Winter Haven Florida Homes for Rent

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View 560 REGGIE ROAD Winter Haven, FL MLS# O6456547
  • Recently Listed with Virtual Tour
1 of 63
$2,150
4

Beds

2.0

Baths

1,933

Sq.Ft.

560 REGGIE ROAD

Winter Haven, FL

Courtesy of GARCIA REALTY GROUP
View 3051 CAPTAIN JAX WAY Winter Haven, FL MLS# O6457058
  • Recently Listed with Virtual Tour
1 of 34
$2,000
3

Beds

2.1

Baths

1,386

Sq.Ft.

3051 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of NEWKEY REAL ESTATE LLC
View 1450 AUSTIN STREET Winter Haven, FL MLS# S5161170
  • Recently Listed with Virtual Tour
1 of 27
$2,500
4

Beds

3.0

Baths

2,509

Sq.Ft.

1450 AUSTIN STREET

Winter Haven, FL

Courtesy of AGENT TRUST REALTY CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 5441 CHANDLER DRIVE Winter Haven, FL MLS# O6456504
  • Recently Listed with Virtual Tour
1 of 39
$2,100
4

Beds

3.1

Baths

3,034

Sq.Ft.

5441 CHANDLER DRIVE

Winter Haven, FL

Courtesy of RENT A FLORIDA HOME
View 347 8TH STREET NE Winter Haven, FL MLS# TB8566854
  • Recently Listed with Virtual Tour
1 of 13
$1,530
3

Beds

2.0

Baths

1,320

Sq.Ft.

347 8TH STREET NE

Winter Haven, FL

Courtesy of PALM LEAF PROPERTY MANAGEMENT
View 5850 CYPRESS GARDENS BOULEVARD 607 Winter Haven, FL MLS# P4940431
  • Recently Listed with Virtual Tour
1 of 25
$1,400
2

Beds

1.1

Baths

1,260

Sq.Ft.

5850 CYPRESS GARDENS BOULEVARD 607

Winter Haven, FL

Courtesy of BROKERS REALTY OF CENTRAL FLOR
View 1798 WHITE ELEPHANT LOOP Winter Haven, FL MLS# O6456474
  • Recently Listed with Virtual Tour
1 of 54
$2,290
3

Beds

2.0

Baths

1,526

Sq.Ft.

1798 WHITE ELEPHANT LOOP

Winter Haven, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 2407 WILLOW WAY Winter Haven, FL MLS# S5161056
  • Recently Listed with Virtual Tour
1 of 32
$1,795
3

Beds

2.1

Baths

1,625

Sq.Ft.

2407 WILLOW WAY

Winter Haven, FL

Courtesy of TRANSCEND REALTY
View 2500 21ST STREET NW 15 Winter Haven, FL MLS# S5161070
  • Recently Listed with Virtual Tour
1 of 26
$1,750
2

Beds

2.1

Baths

1,184

Sq.Ft.

2500 21ST STREET NW 15

Winter Haven, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 1450 HAINES DRIVE Winter Haven, FL MLS# O6456271
  • Recently Listed with Virtual Tour
1 of 20
$2,500
4

Beds

2.0

Baths

2,232

Sq.Ft.

1450 HAINES DRIVE

Winter Haven, FL

Courtesy of EMAJIN REALTY LLC
View 2802 W LAKE ELOISE DRIVE Winter Haven, FL MLS# P4940390
  • Recently Listed with Virtual Tour
1 of 24
$1,125
1

Beds

1.0

Baths

500

Sq.Ft.

2802 W LAKE ELOISE DRIVE

Winter Haven, FL

Courtesy of JULIE MATTHEWS GROUP LLC
View 5860 WINDRIDGE DRIVE Winter Haven, FL MLS# S5160922
$2,200
4

Beds

2.0

Baths

1,836

Sq.Ft.

5860 WINDRIDGE DRIVE

Winter Haven, FL

Courtesy of HONEST EXPERTS REAL ESTATE LLC
View 1416 ENGELBERG STREET Winter Haven, FL MLS# O6455756
  • Recently Listed with Virtual Tour
1 of 25
$2,150
3

Beds

2.0

Baths

1,585

Sq.Ft.

1416 ENGELBERG STREET

Winter Haven, FL

Courtesy of VESTI LLC
View 400 EL CAMINO DRIVE 220 Winter Haven, FL MLS# P4940385
  • Recently Listed with Virtual Tour
1 of 12
$1,050
1

Beds

1.0

Baths

705

Sq.Ft.

400 EL CAMINO DRIVE 220

Winter Haven, FL

Courtesy of PROPERTY MANAGEMENT OF POLK
View 209 WHITMAN ROAD Winter Haven, FL MLS# P4940369
  • Recently Listed with Virtual Tour
1 of 28
$2,700
4

Beds

4.0

Baths

1,942

Sq.Ft.

209 WHITMAN ROAD

Winter Haven, FL

Courtesy of PROPERTY MANAGEMENT OF POLK
View 616 SHAMAN COURT Winter Haven, FL MLS# L4966273
$3,500
4

Beds

3.0

Baths

2,390

Sq.Ft.

616 SHAMAN COURT

Winter Haven, FL

Courtesy of RE/MAX EXPERTS
View 29 ENCLAVE DRIVE Winter Haven, FL MLS# L4966234
  • Recently Listed with Virtual Tour
1 of 25
$1,995
3

Beds

2.0

Baths

1,526

Sq.Ft.

29 ENCLAVE DRIVE

Winter Haven, FL

Courtesy of LOCKHART & ASSOCIATES INC
View 922 MARTIN LUTHER KING BOULEVARD NE Winter Haven, FL MLS# O6455197
  • Recently Listed with Virtual Tour
1 of 14
$1,700
3

Beds

1.1

Baths

1,160

Sq.Ft.

922 MARTIN LUTHER KING BOULEVARD NE

Winter Haven, FL

Courtesy of AROD PARTNERS REALTY
View 3008 SAINT PAUL DRIVE 3014 Winter Haven, FL MLS# S5160671
  • Recently Listed with Virtual Tour
1 of 6
$1,349
2

Beds

1.0

Baths

914

Sq.Ft.

3008 SAINT PAUL DRIVE 3014

Winter Haven, FL

Courtesy of ADAN INVESTMENTS REAL ESTATE GROUP, PLLC
View 3055 CAPTAIN JAX WAY Winter Haven, FL MLS# S5160682
  • Recently Listed with Virtual Tour
1 of 13
$2,050
3

Beds

2.1

Baths

1,386

Sq.Ft.

3055 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of MELIN REALTY LLC

About Winter Haven

Listings in Winter Haven, FL

1,095

Estimated median home price

$279,900
Winter Haven FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Haven, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Haven, FL.

Homes for Sale by Price in Winter Haven, FL

PriceCount
$0 - 100K60
$100K - 200K191
$200K - 300K410
$300K - 400K276
$400K - 500K63
$500K - 600K24
$600K - 700K14
$700K - 800K17
$800K - 900K4
$900K - 1M7
$1M - Max29

Homes for Sale by Type in Winter Haven, FL

Property TypeCount
Single Family793
Townhouse47
Condo73
Commercial22
Rental259
Lots and Land70
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home78
Farms0

(Data as of 11/13/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 11/13/2026.