5 bedroom homes for sale in Winter Park, FL

neoclassical / greek revival house featuring a shingled roof, a lawn, a balcony, a porch, and stucco siding

greek revival house with a porch, a front lawn, a balcony, and stucco siding

exterior space featuring ceiling fan, a patio, a fenced backyard, an outdoor living space, and a fenced in pool

New - 7 hours on Rocket

$10,000 Closing Credit¹

$2,500,000

5 beds • 5 baths • 4,676 sqft

450 Lakewood Dr, Winter Park FL 32789

#O6279653, Vonda Fields, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

view of front of property featuring driveway, fence, and stucco siding

traditional style home featuring a tiled roof and a fenced front yard

New - 1 day on RocketVideo tour

$5,700,000

5 beds • 6.5 baths • 6,406 sqft

1660 Palmer Ave, Winter Park FL 32789

#O6282425, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

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view of front of home featuring a shingled roof, fence, a front lawn, and stucco siding

view of front facade with driveway, a front yard, and stucco siding

view of front of property with a shingled roof and stucco siding

New - 1 day on RocketVideo tour

$10,000 Closing Credit¹

$2,495,000

5 beds • 3.5 baths • 4,168 sqft

140 Cortland Ave, Winter Park FL 32789

#TB8352152, Stephen Hachey, Listing Office: FLAT FEE MLS REALTY

ranch-style house featuring a garage, concrete driveway, fence, and stucco siding

New - 1 day on RocketVideo tour

$6,234 Closing Credit¹

$525,000

5 beds • 2.5 baths • 2,158 sqft

7448 Grand Ct, Winter Park FL 32792

#O6281379, Amaal Barakat, Listing Office: KELLER WILLIAMS ADVANTAGE III

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

kitchen with light tile patterned floors, stainless steel appliances, and white cabinetry

kitchen featuring stainless steel appliances, white cabinets, a breakfast bar, a center island, and light tile patterned floors

New - 2 days on RocketVideo tour

$4,191 Closing Credit¹

$352,890

5 beds • 2.5 baths • 2,112 sqft

1946 Sarah St, Winter Haven FL 33884

#TB8352550, Ben Goldstein, Listing Office: LENNAR REALTY

modern home featuring a garage and a balcony

entrance to property featuring a balcony

$10,000 Closing Credit¹

$2,395,000

5 beds • 6.5 baths • 4,506 sqft

2412 Chantilly Ave, Winter Park FL 32789

#O6278049, Christopher Christensen, Listing Office: COMPASS FLORIDA, LLC

view of front facade featuring a garage and a front lawn

kitchen featuring stainless steel appliances, sink, an island with sink, and white cabinets

living room with beam ceiling, a healthy amount of sunlight, and light hardwood / wood-style floors

Video tour

$10,000 Closing Credit¹

$2,119,000

5 beds • 4.5 baths • 2,964 sqft

785 N Phelps Ave, Winter Park FL 32789

#O6275847, Leighton Hope, Listing Office: COMPASS FLORIDA, LLC

Room to negotiate?

Median Sold Price

$471.4K

Avg. Sale Time

63 Days

Based on our January 2025 Market Report.

mediterranean / spanish-style home with french doors and a front yard

mediterranean / spanish house featuring a front yard

view of exterior entry featuring french doors

$10,000 Closing Credit¹

$2,279,000

5 beds • 4 baths • 3,909 sqft

141 Oakwood Way, Winter Park FL 32789

#O6276417, Nicole Rader, Listing Office: MAINFRAME REAL ESTATE

entryway featuring ornamental molding, hardwood / wood-style floors, and a notable chandelier

Video tour

$10,000 Closing Credit¹

$1,950,000

5 beds • 5 baths • 4,227 sqft

1470 Place Picardy, Winter Park FL 32789

#O6275888, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

view of front of property with a balcony, a porch, and a front yard

foyer entrance with crown molding, plenty of natural light, and dark hardwood / wood-style floors

Video tour

$2,995,000

5 beds • 5.5 baths • 4,411 sqft

1400 Place Picardy, Winter Park FL 32789

#O6265769, Jo Ann Lamar, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

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

back of property with a fenced in pool, a patio area, and a lawn

$10,000 Closing Credit¹

$1,599,900

5 beds • 4 baths • 3,312 sqft

1417 Miller Ave, Winter Park FL 32789

#O6271186, Laura Earl, Listing Office: CORCORAN PREMIER REALTY

view of front of house featuring a garage

view of front of home featuring a garage

Video tour

$4,500,000

5 beds • 5.5 baths • 3,720 sqft

702 Via Bella, Winter Park FL 32789

#O6273466, Dillon Muto, Listing Office: FLORIDIAN REALTY GROUP LLC

living room featuring ceiling fan and light hardwood / wood-style flooring

Video tour

$10,000 Closing Credit¹

$1,125,000

5 beds • 4 baths • 3,270 sqft

1975 Biscayne Dr, Winter Park FL 32789

#O6273072, Ranah Nam, Listing Office: SOGO REAL ESTATE SERVICES LLC

ranch-style house featuring a garage, decorative driveway, and a front lawn

view of front of property featuring a garage and concrete block siding

$9,488 Closing Credit¹

$799,000

5 beds • 3 baths • 2,804 sqft

744 London Rd, Winter Park FL 32792

#O6269464, Randall Shirey, LLC, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

contemporary house with a porch, a balcony, and a front lawn

kitchen featuring a breakfast bar, stainless steel appliances, wall chimney range hood, decorative light fixtures, and a center island

kitchen featuring wall chimney exhaust hood, stainless steel appliances, crown molding, decorative light fixtures, and white cabinets

Video tour

$10,000 Closing Credit¹

$1,395,000

5 beds • 3.5 baths • 2,700 sqft

433 Carolina Ave, Winter Park FL 32789

#O6270087, Thomas Bonner, Listing Office: COLDWELL BANKER RESIDENTIAL RE

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

view of front facade featuring covered porch

$10,000 Closing Credit¹

$1,100,000

5 beds • 3 baths • 3,296 sqft

2330 Westminster Ct, Winter Park FL 32789

#O6266127, Brandon Geers, Listing Office: COMPASS FLORIDA LLC

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

$10,000 Closing Credit¹

$2,000,000

5 beds • 4 baths • 3,246 sqft

2260 Mulbry Dr, Winter Park FL 32789

#O6264761, Farah Bloom, Listing Office: KELLER WILLIAMS WINTER PARK

view of front of house with a front yard

$4,985,000

5 beds • 6.5 baths • 6,338 sqft

2161 Sharon Rd, Winter Park FL 32789

#O6263091, Marcio Tannus, Listing Office: LA ROSA REALTY HORIZONS LLC

deck at dusk featuring an outdoor living space with a fire pit

$2,999,999

5 beds • 3.5 baths • 3,898 sqft

2652 Lake Howell Ln, Winter Park FL 32792

#O6259891, Donna Bryant, Listing Office: COLDWELL BANKER RESIDENTIAL RE

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

modern inspired farmhouse featuring a yard and a garage

kitchen featuring light wood-type flooring, decorative light fixtures, a kitchen island with sink, and sink

3D tour

$10,000 Closing Credit¹

$1,395,000

5 beds • 4.5 baths • 3,161 sqft

777 Halifax Ave, Winter Park FL 32792

#O6258805, Tracy Nuetzi, Listing Office: EXP REALTY LLC

mediterranean / spanish home featuring a garage

Video tour

$10,000 Closing Credit¹

$1,299,000

5 beds • 4.5 baths • 4,435 sqft

7440 Aloma Ave, Winter Park FL 32792

#O6258176, Josh Marzucco, Listing Office: MARZUCCO REAL ESTATE

back of house featuring a pool side deck and outdoor lounge area

$4,100,000

5 beds • 5.5 baths • 4,520 sqft

1751 Glencoe Rd, Winter Park FL 32789

#O6255877, Julie Christensen, Listing Office: COMPASS FLORIDA, LLC

view of front of property with a front yard, a porch, and a garage

dining space featuring light hardwood / wood-style flooring

dining space featuring light wood-type flooring

$10,000 Closing Credit¹

$869,000

5 beds • 3 baths • 1,813 sqft

1795 Walker Ave, Winter Park FL 32789

#O6254742, Tiffany Pantozzi, Listing Office: ALIGN REAL ESTATE LLC

view of front of property with a front yard

mediterranean / spanish-style house featuring a front yard and a garage

Video tour

$5,400,000

5 beds • 5.5 baths • 5,072 sqft

2228 Azalea Pl, Winter Park FL 32789

#O6250411, Quentin Green, II, Listing Office: COMPASS FLORIDA LLC

view of front of house featuring a garage and a yard

view of patio / terrace featuring an outdoor stone fireplace

stairs featuring hardwood / wood-style floors

Video tour

$3,295,000

5 beds • 5.5 baths • 4,080 sqft

1730 Winchester Dr, Winter Park FL 32789

#O6235073, Nick McKee, Listing Office: KELLER WILLIAMS WINTER PARK

view of front facade with a garage and a front lawn

corridor featuring light hardwood / wood-style floors

sitting room featuring hardwood / wood-style floors and a healthy amount of sunlight

Video tour

$10,000 Closing Credit¹

$1,129,000

5 beds • 3 baths • 2,641 sqft

1840 Biscayne Dr, Winter Park FL 32789

#O6226190, Laura Hope, Listing Office: COMPASS FLORIDA, LLC

mediterranean / spanish-style home with french doors

view of mediterranean / spanish-style home

3D tour

$6,950,000

5 beds • 7 baths • 7,916 sqft

1400 Alabama Dr, Winter Park FL 32789

#O6212012, Rachel Peters, LLC, Listing Office: IRON VALLEY REAL ESTATE CENTRAL FLORIDA

entryway featuring light wood-type flooring

kitchen featuring a stone fireplace, pendant lighting, white cabinetry, an island with sink, and light wood-type flooring

Video tour

$6,519 Closing Credit¹

$549,000

5 beds • 3 baths • 2,153 sqft

4041 Yacht Ct, Winter Park FL 32792

#O6194323, Andrew Livingston, Listing Office: COLDWELL BANKER REALTY

Winter Park, FL Real Estate Market Overview

Find your perfect 5 bedroom home in Winter Park, FL. Browse 5 in Winter Park, FL and connect with a Rocket Homes agent to get your dream home. Between December 2024 and January 2025, Winter Park, FL real estate market has seen increase in the number of listings by 0.2%. In January 2025 median list price was $471,465 and the average listing age was 63 days. In January 2025, from all listings sold in Winter Park, FL there were more than 14 sold above asking price, over 43 sold below and more than 12 were sold right at the asked 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

5 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

Overview

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Schools near Winter Park, FL

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