Winterpark

$2,500

Low Rise (1-3)

Beautifully Furnished 2 Bedroom, 2 Bath First-Floor Condo – Move-In Ready! This charming first-floor condo features 2 spacious bedrooms and 2 full baths, fully furnished and ready for you to enjoy. Ideally located just minutes from…

$2,200

Low Rise (1-3)

Charming 2/2 Condo in Winterpark, Naples Marketing DescriptionEscape to this ultra-convenient second-floor condo located in the heart of Naples, FL. This cozy 2-bedroom, 2-bathroom unit features a spacious layout and modern amenities. Property Highlights: Bedrooms: 2 Bathrooms: 2 Comes furnished,…

$280,000

Low Rise (1-3)

2nd Floor Vaulted Ceiling Unit and Impact Windows and Doors! Building has Flood insurance through the HOA necessary for a Fannie/Freddie Mortgage approval and an added plus is New Underground Utilities. This Association is very…

$219,000

Low Rise (1-3)

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…

$240,000

Low Rise (1-3)

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…

$259,500

Low Rise (1-3)

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…

$254,900

Low Rise (1-3)

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. …

$2,680

Low Rise (1-3)

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…

$309,900

Low Rise (1-3)

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…

$2,400

Low Rise (1-3)

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…

$288,000

Low Rise (1-3)

Beautiful remodeled 2 bedroom 2 bath 2nd Floor condo. Enter into the condo with vaulted ceilings, recessed lighting, eat-in kitchen along with counter bar, quartz counter tops, backsplash, large stainless steel sink, new custom cabinets…

$229,000

Low Rise (1-3)

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.…

$3,500

Low Rise (1-3)

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…

$299,000

Low Rise (1-3)

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…

$1,950

Low Rise (1-3)

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…

$305,000

Low Rise (1-3)

Welcome to your serene sanctuary in the heart of Winterpark! This charming condominium offers a beautiful living space and an unbeatable location. You are steps from the largest pool in South Florida. With updated plumbing…

$268,500

Low Rise (1-3)

Great Location within the Development and an END UNIT so it only shares on wall, unlike most that share two. This unit is immaculately clean and sold turnkey furnished with modern coastal feel finishes and…

$239,900

2 Story,Low Rise (1-3)

This unit is THE LOWEST PRICED unit in Winterpark and ready for your personal touch. Great Location near the Wonderful Amenities Winterpark has to offer. A quick walk to the resort size Pool, Bocce Court,…

$279,000

2 Story,Low Rise (1-3)

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…

$1,950

Low Rise (1-3)

May Special 1/2 off first month rent! 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…

$329,000

2 Story,Low Rise (1-3)

Here are 3 reasons why you shouldn't miss this amazing opportunity! 1. Unbeatable Value in a Prime Location – This condo offers modern luxury at an affordable price, making it a rare find in such a…

$2,700

2 Story,Low Rise (1-3)

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,…

$2,100

Low Rise (1-3)

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

$3,200

2 Story,Low Rise (1-3)

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.

$234,000

Low Rise (1-3)

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…

$1,950

Low Rise (1-3)

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…

$245,000

Apartment,Low Rise (1-3)

***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…

$2,200

Low Rise (1-3)

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.…

$270,000

Low Rise (1-3)

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…

$298,000

2 Story,Low Rise (1-3)

Beautiful first floor, 2-bedroom 2-bathroom condo located in the community of Winterpark. One of the few condos in Winterpark with a screened in lanai. The kitchen and bathrooms were remodeled, granite countertops, and impact-resistant windows.…

$1,650

2 Story,Low Rise (1-3)

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,…

$3,500

2 Story,Low Rise (1-3)

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,…

$269,000

Low Rise (1-3)

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…

$274,900

Low Rise (1-3)

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…

$279,500

Low Rise (1-3)

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,…

$229,000

2 Story,Low Rise (1-3)

This charming Winterpark end unit residence is the opportunity you've been waiting for! This charming 2-bedroom/2-bathroom condo is an ideally situated corner residence, offering added privacy and natural light.  Winterpark is an appealing and vibrant…

$265,000

Apartment,Low Rise (1-3)

PET-FRIENDLY -- spacious FIRST floor 2BR/2BA END UNIT condo only a few minutes to downtown Naples and all the wonderful activities, shopping, restaurants, entertainment and of course, the world-renowned beaches! The residence is LIGHT &…

$269,900

Low Rise (1-3)

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…

$259,990

Low Rise (1-3)

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…

$259,000

Low Rise (1-3)

Don’t miss this fantastic opportunity to own a turnkey 2-bedroom, 2-bath condo in the sought-after Winterpark resort community! Situated on the second floor, this condo boasts impressive high ceilings and an updated kitchen featuring white…

$3,500

Low Rise (1-3)

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…

$309,000

2 Story,Low Rise (1-3)

Fantastic location, only five minutes from Downtown and the pristine beaches of Gulf of Mexico. Indulge in the thoughtfully crafted split floor plan that seamlessly accommodates both entertainment and ample bedroom space. Beautifully…

$4,000

Low Rise (1-3)

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…

$250,000

Low Rise (1-3)

Location, Location, Location! This 2-bedroom, 2-bath gem is situated in the highly sought-after Winterpark community. But what sets this home apart? A Private Den! Perfectly enclosed with sliders for ultimate privacy, this den is your…

$295,000

Low Rise (1-3)

Welcome to your dream condo in the heart of Naples! This stunning, beautifully renovated residence at 4049 Northlight Drive in the desirable Winterpark community offers a blend of coastal and comfortable living. Step inside to discover…

$278,900

2 Story,Low Rise (1-3)

Light, Bright, Renovated and Turnkey Furnished! Spacious and MOST DESIRED 1st Floor Western Exposure Cozy Beach Coastal in the highly Desirable Winterpark community, known for having one of the Largest Resort Style Pools in town.…

$239,000

Low Rise (1-3)

This ground-floor (no stairs) condominium is minutes from 5th Avenue- downtown Naples for fine dining, entertainment, and the world-renowned white sand beaches. This 2-Bed, 2-Bath condominium community boasts a resort-style pool, clubhouse, tennis, pickleball, bocce…

$289,000

2 Story,Low Rise (1-3)

Winterpark Condominiums are conveniently located close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. Recently renovated Kicthen with White Shaker soft close cabinets, white subway tile backsplash and gorgeous quartz counter…

$259,900

2 Story,Low Rise (1-3)

PRICE REDUCED! Welcome to Winterpark! This Ground Floor, Turnkey, 2 bed 2 bath 1246 sq ft condo is a 3 minute walk to all of the great amenities that Winterpark has to offer. Ground floor…

$4,200

Low Rise (1-3)

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…

$248,500

Low Rise (1-3)

**EXCELLENT INVESTMENT OPPORTUNITY WITH A HUGE REDUCTION IN PRICE!** This 2 Bedroom/2 Bath downstairs unit is located in the desirable community of Winterpark which features a resort style pool, a Clubhouse & tons of additional…

$309,999

Low Rise (1-3)

Impeccable designer-renovated ground floor turnkey 2 bedroom/2 bath end unit condo in the desirable Winterpark community! This condo features a stunning brand new kitchen with quartz countertops, high-quality white cabinets, herringbone backsplash and stainless steel…

$3,300

Low Rise (1-3)

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…

$309,000

2 Story,Low Rise (1-3)

Discover refined living in this exquisite 2-bed, 2-bath sanctuary on the second floor. As you enter, the soaring ceilings create an immediate sense of openness, complemented by exquisite tile flooring throughout.The kitchen is a masterpiece,…

$265,000

2 Story,Low Rise (1-3)

Seller is motivated! This exquisite second-floor furnished kroner unit offers a well-maintained interior that is sure to impress. Complete with two bedrooms and two baths, providing the perfect retreat just 3 miles away from downtown…

$299,900

2 Story,Low Rise (1-3)

This Winterpark 2 bed, 2 bath unit is a must-see with its private southern rear exposure and recent renovations. The kitchen boasts hard wood cabinets, granite countertops, and a breakfast bar, the split floor plan…

$280,000

2 Story,Low Rise (1-3)

Discover the allure of this 2-bed, 2-bath Winterpark residence featuring a private southern rear exposure and recent enhancements. The kitchen boasts tons of cabinets, new stainless steel appliances, and a convenient breakfast bar. Indulge in…

$299,999

2 Story,Low Rise (1-3)

This unit is what living in Florida is all about. FIRST FLOOR 2 bedroom/2 bath condo in the wonderful WINTERPARK Community. The location of this unit is steps to the incredible RESORT-STYLE pool, clubhouse, bocci…

$260,000

Low Rise (1-3)

This first-floor corner unit is being offered furnished and turnkey, making it the perfect option for those seeking convenience and comfort. Some of the notable features include a new air conditioner, new hot water tank,…

$289,900

Low Rise (1-3)

Welcome to this spacious first-floor end unit condo located just 3 miles from the heart of downtown Fifth Avenue and the stunning Naples beaches. Conveniently situated on Frosty Way just steps away from a…

$290,000

Low Rise (1-3)

This 2 bedroom 2 bath condo features tile throughout. The unit is in the community of Winterpark. Winterpark is close to King's Lake Square with a Publix, dining and shopping.

$285,000

2 Story,Low Rise (1-3)

Welcome to 3805 Snowflake Ln, located in the beautiful Winterpark Community. This 2 bedroom, 2 bath condo is situated on the first floor and within walking distance of the big resort style pool, club house,…

$329,000

2 Story,Low Rise (1-3)

Stunning Designer Renovated And FURNISHED!!!! Large 2/2 1246 sq ft,MOST DESIRED 1st floor Chic Beach Coastal Condo TURNKEY in the very Desirable Winterpark community. Proudly having one of the Larges Resort Style Swimming Pools…

$275,000

Apartment,Low Rise (1-3)

With full price offer, there will be a $10,000 Seller Concession at closing. Exceptional affordable condo in Naples, Florida. This stunning residence offers the perfect combination of convenient location, luxurious amenities, and an enviable coastal…

$320,000

2 Story,Low Rise (1-3)

This is the Best Location in Naples. It's just a 5 minute drive to the beachs, downtown Naples, shopping and more! This Very well maintained Updated 1st floor unit has New Hurricane windows, New plumbing,…

$337,000

Apartment,Low Rise (1-3)

Superbly located close to Downtown Naples shopping, fine dining, entertainment and world-renowned beaches. The Winterpark community amenities include resort-style community pool, tennis & pickle ball courts, bocce and the community clubhouse with regular activities just…

$319,000

2 Story,Low Rise (1-3)

Beautifully renovated condo in much sort after Winterpark community. This unit is turnkey, with everything you need to enjoy your time in Naples. Spacious 2 bed/2 bath condo with open floor plan, and split bedroom…

$199,000

Low Rise (1-3)

First-floor end unit with 2 bedrooms and 2 full baths in the community of Winterpark. Beautifully maintained and updated and uniquely redesigned to create formal dining. Updates include wood flooring in the kitchen and dining…

$192,250

2 Story,Low Rise (1-3)

Lovely unit features nice updates in kitchen & bathrooms. New A/C system 12/2020, shaker cabinets in kitchen with granite counter-tops, subway tile backsplash, stainless appliances and plank flooring throughout. Wintepark offers resort style swimming pool,…

$159,000

Low Rise (1-3)

PRICED TO SELL! This is the lowest priced unit in Winterpark! Being sold turnkey, master walk-in closet, vaulted ceilings, open floor plan. This unit has lots of potential ! Great location !

$179,900

2 Story,Low Rise (1-3)

This well maintained , Spacious 2BR/2Bath Unit is being sold Turnkey. It is well appointed and well stocked. Newly updated kitchen with granite countertops and new stainless steel appliances. Newer A/C unit & hot…

$214,900

Low Rise (1-3)

This 2019 completely remodeled to the studs, ground floor condo, only 10 minutes from the beach and downtown Naples, is waiting for you to call home or make it your vacation home! The gourmet kitchen…

$319,900

2 Story,Low Rise (1-3)

This is a lovely and spacious 2 bedroom first floor condominium in Winterpark V with nice tile flooring, beautiful kitchen with breakfast bar and stainless appliances. There is a large laundry room and the air…

$264,900

Low Rise (1-3)

This is a handyman's dream! What a great opportunity to own just minutes to Naples' award winning white sand beaches! This condo needs some TLC but is very spacious and has many…

$176,900

Low Rise (1-3)

This the best value in Naples - just minutes to the beach and conveniently located to great restaurants, shopping, banks and more! This lovely 2 bedroom condo has been meticulously cared for and is…

$350,000

Low Rise (1-3)

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$282,000

2 Story,Low Rise (1-3)

LOWEST PRICED UNIT ON THE MARKET AND AND END UNIT!!! Ohhhh the view...wide open green space....check this out! You rarely get this view and private feel in Winterpark and this unit is an End…

$327,000

2 Story,Low Rise (1-3)

Move-in ready and completely renovated, this two-bedroom, two-bath condominium is just five miles from downtown Naples and beaches. The sparkling white kitchen has custom cabinets, quartz countertops and stainless steel appliances. Both bathrooms have been…

$349,000

2 Story,Low Rise (1-3)

LOCATION, LOCATION, LOCATION!! Only 3 miles from Naples Down Town, fine dining, shopping and the sandy Naples Beaches . This two bedroom, two bath updated and very well maintained condo located only…

$230,000

Low Rise (1-3)

END UNIT - 2 bedroom/2 bath condo in the highly desired WINTERPARK Community....The unique feature of this condo is it's location...directly across and steps away from the incredible RESORT-STYLE pool, CLUBHOUSE, and TENNIS/PICKLEBALL COURTS. …

$289,000

2 Story,Low Rise (1-3)

FOR SALE!! Nice two bed room two bath second floor condo in WINTERPARK sells turn key furnished. Stunning view and walking distance to pool and tennis courts. Conveniently located only minutes to Naples Down…

$289,000

Low Rise (1-3)

Lowest Priced unit in Winterpark! 2nd Floor Vaulted Ceiling End Unit! It is all about location in this superbly located community close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. The…

$324,000

Low Rise (1-3)

Prepare to be amazed by what this must-see condo has to offer less than 3 miles from 5th Avenue. Move-in ready with recent renovations. Beautifully remodeled kitchen including white shaker cabinets and quartz counters for…

$275,000

2 Story,Low Rise (1-3)

Location, Location, location!! This condo is less than 3 miles from the beach, and the Olde Naples exquisite shopping & dining district. Also only a 20 minute walk (1 mile) to the King's Lake plaza…

$329,999

2 Story,Low Rise (1-3)

This completely renovated unit is just 8 minutes away from the beach, 5th Ave South, and downtown Naples. This 1st floor condo features 2 bedrooms, 2 bathrooms, a walk in master closet, updated title flooring,…

$299,000

Low Rise (1-3)

2 bedroom, 2 bathroom first floor END UNIT condo with A LOT OF PRIVACY!!! Being offered TURNKEY FURNISHED. A front screened in lanai, extra storage closet and a patio setting in the backyard. Great…