View 1850 HESS DRIVE Holiday, FL MLS# TB8445330
  • Virtual Tour
1 of 36
$175,900
3

Beds

2.0

Baths

1,152

Sq.Ft.

1850 HESS DRIVE

Holiday, FL

Courtesy of PENNY GOULD REALTY INC
View 3207 BREWSTER DRIVE Holiday, FL MLS# TB8444939
  • Adult Community with Virtual Tour
1 of 32
$164,900
2

Beds

2.0

Baths

864

Sq.Ft.

3207 BREWSTER DRIVE

Holiday, FL

Courtesy of CITY BREEZE ACTION REALTY
View 3518 EMORY DRIVE Holiday, FL MLS# TB8444920
  • Virtual Tour
1 of 29
$189,000
2

Beds

1.0

Baths

840

Sq.Ft.

3518 EMORY DRIVE

Holiday, FL

Courtesy of FUTURE HOME REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 3968 SAILMAKER LANE 3968 Holiday, FL MLS# W7880153
  • Adult Community with Virtual Tour
1 of 70
$169,900
2

Beds

2.0

Baths

1,318

Sq.Ft.

3968 SAILMAKER LANE 3968

Holiday, FL

Courtesy of RE/MAX MARKETING SPECIALISTS
View 3437 WILTSHIRE DRIVE Holiday, FL MLS# TB8443918
$199,000
2

Beds

1.0

Baths

988

Sq.Ft.

3437 WILTSHIRE DRIVE

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 3116 FAIRMOUNT DRIVE Holiday, FL MLS# W7880307
  • Virtual Tour
1 of 28
$200,000
2

Beds

1.1

Baths

1,094

Sq.Ft.

3116 FAIRMOUNT DRIVE

Holiday, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 3317 CHATFORD DRIVE Holiday, FL MLS# TB8440816
  • Adult Community with Virtual Tour
1 of 60
$145,000
2

Beds

2.0

Baths

1,344

Sq.Ft.

3317 CHATFORD DRIVE

Holiday, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 5817 ELENA DRIVE Holiday, FL MLS# O6355360
  • Virtual Tour
1 of 30
OPEN HOUSE: Friday 1/2 8:00 AM - 7:00 PM
$198,000
2

Beds

1.0

Baths

936

Sq.Ft.

5817 ELENA DRIVE

Holiday, FL

Courtesy of OPENDOOR BROKERAGE LLC
View 3409 BRIAR CLIFF DRIVE Holiday, FL MLS# TB8438139
$190,000
2

Beds

1.0

Baths

908

Sq.Ft.

3409 BRIAR CLIFF DRIVE

Holiday, FL

Courtesy of TOPAZ REALTY LLC
View 3253 MASONVILLE LOOP Holiday, FL MLS# TB8433193
$199,900
2

Beds

1.0

Baths

988

Sq.Ft.

3253 MASONVILLE LOOP

Holiday, FL

Courtesy of OFFERPAD BROKERAGE FL, LLC
View 1542 DERRICK STREET Holiday, FL MLS# W7879895
$199,900
2

Beds

1.0

Baths

1,188

Sq.Ft.

1542 DERRICK STREET

Holiday, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 2122 WATERVIEW DRIVE Holiday, FL MLS# W7879736
  • Adult Community with Virtual Tour
1 of 39
$145,000
2

Beds

2.0

Baths

936

Sq.Ft.

2122 WATERVIEW DRIVE

Holiday, FL

Courtesy of BAM REALTY ADVISORS INC
View 3041 Fairmount Drive Holiday, FL MLS# 2255936
$195,000
2

Beds

1.1

Baths

986

Sq.Ft.

3041 Fairmount Drive

Holiday, FL

Courtesy of REMAX MARKETING SPECIALISTS
View 3041 FAIRMOUNT DRIVE Holiday, FL MLS# W7879373
  • Virtual Tour
1 of 25
$195,000
2

Beds

1.1

Baths

986

Sq.Ft.

3041 FAIRMOUNT DRIVE

Holiday, FL

Courtesy of RE/MAX MARKETING SPECIALISTS
View 5050 BILLINGS DRIVE Holiday, FL MLS# W7879088
  • Virtual Tour
1 of 29
$189,000
2

Beds

2.0

Baths

1,185

Sq.Ft.

5050 BILLINGS DRIVE

Holiday, FL

Courtesy of RE/MAX CHAMPIONS
View 2012 MAUI DRIVE Holiday, FL MLS# TB8429270
  • Adult Community with Virtual Tour
1 of 34
$168,000
2

Beds

2.0

Baths

1,056

Sq.Ft.

2012 MAUI DRIVE

Holiday, FL

Courtesy of PROPERTY LEADERS RE INC
View 1313 CHANCELLOR DRIVE Holiday, FL MLS# TB8426910
$199,000
2

Beds

1.1

Baths

953

Sq.Ft.

1313 CHANCELLOR DRIVE

Holiday, FL

Courtesy of KELLER WILLIAMS SUBURBAN TAMPA
View 2045 KONA DRIVE Holiday, FL MLS# TB8424801
  • Adult Community with Virtual Tour
1 of 60
$150,000
2

Beds

2.0

Baths

1,100

Sq.Ft.

2045 KONA DRIVE

Holiday, FL

Courtesy of HOMEFRONT REALTY
View 4140 CASTLEWOOD DRIVE Holiday, FL MLS# TB8424713
$185,000
2

Beds

2.0

Baths

1,232

Sq.Ft.

4140 CASTLEWOOD DRIVE

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 4848 COLONNADE AVENUE Holiday, FL MLS# O6340883
$184,000
2

Beds

1.0

Baths

831

Sq.Ft.

4848 COLONNADE AVENUE

Holiday, FL

Courtesy of OPENDOOR BROKERAGE LLC

About Holiday

Listings in Holiday, FL

379

Estimated median home price

$234,900
Holiday FL Homes for Sale & Properties

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

Homes for Sale by Price in Holiday, FL

PriceCount
$0 - 100K24
$100K - 200K102
$200K - 300K162
$300K - 400K53
$400K - 500K21
$500K - 600K5
$600K - 700K5
$700K - 800K1
$800K - 900K0
$900K - 1M1
$1M - Max5

Homes for Sale by Type in Holiday, FL

Property TypeCount
Single Family256
Townhouse5
Condo31
Commercial9
Rental74
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home52
Farms0

(Data as of 1/2/2026)

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.

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 1/3/2026.