Winterpark Real Estate

There are 22 active listings in Winterpark, Naples, with a median asking price of $249,450 and an average of 95 days on market.

Active Listings

Median Asking Price

$249,450

Average Asking Price

$249,727

Avg. Days on Market

Closed · Last 90 Days

About Winterpark

Winterpark is a Southwest Florida community in Naples where the NABOR MLS currently shows 22 active listings, asking $199,500 to $329,900, averaging 95 days on market, with 3 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

22 properties shown

$329,900

4140 Looking Glass LN 7

2 bd · 2 ba · 1,246 sf

Listing courtesy of Keller Williams Realty Naples

Source: NABOR MLS

$309,900

4030 Northlight DR

2 bd · 2 ba · 1,200 sf

Listing courtesy of Premier Property Management

Source: NABOR MLS

$299,000

3400 Frosty WAY 5

2 bd · 2 ba · 1,284 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$265,000

4001 Ice Castle WAY 3605

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premiere Plus Realty Company

Source: NABOR MLS

$262,000

3420 Frosty WAY 4902

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premiere Plus Realty Company

Source: NABOR MLS

$259,900

4230 Jack Frost CT 7

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premier Sotheby's Int'l Realty

Source: NABOR MLS

$255,000

3574 Antarctic CIR 2107

2 bd · 2 ba · 1,246 sf

Listing courtesy of KW Elevate Luxury

Source: NABOR MLS

$255,000

4100 Looking Glass LN 3008

2 bd · 2 ba · 1,250 sf

Listing courtesy of Naples Homes and Rentals Inc

Source: NABOR MLS

$250,000

4031 Ice Castle WAY 3306

2 bd · 2 ba · 1,246 sf

Listing courtesy of Realty World Top Producers Rlt

Source: NABOR MLS

$250,000

4065 Northlight DR 1807

2 bd · 2 ba · 1,234 sf

Listing courtesy of Coldwell Banker Realty

Source: NABOR MLS

$249,900

4038 Northlight DR 1506

2 bd · 2 ba · 1,234 sf

Listing courtesy of Marzucco Real Estate

Source: NABOR MLS

$249,000

4073 Northlight DR 1803

2 bd · 2 ba · 1,234 sf

Listing courtesy of Brodersen LLC

Source: NABOR MLS

$248,000

3532 Antarctic CIR 2216

2 bd · 2 ba · 1,246 sf

Listing courtesy of Re/Max Alliance Group

Source: NABOR MLS

$239,900

4100 Looking Glass LN 7

2 bd · 2 ba · 1,246 sf

Listing courtesy of Realty One Group MVP

Source: NABOR MLS

$239,000

4096 Northlight DR 1709

2 bd · 2 ba · 1,246 sf

Listing courtesy of Blue Lighthouse Realty Inc

Source: NABOR MLS

$239,000

4050 Ice Castle WAY 2812

2 bd · 2 ba · 1,246 sf

Source: NABOR MLS

$230,000

4230 Jack Frost CT 4402

2 bd · 2 ba · 1,246 sf

Listing courtesy of William Raveis Real Estate

Source: NABOR MLS

$229,000

4200 LOOKING GLASS LN 4207

2 bd · 2 ba · 1,246 sf

Listing courtesy of William Raveis Real Estate

Source: NABOR MLS

$220,000

4079 Northlight DR 2

2 bd · 2 ba · 1,234 sf

Listing courtesy of Downing Frye Realty Inc.

Source: NABOR MLS

$215,000

4001 Ice Castle WAY 1

2 bd · 2 ba · 1,246 sf

Listing courtesy of Premiere Plus Realty Company

Source: NABOR MLS

$199,999

3816 Snowflake LN 1303

2 bd · 2 ba · 1,246 sf

Listing courtesy of Broker Brothers LLC

Source: NABOR MLS

$199,500

4200 Looking Glass LN 4204

2 bd · 2 ba · 1,246 sf

Listing courtesy of Portside Property Group

Source: NABOR MLS

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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