View 4209 CASTLEWOOD DR Holiday, FL MLS# 226002466
$215,950
2

Beds

2.0

Baths

1,257

Sq.Ft.

4209 CASTLEWOOD DR

Holiday, FL

Naples_Area_Board_of_Realtors
View 2033 MAUI DRIVE Holiday, FL MLS# TB8461374
  • Adult Community with Virtual Tour
1 of 58
$125,000
2

Beds

2.0

Baths

1,056

Sq.Ft.

2033 MAUI DRIVE

Holiday, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View Lot 1511 JACKSON DRIVE Holiday, FL MLS# TB8465494
$90,000
Studio

Beds

0.0

Baths

Lot 1511 JACKSON DRIVE

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY PORTFOLIO COLLECTION
The time to sell is now! THE TIME TO SELL IS NOW!
View 2616 GRETNA PLACE Holiday, FL MLS# W7882024
$220,000
2

Beds

1.1

Baths

1,096

Sq.Ft.

2616 GRETNA PLACE

Holiday, FL

Courtesy of F I GREY & SON RESIDENTIAL
View 2907 FEATHERSTONE DRIVE Holiday, FL MLS# W7881997
$194,900
2

Beds

2.0

Baths

1,159

Sq.Ft.

2907 FEATHERSTONE DRIVE

Holiday, FL

Courtesy of HOMETRUST REALTY GROUP
View 2047 KEPNER DRIVE Holiday, FL MLS# O6372727
  • Virtual Tour
1 of 33
$85,000
2

Beds

1.1

Baths

624

Sq.Ft.

2047 KEPNER DRIVE

Holiday, FL

Courtesy of UNITED REALTY GROUP INC
View 3711 ELMWOOD DRIVE Holiday, FL MLS# TB8463595
  • Virtual Tour
1 of 42
$205,000
2

Beds

2.0

Baths

1,096

Sq.Ft.

3711 ELMWOOD DRIVE

Holiday, FL

Courtesy of COASTAL PROPERTIES GROUP INTER
View 3849 STAYSAIL LANE Holiday, FL MLS# TB8463014
  • Adult Community with Virtual Tour
1 of 38
$149,900
2

Beds

2.0

Baths

1,318

Sq.Ft.

3849 STAYSAIL LANE

Holiday, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 1821 KNOLLWOOD DRIVE Holiday, FL MLS# W7881764
  • Virtual Tour
1 of 16
$199,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

1821 KNOLLWOOD DRIVE

Holiday, FL

Courtesy of DALTON WADE INC
View 2331 BARON DRIVE Holiday, FL MLS# TB8459753
  • Adult Community with Virtual Tour
1 of 8
$78,000
2

Beds

2.0

Baths

960

Sq.Ft.

2331 BARON DRIVE

Holiday, FL

Courtesy of EZ CHOICE REALTY
View 3245 FAIRMOUNT TERRACE Holiday, FL MLS# V4946300
$172,000
2

Beds

1.0

Baths

970

Sq.Ft.

3245 FAIRMOUNT TERRACE

Holiday, FL

Courtesy of TROPIC SHORES REALTY LLC
View 3245 Fairmount Drive Holiday, FL MLS# 2257086
$172,000
2

Beds

2.0

Baths

970

Sq.Ft.

3245 Fairmount Drive

Holiday, FL

Courtesy of TROPIC SHORES REALTY LLC
View 1934 SHADY COVE Holiday, FL MLS# W7881395
  • Virtual Tour
1 of 25
$90,000
2

Beds

2.0

Baths

1,108

Sq.Ft.

1934 SHADY COVE

Holiday, FL

Courtesy of RE/MAX CHAMPIONS
View 5124 DARLINGTON ROAD Holiday, FL MLS# TB8455401
  • Adult Community with Virtual Tour
1 of 27
$140,000
2

Beds

2.0

Baths

960

Sq.Ft.

5124 DARLINGTON ROAD

Holiday, FL

Courtesy of INSPIRED REALTY, LLC
View 1044 BOWSPRIT LANE Holiday, FL MLS# TB8454818
  • Adult Community with Virtual Tour
1 of 26
$99,900
2

Beds

2.0

Baths

1,114

Sq.Ft.

1044 BOWSPRIT LANE

Holiday, FL

Courtesy of HOMEFRONT REALTY
View 1205 CALVARY ROAD Holiday, FL MLS# TB8455069
$225,000
3

Beds

2.0

Baths

1,701

Sq.Ft.

1205 CALVARY ROAD

Holiday, FL

Courtesy of EXP REALTY LLC
View 2400 LEMUR DRIVE Holiday, FL MLS# W7881222
  • Adult Community with Virtual Tour
1 of 39
$165,000
4

Beds

2.0

Baths

1,620

Sq.Ft.

2400 LEMUR DRIVE

Holiday, FL

Courtesy of CITY BREEZE ACTION REALTY
View 4723 AEGEAN AVENUE Holiday, FL MLS# C7518608
$199,000
2

Beds

1.0

Baths

956

Sq.Ft.

4723 AEGEAN AVENUE

Holiday, FL

Courtesy of SOVEREIGN REAL ESTATE GROUP
View 2135 WATERVIEW DRIVE Holiday, FL MLS# TB8453359
  • Adult Community with Virtual Tour
1 of 43
$139,900
2

Beds

2.0

Baths

984

Sq.Ft.

2135 WATERVIEW DRIVE

Holiday, FL

Courtesy of SELECT REAL ESTATE OF PINELLAS
View 3706 CHESWICK DRIVE Holiday, FL MLS# O6364249
  • Virtual Tour
1 of 27
$198,000
2

Beds

1.1

Baths

1,036

Sq.Ft.

3706 CHESWICK DRIVE

Holiday, FL

Courtesy of OPENDOOR BROKERAGE LLC

About Holiday

Listings in Holiday, FL

413

Estimated median home price

$232,499
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 - 100K41
$100K - 200K101
$200K - 300K173
$300K - 400K60
$400K - 500K16
$500K - 600K6
$600K - 700K4
$700K - 800K3
$800K - 900K2
$900K - 1M1
$1M - Max6

Homes for Sale by Type in Holiday, FL

Property TypeCount
Single Family277
Townhouse13
Condo26
Commercial5
Rental77
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home67
Farms0

(Data as of 4/28/2026)

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 4/29/2026.