Luxury Homes in Winter Park, FL

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3 beds New construction With a pool

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4 Listings

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Luxury Homes in Winter Park, FL

4 Listings

39Active
$1,450,000

4 listings

Luxury Homes in Winter Park, FL

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4 Listings

Map

Luxury Homes in Winter Park, FL

4 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

39Active
$1,450,000

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

3 bd · 3 ba · 2,756 sqft

100 S Virginia Ave #201, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

63Active

$2,475,000

3 bd · 3 ba · 2,316 sqft

311 E Morse Blvd #1-5, Winter Park, FL

Skip Kirst · COLLADO REAL ESTATE

36Active

$2,350,000

3 bd · 4 ba · 3,110 sqft

200 S Interlachen Ave #350, Winter Park, FL

Rhonda Chesmore · KELLY PRICE & COMPANY LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced39Active

$1,775,000

3 bd · 4 ba · 3,112 sqft

101 S New York Ave #311, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY 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.

Winter Park housing market

August 2026

Selling at 97.6% of asking price

Buyers here are paying below asking. MLS · 90 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $548,000$350,000–$1,187,500 typical range
Price per sq. ft.: $319
Sales: 110
Paid in cash: 40.9%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

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

Year-over-year: 11.6%

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

Explore Winter Park homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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.

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

Winter Park housing market

August 2026

Selling at 97.6% of asking price

Buyers here are paying below asking. MLS · 90 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $548,000$350,000–$1,187,500 typical range
Price per sq. ft.: $319
Sales: 110
Paid in cash: 40.9%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

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

Year-over-year: 11.6%

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Park housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

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

Winter Park, FL community profile

Explore Winter Park homes

Your local brokerage

Listing data & MLS disclosures

Winter Park, FL community profile

Winter Park housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

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