Winterpark

Winterpark is a condominium building in Naples, Florida, with a range of options priced between $215,000 and $339,000. There are currently a total of 24 condos for sale in Winterpark. The smallest Winterpark condo presently available is a two bedroom two bathroom residence that is 1,200 square feet, and the largest of the Winterpark condos currently on the market has two beds and two baths and is a 1,554 square foot (1,300SF Under Air) residence.

Building amenities include a clubhouse, swimming pool, spa / hot tub, cabana, a state-of-the-art fitness center, business center, and a library. Sports facilities include tennis courts, pickleball courts, Bocce ball, basketball court, and shuffleboard. Onsite dining venues consist of a picnic area, and a barbecue area. There is also a community park, a playground, walking or jogging trails, as well as guest suites for visitors.

Pets are allowed in Winterpark. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are two commercial airports that serve Winterpark - Southwest Florida International Airport (RSW), which is twenty eight miles away, and Page Field (FMY), which is 32 miles away.

Winterpark real estate activity on the Naples MLS during the past year (as of June 2026) reflects twenty one condos changing hands, with an average asking price of $248,995 and an average selling price of $233,481. This represents a healthy list-to-sell price ratio of 94% and $183 per square foot. During this period, Winterpark condos for sale have taken an average of 194 days to sell.

In addition, there are numerous other condo buildings in Naples to choose from, or you may browse all available Condos for sale in Naples. Condos for sale in Winterpark are selling quickly. Set up a new listing alert, and we will notify you immediately when a new condo in Winterpark hits the market. You can also always contact your BEX Realty agent, who would happily assist you further with all your Gulf Coast real estate needs.

Winterpark Condos For Sale

Reduced

$339,000

$349,000

MLS#226005552

4180 Looking Glass Ln 4102
Naples, FL 34112

2

2

1,246 Sq Ft

138 Days

$329,900

MLS#226019156

4140 Looking Glass Ln 7
Naples, FL 34112

2

2

1,326 Sq Ft

42 Days

$309,900

MLS#226015387

4030 Northlight Dr
Naples, FL 34112

2

2

1,200 Sq Ft

432 Days

Reduced

$298,000

$310,000

MLS#226009064

4001 Ice Castle Way 3605
Naples, FL 34112

2

2

1,350 Sq Ft

116 Days

Under Contract

$290,000

$295,000

MLS#226012425

4070 Northlight Dr 1612
Naples, FL 34112

2

2

1,234 Sq Ft

94 Days

$284,900

MLS#226012607

4150 Looking Glass Ln 3903
Naples, FL 34112

2

2

1,342 Sq Ft

91 Days

Reduced

$284,900

$294,900

MLS#225070242

3430 Frosty Way 12
Naples, FL 34112

2

2

1,300 Sq Ft

286 Days

Reduced

$280,000

$299,000

MLS#226014881

4240 Jack Frost Ct 6
Naples, FL 34112

2

2

1,246 Sq Ft

76 Days

$275,000

MLS#226016628

4230 Jack Frost Ct 4402
Naples, FL 34112

2

2

1,246 Sq Ft

61 Days

$270,000

MLS#2025023850

3574 Antarctic Cir 2107
Naples, FL 34112

2

2

1,246 Sq Ft

194 Days

Reduced

$265,000

$269,500

MLS#226007244

3420 Frosty Way 4902
Naples, FL 34112

2

2

1,246 Sq Ft

129 Days

$259,900

MLS#226009042

4100 Looking Glass Ln 3002
Naples, FL 34112

2

2

1,324 Sq Ft

110 Days

24 Active Listings in Winterpark