Winterpark Real Estate

There are 20 active listings in Winterpark, Naples, with a median asking price of $252,500 and an average of 105 days on market.

Active Listings

Median Asking Price

$252,500

Average Asking Price

$262,725

Avg. Days on Market

105

Closed · Last 90 Days

About Winterpark

Winterpark is a Southwest Florida community in Naples where the NABOR MLS currently shows 20 active listings, asking $209,000 to $339,000, averaging 105 days on market, with 4 closed sales recorded here in the last 90 days. Waterfront Realty Group, Inc. has worked this market as an independent, Realtor-owned brokerage since 1986, and pairs every customer with a Sales Associate who knows these streets, waterways, and price trends firsthand.

Figures reflect the active Winterpark inventory shown on this page, drawn live from the Naples Area Board of REALTORS® (NABOR) MLS. Closed-sale counts cover the trailing 90 days.

Available Properties

Winterpark Listings

20 properties shown

$339,000

4180 Looking Glass LN 4102

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premiere Plus Realty Company

$329,900

4140 Looking Glass LN 7

2 bd · 2 ba · 1,246 sf

Listing courtesy of Keller Williams Realty Naples

$310,000

3400 Frosty WAY 5

2 bd · 2 ba · 1,284 sf

Listing courtesy of Realty One Group MVP

$309,900

4030 Northlight DR

2 bd · 2 ba · 1,200 sf

Listing courtesy of Premier Property Management

$284,900

4150 Looking Glass LN 3903

2 bd · 2 ba · 1,246 sf

Listing courtesy of LPT Realty, LLC

$265,000

4073 Northlight DR 1803

2 bd · 2 ba · 1,234 sf

Listing courtesy of Brodersen LLC

$262,000

3420 Frosty WAY 4902

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premiere Plus Realty Company

$259,900

4027 Northlight DR 4

2 bd · 2 ba · 1,234 sf

Listing courtesy of Coffey Real Estate Agency LLC

$255,000

4100 Looking Glass LN 3008

2 bd · 2 ba · 1,250 sf

Listing courtesy of Naples Homes and Rentals Inc

$255,000

3574 Antarctic CIR 2107

2 bd · 2 ba · 1,246 sf

Listing courtesy of KW Elevate Luxury

$250,000

4031 Ice Castle WAY 3306

2 bd · 2 ba · 1,246 sf

Listing courtesy of Realty World Top Producers Rlt

$249,900

4038 Northlight DR 1506

2 bd · 2 ba · 1,234 sf

Listing courtesy of Marzucco Real Estate

$249,000

3420 Frosty WAY 4910

2 bd · 2 ba · 1,246 sf

Listing courtesy of William Raveis Real Estate

$248,000

3532 Antarctic CIR 2216

2 bd · 2 ba · 1,246 sf

Listing courtesy of Re/Max Alliance Group

$245,000

4001 Ice Castle WAY 1

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premiere Plus Realty Company

$240,000

4100 Looking Glass LN 3002

2 bd · 2 ba · 1,246 sf

Listing courtesy of Saggio Realty, Inc

$239,000

4050 Ice Castle WAY 2812

2 bd · 2 ba · 1,246 sf

$230,000

4230 Jack Frost CT 4402

2 bd · 2 ba · 1,246 sf

Listing courtesy of William Raveis Real Estate

$224,000

3816 Snowflake LN 1303

2 bd · 2 ba · 1,246 sf

Listing courtesy of Broker Brothers LLC

$209,000

4200 Looking Glass LN 4204

2 bd · 2 ba · 1,246 sf

Listing courtesy of Portside Property Group

Listing data provided via the Naples Area Board of REALTORS® (NABOR) MLS. Information deemed reliable but not guaranteed. Equal Housing Opportunity. © 2026 Waterfront Realty Group, Inc. License CQ257718. All rights reserved.

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