Florida, Winter Park Waterfront Houses For Sale — from $699K | Broker One

Waterfront Houses For Sale in Florida, Winter Park

Browse waterfront Houses For Sale in Florida, Winter Park — canal-front, bay-front, and oceanfront properties with dock access, water views, and direct ocean access. Filter by price, bedrooms, lot size, and waterfront type.

Waterfront living in Florida, Winter Park

Waterfront homes in Florida, Winter Park range from canal-front properties with private docks to luxury estates on open water. Many include boat lifts, seawalls, and direct access to Biscayne Bay or the Intracoastal Waterway. Waterfront properties typically command a 30-60% premium over comparable inland homes.

What to check on waterfront properties

Verify seawall condition, dock permits, flood zone designation, and elevation certificate before buying. Waterfront homes in South Florida require flood insurance — check FEMA zone maps and recent claims history. Our listings include flood zone data and property details to help you evaluate risk.

New
For Sale
$1,650,000
House
3 bds · 4 ba · 2,467 sqft
SOUTH LAKEMONT SHORES, WINTER PARK
1841 LAKE SPIER DRIVE
For Sale
$699,000
House
3 bds · 2 ba · 1,467 sqft
ALBERT LEE RIDGE ADD 02, WINTER PARK
1009 LAKE BELL DRIVE
For Sale
$1,795,000
House
3 bds · 3 ba · 2,351 sqft
SHERIDAN PLACE, MAITLAND
631 LAKE CATHERINE DRIVE
For Sale
$3,895,000
House
4 bds · 4 ba · 5,347 sqft
SYBELIA SHORES SECOND ADD, MAITLAND
747 N LAKE SYBELIA DRIVE
For Sale
$2,395,000
House
5 bds · 3 ba · 3,456 sqft
FRIES PARK HOUSE PROP, MAITLAND
530 LAKE CATHERINE DRIVE
-$105K
For Sale
$1,790,000
House
4 bds · 5 ba · 4,478 sqft
LAKE COLONY PH 02, MAITLAND
1244 E LAKE COLONY DRIVE
For Sale
$1,350,000
House
3 bds · 2 ba · 1,750 sqft
SOUTH LAKEMONT SHORES, WINTER PARK
1881 LAKE SPIER DRIVE
-$140K
For Sale
$960,000
House
3 bds · 2 ba · 2,021 sqft
ACREAGE & UNREC, MAITLAND
790 S LAKE SYBELIA DRIVE
For Sale
$6,900,000
House
6 bds · 5 ba · 6,396 sqft
J KRONENBERGER SUB, WINTER PARK
1260 ALABAMA DRIVE
-$370K
For Sale
$1,825,000
House
4 bds · 3 ba · 3,754 sqft
MAITLAND COVE, MAITLAND
1111 AUDUBON WAY
For Sale
$1,595,000
House
3 bds · 2 ba · 2,012 sqft
TUSCANY TERRACE, WINTER PARK
1113 VIA DEL MAR
For Sale
$8,950,000
House
7 bds · 9 ba · 11,255 sqft
WINDSONG-PRESERVE POINT, WINTER PARK
1120 PRESERVE POINT DRIVE
-$24K
For Sale
$925,000
House
2 bds · 2 ba · 1,086 sqft
KILLARNEY CIRCLE, WINTER PARK
560 OLOLU DRIVE
-$930K
For Sale
$5,250,000
House
5 bds · 6 ba · 7,278 sqft
MAITLAND SHORES, Winter Park
2211 Azalea Pl, Winter Park FL 32789
-$930K
For Sale
$5,250,000
House
5 bds · 6 ba · 7,278 sqft
MAITLAND SHORES, WINTER PARK
2211 AZALEA PLACE
For Sale
$12,500,000
House
6 bds · 7 ba · 10,172 sqft
LAKE MAITLAND MANOR, Winter Park
570 Manor Rd, Maitland, Winter Park FL 32751
For Sale
$12,500,000
House
6 bds · 7 ba · 11,668 sqft
LAKE MAITLAND MANOR, MAITLAND
570 MANOR ROAD