Florida, Winter Park Houses For Sale — from $300K | 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
$395,000
House
3 bds · 2 ba · 1,346 sqft
ROSEMERE SEC 02, ORLANDO
24 E PRINCETON ST
For Sale
$1,975,000
House
4 bds · 3 ba · 3,815 sqft
ROSE ISLE SEC 09, ORLANDO
2410 LAKE SHORE DRIVE
For Sale
$1,595,000
House
3 bds · 2 ba · 1,944 sqft
WINTER PARK, WINTER PARK
462 W LYMAN AVENUE
New
For Sale
$2,195,000
House
4 bds · 4 ba · 3,691 sqft
CONWILL ESTATES, WINTER PARK
1750 WALNUT AVENUE
New
For Sale
$375,000
House
4 bds · 2 ba · 1,776 sqft
WINTER WOODS UNIT 01, WINTER PARK
2189 SUSSEX ROAD
New
For Sale
$589,000
House
3 bds · 2 ba · 1,637 sqft
FAIRSHORES PLACE, WINTER PARK
2803 RIDDLE DRIVE
New
For Sale
$594,500
House
3 bds · 2 ba · 1,889 sqft
KENILWORTH SHORES SEC 07, WINTER PARK
2010 SUMMERFIELD ROAD
New
For Sale
$2,569,999
House
5 bds · 4 ba · 3,670 sqft
ORANGE GROVE SUB, WINTER PARK
1754 TAYLOR AVENUE
New
For Sale
$770,000
House
5 bds · 3 ba · 2,132 sqft
CARVER TOWN FIRST ADD, WINTER PARK
730 W SWOOPE AVENUE
New
For Sale
$2,549,000
House
5 bds · 4 ba · 3,479 sqft
LAKE KNOWLES TERRACE ADD 02, WINTER PARK
1823 SUNSET DRIVE
For Sale
$449,000
House
3 bds · 2 ba · 1,838 sqft
JUSTAMERE CAMP REP, WINTER PARK
2611 LOTAFUN AVENUE
For Sale
$459,000
House
3 bds · 2 ba · 1,128 sqft
ORWIN MANOR WESTMINSTER SEC, ORLANDO
3365 PELHAM ROAD
For Sale
$825,000
House
4 bds · 3 ba · 2,164 sqft
WINTER PARK PINES, WINTER PARK
722 S RANGER BOULEVARD
For Sale
$695,000
House
3 bds · 1 ba · 1,351 sqft
CONWILL ESTATES, WINTER PARK
1622 ARBOR PARK DRIVE
For Sale
$300,000
House
2 bds · 1 ba · 1,272 sqft
KAROLINA ON KILLARNEY, WINTER PARK
1960 BISCAYNE DRIVE
For Sale
$599,000
House
3 bds · 2 ba · 1,723 sqft
GLENCOE SUBDIVISION, WINTER PARK
2361 ROXBURY ROAD
For Sale
$1,695,000
House
4 bds · 4 ba · 3,723 sqft
CHARMONT, WINTER PARK
341 E READING WAY
For Sale
$470,000
House
3 bds · 1 ba · 1,508 sqft
PINES, WINTER PARK
2041 JEWELL AVENUE
For Sale
$4,900,000
House
5 bds · 5 ba · 4,961 sqft
WOODMERE TERRACE REP, WINTER PARK
1180 VIA LUGANO
-$170K
For Sale
$2,525,000
House
4 bds · 4 ba · 4,094 sqft
ROSE ISLE SEC 03, ORLANDO
2655 LAKE SHORE DRIVE