378 total properties
View 3130 SHIPWATCH DRIVE Holiday, FL MLS# TB8442547
  • Virtual Tour
1 of 18
$5,400,000
Studio

Beds

0.0

Baths

3130 SHIPWATCH DRIVE

Holiday, FL

Courtesy of FISCHBACH LAND COMPANY LLC
View 0 BERRY HILL ROAD Holiday, FL MLS# TB8507322
  • Recently Listed with Virtual Tour
1 of 45
$3,750,000
Studio

Beds

0.0

Baths

0 BERRY HILL ROAD

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY PORTFOLIO COLLECTION
View 2119 GRAND BOULEVARD Holiday, FL MLS# TB8404015
$2,700,000
22,814

Sq.Ft.

2119 GRAND BOULEVARD

Holiday, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View NO ADDRESS ASSIGNED Holiday, FL MLS# W7883129
  • Virtual Tour
1 of 6
$1,900,000
Studio

Beds

0.0

Baths

NO ADDRESS ASSIGNED

Holiday, FL

Courtesy of FUTURE HOME REALTY INC
View 1906 GULFVIEW DRIVE Holiday, FL MLS# TB8482035
$1,859,900
4

Beds

4.0

Baths

3,412

Sq.Ft.

1906 GULFVIEW DRIVE

Holiday, FL

Courtesy of BANNER INT'L REAL ESTATE
View 3143 PINEVIEW DRIVE Holiday, FL MLS# W7879730
  • Virtual Tour
1 of 93
$1,379,990
4

Beds

4.0

Baths

4,204

Sq.Ft.

3143 PINEVIEW DRIVE

Holiday, FL

Courtesy of RE/MAX CHAMPIONS
View 3114 BLUFF BOULEVARD Holiday, FL MLS# TB8486712
  • Virtual Tour
1 of 84
$1,265,000
3

Beds

3.0

Baths

3,234

Sq.Ft.

3114 BLUFF BOULEVARD

Holiday, FL

Courtesy of HOMEFRONT REALTY
View 1204 BAILLIES BLUFF ROAD Holiday, FL MLS# TB8510721
$899,000

1204 BAILLIES BLUFF ROAD

Holiday, FL

Courtesy of BENOOT REALTY
View 2008 US HIGHWAY 19 Holiday, FL MLS# W7883935
$895,000
4,744

Sq.Ft.

2008 US HIGHWAY 19

Holiday, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 000 BLUFF BOULEVARD Holiday, FL MLS# W7883578
  • Virtual Tour
1 of 9
$799,000
Studio

Beds

0.0

Baths

000 BLUFF BOULEVARD

Holiday, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 5001 WHIPPOORWILL DRIVE Holiday, FL MLS# W7884728
  • Virtual Tour
1 of 5
$799,000
Studio

Beds

0.0

Baths

5001 WHIPPOORWILL DRIVE

Holiday, FL

Courtesy of FI GREY & SON INC COMMERCIAL
View FLOTILLA Holiday, FL MLS# TB8498330
  • Virtual Tour
1 of 31
$799,000
Studio

Beds

0.0

Baths

FLOTILLA

Holiday, FL

Courtesy of RE/MAX ACTION FIRST OF FLORIDA
View 0 SILHOUETTE LANE Holiday, FL MLS# TB8320392
  • Virtual Tour
1 of 17
$699,900
Studio

Beds

0.0

Baths

0 SILHOUETTE LANE

Holiday, FL

Courtesy of PAPPAS REAL ESTATE LLC
View 3236 MADISON STREET Holiday, FL MLS# W7876795
$650,000
Studio

Beds

0.0

Baths

3236 MADISON STREET

Holiday, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 2401 SAND BAY DRIVE Holiday, FL MLS# TB8507031
  • Virtual Tour
1 of 44
$629,999
4

Beds

3.0

Baths

2,451

Sq.Ft.

2401 SAND BAY DRIVE

Holiday, FL

Courtesy of 3 POINT REAL ESTATE SOLUTION
View 1734 RUMAR LANE Holiday, FL MLS# P4937355
  • Virtual Tour
1 of 100
$610,000
6

Beds

4.0

Baths

3,384

Sq.Ft.

1734 RUMAR LANE

Holiday, FL

Courtesy of COLDWELL BANKER REALTY
View 0 BLUFF Holiday, FL MLS# TB8414141
  • Virtual Tour
1 of 11
$590,000
Studio

Beds

0.0

Baths

0 BLUFF

Holiday, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 5657 OCEANIC ROAD Holiday, FL MLS# A4692916
  • Virtual Tour
1 of 32
$579,000
4

Beds

4.0

Baths

3,553

Sq.Ft.

5657 OCEANIC ROAD

Holiday, FL

Courtesy of JOSEPH WALTER REALTY LLC
View 1914 OSWEGO DRIVE Holiday, FL MLS# W7883046
  • Virtual Tour
1 of 44
$575,000
5

Beds

3.0

Baths

3,072

Sq.Ft.

1914 OSWEGO DRIVE

Holiday, FL

Courtesy of INVESTMENT FLORIDA REALTY LLC
View 3025 SHEPPARDS CROOK COURT Holiday, FL MLS# TB8493709
$549,000
3

Beds

3.0

Baths

2,218

Sq.Ft.

3025 SHEPPARDS CROOK COURT

Holiday, FL

Courtesy of AZURE WATERFRONT REALTY, LLC

About Holiday

Listings in Holiday, FL

378

Estimated median home price

$239,950
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

Price Count
$0 - 100K 29
$100K - 200K 91
$200K - 300K 165
$300K - 400K 54
$400K - 500K 18
$500K - 600K 5
$600K - 700K 4
$700K - 800K 3
$800K - 900K 2
$900K - 1M 0
$1M - Max 7

Homes for Sale by Type in Holiday, FL

Property Type Count
Single Family 256
Townhouse 18
Condo 23
Commercial 4
Rental 75
Lots and Land 22
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 54
Farms 0

(Data as of 6/14/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 6/15/2026.