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4 Bedroom Homes in Winter Park, FL

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24 of 105 Listings

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24 of 105 Listings

73Active

4 Bedroom Homes in Winter Park, FL — Page 2

105 listings

4 Bedroom Homes in Winter Park, FL

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24 of 105 Listings

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4 Bedroom Homes in Winter Park, FL

24 of 105 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

73Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$789,000

4 bd · 3 ba · 2,141 sqft

2410 Sherbrooke Rd, Winter Park, FL

Li Ju Huang · AMERICA REAL ESTATE COMPANY LL

35Active

$699,000

4 bd · 2 ba · 1,509 sqft

2260 Coldstream Dr, Winter Park, FL

Steven Ritz · KELLER WILLIAMS WINTER PARK

55Active

$495,000

4 bd · 2 ba · 1,756 sqft

3020 Nicholson Dr, Winter Park, FL

Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

68Active

$5,999,990

4 bd · 5 ba · 3,880 sqft

2661 Via Tuscany, Winter Park, FL

Nohora Gomez · COLDWELL BANKER REALTY

27Active

$360,000

4 bd · 3 ba · 1,664 sqft

2122 Ridge Dr, Winter Park, FL

Dave Vobornik · ABSOLUTE REALTY GROUP, LLC

33Active

$1,350,000

4 bd · 4 ba · 2,998 sqft

1320 Orchid Ave, Winter Park, FL

Isis Sarcos · EXP REALTY LLC

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

27Active

$975,000

4 bd · 3 ba · 2,528 sqft

471 Holt Ave, Winter Park, FL

Tina Bollet · FLORIDA HOME TEAM REALTY LLC

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 Reduced47Active

$650,000

4 bd · 3 ba · 2,067 sqft

943 Fairway Dr, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

28Active

$419,000

4 bd · 2 ba · 1,836 sqft

1842 Puritan Ave, Winter Park, FL

Karan Jodha · MOBED REALTY, P.A.

Price Reduced38Active

$550,000

4 bd · 2 ba · 2,126 sqft

2641 Carvell Ct, Winter Park, FL

Christina Perez · CHAMBERLAIN REALTY LLC

26Active

$520,000

4 bd · 2 ba · 1,774 sqft

1905 Bonanza Ct, Winter Park, FL

Bailey Briscoe · ORCHARD BROKERAGE, LLC

41Active

$770,000

4 bd · 3 ba · 2,192 sqft

2286 Marsh Sedge Ln, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

16Active

$575,000

4 bd · 3 ba · 1,745 sqft

2627 Ambergate Rd, Winter Park, FL

Steven Thetford · KELLER WILLIAMS WINTER PARK

Price Reduced72Active

$3,750,000

4 bd · 3 ba · 3,377 sqft

2622 Lake Howell Ln, Winter Park, FL

Brian Hyser · THE AGENCY FL

Price Reduced43Active

$1,750,000

4 bd · 4 ba · 3,307 sqft

2343 Versailles Ave, Winter Park, FL

MaryStuart Day · FANNIE HILLMAN & ASSOCIATES

12Active

$1,699,000

4 bd · 4 ba · 2,530 sqft

2308 Mulbry Dr, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

53Active

$1,725,000

4 bd · 4 ba · 3,727 sqft

1840 Bryan Ave, Winter Park, FL

Jennifer Draper · REAL BROKER, LLC

1 2 3…5

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

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 40.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 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

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 40.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,731 sq. ft.