Waterfront Homes in Winter Park, FL

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23 of 26 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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32Active
$335,000
2 bd · 2 ba · 1,140 sqft
220 Killarney Bay Ct #6-2, Winter Park, FL
Cindy Gold · COLDWELL BANKER REALTY
16Active
$5,950,000
5 bd · 6 ba · 5,796 sqft
1441 Grove Ter, Winter Park, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
99Active
$5,695,000
4 bd · 4 ba · 4,725 sqft
541 Virginia Dr, Winter Park, FL
Scott Brazdo · EXP REALTY 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 Waterfront Homes in Winter Park, FL

Waterfront Homes in Winter Park, FL: 26 active listings as of November 5, 2026, 06:40 UTC.

Property types among these 26 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	16	61.5%
Condominium	9	34.6%

Winter Park housing market

October 2026 · This period is still settling

Selling at 96.8% of asking price

Buyers here are paying below asking. MLS · 65 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 19, 2026

Median sale price: $510,000$355,250–$992,500 typical range
Price per sq. ft.: $313
Sales: 44
Paid in cash: 47.7%

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Median list price: $587,000
Homes for sale: 334
Median days on market: 24 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year: -1.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 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

Waterfront Homes in Winter Park, FL

Your local brokerage

Listing data & MLS disclosures

About Waterfront Homes in Winter Park, FL

Winter Park housing market

Homes that sold · County records, as of Oct 19, 2026

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Price trend · Assessor repeat sales, as of Oct 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 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 Oct 19, 2026

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Price trend · Assessor repeat sales, as of Oct 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026