community roof replaced in 2018. Amenities: Resort-style heated pool, tennis, pickleball, bocce, clubhouse. Location: Minutes to 5th Ave South, Bayfront, and beaches; walk to Publix and dining at Kings Lake Square. Community: Leasing permitted 3 times per year (30-day minimum / 180-day maximum). Pets: one dog (up to 50 lbs) or cat for owners (no pets for tenants).

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 Winterpark, one of Naples most sought-after communities just minutes from downtown and the pristine Gulf beaches. This beautifully updated 2-bedroom, 2-bath 1st floor condo offers a perfect blend of modern style and effortless Florida living. Step inside to an open, light-filled layout designed for both comfort and entertaining. Darkwood accents & cabinetry in the kitchen and breakfast bar, custom tile work and exquisite finishes throughout. Enjoy your morning coffee or unwind in the evening on the spacious lanai, a perfect private retreat with a relaxing, tropical feel. Winterpark is known for its resort-style amenities, including one of the largest pools in Naples, newly updated pickleball and tennis courts, and a vibrant, active social atmosphere. Surrounded by lush green spaces and charming scenery, the community captures the essence of classic Florida living. Ideally located just minutes from 5th Avenue South, Olde Naples, shopping, dining, and the beach, this property is perfect as a full-time residence, seasonal getaway, or investment opportunity. Come experience it for yourself—this one won’t last.

Winterpark Naples Condos for Sale: One or more photo(s) has been virtually staged, AI generated or rendered. Charming second-floor 2-bedroom, 2-bath condominium located in the highly desirable Winterpark community, specifically within Winterpark VIII, which offers the lowest HOA fees in the neighborhood. Ideally positioned for convenient access to the vibrant downtown Naples area, this residence is set within a beautifully maintained, amenity-rich environment featuring a resort-style pool, clubhouse, scenic walking paths, bocce courts, pickleball, and tennis. This move-in-ready property presents an exceptional opportunity for a variety of lifestyles in beautiful Southwest Florida.

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: 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: Experience effortless Florida living in this charming 2-bedroom, 2-bath first-floor condo located in the desirable Winterpark community. Offered beautifully furnished and turnkey, this home presents a rare opportunity for immediate enjoyment with a seamless move-in experience or investment. The entire condo features new plank-style tile floors, creating a cohesive and modern look with the latest style. The kitchen has been tastefully refreshed with professionally painted cabinetry, a new faucet, and a new vent hood, creating a clean and modern aesthetic. Both bathrooms now feature new Quartz Custom Countertops and cabinets and and modern lighting. adding a touch of elegance and style. Additional updates include updated lighting, and plantation shutters that add both style and functionality. The spacious primary suite offers a serene retreat, complete with a walk-in closet for ample storage and organization. Additional highlights include a spacious in-residence laundry room with ample storage, as well as a large, convenient outdoor storage area—perfect for bicycles, beach gear, or seasonal items. The unit also benefits from a full replacement of polybutylene plumbing for added peace of mind. Enjoy the screened-in front porch, an ideal space to relax with your morning coffee or unwind in the evening. Residents of Winterpark enjoy an exceptional array of amenities, including a resort-style pool, clubhouse, tennis and pickleball courts, bocce, and scenic walking paths, all within a beautifully maintained, amenity-rich environment. The property’s convenient location, is just a short drive away from Fifth Avenue and Third Street, where you can indulge in a variety of restaurants, parades, upscale shopping and holiday events. Close to the beautiful Napes Gulf beaches, offering a perfect spot for relaxation and breathtaking sunsets. This move-in-ready condo is an excellent opportunity for a variety of lifestyles. schedule your showing today!

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: Welcome to an exceptional opportunity to own an upstairs residence in the highly sought-after Winterpark community—where value meets vision and the potential to create your dream Naples retreat awaits. Positioned in a prime Naples location, this 2-bedroom, 2-bath condominium offers a light-filled layout with an expansive living and dining area, ready to be reimagined with your personal style and design vision. The screened balcony provides a peaceful outdoor space overlooking lush tropical landscaping—perfect for morning coffee or unwinding after a day at the beach. Inside, you’ll find a spacious primary suite, in-unit laundry, and a functional floor plan that serves as the perfect canvas for updates, renovations, or a full custom transformation. What truly sets this property apart is its placement within Winterpark—one of Naples’ most desirable, amenity-rich communities known for its vibrant lifestyle and classic Florida charm. Residents enjoy access to one of the largest resort-style pools in Naples, beautifully maintained grounds, newly updated pickleball and tennis courts, and an active social atmosphere that makes it easy to feel at home. Located just minutes from 5th Avenue South and Olde Naples, as well as world-renowned Gulf beaches, this property offers unmatched convenience to fine dining, boutique shopping, art galleries, and coastal living at its finest. Whether you’re seeking a seasonal escape, investment opportunity, or a full-time residence to customize and make your own, this is your chance to unlock the full potential of Naples living in a community that truly embodies the Florida lifestyle.

Winterpark Naples Condos for Sale: One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. Beautiful lake-view condo just minutes from everything Naples has to offer! Located only 8 minutes from the beach and close to 5th Ave South and downtown, this desirable second-floor unit offers privacy, natural light, and beautiful Lake views. Featuring 2 bedrooms and 2 bathrooms, this home boasts vaulted ceilings, an updated Tile and carpet flooring throughout, and a spacious primary suite with a walk-in closet. The living area is enhanced with impact windows, providing both peace of mind and energy efficiency. Whether you're looking for a full-time residence, seasonal getaway, or income-producing rental investment, this unit checks all the boxes. Allows up to 12 rentals per year with a 30-day minimum, offering excellent flexibility and strong income potential making it a fantastic opportunity for investors seeking Airbnb-style or seasonal rental income.

Winterpark Naples Condos for Sale: PRICE IMPROVED!! BRING AN OFFER!! 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 $240K. 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: 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: 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 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 Under Contract: 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 Under Contract: 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!