Homes for sale in Holiday.

274 active listings in Holiday, FL — live Stellar MLS inventory.

Communities in Holiday

60 subdivisions with active listings

Beacon Square31 Holiday Lake Estates28 Aloha Gardens26 Tanglewood Mobile Village11 Tahitian Gardens Condo10 Forest Hills8 Gulfwinds8 Lake Conley Mhp8 Tahitian Homes8 Holiday Lake Villas Condo7 Townes/Darlington7 Buena Vista 2nd Add6 Buena Vista Manor6 La Villa Gardens6 Tiki Village Mhp Condo6 Baileys Bluff Estates5 Tahitian Dev5 Anclote Square4 Crest Ridge Gardens4 Tahitian Dev Sub4 Acreage3 Colonial Hills3 Forest Hills East3 Holiday Gardens3 Orangewood Village3 Park Place3 Tampa Tarpon Spgs Land Co3 Bay Park Estates2 Buena Vista2 Colonial Manor2 Dixie Groves Estates2 Holiday Lake Estates 212 Key Vista Ph 012 Key Vista Ph 022 Pinewood Villas2 Sunrise Square Villas2 Bonita Village1 Buena Vista 5th Add1 Buena Vista Fourth Add1 Buena Vista Melody Manor Add1 Buena Vista Second Add1 Dixie Grove Estates Pb6pg27lot2 Block D1 Dodge City First Add1 Eastwood Acres1 Edgewood Gulf Trace Rep1 Forest Hills Un #221 Glenwood Gulf Trace1 Gulfwinds Pb 58 Pg 095 Lot 139 Or 9602 Pg 37551 Holiday1 Holiday Lake Villas Ph 21 Holiday Lakes West1 Holyday Oaks Condo1 Jacobs Sub1 Key Vista Ph 03 Prcl 051 Key Vista Ph 41 Key Vista Prcl 181 Lake Conley Mobile Home Park Condos1 Lullaby Gardens Add1 Lullaby Gardens Addn1 N/A1

Listings in Holiday

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Active360°

$5,400,000

3130 Shipwatch Dr

Holiday, FL 34691

80 acres

MLS# TB8442547

🌳 Land · 35.6 acres

Active360°

$1,900,000

No Address Assigned

Holiday, FL 34691

35.6 acres

MLS# W7883129

Photo coming soon

ActiveSingle Family Residence

$1,859,900

1906 Gulfview Dr

Holiday, FL 34691

4 bd · 4 ba · 3,412 sqft

Baileys Bluff Estates

MLS# TB8482035

Photo coming soon

ActiveSingle Family Residence360°

$1,389,990

3143 Pineview Dr

Holiday, FL 34691

4 bd · 4 ba · 4,204 sqft

Baileys Bluff Estates

MLS# W7879730

Photo coming soon

ActiveSingle Family Residence360°

$1,265,000

3114 Bluff Blvd

Holiday, FL 34691

3 bd · 3 ba · 3,234 sqft

Baileys Bluff Estates

MLS# TB8486712

Photo coming soon

ActiveSingle Family Residence360°

$995,000

1238 Flotilla Dr

Holiday, FL 34690

6 bd · 6 ba · 5,360 sqft

Forest Hills Un #22

MLS# TB8485598

Photo coming soon

ActiveSingle Family Residence360°

$844,900

2138 Bayou Dr

Holiday, FL 34691

3 bd · 3 ba · 2,583 sqft

Baileys Bluff Estates

MLS# TB8469784

Active360°

$799,000

Flotilla

Holiday, FL 34690

1.46 acres

MLS# TB8498330

Active360°

$799,000

5001 Whippoorwill Dr

Holiday, FL 34690

10.47 acres

Tampa Tarpon Spgs Land Co

MLS# W7884728

🌳 Land · 0.35 acres

Active360°

$799,000

000 Bluff Blvd

Holiday, FL 34691

0.35 acres

Baileys Bluff Estates

MLS# W7883578

Active360°

$749,000

0 Silhouette Lane

Holiday, FL 34691

5 acres

Tampa Tarpon Springs Land Company

MLS# TB8320392

🌳 Land · 6 acres

Active

$650,000

3236 Madison St

Holiday, FL 34690

6 acres

MLS# W7876795

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively 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.

Based on information submitted to the MLS GRID as of May 20, 2026 at 9:16 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA