5 Bedroom Homes in Winter Park, FL

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2 Listings

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2 Listings

69Active
$795,000
5 bd · 4 ba · 2,840 sqft

2 listings

5 Bedroom Homes in Winter Park, FL

Show Map

2 Listings

Map

5 Bedroom Homes in Winter Park, FL

2 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

69Active
$795,000
5 bd · 4 ba · 2,840 sqft

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

1164 Dodd Road, Winter Park, FL

Michael John Rothenburg · Charles Rutenberg Realty FTL

44Active

$2,995,000

5 bd · 3 ba · 3,523 sqft

1591 Cardinal Court, Winter Park, FL

DJ Diamond · Sunset Lakes Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Listing data & MLS disclosures

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-09-17 21:52:55 UTC
Space Coast MLS (Space Coast Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-06-20 07:15:48 UTC

Winter Park housing market

July 2026 · This period is still settling

Selling at 99.3% of asking price

Buyers here are paying below asking. MLS · 51 sales · as of Jul 20, 2026

Homes that sold · County records, as of Jul 6, 2026

Median sale price: $519,000$385,000–$850,000 typical range
Price per sq. ft.: $344
Sales: 25
Paid in cash: 36.0%

Homes on the market · MLS, as of Jul 20, 2026

Median list price: $625,000
Homes for sale: 313
Median days on market: 39 days

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

Year-over-year: 19.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Median home size: 1,704 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

Explore Winter Park homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Listing data & MLS disclosures

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-09-17 21:52:55 UTC
Space Coast MLS (Space Coast Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-06-20 07:15:48 UTC

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

July 2026 · This period is still settling

Selling at 99.3% of asking price

Buyers here are paying below asking. MLS · 51 sales · as of Jul 20, 2026

Homes that sold · County records, as of Jul 6, 2026

Median sale price: $519,000$385,000–$850,000 typical range
Price per sq. ft.: $344
Sales: 25
Paid in cash: 36.0%

Homes on the market · MLS, as of Jul 20, 2026

Median list price: $625,000
Homes for sale: 313
Median days on market: 39 days

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

Year-over-year: 19.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Median home size: 1,704 sq. ft.

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 Jul 6, 2026

Homes on the market · MLS, as of Jul 20, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 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 Jul 6, 2026

Homes on the market · MLS, as of Jul 20, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026