Florida, Winter Park Houses For Sale — from $439K | Broker One

Houses For Sale in Florida, Winter Park

Search Houses currently For Sale in Florida, Winter Park with photos, pricing, and property details updated daily. Filter by price, bedrooms, bathrooms, lot size, year built, and waterfront access to find exactly what you need.

Why buy in Florida, Winter Park?

Florida, Winter Park offers a mix of established neighborhoods and new construction, with proximity to top-rated schools, parks, dining, and major commute routes. Whether you are a first-time buyer, upsizing for a growing family, or looking for an investment property, the local market has options across every price range.

What to know before buying in Florida, Winter Park

Check property tax history, flood zone status, HOA rules, and recent comparable sales before making an offer. Our listings include assessed values, building details, and owner history to help you make informed decisions. Check for unpermitted work and review code violations on any property you are considering.

For Sale
$625,000
House
5 bds · 2 ba · 1,938 sqft
WINTER PARK PINES MERRIE OAKS, WINTER PARK
2652 ABBEY ROAD
New
For Sale
$729,900
House
4 bds · 2 ba · 1,764 sqft
KENILWORTH ESTATES 1ST ADD, WINTER PARK
2344 WOODCREST DRIVE
New
For Sale
$1,386,000
House
4 bds · 3 ba · 2,473 sqft
KINGS ROW, MAITLAND
1615 KING ARTHUR CIRCLE
New
For Sale
$539,900
House
2 bds · 1 ba · 1,240 sqft
ANDERSON PARK, ORLANDO
2819 ELIZABETH AVENUE
New
For Sale
$1,549,000
House
5 bds · 4 ba · 3,283 sqft
BONITA PARK, ORLANDO
9 E STEELE STREET
New
For Sale
$699,000
House
3 bds · 2 ba · 1,787 sqft
AMHERST LT SPLITS, ORLANDO
2401 AMHERST AVENUE
New
For Sale
$1,950,000
House
4 bds · 4 ba · 3,460 sqft
WINTER PARK PLACE 45/148, WINTER PARK
2625 PARK PLACE DRIVE
New
For Sale
$1,800,000
House
5 bds · 4 ba · 3,402 sqft
ANDERSON PARK, ORLANDO
3300 OBERLIN AVENUE
New
For Sale
$595,000
House
4 bds · 2 ba · 2,355 sqft
WINTER PARK PINES MERRIE OAKS, WINTER PARK
332 FLEET ROAD
New
For Sale
$439,000
House
2 bds · 1 ba · 710 sqft
ANDERSON PARK, ORLANDO
2534 HARRISON AVENUE
New
For Sale
$1,275,000
House
4 bds · 4 ba · 3,024 sqft
KENILWORTH SHORES SEC 07, WINTER PARK
2015 SUMMERFIELD ROAD
New
For Sale
$1,795,000
House
4 bds · 4 ba · 2,819 sqft
WINTER PARK VILLAGE, WINTER PARK
2501 LAFAYETTE AVENUE
New
For Sale
$849,000
House
3 bds · 2 ba · 1,904 sqft
CANTON AVE COTTAGES 1, WINTER PARK
437 N CAPEN AVENUE
New
For Sale
$5,500,000
House
4 bds · 4 ba · 4,775 sqft
SYLVAN PARK, WINTER PARK
313 SYLVAN DRIVE
For Sale
$3,500,000
House
5 bds · 6 ba · 4,168 sqft
KENILWORTH SHORES SEC 06, WINTER PARK
1836 WHITEHALL DRIVE
For Sale
$3,995,000
House
5 bds · 5 ba · 4,483 sqft
GREEN OAKS REP, WINTER PARK
1600 LEGION DRIVE
For Sale
$1,550,000
House
4 bds · 3 ba · 3,578 sqft
WINDSONG ELIZABETHS WALK 43/81, WINTER PARK
1421 CHAPMAN CIRCLE
For Sale
$1,499,000
House
5 bds · 4 ba · 4,814 sqft
REPLAT BLK B POORS ADD, MAITLAND
255 W GEORGE AVENUE
For Sale
$3,490,000
House
5 bds · 5 ba · 4,191 sqft
CHARMONT, WINTER PARK
121 E FAWSETT ROAD
For Sale
$2,250,000
House
5 bds · 4 ba · 2,889 sqft
SYLVAN HEIGHTS, WINTER PARK
240 N PHELPS AVENUE