Winterpark

List Price:  $349,000

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…

List Price:  $2,700

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…

List Price:  $254,900

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…

List Price:  $3,500

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…

List Price:  $257,777

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…

List Price:  $1,950

Available as a furnished, annual rental beginning on April 1st! Lovely updated ground-floor condo in the popular Winterpark community! This unit is beautifully furnished, tastefully decorated & well maintained, with tile floors, updated bathrooms and kitchen featuring nice cabinets, granite countertops & stainless steel appliances. Comes with a storage unit. Enjoy all the wonderful amenities…

List Price:  $1,895

FIRST FLOOR Annual Rental. Western Exposure Cozy Beach Coastal in the active and friendly Winterpark community, with one of the Largest Resort Style Pools in town. This friendly neighborhood is minutes from downtown 5th Ave., and 25 mins. from the airport. Plenty of storage within the walk in master closet, large utility/laundry room, and additional…

List Price:  $1,800

Beautiful 2-bedroom, 2-bath unit in Winterpark, Naples. This property offers a functional floor plan and a great location near shopping centers, restaurants, and major roads. Perfect for those seeking comfort, convenience, and the Naples lifestyle.

List Price:  $220,000

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:…

List Price:  $2,700

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 guests. There is a big walk-in…

List Price:  $2,000

Welcome Home to Your Naples Oasis! Step into this beautifully renovated 2-bedroom, 2-bath condo—bright, airy, and refreshed from top to bottom. Vaulted ceilings and an abundance of natural light create a spacious, uplifting atmosphere the moment you walk in. With so many high-quality updates, it truly feels like a brand-new home. The all-new…

List Price:  $3,000

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…

List Price:  $2,000

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…

List Price:  $279,000

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…

List Price:  $1,850

Available NOW! This spacious, freshly painted 2-bedroom, 2-bath first-floor WINTER PARK condo is ready for you to move in! Step inside from the front lanai into a well-sized kitchen with a breakfast bar — perfect for your morning coffee or entertaining guests. Enjoy the added comfort and convenience of in-unit laundry and tile flooring throughout.…

List Price:  $3,000

Stay the season in Naples! Seasonal rates (December 2025- April 2026) $3,000.00 A 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,…

List Price:  $3,200

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…

List Price:  $1,800

Beautiful ground floor 2 bedroom and 2 bathrooms with new tile floor and paint throughout. Available now after association approval. This unit is fully furnished. Just bring your suitcase! Winterpark has lots of amenities: huge resort style swimming pool, tennis courts, pickleball courts, bocce courts and clubhouse. Centrally located, close to downtown, 5th Ave and…

List Price:  $274,500

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,…

List Price:  $195,000

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…

List Price:  $270,000

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…

List Price:  $2,400

Long Term Rental Available. 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 . The Kitchen has granite countertops, newer refrigerator, microwave and dishwasher. There are 3 televisions…

List Price:  $2,450

FEBRUARY SPECIAL PRICE. Must book this week! Escape the Cold in this Light, Bright, Renovated and Turnkey Furnished! Spacious and most desired FIRST FLOOR Western Exposure Cozy Beach Coastal in the active and friendly Winterpark community, with one of the Largest Resort Style Pools in town. This friendly neighborhood is minutes from downtown 5th Ave.,…

List Price:  $239,900

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…

List Price:  $3,450

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…

List Price:  $2,680

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…

List Price:  $229,999

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…

List Price:  $299,000

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…

List Price:  $235,000

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…

List Price:  $284,999

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…

List Price:  $239,000

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…

List Price:  $264,900

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…

List Price:  $289,900

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…

List Price:  $309,900

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…