4 bedroom homes for sale in Winter Park, FL

1 day on RocketTour

$10,000 Closing Credit¹

$1,500,000

4 beds • 3.5 baths • 3,349 sqft

2401 Lafayette Ave, Winter Park, FL 32789

#TB8395492, Nehad Darwish, Listing office: DIVINE ESTATES REALTY LLC

1 day on RocketTour

$3,894 Closing Credit¹

$327,950

4 beds • 2 baths • 1,919 sqft

5135 Kinsley Dr, Winter Haven, FL 33884

#S5127745, Stephanie Morales, LLC, Listing office: THE REALTY EXPERIENCE POWERED BY LRR

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1 day on RocketTour

$10,000 Closing Credit¹

$1,210,000

4 beds • 3.5 baths • 3,321 sqft

4048 Gilder Rose Pl, Winter Park, FL 32792

#O6316911, Abby Greenberg, Listing office: COMPASS FLORIDA LLC

3 days on RocketTour

$10,000 Closing Credit¹

$1,425,000

4 beds • 3.5 baths • 3,153 sqft

2922 Reef Knot Pl, Winter Park, FL 32792

#O6316445, Ellen Bessette, Listing office: CHARLES RUTENBERG REALTY ORLANDO

4 days on RocketTour

$10,000 Closing Credit¹

$998,000

4 beds • 3.5 baths • 4,088 sqft

1319 Heavenly Cv, Winter Park, FL 32792

#TB8394560, Douglas Addeo, Listing office: COMMUNITY REALTY ASSOCIATES

6 days on RocketTour

$5,344 Closing Credit¹

$450,000

4 beds • 2.5 baths

2512 Eastbrook Blvd, undefined, FL 32792

#A11713727, Ligia Trask, Listing office: Robert Slack LLC

7 days on Rocket

$10,000 Closing Credit¹

$950,000

4 beds • 2 baths • 2,237 sqft

1018 Turner Rd, Winter Park, FL 32789

#O6314546, Jenny Wemert, Listing office: WEMERT GROUP REALTY LLC

Room to negotiate?

Median Sold Price

$465.6K

Avg. Sale Time

47 Days

Based on our May 2025 Market Report.

$10,000 Closing Credit¹

$1,180,000

4 beds • 3.5 baths • 2,770 sqft

2607 Lafayette Ave, Winter Park, FL 32789

#O6314734, Maggie Walas, Listing office: FORTUNE INTERNATIONAL REALTY

$6,769 Closing Credit¹

$570,000

4 beds • 2 baths • 1,749 sqft

3231 Lowndes Dr, Winter Park, FL 32792

#S5125689, Sergio Morante, Listing office: LA ROSA REALTY KISSIMMEE

Tour

$5,225 Closing Credit¹

$439,999

4 beds • 2 baths • 2,027 sqft

2209 Fairglenn Way, Winter Park, FL 32792

#O6313561, Benjamin Benami, Listing office: HIVE REALTY LLC

$5,023 Closing Credit¹

$423,000

4 beds • 2 baths • 1,996 sqft

5436 Tangerine Ave, Winter Park, FL 32792

#O6313878, Amy Phillips, Listing office: CALL IT CLOSED INTL REALTY

Tour

$3,927 Closing Credit¹

$330,728

4 beds • 2 baths • 1,919 sqft

5147 Kinsley Dr, Winter Haven, FL 33884

#S5127810, Stephanie Morales, LLC, Listing office: THE REALTY EXPERIENCE POWERED BY LRR

Tour

$10,000 Closing Credit¹

$1,495,000

4 beds • 3.5 baths • 2,953 sqft

1420 Palmer Ave, Winter Park, FL 32789

#O6313031, Amy Turner, Listing office: KELLER WILLIAMS WINTER PARK

Tour

$9,441 Closing Credit¹

$795,000

4 beds • 2 baths • 2,509 sqft

627 Darcey Dr, Winter Park, FL 32792

#O6306441, Ingrid Livingston, Listing office: COLDWELL BANKER RESIDENTIAL RE

Tour

$4,750 Closing Credit¹

$399,990

4 beds • 2 baths • 1,704 sqft

1017 Manchester Cir, Winter Park, FL 32792

#O6313211, Jenaia Fowlkes, Listing office: FOWLKES REALTY CO

$4,175,000

4 beds • 5 baths • 4,683 sqft

1581 Forest Ave, Winter Park, FL 32789

#O6298754, Glenda Massie, Listing office: BHHS FLORIDA REALTY

Tour

$6,411 Closing Credit¹

$539,900

4 beds • 2.5 baths • 2,616 sqft

7679 Bent Bow Trl, Winter Park, FL 32792

#O6312217, Jason Gilkey, Listing office: GILKEY REAL ESTATE

Tour

$10,000 Closing Credit¹

$1,199,000

4 beds • 4 baths • 4,015 sqft

4052 Gilder Rose Pl, Winter Park, FL 32792

#O6312182, Steve Lang, Listing office: HOMEVEST REALTY

Tour

$10,000 Closing Credit¹

$980,000

4 beds • 4 baths • 3,646 sqft

5510 Howell Branch Rd, Winter Park, FL 32792

#1047087, Shaun Shaffner, Listing office: Blue Marlin Real Estate

Tour

$3,656 Closing Credit¹

$307,890

4 beds • 3 baths • 2,174 sqft

1523 Jessica Blvd, Winter Haven, FL 33884

#O6312034, Ben Goldstein, Listing office: LENNAR REALTY

Tour

$5,332 Closing Credit¹

$448,990

4 beds • 2.5 baths • 1,678 sqft

1315 Tarflower Dr, Winter Springs, FL 32708

#O6312003, Elizabeth Manchester, Listing office: MATTAMY REAL ESTATE SERVICES

Tour

$5,219 Closing Credit¹

$439,500

4 beds • 2 baths • 1,836 sqft

1842 Puritan Ave, Winter Park, FL 32792

#S5127384, Marissa Crawford, Listing office: COMPASS FLORIDA LLC

Tour

$10,000 Closing Credit¹

$1,594,950

4 beds • 3 baths • 3,474 sqft

952 Moss Ln, Winter Park, FL 32789

#TB8388549, Terry Connors, II, Listing office: THE SHOP REAL ESTATE CO.

Tour

$10,000 Closing Credit¹

$2,100,000

4 beds • 2.5 baths • 2,674 sqft

633 Balmoral Rd, Winter Park, FL 32789

#O6308662, Laura Hope, Listing office: COMPASS FLORIDA LLC

Tour

$4,311 Closing Credit¹

$362,990

4 beds • 3 baths • 2,174 sqft

1523 Jessica Blvd, Winter Haven, FL 33884

#O6311304, Ben Goldstein, Listing office: LENNAR REALTY

$10,000 Closing Credit¹

$2,455,000

4 beds • 4.5 baths • 3,883 sqft

521 S Phelps Ave, Winter Park, FL 32789

#O6311128, Marcio Tannus, Listing office: LA ROSA REALTY HORIZONS LLC

$2,590,000

4 beds • 4.5 baths • 3,138 sqft

185 Sylvan Blvd, Winter Park, FL 32789

#O6304627, Christopher Christensen, Listing office: COMPASS FLORIDA LLC

Tour

$6,056 Closing Credit¹

$510,000

4 beds • 2 baths • 2,313 sqft

1742 Willa Cir, Winter Park, FL 32792

#O6309904, Bo Zhang, Listing office: CENTURY 21 CARIOTI

Tour

$10,000 Closing Credit¹

$1,999,900

4 beds • 3 baths • 3,117 sqft

1521 Chestnut Ave, Winter Park, FL 32789

#A4651868, Sue Silberbusch, Listing office: COMPASS FLORIDA LLC

Tour

$10,000 Closing Credit¹

$1,200,000

4 beds • 3.5 baths • 3,074 sqft

4107 Gabriella Ln, Winter Park, FL 32792

#O6307317, Barrett Spray, Listing office: KELLER WILLIAMS ADVANTAGE REALTY

$10,000 Closing Credit¹

$2,375,000

4 beds • 3 baths • 3,182 sqft

104 Cortland Ave, Winter Park, FL 32789

#O6307403, Mick Night, Listing office: PREMIER SOTHEBY'S INTL. REALTY

Tour

$4,382 Closing Credit¹

$369,000

4 beds • 2 baths • 1,349 sqft

657 Overspin Dr, Winter Park, FL 32789

#O6308079, Abby Nelson, Listing office: RE/MAX 200 REALTY

Tour

$6,055 Closing Credit¹

$509,900

4 beds • 2 baths • 2,195 sqft

5338 Tangerine Ave, Winter Park, FL 32792

#O6308136, Mystique Barba, Listing office: CENTURY 21 CARIOTI

Tour

$2,900,000

4 beds • 5.5 baths • 5,416 sqft

1401 Green Cove Rd, Winter Park, FL 32789

#O6306675, Terry Yonker, Listing office: BUCKEYE REALTY LLC

Tour

$3,150,000

4 beds • 3.5 baths • 3,553 sqft

541 W Canton Ave, Winter Park, FL 32789

#O6307816, Bianca Khoury, Listing office: KELLER WILLIAMS WINTER PARK

$9,619 Closing Credit¹

$810,000

4 beds • 3 baths • 3,020 sqft

2144 Ridge Dr, Winter Park, FL 32792

#1213234, Sahil Rama, Listing office: EXP Realty LLC

Tour

$3,095,000

4 beds • 4.5 baths • 3,551 sqft

940 Lincoln Cir, Winter Park, FL 32789

#O6306740, Padgett McCormick, Listing office: KELLY PRICE & COMPANY LLC

$9,203 Closing Credit¹

$775,000

4 beds • 3.5 baths • 2,587 sqft

1340 Blue Stem Ln, Winter Park, FL 32792

#O6307026, Andrea Luna, Listing office: AGL BROKERAGE CORP

Tour

$5,106 Closing Credit¹

$430,000

4 beds • 2 baths • 1,508 sqft

7249 Abbey Ln, Winter Park, FL 32792

#O6306995, Jackie Criswell, Listing office: RE/MAX TOWN & COUNTRY REALTY

$10,000 Closing Credit¹

$1,695,000

4 beds • 3.5 baths • 3,204 sqft

1831 Mizell Ave, Winter Park, FL 32789

#O6305970, Bryan DeCorso, Listing office: EXP REALTY LLC

Winter Park, FL Real Estate Market Overview

There are 111 4-bedroom homes for sale in Winter Park, FL. The following market insights reflect all property types in the Winter Park, FL real estate market. The number of homes for sale in Winter Park, FL increased by 3.5% between April 2025 and May 2025. While the average time on the market in May 2025 was 47 days, the median list price was $465,611. In May 2025 more than 11 listings in Winter Park, FL were sold above the asking price. During the same period more than 27 listings were sold at asking price, while more than 74 were sold below.

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

What is it like to live in Winter Park, FL

Overview

Winter Park is located in Orange County, Florida. There are roughly 30,427 residents, living in 13,373 households. The average temperature for Winter Park this time of the year is low of 71F and high of 90F. On average, Winter Park gets about 7.22 inches of precipitation in June. Most residents are home owners (62%), have a post secondary degree (63%) and are single, no kids (51%).

Data provided by Home Junction

Schools near Winter Park, FL