What are home prices like in Winterpark?

Winterpark is in the entry price tier, typically Typically $200K – $450K. List prices vary by size, age, condition, and inventory. Search current listings at /search.

What FEMA flood zone is Winterpark in?

Winterpark is mapped primarily in FEMA Zone AE, High risk · 1% annual chance · BFE established. Parcels can differ; Rick verifies the exact zone for any address.

What schools are near Winterpark?

Closest schools to Winterpark: Cape Coral High School (4.1 mi), Heritage Charter Academy of Cape Coral (4.2 mi). Browse all at /schools.

What does it cost to own a home in Winterpark?

For a $350,000 home in Winterpark: ~$4,550/yr property tax, $4,200-$7,700/yr insurance incl. flood, and $300-900/mo HOA. See the cost cheatsheet at /swfl-relocation-cost-cheatsheet.

What amenities does Winterpark offer?

Amenities vary; refer to HOA documents or explore similar communities at /communities.

Naples, FL · Condo & Villa Communities

Winterpark

Winterpark is a residential community in Naples, Collier County, Southwest Florida.

Condo & Villa CommunitiescondoEntry · $200K – $450KFEMA Zone AE

Market Snapshot

Winterpark market data

Live from the MLS · updated continuously. See all 17 listings →

Active Listings

for sale now

Median List Price

$250,000

active inventory

Median $/Sq Ft

$201

list price ÷ sqft

Avg Days on Market

days listed

Price Range

$209,000-$339,000

low to high

Sold (90 days)

$217,500

6 closed · median

Homes Built

1985-1989

Typical Home

2 bed · 1,246 sq ft

Median sold price · Winterpark

$217,500last 3 monthsnot enough sold data to compare

Figures reflect current active listings (and recent closed sales where available) tagged to Winterpark. Medians are indicative, not an appraisal, ask Rick for a comparative market analysis on a specific home.

On the Map

Where Winterpark sits

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Available Now

Homes for sale in Winterpark(17)

Newest listings first, showing 12 of 17.

See all 17 homes →View on map →

Swipe to see more →

Recently Sold

Recent sales in Winterpark

Home	Bd / Ba	Sq Ft	Sold	Sold Price
3420 Frosty Way 12, Naples	2 / 2	1,246	Sep 2026	$190,000
4070 Looking Glass Lane 3101, Naples	2 / 2	1,246	Sep 2026	$190,000
4240 Jack Frost Court 6, Naples	2 / 2	1,246	Sep 2026	$253,000
3450 Frosty Way 5210, Naples	2 / 2	1,246	Jul 2026	$225,000

Closed sales from the last 12 months. Ask Rick for a full comparable-sales report on any home you're considering.

At a Glance

Winterpark at a glance

Price Range

Entry

Typically $200K – $450K

Flood Zone

Zone AE

High risk · 1% annual chance · BFE established

high-confidence estimate, verify by address

Community Type

condo

Region

Naples

Amenities & Lifestyle

What you get living in Winterpark

Amenity details vary by HOA / phase. Contact for current specs.

Drive Times

Location & access

🏖️ Nearest Beach14 min
✈️ RSW Airport41 min
🏙️ Downtown Fort Myers9 min
🏥 Nearest Hospital10 min
🛣️ I-75 Access18 min

Cost of Ownership

Estimated yearly costs for a entry-tier home

Florida estimates based on a $350,000 home in Winterpark. Actual numbers vary, book a Strategy Session for a live, parcel-specific quote.

Property Tax

$4,550

~$379/mo · Collier County millage ~1.3%

Insurance (incl. flood)

$4,200, $7,700

Flood + wind in high-risk zone

HOA Estimate

$300, $900/mo

Condo association range

Estimates only. Florida Homestead Exemption (when you qualify) can knock $750-1,500 off the annual tax bill.

⚠️ Flood Zone Accuracy Note

Winterpark is mapped primarily in Zone AE

All sample points within Winterpark returned Zone AE. Individual parcels may differ, flood zones are assigned per parcel by FEMA, not per community.

Before making an offer, always verify the exact flood zone for the specific property address:

🔍 Verify on FEMA Map Service Center →Ask Rick for the Exact Zone →

Source: FEMA National Flood Hazard Layer · sampled at 5 points per community · confidence: high

Schools Nearby

Top schools within 8 miles of Winterpark

Cape Coral High School

4.1 mi

Highpublic· DOE Grade B· Score 65/100

Heritage Charter Academy of Cape Coral

4.2 mi

K-8charter· Score 40/100

Compare

Ready to Look Closer?

Get live numbers for Winterpark

HOA dues, current listings, recent sales, builder incentives, all change weekly. Book a free Strategy Session and I'll pull a live snapshot for Winterpark tailored to your timeline and budget.

Ask About Winterpark →Find Communities Like This (90-sec quiz)

Good Questions

Winterpark, frequently asked questions

What are home prices like in Winterpark?: Winterpark is in the entry price tier, typically Typically $200K – $450K. List prices vary by size, age, condition, and current inventory; search current listings or ask Rick for live comps.
What FEMA flood zone is Winterpark in?: Winterpark is mapped primarily in FEMA Zone AE, High risk · 1% annual chance · BFE established. Individual parcels can differ; Rick verifies the exact zone for any address.
What schools are near Winterpark?: Closest schools include Cape Coral High School (4.1 mi), Heritage Charter Academy of Cape Coral (4.2 mi). Browse all on the schools directory.
What does it cost to own a home in Winterpark?: For a $350,000 home, estimate roughly $4,550/yr property tax, $4,200-$7,700/yr insurance (incl. flood), and $300-$900/mo HOA. Full breakdown in the SWFL cost cheatsheet.
What amenities does Winterpark offer?: Amenities vary, refer to HOA documents or explore similar communities.