4 bedroom homes for sale in Winter Park, FL

ranch-style house with a garage, concrete driveway, and a front lawn

view of front of home featuring a front lawn, concrete block siding, a garage, and driveway

ranch-style home with an attached garage, concrete block siding, a front yard, and concrete driveway

6 hours on Rocket

$4,869 Closing Credit¹

$410,000

4 beds • 2.5 baths • 1,730 sqft

1021 Mare Bello Dr, Winter Park FL 32792

#O6289497, Lori Hutchinson, Listing Office: THE WILKINS WAY LLC

ranch-style house with an attached garage, a lawn, driveway, and stucco siding

ranch-style home with stucco siding, driveway, stone siding, a yard, and a garage

view of front of home featuring fence, driveway, stucco siding, stone siding, and a lawn

12 hours on RocketVideo tour

$5,344 Closing Credit¹

$450,000

4 beds • 2 baths • 2,124 sqft

4991 Tangerine Ave, Winter Park FL 32792

#O6288881, Darein Washington, Listing Office: KELLER WILLIAMS ADVANTAGE REALTY

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view of front of house with a lawn and brick siding

neoclassical / greek revival house featuring brick siding, a chimney, and a front yard

view of front facade featuring decorative driveway, stone siding, a chimney, and a front lawn

12 hours on Rocket

$10,000 Closing Credit¹

$1,475,000

4 beds • 3.5 baths • 3,014 sqft

1600 Barcelona Way, Winter Park FL 32789

#O6288843, Laura Ascenso, Listing Office: LPT REALTY, LLC

single story home featuring an attached carport, fence, and driveway

view of front of property featuring a carport, fence, a front lawn, and driveway

13 hours on Rocket

$6,994 Closing Credit¹

$589,000

4 beds • 2 baths • 1,710 sqft

3006 Northwood Blvd, Winter Park FL 32789

#O6289061, Chris Creegan, Listing Office: CREEGAN GROUP

ranch-style home with concrete driveway, brick siding, a garage, and stucco siding

view of exterior entry featuring brick siding and stucco siding

living room featuring visible vents, carpet floors, and a textured ceiling

1 day on RocketVideo tour

$4,501 Closing Credit¹

$379,000

4 beds • 3 baths • 1,904 sqft

1873 Poinciana Rd, Winter Park FL 32792

#O6288529, Benondre Cerezo, Listing Office: COLDWELL BANKER REALTY

single story home featuring a front lawn, a chimney, and an attached garage

aerial view featuring a water view and a wooded view

ranch-style house with a front yard, driveway, a chimney, a garage, and brick siding

1 day on RocketVideo tour

$10,000 Closing Credit¹

$1,095,000

4 beds • 4.5 baths • 3,121 sqft

1444 Pelican Bay Trl, Winter Park FL 32792

#S5122502, Jacob Hara, Listing Office: TRANSCEND REALTY

view of front of property featuring stucco siding, a front lawn, driveway, roof with shingles, and an attached garage

view of exterior entry featuring a porch, stone siding, and roof with shingles

entryway featuring visible vents, an inviting chandelier, decorative columns, crown molding, and light wood-type flooring

3 days on RocketVideo tour

$10,000 Closing Credit¹

$1,500,000

4 beds • 3 baths • 3,297 sqft

1741 Pine Ave, Winter Park FL 32789

#O6287861, Wendy Williams Crumit, Listing Office: FANNIE HILLMAN & ASSOCIATES

Room to negotiate?

Median Sold Price

$469.6K

Avg. Sale Time

62 Days

Based on our February 2025 Market Report.

modern farmhouse style home featuring a garage, stone siding, driveway, and a porch

kitchen with a raised ceiling, light stone counters, stove, a kitchen island with sink, and backsplash

living room featuring recessed lighting, a large fireplace, and light wood-style flooring

4 days on Rocket

$10,000 Closing Credit¹

$1,775,000

4 beds • 3.5 baths • 2,950 sqft

1682 Arbor Park Dr, Winter Park FL 32789

#O6285459, Christopher Christensen, Listing Office: COMPASS FLORIDA LLC

modern farmhouse style home with driveway, a garage, and roof with shingles

kitchen with stove, decorative backsplash, light stone countertops, a tray ceiling, and a center island with sink

living room featuring recessed lighting, a fireplace, and light wood-style floors

4 days on Rocket

$10,000 Closing Credit¹

$1,775,000

4 beds • 3.5 baths • 2,950 sqft

1702 Arbor Park Dr, Winter Park FL 32789

#O6285557, Christopher Christensen, Listing Office: COMPASS FLORIDA LLC

ranch-style house featuring roof with shingles, stucco siding, a garage, driveway, and a front lawn

kitchen featuring light tile patterned flooring, stove, white cabinetry, a kitchen breakfast bar, and stainless steel refrigerator with ice dispenser

kitchen featuring appliances with stainless steel finishes, white cabinetry, a center island with sink, and a kitchen breakfast bar

5 days on RocketVideo tour

$3,931 Closing Credit¹

$330,990

4 beds • 3 baths • 2,174 sqft

2327 Scarlet Ave, Winter Haven FL 33884

#TB8359425, Ben Goldstein, Listing Office: LENNAR REALTY

view of front of property with an attached garage, a front yard, board and batten siding, and concrete driveway

kitchen with stainless steel appliances, a breakfast bar area, and white cabinetry

kitchen with a center island, appliances with stainless steel finishes, white cabinetry, vaulted ceiling, and a kitchen breakfast bar

5 days on RocketVideo tour

$3,408 Closing Credit¹

$286,990

4 beds • 2 baths • 1,824 sqft

1993 Sarah St, Winter Haven FL 33884

#TB8359423, Ben Goldstein, Listing Office: LENNAR REALTY

ranch-style home with a garage, concrete driveway, roof with shingles, a front lawn, and board and batten siding

kitchen with a breakfast bar, stainless steel refrigerator with ice dispenser, light tile patterned floors, stove, and white cabinetry

kitchen featuring appliances with stainless steel finishes, a kitchen island with sink, a kitchen bar, and white cabinetry

5 days on RocketVideo tour

$3,859 Closing Credit¹

$324,990

4 beds • 3 baths • 2,174 sqft

1950 Sarah St, Winter Haven FL 33884

#TB8359422, Ben Goldstein, Listing Office: LENNAR REALTY

view of front facade with a garage, decorative driveway, and stucco siding

view of exterior entry featuring stucco siding

kitchen featuring visible vents, appliances with stainless steel finishes, a peninsula, under cabinet range hood, and a sink

6 days on Rocket

$9,441 Closing Credit¹

$795,000

4 beds • 3.5 baths • 2,589 sqft

1344 Blue Stem Ln, Winter Park FL 32792

#O6287330, Denae Zoellner, Listing Office: CASTLE & COTTAGE REALTY LLC

view of front facade with driveway, stucco siding, cooling unit, and fence

view of front of home with stucco siding, an attached garage, fence, driveway, and a front lawn

hallway featuring a textured wall and wood finished floors

7 days on Rocket

$10,000 Closing Credit¹

$1,375,000

4 beds • 3 baths • 3,204 sqft

1213 Richmond Rd, Winter Park FL 32789

#O6287413, Jennifer Sloan, Listing Office: KELLY PRICE & COMPANY LLC

ranch-style home featuring an attached garage, concrete driveway, and roof with shingles

single story home featuring concrete driveway, roof with shingles, an attached garage, a front yard, and brick siding

$6,975 Closing Credit¹

$587,400

4 beds • 2.5 baths • 2,260 sqft

3822 Kinsley Pl, Winter Park FL 32792

#A4641055, Donna Mink, Listing Office: MINK REALTY

single story home with a front yard, roof with shingles, and stucco siding

foyer with a textured ceiling, baseboards, and light tile patterned floors

entrance foyer featuring a textured ceiling, a notable chandelier, visible vents, and light wood-style floors

$5,522 Closing Credit¹

$465,000

4 beds • 2.5 baths • 1,948 sqft

7565 Dockside St, Winter Park FL 32792

#O6285857, Maurince Pierre, LLC, Listing Office: PREMIUM PROPERTIES REAL ESTATE

exterior space featuring a yard, a chimney, a balcony, and stucco siding

exterior space featuring a balcony and stucco siding

exterior space featuring driveway, a chimney, and stucco siding

Video tour

$4,875,000

4 beds • 5 baths • 4,431 sqft

229 Alexander Pl, Winter Park FL 32789

#O6281892, Julie Bombardo, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

ranch-style home with brick siding, a shingled roof, a garage, driveway, and a front lawn

single story home featuring a shingled roof and brick siding

foyer entrance with arched walkways, a textured ceiling, wood finished floors, baseboards, and wallpapered walls

$8,894 Closing Credit¹

$749,000

4 beds • 2 baths • 2,446 sqft

1321 Medinah Ct, Winter Park FL 32792

#O6285649, Courtney Pelfrey, Listing Office: MILLER GRANT AND COMPANY

living area with a notable chandelier, crown molding, a glass covered fireplace, and a decorative wall

kitchen with a tray ceiling, open shelves, tasteful backsplash, oven, and under cabinet range hood

3D tour

$10,000 Closing Credit¹

$1,799,000

4 beds • 3.5 baths • 3,669 sqft

1731 Windsor Dr, Winter Park FL 32789

#O6285883, James Condino, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

view of front of home featuring decorative driveway, an attached garage, fence, and stucco siding

view of front of home featuring a garage, fence, decorative driveway, and stucco siding

view of front of house featuring a garage, decorative driveway, fence, and stucco siding

Video tour

$7,719 Closing Credit¹

$650,000

4 beds • 2.5 baths • 1,881 sqft

2739 Riddle Dr, Winter Park FL 32789

#TB8355970, JASON OLD, Listing Office: BRAINARD REALTY

ranch-style house featuring a front yard, covered porch, driveway, and an attached garage

entrance to property with covered porch and a garage

property entrance featuring covered porch and ceiling fan

Video tour

$10,000 Closing Credit¹

$1,580,000

4 beds • 3.5 baths • 2,637 sqft

1750 Winchester Dr, Winter Park FL 32789

#O6285335, Michael Ford, Listing Office: FANNIE HILLMAN & ASSOCIATES

contemporary home with a front lawn, decorative driveway, an attached garage, and stucco siding

view of front of house with stucco siding, fence, decorative driveway, and a front yard

hall featuring recessed lighting and baseboards

Video tour

$10,000 Closing Credit¹

$1,500,000

4 beds • 4 baths • 2,958 sqft

2015 Summerfield Rd, Winter Park FL 32792

#O6285086, Steven Koleno, Listing Office: BEYCOME OF FLORIDA LLC

ranch-style house featuring brick siding, driveway, and an attached garage

ranch-style home with concrete driveway, brick siding, and an attached garage

kitchen featuring appliances with stainless steel finishes, brown cabinets, light countertops, and a sink

Video tour

$4,418 Closing Credit¹

$372,000

4 beds • 2 baths • 1,782 sqft

5339 Cypress Dr, Winter Park FL 32792

#O6284337, Fredric Crawford, Listing Office: FUTURE HOME REALTY INC

view of front of property with a garage, stone siding, roof with shingles, decorative driveway, and a front lawn

french country style house featuring an attached garage, driveway, stone siding, stucco siding, and a front yard

bedroom featuring access to exterior, crown molding, visible vents, and wood finished floors

Video tour

$10,000 Closing Credit¹

$995,000

4 beds • 3 baths • 2,838 sqft

210 Laurel Park Ct, Winter Park FL 32792

#O6279127, Lizzie Beaudoin, Listing Office: PR REAL ESTATE SERVICES

view of front of house featuring stucco siding

tudor house featuring a tile roof and stucco siding

back of property featuring a tiled roof, a lawn, a patio area, and a fenced in pool

$4,500,000

4 beds • 4 baths • 3,181 sqft

1336 College Pt, Winter Park FL 32789

#O6277515, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of front of property featuring a garage, decorative driveway, and stucco siding

property view of water with a residential view

view of front facade with decorative driveway, a tile roof, stucco siding, an attached garage, and a front lawn

Video tour

$8,906 Closing Credit¹

$750,000

4 beds • 2.5 baths • 2,197 sqft

1312 Blue Stem Ln, Winter Park FL 32792

#O6268066, Maggie Walas, Listing Office: FORTUNE INTERNATIONAL REALTY

view of front facade featuring driveway, a shingled roof, an attached garage, and a front yard

garage featuring concrete driveway and visible vents

Video tour

$7,125 Closing Credit¹

$599,999

4 beds • 2.5 baths • 2,141 sqft

7531 Lodge Pole Trl, Winter Park FL 32792

#O6283589, Austin Cummings, Listing Office: NEXTDWELL

modern inspired farmhouse featuring a fenced front yard, a front yard, and driveway

view of dock featuring a yard, a water view, fence, and boat lift

rear view of property with a lawn, a fenced in pool, a patio, fence, and stucco siding

Video tour

$10,000 Closing Credit¹

$2,399,900

4 beds • 5 baths • 3,694 sqft

301 Rippling Ln, Winter Park FL 32789

#A4637563, Cynthia Fernandez, Listing Office: XCLUSIVE HOMES LLC

ranch-style house featuring a front lawn

single story home with a garage, concrete driveway, and a front yard

Video tour

$10,000 Closing Credit¹

$925,000

4 beds • 2 baths • 2,133 sqft

625 Worthington Dr, Winter Park FL 32789

#O6282822, Jennifer Sloan, Listing Office: KELLY PRICE & COMPANY LLC

ranch-style house featuring a front lawn and a garage

single story home with a front yard and a garage

ranch-style house with a yard and a garage

$6,472 Closing Credit¹

$545,000

4 beds • 3 baths • 1,945 sqft

4200 Bear Gully Rd, Winter Park FL 32792

#O6280157, Renee Killiri, Listing Office: RED BIRD REALTY OF FLORIDA INC

doorway to property featuring ceiling fan

Video tour

$10,000 Closing Credit¹

$1,350,000

4 beds • 4 baths • 3,000 sqft

181 N Phelps Ave, Winter Park FL 32789

#O6278498, Iluska Kruse, Listing Office: ORLANDO BROTHERS REAL ESTATE LLC

view of front of home with decorative driveway, an attached garage, fence, and stucco siding

Video tour

$10,000 Closing Credit¹

$1,295,000

4 beds • 4 baths • 2,916 sqft

1611 Chestnut Ave, Winter Park FL 32789

#O6281275, Didem Isik-Widener, Listing Office: PARK AVENUE REALTY LLC

contemporary home with a garage and a front lawn

$10,000 Closing Credit¹

$1,675,000

4 beds • 4 baths • 2,812 sqft

607 Ellen Dr, Winter Park FL 32789

#TB8350945, Douglas Addeo, Listing Office: COMMUNITY REALTY ASSOCIATES

mediterranean / spanish-style home with a garage and a front yard

view of front of home featuring a garage and a front lawn

mediterranean / spanish house featuring a garage and a front yard

Video tour

$10,000 Closing Credit¹

$1,195,000

4 beds • 3 baths • 2,703 sqft

1690 Oneco Ave, Winter Park FL 32789

#O6279805, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of front of home featuring a garage

view of front of home with a garage and a front lawn

Video tour

$10,000 Closing Credit¹

$1,250,000

4 beds • 2.5 baths • 2,220 sqft

1585 Chestnut Ave, Winter Park FL 32789

#O6280166, Ashley Landers, Listing Office: KELLER WILLIAMS WINTER PARK

kitchen featuring white cabinetry, a breakfast bar area, and stainless steel appliances

kitchen with light tile patterned floors, a kitchen island, white cabinets, and appliances with stainless steel finishes

Video tour

$3,622 Closing Credit¹

$304,990

4 beds • 2.5 baths • 1,874 sqft

1938 Sarah St, Winter Haven FL 33884

#TB8348116, Ben Goldstein, Listing Office: LENNAR REALTY

view of front facade with a garage and a front lawn

$6,638 Closing Credit¹

$559,000

4 beds • 2.5 baths • 2,213 sqft

3901 Woodglade Cv, Winter Park FL 32792

#G5092637, Jen Gotlewski, Listing Office: OLYMPUS EXECUTIVE REALTY INC

back of property with a lawn and a patio

view of property with a front yard and a porch

$6,352 Closing Credit¹

$534,900

4 beds • 3 baths • 1,900 sqft

1481 Harmon Ave, Winter Park FL 32789

#O6276943, Laura Napoleon, Listing Office: KELLER WILLIAMS WINTER PARK

interior space featuring decorative columns

sitting room with hardwood / wood-style flooring

Video tour

$10,000 Closing Credit¹

$1,895,000

4 beds • 3 baths • 3,971 sqft

817 Antonette Ave, Winter Park FL 32789

#O6276468, Mary Colton, Listing Office: FANNIE HILLMAN & ASSOCIATES

entryway with tile patterned flooring and vaulted ceiling

tiled dining room featuring an inviting chandelier, plenty of natural light, and lofted ceiling with beams

Video tour

$10,000 Closing Credit¹

$1,380,000

4 beds • 3 baths • 2,060 sqft

1400 S Pennsylvania Ave, Winter Park FL 32789

#TB8344918, John Keller, Listing Office: JACK KELLER INC

Winter Park, FL Real Estate Market Overview

Find your perfect 4 bedroom home in Winter Park, FL. Browse 4 in Winter Park, FL and connect with a Rocket Homes agent to get your dream home. In February 2025 in Winter Park, FL there were 2.1% more homes for sale than in January 2025. In February 2025 median list price was $469,642 and the average listing age was 62 days. Over 7 listings were sold over their listed price in February 2025 in Winter Park, FL. In the same period over 53 listings were sold below the listed price and 23 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

4 bedroom homes for sale in Winter Park, FL

Winter Park, FL Real Estate Market Overview

What is it like to live in Winter Park, FL

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