Winterpark

List Price:  $240,000

Huge price reduction on a Winterpark condo with value-added updates! Nothing compares in the area with these features at this price. This well-maintained home will delight you - updated kitchen and baths with Uba Tuba granite, large owners suite with walk in closet, engineered wood floors, high ceilings, impact windows and slider, plumbing and AC…

List Price:  $259,500

Wonderful furnished, 2 bedroom/ 2 bath, end unit, 1st floor condo in Winterpark. Impact windows and doors, new plumbing throughout, new AC, mostly new appliances. Fully furnished, turn key. Secluded condo location with landscape view in front and back and a screened porch off of the kitchen. Easy to rent seasonally or annually. Close to…

List Price:  $254,900

you will be impressed with the light and bright and spacious feel in this 2 bedroom, 2 bath condo. It has vaulted ceilings and is tastefully turnkey furnished. The furniture is negotiable. There is extra storage too. Shopping and restaurants are within walking distance of the condo. There is a resort…

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:  $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…

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:  $229,000

Gorgeous 2 bedroom, 2 bath residence centrally located near all that Naples has to offer! Upon entering, you will be greeted by ample natural light and the freshly painted interior with tile flooring throughout. The living room features beautiful views of manicured landscaping. The kitchen is fully equipped with white cabinetry and…

List Price:  $3,500

RESERVE NOW FOR 2026 SEASON. 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., and 25 mins. from the airport. …

List Price:  $299,000

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…

List Price:  $2,250

Welcome to Your Private Oasis in Paradise Step into elegance with this stunningly appointed 2-bedroom, 2-bathroom condo—a refined sanctuary designed for those who crave style, comfort, and the ultimate in South Florida living. This unfurnished gem features a modern, entertainer’s dream kitchen, beautifully updated with sleek white cabinetry, quartz countertops, and a convenient in-unit washer and…

List Price:  $279,000

A bright and beautiful 2 bedroom condominium is being offered for sale in the wonderful Winterpark community. This tastefully decorated and well-appointed residence features large spaces and functional rooms. The well-lit kitchen boasts quartz countertops and breakfast bar, tiled backsplash, a stainless steel sink and stainless steel appliances. Large plank ceramic flooring runs throughout the…

List Price:  $1,950

Welcome to Winterpark, Naples, Florida! This charming annual rental offers the perfect blend of comfort and convenience. Nestled in a tranquil neighborhood, this 2 bedroom, 2 bathroom home is ideal retreat for those seeking a serene and welcoming living space. Enjoy the beautiful Florida weather in your private oasis, complete with a full amenities…

List Price:  $2,700

AVAILABLE FOR 6 MONTHS AT A TIME. AVAILABLE APRIL-DEC 2025. Recently updated with tile flooring, granite counter tops and painted in neutral gray tones. Winter Park has one of the largest pools in Southwest Florida, with tennis, pickleball, bocce Courts and a clubhouse. It is only 5 miles from 5th Avenue and Downtown Naples! Book…

List Price:  $2,150

Completely remodeled condo. Close to downtown and beaches. Water and trash included.

List Price:  $3,200

Available short term or long term. 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.

List Price:  $234,000

This is the best value in Winterpark! This spacious well cared for 2 bedroom condo offers soaring ceilings, an open, efficient floor plan, updated kitchen, hurricane impact windows and more! The bedrooms are spacious with large closets and the laundry room offers additional storage, as well as outdoor storage under the stairs. This condo…

List Price:  $219,000

BEST DEAL 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. Seller never had any flood damage or water intrusion at all, in the 15…

List Price:  $1,950

AVAILABLE immediately!. Beautiful condo, spacious and bright. Fully furnished available for a yearly lease. Close to downtown Naples, Beaches, Restaurants and shopping. Great floor plan, good size bedrooms and spacious laundry room and storage. Water included in monthly rent. Rented turnkey. Computer and printer do not convey.

List Price:  $245,000

***WINTERPARK***QUAINT CONDO***2BEDS/2BATHS***FULLY FURNISHED***DOGS ALLOWED*** Welcome to this charming 2-bedroom, 2-bathroom condo located in the beautiful city of Naples, FL. This cozy home is perfect for those seeking a comfortable and convenient living space. The unit comes fully furnished, allowing you to move in hassle-free and start enjoying your new home right away. The community offers a…

List Price:  $2,200

Short Term or Long 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…

List Price:  $288,000

Light and Bright First Floor Condo. This large 2 bedroom/ 2 bath Split Bedroom home has Sunny Southern Exposure and Private backyard landscape views. Winterpark is located just 3 miles from 5th Avenue and The Pristine Gulf Beaches. It is an amenity rich community with a Newly Refurbished, large Resort Style Pool, Brand New Pickleball Courts,…

List Price:  $1,650

GREAT PRICE ON THIS LONG TERM TWO BEDROOM, TWO BATH CONDO AVAILABLE APRIL 2 TO DECEMBER 27, 2025! FULLY FURNISHED FOR YOUR COMFORT AND CONVENIENCE. WINTERPARK HAS MANY AMENITIES INCLUDING CLUBHOUSE, COMMUNITY POOL, COMMUNITY SPA, EXERCISE ROOM, TENNIS AND MORE.... JUST A SHORT DRIVE TO FIFTH AVE, TIN CITY, BAYFRONT, DOWNTOWN, AND THE BEAUTIFUL WHITE…

List Price:  $3,500

AVAILABLE FOR JANUARY, FEBRUARY, AND MARCH 2026 AND NOW TAKING RESERVATIONS FOR THOSE DATES. THIS IS A NICE TWO BEDROOM UNIT IN WINTERPARK DEVELOPMENT WITH A CLOSE PROXIMITY TO DOWNTOWN, BAYFRONT, TIN CITY, FIFTH AVE, AND THE BEAUTIFUL WHITE SAND BEACHES OF NAPLES. THIS CONDO IS FULLY FURNISHED AND READY FOR YOUR COMFORTABLE STAY.

List Price:  $269,000

WINTERPARK IS A HIDDEN GEM WITH A VERY DESIRABLE LOCATION... 2 BDRM 2 BATH FIRST FLOOR UNIT WITH LARGE SCREENED IN PATIO LOOKING OUT TO LUSH LANDSCAPING... 2-3 MILES TO BAYFRONT, 5TH AVE, DOWNTOWN RESTAURANTS AND SHOPS, AND THE BEACHES... ... WALK TO RESORT STYLE POOL (ONE OF THE LARGEST IN NAPLES) / FIVE TENNIS…

List Price:  $274,900

This is an amazing listing! Winterpark in Naples truly seems like a dream for someone looking to enjoy an active and vibrant lifestyle. The proximity to the pool (right in the back yard) plus all the fantastic amenities like pickleball, tennis, bocce, and that huge resort pool, make it very attractive. The updates (new air conditioner,…

List Price:  $279,500

Bright and spacious 2 bdrm/2 bth 2nd floor condo with all new storm impact windows, newly renovated bathrooms, tile throughout, laundry rm in residence... spectacular location only 2 miles to Bayfront, 5th Ave shops, dining, and beaches... the Winterpark community amenities include tennis courts, pickleball, shuffleboard, bocce, large resort style community pool surrounded by palm…

List Price:  $269,900

Newly renovated 2 bedroom, 2 bath Condo Available! Just 4 miles to beautiful downtown Naples! 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, Bocce, Walking and Bike Paths, and a resort style community pool. Great for…

List Price:  $259,990

Discover this investor's dream in the heart of Winterpark! This 2 bedroom 2 bathroom end unit, top floor condo is READY TO SELL! CASH BUYERS ONLY... No financing contingency. With high ceilings and an abundance of natural sunlight streaming through every room, you'll immediately feel the warmth and openness of this inviting space. NEWLY added…

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…

List Price:  $4,000

SEASONAL RENTAL AVAILABLE (APRIL 2025) 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 resort style…

List Price:  $4,200

Check out this charming second-floor condo in Winterpark Community. It's super spacious, filled with light, and features a split-level layout. Just a short walk to the pool and tennis courts, Winterpark boasts a resort-style pool and lovely open spaces. Plus, it's conveniently located just minutes from 5th Avenue, where you can enjoy dining, shopping,…

List Price:  $3,300

Very nice 2 bedroom, 2 bath 2nd floor condo with resort style community pool and tennis courts. Close to shopping and restaurants and only a short drive to Naples famous pristine beaches and fabulous world renowned restaurants and boutiques. Turnkey furnished.