Florida, Winter Park Houses For Sale — from $299K | 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
$1,495,000
House
3 bds · 2 ba · 2,080 sqft
CHARMONT, WINTER PARK
150 E READING WAY
New
For Sale
$475,000
House
2 bds · 2 ba · 1,438 sqft
WINTER PARK PINES REP, WINTER PARK
2824 PRINCE JOHN ROAD
New
For Sale
$1,375,000
House
4 bds · 2 ba · 2,676 sqft
BALDWIN PARK, ORLANDO
4036 HAWS LANE
-$11K
For Sale
$739,000
House
3 bds · 2 ba · 2,066 sqft
DOMMERICH ESTS 1ST ADD, MAITLAND
1761 TIPPICANOE TRAIL
New
For Sale
$1,875,000
House
3 bds · 3 ba · 3,127 sqft
CHARMONT, WINTER PARK
1661 LAUREL ROAD
New
For Sale
$950,000
House
5 bds · 3 ba · 3,379 sqft
OAKLEIGH THIRD ADD, MAITLAND
60 OAKLEIGH LANE
New
For Sale
$589,900
House
3 bds · 2 ba · 1,700 sqft
ELIZABETH HEIGHTS SUB, WINTER PARK
1313 S DENNING DRIVE
New
For Sale
$340,000
House
2 bds · 1 ba · 780 sqft
OLYMPIA HEIGHTS, WINTER PARK
1941 OGLESBY AVENUE
New
For Sale
$1,639,900
House
5 bds · 4 ba · 3,252 sqft
ANDERSON PARK, ORLANDO
2931 HELEN AVENUE
New
For Sale
$689,000
House
3 bds · 3 ba · 1,794 sqft
MAGNOLIA GARDENS SUB, WINTER PARK
900 CARVER STREET
New
For Sale
$675,000
House
3 bds · 1 ba · 1,243 sqft
WINTER PARK VILLAGE, WINTER PARK
1416 BORDER DRIVE
New
For Sale
$1,449,900
House
5 bds · 4 ba · 3,104 sqft
DUBSDREAD ADD, ORLANDO
515 W WINTER PARK STREET
New
For Sale
$899,000
House
3 bds · 2 ba · 2,022 sqft
LAKE KNOWLES TERRACE, WINTER PARK
1621 CHESTNUT AVENUE
New
For Sale
$1,574,900
House
5 bds · 4 ba · 3,252 sqft
LAWNDALE, WINTER PARK
1526 MILLER AVENUE
New
For Sale
$664,900
House
4 bds · 2 ba · 1,877 sqft
GLENCOE SUB, WINTER PARK
2333 WESTMINSTER COURT
New
For Sale
$3,999,000
House
5 bds · 5 ba · 4,891 sqft
PARK GROVE, WINTER PARK
1417 WILLIAMS DRIVE
For Sale
$299,000
House
3 bds · 1 ba · 1,208 sqft
RIDGE HIGH 1ST ADD, WINTER PARK
2168 RIDGE DRIVE
For Sale
$575,000
House
4 bds · 2 ba · 2,126 sqft
WINTER PARK ESTATES, WINTER PARK
2641 CARVELL COURT
For Sale
$439,000
House
3 bds · 2 ba · 1,494 sqft
LAKE BELL TERRACE, WINTER PARK
1955 ELAND AVENUE
For Sale
$2,950,000
House
5 bds · 5 ba · 3,501 sqft
BEVERLY SHORES, ORLANDO
1236 CHICHESTER STREET