Winterpark
The community of Winterpark is situated in Naples. Ideally located for access to all of the Naples area amenities and comforts available.
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4085 Northlight Naples
$289,000
Low Rise (1-3)
Investor’s Tropical Paradise - Winterpark IX ! A rare opportunity in one of the most desirable buildings, where condos are often sold before they even hit the market. Up to 12 leases allowed per year,…
4001 Ice Castle Naples
$275,000
Low Rise (1-3)
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…
3560 Antarctic Naples
$239,000
Low Rise (1-3)
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…
3400 Frosty Naples
$250,000
Low Rise (1-3)
Welcome to Winterpark in Naples, a highly sought-after community just minutes from downtown and the Gulf of Mexico. This spacious 2-bedroom, 2-bath condo offers vaulted ceilings, an open floor plan, and a split-bedroom design for…
3676 Arctic Naples
$264,900
Low Rise (1-3)
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…
4079 Northlight Naples
$289,000
Low Rise (1-3)
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…
3750 Northwinds Naples
$243,500
Low Rise (1-3)
Welcome to your slice of paradise in the sought-after Winterpark community! This beautifully maintained 2nd-floor condominium offers serene views of the resort-style pool and is ideally situated in a premier location within the community—tucked away…
4040 Ice Castle Naples
$265,000
Low Rise (1-3)
Stop searching for an affordable condo in Naples—this one has already been beautifully updated and is truly move-in ready! This 2-bedroom, 2-bath end-unit on the 2nd floor offers both privacy and natural light, along with…
4180 Looking Glass Naples
$289,000
Low Rise (1-3)
Welcome Home! This 2-bedroom 2-bathroom unfurnished condo with vaulted ceilings and tons of natural sunlight is ready for you. So many updates, you will feel like you are in a brand-new home! All-new kitchen and…
3430 Frosty Way Naples
$294,900
Low Rise (1-3)
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…
4001 Ice Castle Naples
$214,000
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…
4200 Looking Glass Naples
$259,900
Low Rise (1-3)
Welcome to your dream condo close to Beautiful Downtown Naples and Downtown Naples' Beach! This stunning 2 bedroom, 2 bath condominium with Open Floor Plan and Split Bedrooms offers a remodeled kitchen with upgraded Granite…
3612 Arctic Naples
$309,000
Low Rise (1-3)
Winterpark Condominiums are conveniently located close to Downtown Naples shopping, fine dining, entertainment and world-renowned white sand beaches. The kitchen is a dream, newly updated. The living-dining area is extremely spacious and the unit is…
4092 Northlight Naples
$258,800
Low Rise (1-3)
Escape to Your Naples Oasis. A Turnkey Treasure in WINTERPARK. Get ready to fall in love with this stunning, immaculately maintained 2 bedroom, 2 bathroom, first-floor condominium in the vibrant WINTERPARK community, a true gem…
3532 Antarctic Naples
$240,000
Low Rise (1-3)
Don’t miss this opportunity in Naples! This fully furnished, turnkey two-bedroom, two-bath condo is an investor’s dream. Enjoy it as your own retreat, and when you’re away, rent it seasonally to generate income. Ideally located…
4200 Looking Glass Naples
$230,000
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…
4220 Looking Glass Naples
$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.…
4031 Ice Castle Naples
$299,000
Low Rise (1-3)
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…
3450 Frosty Naples
$265,000
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…
4021 Ice Castle Naples
$263,000
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…
4150 Looking Glass Naples
$209,000
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…
3832 Snowflake Naples
$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…
4070 Looking Glass Naples
$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…
4030 Northlight Naples
$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…
3603 Arctic Naples
$257,500
Low Rise (1-3)
LOCATION, LOCATION, LOCATION! This is the one! It's all about the location of your home within the Winterpark community! This 2nd floor, END condo features a coveted location close enough to all the amenities to…
4040 Ice Castle Naples
$220,000
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…
3410 Frosty Naples
$284,999
Low Rise (1-3)
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…
3480 Frosty Naples
$259,900
Low Rise (1-3)
Welcome to WinterPark! This spacious and bright turnkey 2-bedroom condo features soaring volume ceilings, an open and efficient floor plan, hurricane impact windows, a screened-in front porch and additional storage under stairs. The bedrooms are…
4084 Northlight Naples
$299,900
Low Rise (1-3)
Just a short walk to the stunning resort-style pool, this beautifully updated First-Floor condo is your chance to enjoy the highly sought-after Winterpark lifestyle! The community is packed with amenities including pickleball, tennis, bocce ball, and…
4051 Northlight Naples
$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…
3840 Snowflake Naples
$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…
4080 Looking Glass Naples
$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…
3539 Antarctic Naples
$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,…
3804 Snowflake Naples
$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…
3609 Arctic Naples
$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.…
4230 Jack Frost Naples
$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…
4110 Looking Glass Naples
$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 &…
3512 Antarctic Naples
$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…
4053 Northlight Naples
$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…
3659 Arctic Naples
$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…
4049 Northlight Naples
$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…
4230 Jack Frost Naples
$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.…
4040 Ice Castle Naples
$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…
4030 Ice Castle Naples
$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…
3470 Frosty Naples
$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…
4210 Looking Glass Naples
$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…
3558 Antarctic Naples
$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…
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These data up-to-date as of 11/07/25. Some properties that appear for sale on this website may subsequently have sold and may no longer be available. For the most current information, contact RWS demo.