4 Bedroom Homes in Winter Park, FL

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4 Bedroom Homes in Winter Park, FL

24 of 55 Listings

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55 listings

4 Bedroom Homes in Winter Park, FL

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24 of 55 Listings

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4 Bedroom Homes in Winter Park, FL

24 of 55 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

4Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$1,995,000

4 bd · 4 ba · 3,314 sqft

2007 Edwin Blvd, Winter Park, FL

Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP

15Active

$850,000

4 bd · 3 ba · 2,301 sqft

870 N Phelps Ave, Winter Park, FL

Christina Frucci · RE/MAX TOWN & COUNTRY REALTY

96Active

$2,095,000

4 bd · 4 ba · 3,776 sqft

555 E Lake Sue Ave, Winter Park, FL

Claudia Davidson · KELLER WILLIAMS WINTER PARK

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

55Active

$1,890,000

4 bd · 4 ba · 3,307 sqft

2614 Parkland Dr, Winter Park, FL

Ryan Gaston · JW GASTON LLC

12Active

$449,900

4 bd · 2 ba · 1,627 sqft

3209 Heartwood Ave, Winter Park, FL

James Fitzgibbon · LEDGE REAL ESTATE SOLUTIONS LLC

73Active

$2,089,000

4 bd · 4 ba · 3,479 sqft

1951 Winter Park Rd, Winter Park, FL

Holly Wilton · KELLER WILLIAMS WINTER PARK

31Active

$1,599,000

4 bd · 4 ba · 2,942 sqft

533 Country Club Dr, Winter Park, FL

Jill Healey · KELLER WILLIAMS WINTER PARK

41Active

$3,695,999

4 bd · 5 ba · 3,658 sqft

1742 Temple Dr, Winter Park, FL

Mark Anthony Buot · ROI AVE LLC

41Active

$675,000

4 bd · 2 ba · 1,688 sqft

2215 Woodcrest Dr, Winter Park, FL

Shari Klafter · KELLER WILLIAMS WINTER PARK

64Active

$895,000

4 bd · 3 ba · 1,876 sqft

618 Blairshire Cir, Winter Park, FL

Ken Pozek · REAL BROKER, LLC

10Active

$1,579,000

4 bd · 4 ba · 2,718 sqft

2417 Chantilly Ave, Winter Park, FL

Amanda Wood · RE/MAX EXCLUSIVE COLLECTION

61Active

$2,195,000

4 bd · 5 ba · 2,850 sqft

1271 Palmer Ave, Winter Park, FL

JR Keelin · KELLY PRICE & COMPANY LLC

Price Reduced28Active

$440,000

4 bd · 2 ba · 2,189 sqft

2301 Conifer Ave, Winter Park, FL

Gregory Buckley · LOKATION

41Active

$4,400,000

4 bd · 6 ba · 3,720 sqft

702 Via Bella, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

55Active

$495,000

4 bd · 2 ba · 1,756 sqft

3020 Nicholson Dr, Winter Park, FL

Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

68Active

$5,999,990

4 bd · 5 ba · 3,880 sqft

2661 Via Tuscany, Winter Park, FL

Nohora Gomez · COLDWELL BANKER REALTY

48Active

$739,777

4 bd · 2 ba · 2,267 sqft

4039 Cool Water Ct, Winter Park, FL

Karen Arbutine · RE/MAX CENTRAL REALTY

Price Reduced40Active

$529,000

4 bd · 2 ba · 1,845 sqft

2211 King Richards Ct, Winter Park, FL

Nicole Howell · FANNIE HILLMAN & ASSOCIATES

64Active

$1,598,000

4 bd · 4 ba · 2,916 sqft

2430 Chantilly Ave, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

81Active

$3,600,000

4 bd · 5 ba · 4,202 sqft

276 Detmar Dr, Winter Park, FL

Melanie Johnston · CALL IT CLOSED INTL REALTY

10Active

$1,829,000

4 bd · 4 ba · 2,706 sqft

1550 Palm Ave, Winter Park, FL

Brian Mitnik · RE/MAX 200 REALTY

32Active

$660,000

4 bd · 4 ba · 1,840 sqft

1016 Aragon Ave, Winter Park, FL

Pam Stewart · PALMANO GROUP RE BROKERAGE LLC

Price Reduced38Active

$575,000

4 bd · 2 ba · 1,936 sqft

7525 Lodge Pole Trl, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

Price Reduced38Active

$550,000

4 bd · 2 ba · 2,126 sqft

2641 Carvell Ct, Winter Park, FL

Christina Perez · CHAMBERLAIN 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: $539,000$337,000–$1,175,000 typical range
Price per sq. ft.: $315
Sales: 111
Paid in cash: 40.5%

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

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: $539,000$337,000–$1,175,000 typical range
Price per sq. ft.: $315
Sales: 111
Paid in cash: 40.5%

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

Winter Park, FL community profile

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