Mindy DolleDomain Realty · Naples
(239) 851-2556
Naples, FL · condominium community

Winterpark homes for sale

As of October 14, 2026, 20 homes are for sale in Winterpark, Naples, FL, priced from $209K to $339K with a median asking price of $250K (about $202 per square foot).

4180 Looking Glass Ln #4102, Winterpark
Current listing in Winterpark: 4180 Looking Glass Ln #4102 $339K · Listing courtesy of Premiere Plus Realty Company
20Active homes
$209K – $339KList price range
$202Median list $ / sq ft
24Closed sales, 12 months

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For sale

Homes for sale in Winterpark

All Naples homes $3M+ →
4180 Looking Glass Ln #4102, Naples1 / 12
$339,000
4180 Looking Glass Ln #4102Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Premiere Plus Realty Company
4140 Looking Glass Ln #7, Naples1 / 29
$329,900
4140 Looking Glass Ln #7Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Keller Williams Realty Naples
4030 Northlight Dr, Naples1 / 22
$309,900
4030 Northlight DrWinterpark · Naples
2 bd2 ba1,200 sf
Listing courtesy of Premier Property Management
3400 Frosty Way #5, Naples1 / 31
$299,000
3400 Frosty Way #5Winterpark · Naples
2 bd2 ba1,284 sf
Listing courtesy of Realty One Group MVP
4073 Northlight Dr #1803, Naples1 / 24
$265,000
4073 Northlight Dr #1803Winterpark · Naples
2 bd2 ba1,234 sf
Listing courtesy of Brodersen LLC
4001 Ice Castle Way #3605, NaplesNew · 5 days1 / 36
$265,000
4001 Ice Castle Way #3605Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Premiere Plus Realty Company
3420 Frosty Way #4902, Naples1 / 43
$262,000
3420 Frosty Way #4902Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Premiere Plus Realty Company
4100 Looking Glass Ln #3008, Naples1 / 13
$255,000
4100 Looking Glass Ln #3008Winterpark · Naples
2 bd2 ba1,250 sf
Listing courtesy of Naples Homes and Rentals Inc
3574 Antarctic Cir #2107, Naples1 / 19
$255,000
3574 Antarctic Cir #2107Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of KW Elevate Luxury
4031 Ice Castle Way #3306, Naples1 / 25
$250,000
4031 Ice Castle Way #3306Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Realty World Top Producers Rlt
4038 Northlight Dr #1506, Naples1 / 39
$249,900
4038 Northlight Dr #1506Winterpark · Naples
2 bd2 ba1,234 sf
Listing courtesy of Marzucco Real Estate
3532 Antarctic Cir #2216, Naples1 / 50
$248,000
3532 Antarctic Cir #2216Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Re/Max Alliance Group
4079 Northlight Dr #2, NaplesNew · 13 days1 / 41
$247,000
4079 Northlight Dr #2Winterpark · Naples
2 bd2 ba1,234 sf
Listing courtesy of Downing Frye Realty Inc.
4100 Looking Glass Ln #3002, Naples1 / 31
$240,000
4100 Looking Glass Ln #3002Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Saggio Realty, Inc
4050 Ice Castle Way #2812, NaplesWaterfront1 / 49
$239,000
4050 Ice Castle Way #2812Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Waterfront Realty Group Inc
4096 Northlight Dr #1709, Naples1 / 5
$239,000
4096 Northlight Dr #1709Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Blue Lighthouse Realty Inc
4001 Ice Castle Way #1, Naples1 / 25
$235,000
4001 Ice Castle Way #1Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Premiere Plus Realty Company
4230 Jack Frost Ct #4402, Naples1 / 27
$230,000
4230 Jack Frost Ct #4402Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of William Raveis Real Estate
3816 Snowflake Ln #1303, NaplesWaterfront1 / 27
$224,000
3816 Snowflake Ln #1303Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Broker Brothers LLC
4200 Looking Glass Ln #4204, Naples1 / 15
$209,000
4200 Looking Glass Ln #4204Winterpark · Naples
2 bd2 ba1,246 sf
Listing courtesy of Portside Property Group

Listings are shown courtesy of the listing brokerages. Information is deemed reliable but not guaranteed.

Questions about Winterpark

How many homes over $3M are for sale in Winterpark?

There are no homes listed at $3M or more in Winterpark right now, and 20 active listings overall. Listings change daily.

What do luxury homes cost in Winterpark?

Current asking prices run $209K to $339K, with a median of $250K or roughly $202 per square foot. Floor, view, finish and, for single-family homes, lot and water frontage account for most of the spread.

What kinds of homes are in Winterpark?

Winterpark is a condominium community in Naples, FL. Current listings include homes with 2 bedrooms, 1,200 sq ft to 1,284 sq ft, built 1985 to 1989.

Are homes in Winterpark on the water?

Of the 20 current listings, 2 are waterfront, per MLS data. Water type and access vary by street and building, so confirm each home's details before relying on them.

What are the association fees in Winterpark?

Current listings report association fees of $1,460 to $1,920 per quarter. What a fee covers differs by building or community, so ask for the budget and the reserve and milestone-inspection documents before you buy.

How fast do homes sell in Winterpark?

24 sales closed in the past 12 months at a median of $231K, with a median of about 95 days on market and a median sale-to-list ratio of 94.1%. A small number of sales means these medians are only a guide.

Who can show me homes in Winterpark?

Mindy Dolle, a licensed Florida real estate sales associate with Domain Realty, can arrange showings, pull comparable sales and review association documents for homes in Winterpark. Call or text (239) 851-2556.

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