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® #: O6420593

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660 OSCEOLA AVENUE UNIT 101
WINTER PARK FL 32789
$9,500
3 Beds | 2.5 Baths | 2,714 SqFt
0 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® #: 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® #: 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® #: 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® #: O6410619

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2344 WOODCREST DRIVE
WINTER PARK FL 32792
$4,100
4 Beds | 2 Baths | 1,764 SqFt
0.26 Acres

MLS® #: O6423443

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3131 LOWNDES DRIVE
WINTER PARK FL 32792
$3,995
4 Beds | 2 Baths | 2,126 SqFt
0.18 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® #: 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® #: 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® #: 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

MLS #O6414626 image #0

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® #: 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® #: 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® #: O6423719

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508 DUNBLANE DRIVE
WINTER PARK FL 32792
$2,900
3 Beds | 2 Baths | 1,600 SqFt
0.22 Acres

MLS® #: O6421113

MLS #O6421113 image #0

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

MLS® #: O6408378

MLS #O6408378 image #0

1351 MERRYDALE WAY
WINTER PARK FL 32792
$2,875
3 Beds | 2.5 Baths | 1,755 SqFt
0.06 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-09-2026 12:13:16 PM.