Homes with a Pool in Winter Park, FL

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24 of 113 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

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New17Active
$2,295,000
4 bd · 6 ba · 3,295 sqft
2234 Howard Dr, Winter Park, FL
Raquel Elliott · COLDWELL BANKER REALTY
38Active
$1,399,900
4 bd · 4 ba · 2,984 sqft
1737 Indiana Ave, Winter Park, FL
Tori Nguyen · LOKATION
51Active
$519,900
4 bd · 3 ba · 1,842 sqft
731 Bongart Rd, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

About Homes with a Pool in Winter Park, FL

Homes with a Pool in Winter Park, FL: 113 active listings as of October 13, 2026, 12:28 UTC.

Property types among these 113 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property type	Listings	Share
Single Family Residence	107	94.7%
Condominium	6	5.3%

Winter Park housing market

September 2026

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 28, 2026

Median sale price: $565,000$410,000–$952,600 typical range
Price per sq. ft.: $342
Sales: 92
Paid in cash: 44.6%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 18 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 28.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,731 sq. ft.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Homes with a Pool in Winter Park, FL

Your local brokerage

Listing data & MLS disclosures

About Homes with a Pool in Winter Park, FL

Winter Park housing market

Homes that sold · County records, as of Sep 28, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Winter Park, FL community profile

Explore Winter Park homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Winter Park, FL community profile

Winter Park housing market

Homes that sold · County records, as of Sep 28, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026