Condos in Winter Park, FL

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3 beds New construction With a pool

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5 Listings

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Condos in Winter Park, FL

5 Listings

31Active

5 listings

Condos in Winter Park, FL

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5 Listings

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Condos in Winter Park, FL

5 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

31Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$245,000

2 bd · 2 ba · 913 sqft

1250 S Denning Dr #Unit 233, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

30Active

$199,900

1 bd · 1 ba · 582 sqft

151 North Orlando Avenue #142, Winter Park, FL

Chris Creegan · CREEGAN GROUP

44Active

$989,500

1 bd · 2 ba · 1,109 sqft

269 E Canton Ave #269, Winter Park, FL

Cathy Sawruk Williams · COLDWELL BANKER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

20Active

$299,999

2 bd · 1 ba · 710 sqft

151 N Orlando Ave #118, Winter Park, FL

Adriana Montes · FLORIDA DREAMS REALTY GRP INC

Price Reduced37Active

$182,900

2 bd · 2 ba · 927 sqft

205 Lewfield Cir #205, Winter Park, FL

Eimi Moreno Carrera · LPT 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.

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

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

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

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