View 265 MEADOWBROOK BOULEVARD Winter Haven, FL MLS# S5147785
$239,990
3

Beds

2.0

Baths

1,426

Sq.Ft.

265 MEADOWBROOK BOULEVARD

Winter Haven, FL

Courtesy of LPT REALTY, LLC
View 4038 ROLLING OAKS DRIVE Winter Haven, FL MLS# B4902243
  • Recently Listed with Virtual Tour
1 of 5
$94,900
2

Beds

2.0

Baths

1,056

Sq.Ft.

4038 ROLLING OAKS DRIVE

Winter Haven, FL

Courtesy of SOUTHERN BELLE REALTY
View 283 WINTER RIDGE BOULEVARD 283 Winter Haven, FL MLS# L4961145
  • Recently Listed with Virtual Tour
1 of 20
$147,500
2

Beds

2.0

Baths

1,073

Sq.Ft.

283 WINTER RIDGE BOULEVARD 283

Winter Haven, FL

Courtesy of ENGEL & VOELKERS LAKELAND
The time to sell is now! THE TIME TO SELL IS NOW!
View 26-28-22-000000-034060 BUCKEYE ROAD Winter Haven, FL MLS# A4690806
$69,000
Studio

Beds

0.0

Baths

26-28-22-000000-034060 BUCKEYE ROAD

Winter Haven, FL

Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE
View 3040 CAPTAIN JAX WAY Winter Haven, FL MLS# O6400954
  • Recently Listed with Virtual Tour
1 of 22
$252,490
3

Beds

2.1

Baths

1,423

Sq.Ft.

3040 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of LENNAR REALTY
View 3060 CAPTAIN JAX WAY Winter Haven, FL MLS# O6400964
  • Recently Listed with Virtual Tour
1 of 22
$247,490
3

Beds

2.1

Baths

1,423

Sq.Ft.

3060 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of LENNAR REALTY
View 6002 GRAND OAKS DRIVE SE Winter Haven, FL MLS# P4938477
  • Recently Listed with Virtual Tour
1 of 33
$135,000
2

Beds

2.0

Baths

1,260

Sq.Ft.

6002 GRAND OAKS DRIVE SE

Winter Haven, FL

Courtesy of JUDY B CLEAVES PROPERTIES INC
View 323 ORANGE BLOSSOM DRIVE 323 Winter Haven, FL MLS# P4938498
  • Recently Listed with Virtual Tour
1 of 30
$209,900
2

Beds

2.1

Baths

1,280

Sq.Ft.

323 ORANGE BLOSSOM DRIVE 323

Winter Haven, FL

Courtesy of CROSBY & ASSOCIATES, INC.
View 3044 CAPTAIN JAX WAY Winter Haven, FL MLS# O6401015
  • Recently Listed with Virtual Tour
1 of 20
$227,490
3

Beds

2.1

Baths

1,386

Sq.Ft.

3044 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of LENNAR REALTY
View 3048 CAPTAIN JAX WAY Winter Haven, FL MLS# O6401056
  • Recently Listed with Virtual Tour
1 of 20
$227,490
3

Beds

2.1

Baths

1,386

Sq.Ft.

3048 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of LENNAR REALTY
View 3056 CAPTAIN JAX WAY Winter Haven, FL MLS# O6401065
  • Recently Listed with Virtual Tour
1 of 20
$227,490
3

Beds

2.1

Baths

1,386

Sq.Ft.

3056 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of LENNAR REALTY
View 3052 CAPTAIN JAX WAY Winter Haven, FL MLS# O6401061
  • Recently Listed with Virtual Tour
1 of 20
$227,490
3

Beds

2.1

Baths

1,386

Sq.Ft.

3052 CAPTAIN JAX WAY

Winter Haven, FL

Courtesy of LENNAR REALTY
View 731 30TH STREET NW Winter Haven, FL MLS# S5148315
  • Recently Listed with Virtual Tour
1 of 32
$230,000
3

Beds

2.0

Baths

1,343

Sq.Ft.

731 30TH STREET NW

Winter Haven, FL

Courtesy of RE/MAX HERITAGE PROFESSIONALS
View 3834 AVENUE O NW Winter Haven, FL MLS# P4938516
  • Recently Listed with Virtual Tour
1 of 19
$135,000
1

Beds

1.0

Baths

480

Sq.Ft.

3834 AVENUE O NW

Winter Haven, FL

Courtesy of KELLER WILLIAMS REALTY SMART 1
View 6114 GRAND OAKS DRIVE SE Winter Haven, FL MLS# L4961323
  • Recently Listed with Virtual Tour
1 of 43
$175,000
2

Beds

2.0

Baths

1,288

Sq.Ft.

6114 GRAND OAKS DRIVE SE

Winter Haven, FL

Courtesy of CROSBY & ASSOCIATES, INC.
View 3420 AVENUE R NW Winter Haven, FL MLS# S5148239
  • Recently Listed with Virtual Tour
1 of 14
$215,000
2

Beds

1.0

Baths

672

Sq.Ft.

3420 AVENUE R NW

Winter Haven, FL

Courtesy of LPT REALTY, LLC
View 1213 8TH STREET NW Winter Haven, FL MLS# L4961397
  • Recently Listed with Virtual Tour
1 of 25
$199,900
2

Beds

2.0

Baths

972

Sq.Ft.

1213 8TH STREET NW

Winter Haven, FL

Courtesy of KELLER WILLIAMS REALTY SMART
View 4925 CYPRESS GARDENS ROAD 20 Winter Haven, FL MLS# P4938460
  • Adult Community with Virtual Tour
1 of 49
$60,000
2

Beds

1.0

Baths

378

Sq.Ft.

4925 CYPRESS GARDENS ROAD 20

Winter Haven, FL

Courtesy of COLDWELL BANKER REALTY
View 212 SE H SE Winter Haven, FL MLS# S5148125
  • Recently Listed with Virtual Tour
1 of 21
$189,990
3

Beds

2.0

Baths

1,136

Sq.Ft.

212 SE H SE

Winter Haven, FL

Courtesy of G FIRST REALTY LLC
View 2208 SAN MARCOS CIRCLE SE Winter Haven, FL MLS# P4938481
  • Recently Listed with Virtual Tour
1 of 29
$200,000
2

Beds

2.0

Baths

1,224

Sq.Ft.

2208 SAN MARCOS CIRCLE SE

Winter Haven, FL

Courtesy of BROKERS REALTY OF CENTRAL FLOR

About Winter Haven

Listings in Winter Haven, FL

1,191

Estimated median home price

$289,900
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 - 100K64
$100K - 200K187
$200K - 300K437
$300K - 400K327
$400K - 500K79
$500K - 600K24
$600K - 700K16
$700K - 800K22
$800K - 900K4
$900K - 1M6
$1M - Max25

Homes for Sale by Type in Winter Haven, FL

Property TypeCount
Single Family871
Townhouse31
Condo68
Commercial28
Rental196
Lots and Land67
Condo/Town/CoOp0
CoOp0
Multi Family20
Mobile Home105
Farms0

(Data as of 5/4/2026)

Information deemed reliable but not guaranteed.

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

Copyright 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved.

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

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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

Data is updated as of 5/4/2026.

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 5/4/2026.