Winter Park, FL homes for sale & real estate

7 hours on Rocket

$2,731 Closing Credit¹

$230,000

2 beds • 2 baths • 956 sqft

2500 Lee Rd Unit 208, Winter Park, FL 32789

#O6297570, Debbie Jones, Listing Office: KELLER WILLIAMS REALTY AT THE PARKS

7 hours on Rocket

$3,384 Closing Credit¹

$285,000

2 beds • 1 bath • 710 sqft

151 N Orlando Ave Unit 115, Winter Park, FL 32789

#O6299179, Jackie O'Leary, Listing Office: FANNIE HILLMAN & ASSOCIATES

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8 hours on Rocket

$4,571 Closing Credit¹

$384,900

3 beds • 2 baths • 1,434 sqft

7543 Dockside St, Winter Park, FL 32792

#S5124738, Juan Matias, Listing Office: LPT REALTY, LLC

8 hours on Rocket

$2,968 Closing Credit¹

$249,900

2 beds • 2.5 baths • 1,031 sqft

3254 Oak Lake Pl Unit 137, Winter Park, FL 32792

#O6298927, Darryl Henderson, Jr, Listing Office: GLOBAL ENTERPRISE REALTY GROUP

view of exterior entry with a balcony and stucco siding

8 hours on Rocket

$1,247 Closing Credit¹

$105,000

1 bed • 1 bath • 785 sqft

337 Scottsdale Sq Unit 337, Winter Park, FL 32792

#TB8373292, Michel Pineda Monsalve, Listing Office: HOMERIVER GROUP

14 hours on Rocket

$5,938 Closing Credit¹

$500,000

4 beds • 2 baths • 1,699 sqft

2011 Harmon Ave, Winter Park, FL 32789

#O6298958, Catherine D'Amico, Listing Office: FANNIE HILLMAN & ASSOCIATES

14 hours on RocketTour

$6,886 Closing Credit¹

$579,900

3 beds • 2 baths • 1,906 sqft

7584 Lodge Pole Trl, Winter Park, FL 32792

#O6297478, Robert Arnold, Jr, Listing Office: SAND DOLLAR REALTY GROUP INC

Room to negotiate?

Median Sold Price

$467.8K

Avg. Sale Time

53 Days

Based on our March 2025 Market Report.

17 hours on Rocket

$3,324 Closing Credit¹

$279,900

2 beds • 2 baths • 939 sqft

2404 Gallery View Dr Unit 1, Winter Park, FL 32792

#O6298040, Lolita Clay, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

1 day on RocketTour

$7,422 Closing Credit¹

$625,000

3 beds • 2 baths • 1,670 sqft

2707 Prince John Rd, Winter Park, FL 32792

#O6297692, Amy Turner, Listing Office: KELLER WILLIAMS WINTER PARK

1 day on RocketTour

$8,016 Closing Credit¹

$675,000

3 beds • 2.5 baths • 1,910 sqft

796 Mcintyre Ave, Winter Park, FL 32789

#O6297200, Catherine D'Amico, Listing Office: FANNIE HILLMAN & ASSOCIATES

1 day on Rocket

$10,000 Closing Credit¹

$2,490,000

5 beds • 4 baths • 3,784 sqft

1299 Harding St, Winter Park, FL 32789

#O6298410, Nancy Bagby, Listing Office: FANNIE HILLMAN & ASSOCIATES

1 day on RocketTour

$3,384 Closing Credit¹

$285,000

2 beds • 2 baths • 1,669 sqft

2309 Sun Valley Cir Unit 2309, Winter Park, FL 32792

#O6298238, Kristin Vogt, Listing Office: CENTURY 21 INTEGRA

1 day on Rocket

$8,016 Closing Credit¹

$675,000

3 beds • 1.5 baths • 1,662 sqft

3019 Northwood Blvd, Winter Park, FL 32789

#O6290544, Robert Arnold, Jr, Listing Office: SAND DOLLAR REALTY GROUP INC

1 day on RocketTour

$5,344 Closing Credit¹

$450,000

3 beds • 1 bath • 960 sqft

710 W Swoope Ave W, Winter Park, FL 32789

#O6297911, Firmin Emanuel, Listing Office: FIRMAN A. EMANUEL

1 day on RocketTour

$5,177 Closing Credit¹

$435,990

3 beds • 2.5 baths • 1,678 sqft

1291 Tarflower Dr, Winter Springs, FL 32708

#O6298434, Elizabeth Manchester, Listing Office: MATTAMY REAL ESTATE SERVICES

1 day on RocketTour

$5,391 Closing Credit¹

$453,990

3 beds • 2.5 baths • 1,678 sqft

1342 Tarflower Dr, Winter Springs, FL 32708

#O6298420, Elizabeth Manchester, Listing Office: MATTAMY REAL ESTATE SERVICES

1 day on RocketTour

$6,882 Closing Credit¹

$579,500

4 beds • 2 baths • 2,126 sqft

3131 Lowndes Dr, Winter Park, FL 32792

#O6296742, Rene Fossey, Listing Office: A +ROI PROPERTY

1 day on RocketTour

$1,164 Closing Credit¹

$98,000

1 bed • 1 bath • 581 sqft

7341 Daniel Webster Dr Unit 4, Winter Park, FL 32792

#S5124417, Delfina Tata, Listing Office: PROFESSIONAL PROPERTY MGMT & L

1 day on RocketTour

$6,757 Closing Credit¹

$569,000

3 beds • 2 baths • 1,642 sqft

1368 Devon Rd, Winter Park, FL 32789

#O6298142, Karen Ripperger, Listing Office: LPT REALTY, LLC

2 days on RocketTour

$10,000 Closing Credit¹

$849,000

3 beds • 2.5 baths • 1,957 sqft

1276 S Pennsylvania Ave Unit 12, Winter Park, FL 32789

#O6298418, Chase Tate, PLLC, Listing Office: COMPASS FLORIDA LLC

2 days on RocketTour

$10,000 Closing Credit¹

$1,349,000

4 beds • 4 baths • 3,046 sqft

1077 Minnesota Ave, Winter Park, FL 32789

#O6298314, Jacob Johnson, Listing Office: SHORES REAL ESTATE

2 days on RocketTour

$500,000

Land • 0.33 Acres

2011 Harmon Ave, Winter Park, FL 32789

#O6297201, Catherine D'Amico, Listing Office: FANNIE HILLMAN & ASSOCIATES

2 days on RocketTour

$5,699 Closing Credit¹

$479,900

4 beds • 2.5 baths • 2,035 sqft

1532 Lawndale Cir, Winter Park, FL 32792

#O6297580, David Coker, Listing Office: KELLER WILLIAMS WINTER PARK

2 days on Rocket

$4,976 Closing Credit¹

$419,000

3 beds • 2 baths • 1,592 sqft

1566 Lawndale Cir, Winter Park, FL 32792

#G5095140, Joshua Earley, LLC, Listing Office: OPTIMA ONE REALTY, INC.

2 days on RocketTour

$4,100,000

5 beds • 6.5 baths • 4,782 sqft

1782 Pine Ave, Winter Park, FL 32789

#O6297161, Prentice Williams, Listing Office: EXP REALTY LLC

3 days on RocketTour

$10,000 Closing Credit¹

$2,199,000

5 beds • 4 baths • 3,907 sqft

1394 Stewart St, Winter Park, FL 32789

#O6295451, Richard Vaughn, Listing Office: REALTY ONE GROUP INSPIRATION

3 days on RocketTour

$1,306 Closing Credit¹

$110,000

2 beds • 2 baths • 1,020 sqft

330 Scottsdale Sq Unit 330, Winter Park, FL 32792

#O6297922, Emad Terkawi, Listing Office: CENTURY 21 CARIOTI

3 days on Rocket

$10,000 Closing Credit¹

$915,000

2 beds • 2 baths • 1,143 sqft

100 S Interlachen Ave Unit 503, Winter Park, FL 32789

#O6292044, Drew Henner, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of front facade with an attached carport, a front lawn, and concrete driveway

3 days on Rocket

$9,500 Closing Credit¹

$799,999

3 beds • 1 bath • 1,128 sqft

2838 Wright Ave, Winter Park, FL 32789

#O6297710, Jordan Suglio, Listing Office: BALDWIN PARK REALTY LLC

4 days on RocketTour

$10,000 Closing Credit¹

$1,360,000

6 beds • 4 baths • 4,468 sqft

1269 Wading Waters Cir, Winter Park, FL 32792

#S5123766, James Baillie, Listing Office: HAMILTON REALTY

4 days on RocketTour

$3,205 Closing Credit¹

$269,900

2 beds • 2.5 baths • 960 sqft

255 Sandlewood Trl, Winter Park, FL 32789

#O6296680, Freddie Crespo, Listing Office: INVESTOR'S REAL ESTATE LLC

4 days on RocketTour

$5,676 Closing Credit¹

$478,000

3 beds • 2 baths • 1,919 sqft

7320 Fieldcrest Ave, Winter Park, FL 32792

#O6292558, Winnie Mai, Listing Office: COLDWELL BANKER REALTY

4 days on Rocket

$3,088 Closing Credit¹

$260,000

2 beds • 2 baths • 908 sqft

1250 S Denning Dr Unit 111, Winter Park, FL 32789

#O6297033, Alayna Phillips, Listing Office: EXP REALTY LLC

5 days on Rocket

$350,000

Land • 0.20 Acres

1807 Magnolia Ave, Winter Park, FL 32789

#TB8371067, Kristen Hamilton, Listing Office: LOMBARDO TEAM REAL ESTATE LLC

6 days on Rocket

$595,000

Land • 0.21 Acres

1821 Goodrich Ave, Winter Park, FL 32789

#O6296858, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

6 days on RocketTour

$4,453 Closing Credit¹

$375,000

3 beds • 2.5 baths • 1,456 sqft

156 Oak Grove Rd, Winter Park, FL 32789

#TB8370885, Serge Osaulenko, Listing Office: EVERLANE REALTY LLC

7 days on Rocket

$5,936 Closing Credit¹

$499,900

4 beds • 3 baths • 2,256 sqft

4887 Seminole Ave, Winter Park, FL 32792

#O6294630, Timothy Oster, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

7 days on RocketTour

$260,000

Land • 0.81 Acres

3580 Wilde Ave, Winter Park, FL 32792

#O6296776, Gwen Flynn, Listing Office: COLDWELL BANKER RESIDENTIAL RE

7 days on RocketTour

$8,016 Closing Credit¹

$675,000

3 beds • 2 baths • 1,232 sqft

843 W Swoope Ave, Winter Park, FL 32789

#O6296025, Jean Chalifour, Listing Office: COLDWELL BANKER RESIDENTIAL RE

7 days on RocketTour

$6,828 Closing Credit¹

$575,000

4 beds • 2 baths • 1,699 sqft

2007 Strathaven Rd, Winter Park, FL 32792

#O6295781, Mark Ramey, Listing Office: EXP REALTY LLC

Winter Park, FL Real Estate Market Overview

Find your perfect home in Winter Park, FL on RocketHomes.com. Browse homes and listings in Winter Park, FL and connect with a Rocket Homes agent to get your dream home. The number of listings in Winter Park, FL increased by 10.4% between February 2025 and March 2025. While the average time on the market in March 2025 was 53 days, the median list price was $467,846. Over 7 listings were sold over their listed price in March 2025 in Winter Park, FL. In the same period over 58 listings were sold below the listed price and 28 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

Schools near Winter Park, FL

Elementary Schools

Brookshire Elementary School
2500 Cady Way
Public District PK-5
Aloma Elementary School
2949 Scarlet Rd
Public District KG-5
Hungerford Elementary School
230 S College Ave
Public District PK-5

Middle Schools

Glenridge Middle School
2900 Upper Park Rd
Public District 6-8

High Schools

Winter Park High School
2100 Summerfield Rd
Public Magnet 9-12

Data provided by Great Schools

Homes for sale in Winter Park, FL

Winter Park, FL Real Estate Market Overview

What is it like to live in Winter Park, FL

Overview

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