Winterpark

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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44 listings match your search criteria.
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      4180 Looking Glass Naples

      Active 4180 Looking Glass Ln Naples
      21 photos

      $279,000

      Low Rise (1-3)

      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…

      1246 2 2 1989
      Courtesy of Tropics Real Estate, LLC

      4150 Looking Glass Naples

      Active 4150 Looking Glass Ln Naples
      28 photos

      $209,000

      Low Rise (1-3)

      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…

      1346 2 2 1989
      Courtesy of Downing Frye Realty Inc.

      3574 Antarctic Naples

      Active 3574 Antarctic Cir Naples
      27 photos

      $270,000

      Low Rise (1-3)

      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…

      1246 2 2 1986
      Courtesy of EXP Realty, LLC

      3750 Northwinds Naples

      Active 3750 Northwinds Dr Naples
      20 photos

      $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…

      1246 2 2 1985
      Courtesy of John R Wood Properties

      4200 Looking Glass Naples

      Closed 4200 Looking Glass Ln Naples
      12 photos

      $279,900

      Low Rise (1-3)

      Newly renovated 2 bedroom, 2 bathroom Condo Available! Just 4 miles to beautiful downtown Naples, 5th Avenue! Complete renovation includes a beautiful new kitchen with updated cabinetry, countertops and appliances. New flooring, lighting, plumbing fixtures,…

      1246 2 2 1989
      Courtesy of Waterfront Realty Group Inc

      4200 Looking Glass Naples

      Active 4200 Looking Glass Ln Naples
      15 photos

      $249,900

      Low Rise (1-3)

      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…

      1246 2 2 1989
      Courtesy of Downing Frye Realty Inc.

      4180 Looking Glass Naples

      Active 4180 Looking Glass Ln Naples
      25 photos

      $229,999

      Low Rise (1-3)

      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…

      1246 2 2 1989
      Courtesy of Riverside Realty Of Naples,LLC

      3400 Frosty Naples

      Active 3400 Frosty Way Naples
      26 photos

      $249,000

      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…

      1350 2 2 1987
      Courtesy of Mato Realty, LLC

      4092 Northlight Naples

      Active 4092 Northlight Dr Naples
      14 photos

      $249,700

      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…

      1330 2 2 1987
      Courtesy of Berkshire Hathaway FL Realty

      4031 Ice Castle Naples

      Active 4031 Ice Castle Way Naples
      28 photos

      $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…

      1246 2 2 1986
      Courtesy of Exit King Realty

      4200 Looking Glass Naples

      Active 4200 Looking Glass Ln Naples
      27 photos

      $250,000

      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…

      1246 2 2 1989
      Courtesy of Premiere Plus Realty Company

      3410 Frosty Naples

      Active 3410 Frosty Way Naples
      27 photos

      $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…

      1246 2 2 1987
      Courtesy of William Raveis Real Estate

      4021 Ice Castle Naples

      Active 4021 Ice Castle Way Naples
      27 photos

      $240,000

      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…

      1246 2 2 1988
      Courtesy of Waterfront Realty Group Inc

      3560 Antarctic Naples

      Active 3560 Antarctic Cir Naples
      24 photos

      $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…

      1246 2 2 1986
      Courtesy of REMAX Affinity Mercato

      3676 Arctic Naples

      Active 3676 Arctic Cir Naples
      23 photos

      $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…

      1246 2 2 1985
      Courtesy of Realty One Group MVP

      3832 Snowflake Naples

      Active 3832 Snowflake Ln Naples
      22 photos

      $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…

      1300 2 2 1985
      Courtesy of ERA Naples Realty Services

      3430 Frosty Way Naples

      Active 3430 Frosty Way  Naples
      18 photos

      $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…

      1300 2 2 1987
      Courtesy of Downing Frye Realty Inc.

      4070 Looking Glass Naples

      Active 4070 Looking Glass Ln Naples
      23 photos

      $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…

      1246 2 2 1988
      Courtesy of Downing Frye Realty Inc.

      4030 Northlight Naples

      Active 4030 Northlight Dr Naples
      22 photos

      $309,900

      Low Rise (1-3)

      Charming 2 Bed, 2 Bath in Desirable Winterpark – Prime Naples LocationNestled 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…

      1200 2 2 1986
      Courtesy of Premier Property Management

      4220 Looking Glass Naples

      Closed 4220 Looking Glass Ln Naples
      20 photos

      $299,000

      Low Rise (1-3)

      THIS WINTERPARK VIII ASSOC CONDO HAS LOWEST HOA FEES IN WINTERPARK + INCLUDES FLOOD INSURANCE!!! Perfectly positioned with easy access to downtown Naples and area beaches, this 2B/2BA unit is ideal for buyers looking to…

      1246 2 2 1989
      Courtesy of John R. Wood Properties

      4001 Ice Castle Naples

      Closed 4001 Ice Castle Way Naples
      29 photos

      $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…

      1350 2 2 1987
      Courtesy of Realty One Group MVP

      3612 Arctic Naples

      Closed 3612 Arctic Cir Naples
      30 photos

      $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…

      1346 2 2 1985
      Courtesy of Downing Frye Realty Inc.

      4200 Looking Glass Naples

      Closed 4200 Looking Glass Ln Naples
      21 photos

      $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…

      1246 2 2 1989
      Courtesy of Coldwell Banker Realty

      4220 Looking Glass Naples

      Closed 4220 Looking Glass Ln Naples
      15 photos

      $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.…

      1246 2 2 1989
      Courtesy of Re/Max Alliance Group

      3480 Frosty Naples

      Closed 3480 Frosty Way Naples
      7 photos

      $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…

      1350 2 2 1987
      Courtesy of Premiere Plus Realty Company

      4084 Northlight Naples

      Closed 4084 Northlight Dr Naples
      34 photos

      $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…

      1246 2 2 1987
      Courtesy of Sellstate Tropical Waters Rlty

      4051 Northlight Naples

      Closed 4051 Northlight Dr Naples
      35 photos

      $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…

      1234 2 2 1987
      Courtesy of Coldwell Banker Realty

      3840 Snowflake Naples

      Closed 3840 Snowflake Ln Naples
      22 photos

      $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…

      1246 2 2 1985
      Courtesy of Douglas Elliman Florida,LLC

      4080 Looking Glass Naples

      Closed 4080 Looking Glass Ln Naples
      42 photos

      $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…

      1346 2 2 1989
      Courtesy of Downing Frye Realty Inc.

      3539 Antarctic Naples

      Closed 3539 Antarctic Cir Naples
      18 photos

      $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,…

      1326 2 2 1986
      Courtesy of Downing Frye Realty Inc.

      3804 Snowflake Naples

      Closed 3804 Snowflake Ln Naples
      12 photos

      $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…

      1246 2 2 1985
      Courtesy of Compass Florida LLC

      3609 Arctic Naples

      Closed 3609 Arctic Cir Naples
      31 photos

      $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.…

      1246 2 2 1985
      Courtesy of Staton Properties, LLC

      4230 Jack Frost Naples

      Closed 4230 Jack Frost Ct Naples
      25 photos

      $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…

      1296 2 2 1988
      Courtesy of Downing Frye Realty Inc.

      4110 Looking Glass Naples

      Closed 4110 Looking Glass Ln Naples
      25 photos

      $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 &…

      1350 2 2 1990
      Courtesy of Coldwell Banker Realty

      3512 Antarctic Naples

      Closed 3512 Antarctic Cir Naples
      31 photos

      $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…

      1246 2 2 1986
      Courtesy of Realty One Group MVP

      4053 Northlight Naples

      Closed 4053 Northlight Dr Naples
      25 photos

      $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…

      1234 2 2 1987
      Courtesy of Royal Shell Real Estate, Inc.

      3659 Arctic Naples

      Closed 3659 Arctic Cir Naples
      32 photos

      $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…

      1246 2 2 1986
      Courtesy of Sellstate Tropical Waters Rlty

      4049 Northlight Naples

      Closed 4049 Northlight Dr Naples
      14 photos

      $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…

      1350 2 2 1987
      Courtesy of Realty One Group MVP

      4230 Jack Frost Naples

      Closed 4230 Jack Frost Ct Naples
      23 photos

      $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.…

      1296 2 2 1988
      Courtesy of DomainRealty.com LLC

      4040 Ice Castle Naples

      Closed 4040 Ice Castle Way Naples
      31 photos

      $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…

      1246 2 2 1990
      Courtesy of Sellstate Priority Realty

      4030 Ice Castle Naples

      Closed 4030 Ice Castle Way Naples
      27 photos

      $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…

      1298 2 2 1988
      Courtesy of Downing Frye Realty Inc.

      3470 Frosty Naples

      Closed 3470 Frosty Way Naples
      26 photos

      $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…

      1246 2 2 1987
      Courtesy of MVP Realty Associates LLC

      4210 Looking Glass Naples

      Closed 4210 Looking Glass Ln Naples
      19 photos

      $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…

      1298 2 2 1985
      Courtesy of Premiere Plus Realty Company

      3558 Antarctic Naples

      Closed 3558 Antarctic Cir Naples
      28 photos

      $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…

      1246 2 2 1986
      Courtesy of Dream Street Realty LLC

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