Rental listings in Winter Park FL

MLS® #: O6395037

MLS #O6395037 image #0

1814 BARKER DRIVE
WINTER PARK FL 32789
$10,000
5 Beds | 4 Baths | 4,200 SqFt
0.28 Acres

MLS® #: O6419042

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2234 HOWARD DRIVE
WINTER PARK FL 32789
$8,295
4 Beds | 5.5 Baths | 3,295 SqFt
0.2 Acres

MLS® #: O6386721

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2075 JEWELL AVENUE
WINTER PARK FL 32789
$6,600
5 Beds | 4 Baths | 2,918 SqFt
0.25 Acres

MLS® #: O6418569

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501 W CANTON AVENUE
WINTER PARK FL 32789
$6,500
3 Beds | 2.5 Baths | 2,372 SqFt
0.07 Acres

MLS® #: O6385827

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301 W COMSTOCK AVENUE
WINTER PARK FL 32789
$6,000
2 Beds | 2.5 Baths | 1,500 SqFt
0.44 Acres

MLS® #: O6373029

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1049 N KENTUCKY AVENUE
WINTER PARK FL 32789
$6,000
3 Beds | 2.5 Baths | 2,112 SqFt
0.07 Acres

MLS® #: O6408937

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784 S PENNSYLVANIA AVENUE
WINTER PARK FL 32789
$5,500
3 Beds | 2.5 Baths | 1,940 SqFt
0.06 Acres

MLS® #: O6380197

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782 S PENNSYLVANIA AVENUE UNIT 1
WINTER PARK FL 32789
$5,490
3 Beds | 2.5 Baths | 2,354 SqFt
0.38 Acres

MLS® #: O6420234

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1791 SPRUCE AVENUE
WINTER PARK FL 32789
$4,900
3 Beds | 2 Baths | 1,776 SqFt
0.22 Acres

MLS® #: O6415814

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418 R GILBERT ROAD
WINTER PARK FL 32792
$4,000
3 Beds | 3 Baths | 1,680 SqFt
0.21 Acres

MLS® #: O6406209

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7864 BROKEN ARROW TRAIL
WINTER PARK FL 32792
$3,400
4 Beds | 2.5 Baths | 2,219 SqFt
0.56 Acres

MLS® #: O6406909

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1843 SHADYHILL TERRACE
WINTER PARK FL 32792
$3,300
4 Beds | 2.5 Baths | 1,891 SqFt
0.18 Acres

MLS® #: O6411306

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640 N PARK AVENUE UNIT 5
WINTER PARK FL 32789
$3,200
1 Beds | 1 Baths | 673 SqFt
0.02 Acres

MLS® #: O6422217

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2251 NAIRN DRIVE
WINTER PARK FL 32792
$3,200
4 Beds | 2.5 Baths | 1,978 SqFt
0.2 Acres

MLS® #: O6396001

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438 LAKEVIEW AVENUE
WINTER PARK FL 32789
$3,200
2 Beds | 1 Baths | 1,250 SqFt
0.17 Acres

MLS® #: O6421116

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240 ORANGE TERRACE DRIVE
WINTER PARK FL 32789
$3,000
4 Beds | 2 Baths | 1,718 SqFt
0.25 Acres

MLS® #: O6414626

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1137 SOUTH PENNSYLVANIA AVENUE
WINTER PARK FL 32789
$2,995
3 Beds | 2 Baths | 1,500 SqFt
0.21 Acres

MLS® #: O6407196

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3463 ARNEL DRIVE
WINTER PARK FL 32792
$2,950
3 Beds | 2 Baths | 1,770 SqFt
0.19 Acres

MLS® #: GC538622

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540 W COMSTOCK AVENUE
WINTER PARK FL 32789
$2,900
3 Beds | 1 Baths | 1,056 SqFt
0.16 Acres

MLS® #: O6421113

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1463 E BROOKSHIRE COURT
WINTER PARK FL 32792
$2,900
3 Beds | 2.5 Baths | 1,673 SqFt
0.17 Acres

MLS® #: S5152229

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2028 SUSSEX ROAD
WINTER PARK FL 32792
$2,900
3 Beds | 2 Baths | 1,674 SqFt
0.41 Acres

MLS® #: O6412826

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2233 SHADOWLAND LOOP
WINTER PARK FL 32792
$2,900
3 Beds | 2.5 Baths | 2,312 SqFt
0.08 Acres

MLS® #: O6408378

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1351 MERRYDALE WAY
WINTER PARK FL 32792
$2,875
3 Beds | 2.5 Baths | 1,755 SqFt
0.06 Acres

MLS® #: O6410414

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1404 CLAY STREET
WINTER PARK FL 32789
$2,800
3 Beds | 2 Baths | 1,440 SqFt
0.21 Acres

The data relating to real estate for sale on this site comes from Stellar MLS. All properties are subject to prior sale, changes, or withdrawal.
This site was last updated Jul-05-2026 10:09:09 PM.