View 1408 JENNINGS DRIVE Holiday, FL MLS# TB8439874
  • Virtual Tour
1 of 36
$339,900
3

Beds

2.0

Baths

1,102

Sq.Ft.

1408 JENNINGS DRIVE

Holiday, FL

Courtesy of COASTAL FLORIDA REAL ESTATE
View 3707 PINEHURST DRIVE Holiday, FL MLS# TB8436690
$284,500
3

Beds

2.0

Baths

1,534

Sq.Ft.

3707 PINEHURST DRIVE

Holiday, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 3449 SPRINGFIELD DRIVE Holiday, FL MLS# TB8438704
$259,000
3

Beds

2.0

Baths

1,334

Sq.Ft.

3449 SPRINGFIELD DRIVE

Holiday, FL

Courtesy of RE/MAX REALTEC GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2514 SANDY HILL COURT Holiday, FL MLS# TB8439068
  • Adult Community with Virtual Tour
1 of 26
$345,900
2

Beds

2.0

Baths

1,555

Sq.Ft.

2514 SANDY HILL COURT

Holiday, FL

Courtesy of PREMIER REALTY
View 1818 AND 1816 HACIENDA WAY Holiday, FL MLS# TB8437960
$350,000
6

Beds

3.0

Baths

1,527

Sq.Ft.

1818 AND 1816 HACIENDA WAY

Holiday, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 3608 EDENWOOD DRIVE Holiday, FL MLS# TB8438367
$279,900
2

Beds

2.0

Baths

1,200

Sq.Ft.

3608 EDENWOOD DRIVE

Holiday, FL

Courtesy of FUTURE HOME REALTY INC
View 3447 COLUMBUS DRIVE Holiday, FL MLS# TB8435710
  • Virtual Tour
1 of 46
$258,000
2

Beds

1.1

Baths

974

Sq.Ft.

3447 COLUMBUS DRIVE

Holiday, FL

Courtesy of MYREALTY 2 LLC
View 2211 PLEASANT HILL LANE Holiday, FL MLS# TB8437813
  • Adult Community
1 of 34
$341,900
2

Beds

2.0

Baths

1,500

Sq.Ft.

2211 PLEASANT HILL LANE

Holiday, FL

Courtesy of EXP REALTY LLC
View 2735 PLANTAIN DRIVE Holiday, FL MLS# TB8434075
  • Adult Community with Virtual Tour
1 of 45
$319,900
2

Beds

2.0

Baths

1,555

Sq.Ft.

2735 PLANTAIN DRIVE

Holiday, FL

Courtesy of REALTY ONE GROUP BEYOND
View 1305 BASSWOOD DRIVE Holiday, FL MLS# TB8433779
  • Virtual Tour
1 of 37
$325,000
2

Beds

1.0

Baths

1,225

Sq.Ft.

1305 BASSWOOD DRIVE

Holiday, FL

Courtesy of EXP REALTY LLC
View 4936 MILE STRETCH DRIVE Holiday, FL MLS# W7879422
$265,000
3

Beds

2.0

Baths

1,244

Sq.Ft.

4936 MILE STRETCH DRIVE

Holiday, FL

Courtesy of F I GREY & SON RESIDENTIAL
View 3800 DARLINGTON ROAD Holiday, FL MLS# TB8431207
$279,000
3

Beds

2.0

Baths

1,252

Sq.Ft.

3800 DARLINGTON ROAD

Holiday, FL

Courtesy of ACREAGE REALTY LLC
View 1817 DARTMOUTH DRIVE Holiday, FL MLS# W7879113
  • Virtual Tour
1 of 49
$264,000
3

Beds

2.0

Baths

1,457

Sq.Ft.

1817 DARTMOUTH DRIVE

Holiday, FL

Courtesy of HOMETRUST REALTY GROUP
View 3220 FAIRMOUNT DRIVE Holiday, FL MLS# TB8431248
$279,900
3

Beds

1.1

Baths

1,383

Sq.Ft.

3220 FAIRMOUNT DRIVE

Holiday, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 3520 OVERLAND DRIVE Holiday, FL MLS# TB8432018
  • Virtual Tour
1 of 42
$279,000
2

Beds

2.0

Baths

1,068

Sq.Ft.

3520 OVERLAND DRIVE

Holiday, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 3309 JACKSON DRIVE Holiday, FL MLS# TB8427610
  • Virtual Tour
1 of 29
$269,999
2

Beds

1.0

Baths

1,140

Sq.Ft.

3309 JACKSON DRIVE

Holiday, FL

Courtesy of DEAN & DEWITT PROPERTIES
View 1810 CEMETERY ROAD Holiday, FL MLS# TB8427428
  • Virtual Tour
1 of 18
$299,000
Studio

Beds

0.0

Baths

1810 CEMETERY ROAD

Holiday, FL

Courtesy of COMPASS FLORIDA LLC
View 1814 CEMETERY ROAD Holiday, FL MLS# TB8426385
  • Virtual Tour
1 of 18
$299,000
Studio

Beds

0.0

Baths

1814 CEMETERY ROAD

Holiday, FL

Courtesy of COMPASS FLORIDA LLC
View 3518 MOOG ROAD Holiday, FL MLS# TB8419861
  • Virtual Tour
1 of 33
$275,000
3

Beds

2.0

Baths

1,518

Sq.Ft.

3518 MOOG ROAD

Holiday, FL

Courtesy of REALTY ONE GROUP SUNSHINE
View 2627 CHARLAN COURT Holiday, FL MLS# TB8427214
  • Virtual Tour
1 of 48
$280,000
2

Beds

2.1

Baths

1,541

Sq.Ft.

2627 CHARLAN COURT

Holiday, FL

Courtesy of COLDWELL BANKER REALTY

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.

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.