358 total properties
View 3000 JACOB CROSSING LANE Holiday, FL MLS# TB8496091
$319,000
3

Beds

2.1

Baths

1,813

Sq.Ft.

3000 JACOB CROSSING LANE

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 3111 KILBURN ROAD Holiday, FL MLS# W7878400
  • Virtual Tour
1 of 32
$315,999
3

Beds

2.0

Baths

1,284

Sq.Ft.

3111 KILBURN ROAD

Holiday, FL

Courtesy of F I GREY & SON RESIDENTIAL
View 2211 PLEASANT HILL LANE Holiday, FL MLS# TB8485823
  • Adult Community with Virtual Tour
1 of 40
$315,000
2

Beds

2.0

Baths

1,500

Sq.Ft.

2211 PLEASANT HILL LANE

Holiday, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1050 DEAL LANE Holiday, FL MLS# O6391641
  • Virtual Tour
1 of 23
$315,000
3

Beds

3.0

Baths

1,667

Sq.Ft.

1050 DEAL LANE

Holiday, FL

Courtesy of DJ & LINDSEY REAL ESTATE
View 3429 DEVONSHIRE DRIVE Holiday, FL MLS# TB8497350
  • Virtual Tour
1 of 44
$315,000
4

Beds

3.0

Baths

1,572

Sq.Ft.

3429 DEVONSHIRE DRIVE

Holiday, FL

Courtesy of HOME PRIME REALTY LLC
View 1741 FAIRFIELD STREET Holiday, FL MLS# TB8498724
  • Virtual Tour
1 of 67
$315,000
4

Beds

3.0

Baths

1,882

Sq.Ft.

1741 FAIRFIELD STREET

Holiday, FL

Courtesy of EXP REALTY LLC
View 2406 ARCADIA ROAD Holiday, FL MLS# TB8508702
  • Recently Listed with Virtual Tour
1 of 8
$315,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

2406 ARCADIA ROAD

Holiday, FL

Courtesy of EXP REALTY LLC
View 2930 PLANTAIN DRIVE Holiday, FL MLS# W7884303
  • Adult Community with Virtual Tour
1 of 42
$309,111
2

Beds

2.0

Baths

1,341

Sq.Ft.

2930 PLANTAIN DRIVE

Holiday, FL

Courtesy of SANDPEAK REALTY
View 3339 HONEYMOON LANE Holiday, FL MLS# W7882785
  • Virtual Tour
1 of 34
$308,000
3

Beds

2.0

Baths

1,695

Sq.Ft.

3339 HONEYMOON LANE

Holiday, FL

Courtesy of SIRROM REALTY LLC
View 4803 GUARDIAN AVENUE Holiday, FL MLS# TB8487126
$307,900
3

Beds

3.0

Baths

1,712

Sq.Ft.

4803 GUARDIAN AVENUE

Holiday, FL

Courtesy of BUILDING NEST REALTY LLC
View 3530 UMBER ROAD Holiday, FL MLS# TB8456171
  • Virtual Tour
1 of 41
$304,999
3

Beds

2.0

Baths

1,424

Sq.Ft.

3530 UMBER ROAD

Holiday, FL

Courtesy of STAR BAY REALTY CORP.
View 2453 PLEASANT HILL LANE Holiday, FL MLS# O6364058
  • Adult Community with Virtual Tour
1 of 25
$300,000
2

Beds

2.0

Baths

1,555

Sq.Ft.

2453 PLEASANT HILL LANE

Holiday, FL

Courtesy of LOKATION
View 4539 MILE STRETCH DRIVE Holiday, FL MLS# TB8450043
  • Virtual Tour
1 of 70
$299,999
1,654

Sq.Ft.

4539 MILE STRETCH DRIVE

Holiday, FL

Courtesy of EXP REALTY LLC
View 3332 WILSON DRIVE Holiday, FL MLS# W7884874
  • Virtual Tour
1 of 28
$299,990
3

Beds

2.0

Baths

1,444

Sq.Ft.

3332 WILSON DRIVE

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 1414 WHITEHALL LANE Holiday, FL MLS# TB8498792
$299,990
3

Beds

2.0

Baths

1,636

Sq.Ft.

1414 WHITEHALL LANE

Holiday, FL

Courtesy of COLDWELL BANKER REALTY
View 5338 SPANISH TRAIL Holiday, FL MLS# TB8462546
  • Virtual Tour
1 of 34
$299,900
2

Beds

2.0

Baths

1,212

Sq.Ft.

5338 SPANISH TRAIL

Holiday, FL

Courtesy of CENTURY 21 COASTAL ALLIANCE
View 3127 DOLE STREET Holiday, FL MLS# TB8482547
  • Virtual Tour
1 of 39
$299,900
2

Beds

2.0

Baths

1,184

Sq.Ft.

3127 DOLE STREET

Holiday, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 4301 WESTWOOD DRIVE Holiday, FL MLS# TB8484815
  • Virtual Tour
1 of 13
$299,900
2

Beds

1.1

Baths

1,259

Sq.Ft.

4301 WESTWOOD DRIVE

Holiday, FL

Courtesy of AVENUE HOMES LLC
View 3625 RICHBORO DRIVE Holiday, FL MLS# TB8463808
  • Virtual Tour
1 of 24
$299,000
3

Beds

2.0

Baths

1,587

Sq.Ft.

3625 RICHBORO DRIVE

Holiday, FL

Courtesy of PEOPLE'S TRUST REALTY
View 3228 ROCK VALLEY DRIVE Holiday, FL MLS# TB8467302
  • Virtual Tour
1 of 28
$299,000
2

Beds

2.0

Baths

1,334

Sq.Ft.

3228 ROCK VALLEY DRIVE

Holiday, FL

Courtesy of ENGEL & VOLKERS BELLEAIR

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

Price Count
$0 - 100K 37
$100K - 200K 92
$200K - 300K 157
$300K - 400K 53
$400K - 500K 16
$500K - 600K 7
$600K - 700K 4
$700K - 800K 4
$800K - 900K 2
$900K - 1M 1
$1M - Max 6

Homes for Sale by Type in Holiday, FL

Property Type Count
Single Family 253
Townhouse 15
Condo 22
Commercial 5
Rental 61
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 59
Farms 0

(Data as of 5/18/2026)

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 5/18/2026.