Winterpark

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…

4140 Looking Glass Ln #3815 is a move-in-ready 2-bedroom, 2-bath condo for sale in Winterpark, one of Naples’ established communities with resort-style amenities and a convenient location. Offered at $329,900, this updated Naples condo features a fully redesigned kitchen with white cabinetry, stainless steel appliances, a stylish backsplash, large breakfast bar, and an open layout…

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…

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…

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…

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…

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…

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.

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…

Discover a pristine Naples paradise with this meticulously maintained 2 bedroom, 2 bathroom condominium at Winter Park that shines with amazing amenities and a luxurious location. Enjoy a condo that benefits from splendid design choices, including vaulted ceilings, plentiful natural light, and split bedrooms. The primary suite is a relaxing retreat, featuring a walk-in closet…

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…

Seller Says Sell! Price reduction for this amazing condo in highly sought after Winterpark. 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…

Welcome home to this beautifully maintained Winter Park condo offering over 1,200 square feet of comfortable living space with peaceful green space views. This spacious residence features 2 bedrooms and 2 bathrooms, providing an ideal layout for both everyday living and entertaining. Enjoy a vibrant, resort-style community with exceptional amenities, including a sparkling resort swimming pool,…

Best Value in Winterpark – First Floor • Turnkey • Impact Windows • New A/C • Conventional Financing On of the Lowest-priced first-floor condo in Winterpark. This turnkey-furnished home offers an incredible opportunity to own in one of Naples’ most desirable communities while leaving room in your budget to update and personalize it over time. The home…

Welcome to 3608 Arctic, a beautifully furnished rental offering flexible short-term accommodations in a highly desirable location. This well-maintained home features a bright, open living space, a fully equipped kitchen, and comfortable sleeping arrangements—perfect for vacationers, relocating professionals, or seasonal residents. Enjoy a move-in-ready experience with stylish furnishings, modern conveniences, and inviting indoor-outdoor living areas designed…

SEASONAL RENTAL AVAILABLE JANUARY - APRIL 2027. LOCATED IN CLOSE PROXIMITY TO NAPLES BEACHES, 5TH AVE IN DOWNTOWN NAPLES, & THE BEST SHOPPING & DINING NAPLES HAS TO OFFER! This condo has been completely remodeled and is fully furnished with designer quality finished and equipped for your winter getaway. The community features a newly renovated…

What a great rental opportunity in the highly sought after community of Winterpark! This 2 bedroom, 2 bathroom condo is a second floor end unit and is immaculate! Wood floors with custom wood working all throughout the condo. The kitchen is beautifully updated with stainless steel appliances and a massive granite countertop. Entertain your guests…

Short Term Rental Available. Perfectly appointed 2 bedroom, 2 bath condo. This entire home has been renovated and tastefully decorated. Primary bedroom offers King size bed, bathroom with walk in shower. The 2nd bedroom has a Queen size bed. The guest bathroom will surprise you with a wonderful Jacuzzi tub for your relaxation. The Kitchen…

Gorgeous 1st floor 2 bedroom / 2 bath turnkey furnished condo in Winterpark. Property features granite countertops, stainless steel appliances, wood plank tile, and a split floorplan that is perfect for entertaining guests. The primary suite has a spacious walk-in closet and a tranquil landscaped view. Property features two screened in outdoor areas that are…

Spacious first floor condo with 2 large bedrooms, screened porch, large living room, short walk to the huge Winterpark pool. $3450 per month for 3 months, $3200. per month for 4 months total, $2750. per month for 6 months total, Maximum 6 months. No pets allowed. Great location, short drive to beaches…

Lovely 2 bedroom 2 bath close to Downtown, Beaches and shopping. 1st floor, newer kitchen, all tile. Fabulous resort style amenities. Walk to shopping and dining.

Available Seasonally! This quaint 2-bedroom, 2-bath first-floor condo in the highly desirable Winterpark community is waiting for you. The home features a well-designed layout with a comfortable living and dining area, a practical and nicely appointed kitchen, and two inviting bedrooms with generous closet space. Residents enjoy access to Winterpark’s impressive amenities, including one of…

This 2 bedroom, 2 bath condo has brand new appliances in the kitchen and updated flooring in the living room-dining room area. There is a resort style swimming pool and tennis and pickleball courts available for your enjoyment. A vaulted ceiling in the living-dining area gives this condo a light and bright…

Centrally located in sunny Naples lies a 2 Bed 2 Bath property in Winterpark that is welcoming to your seasonal desires! Screened in Lani is set for your enjoyment and remodeled open concept is open to entertaining guests. Neighborhood amenities such as a heated pool and fitness center. This is a highly sought after community…

Available from June 1, 2026! Enjoy the best of Naples living in this fully renovated condo, ideally located in the sought-after Winterpark community -just minutes from Downtown Naples and the beaches! This bright and spacious home features modern finishes throughout, an updated kitchen with stainless steel appliances, stylish bathrooms, and open-concept living. Winterpark offers resort style…

Discover easy Florida living in this inviting 2-bedroom, 2-bath first-floor condo available for lease in the highly desirable Winterpark community. The home features a well-designed layout with a comfortable living and dining area, a practical and nicely arranged kitchen, and two welcoming bedrooms with generous closet space. The primary suite includes its own private bath…

Live the Naples lifestyle year-round in this furnished 2-bedroom, 2-bath first-floor condo available for annual rental in a prime location. Offering easy ground-level access and a spacious, inviting layout, this residence is move-in ready and designed for comfortable living. Enjoy exceptional community amenities including a resort-style pool, tennis courts, pickleball, and bocce — all just…

Welcome to your dream condo in Naples/Winter Park! This stunning unit boasts 2 bedrooms, 2 bathrooms, granite counters, stainless steel appliances, and tile flooring throughout. The screened-in front lanai is the perfect spot to enjoy your morning coffee or evening cocktail. Located on the first floor, this condo offers easy access to the lanai from…

This spacious second floor, 2 bedroom/2 bathroom condo is available now as an annual rental!! The floor plan has split bedrooms, a large living and dining area and a laundry room with lots of storage space. Winterpark is in a desirable location as it is less then 5 miles to downtown Naples and the…

Brand new kitchen appliances and flooring in living-dining area. Turnkey furnished, You can move right in and start living the Florida lifestyle!. Vaulted ceilings in living-dining area. Extra storage inside and outside and walk-in closet in master bedroom. Excellent condition throughout. Resort style swimming pool and tennis and…

*Available August-December 2026 and April-May 2027* Beautifully updated condo in the popular Winterpark community! This second floor condo has vaulted ceilings, tile throughout, granite countertops, stainless steel appliances, updated kitchen and bathrooms, and is tastefully furnished and decorated. Large spacious living room with open floor plan to the dining & kitchen, is perfect for entertaining…

Welcome to your opportunity to lease an upstairs residence in the highly sought-after Winterpark community—where resort-style living meets everyday convenience in the heart of Naples. This 2-bedroom, 2-bath condo offers a bright, open layout with an expansive living and dining area, ideal for comfortable living and easy entertaining. The screened balcony provides a tranquil outdoor…