Waterfront Homes for Sale in Holiday, FL

This page tracks every Holiday listing whose MLS record reports waterfront (ocean, bay, Intracoastal, river, canal or lake frontage), by community, with live counts and asking prices, and the costs that come with the water.

44 waterfront homes are for sale or pending in Holiday, FL today across 19 communities. The median asking price is $255,000, from $113,900 to $1,299,999. Listings in Holiday without that feature have a median of $229,150. Most listings right now: Forest Hills (5), Beacon Square (5), Tanglewood Mobile Village (5). Updated October 17, 2026 from the MLS.

Live waterfront homes in Holiday: the listings

37 active listings carry the flag today (13% of Holiday inventory), median asking $260,000, $197/sq ft, median 52 days on market. Photo cards link to the listing; refreshed nightly.

Newest waterfront homes in Holiday

3143 Pineview Drive, waterfront for sale in Holiday
$1,299,999 New
4 bd · 4 ba · 4,204 sq ft · built 2006
3143 Pineview Drive, 34691
Baileys Bluff Estates
Listing courtesy of RE/MAX CHAMPIONS
4036 Sunray Drive, waterfront for sale in Holiday
$300,000 New
3 bd · 2 ba · 1,842 sq ft · built 1970
4036 Sunray Drive, 34691
Aloha Gardens
Listing courtesy of DALTON WADE INC
2217 Harrison Drive, waterfront for sale in Holiday
$245,995 New
4 bd · 2 ba · 1,566 sq ft · built 1979
2217 Harrison Drive, 34691
Tahitian Homes
Listing courtesy of IMPACT REALTY TAMPA BAY
3211 Southport Drive, waterfront for sale in Holiday
$179,900 New
2 bd · 2 ba · 1,329 sq ft · built 1983
3211 Southport Drive, 34690
Tanglewood Mobile Village
Listing courtesy of CITY BREEZE ACTION REALTY
1022 Bowsprit Lane #1022, waterfront for sale in Holiday
$175,000 New
2 bd · 2 ba · 1,114 sq ft · built 1986
1022 Bowsprit Lane #1022, 34691
Holiday Lake Villas Condo
Listing courtesy of BAY TO SHORE PROPERTY MANAGEMENT AND LEASING LLC
3207 Brewster Drive, waterfront for sale in Holiday
$149,900 New
2 bd · 2 ba · 1,018 sq ft · built 1981
3207 Brewster Drive, 34690
Tanglewood Mobile Village
Listing courtesy of COLDWELL BANKER REALTY
3201 Brewster Drive, waterfront for sale in Holiday
$145,500 New
2 bd · 2 ba · 864 sq ft · built 1981
3201 Brewster Drive, 34690
Tanglewood Mobile Village
Listing courtesy of CITY BREEZE ACTION REALTY
3852 Sunray Drive, waterfront for sale in Holiday
$239,900
2 bd · 1.5 ba · 1,088 sq ft · built 1971
3852 Sunray Drive, 34691
Aloha Gardens
Listing courtesy of KELLER WILLIAMS REALTY- PALM HARBOR
2228 Society Drive, waterfront for sale in Holiday
$240,000
2 bd · 1.5 ba · 1,039 sq ft · built 1977
2228 Society Drive, 34691
Aloha Gardens
Listing courtesy of LPT REALTY, LLC
2578 Charlan Court, waterfront for sale in Holiday
$255,000
3 bd · 2.5 ba · 1,634 sq ft · built 2023
2578 Charlan Court, 34690
Townes/Darlington
Listing courtesy of BEST OF THE GULF REALTY INC
2044 Pamela Drive, waterfront for sale in Holiday
$219,900
2 bd · 2 ba · 1,116 sq ft · built 1968
2044 Pamela Drive, 34690
Holiday Gardens
Listing courtesy of KELLER WILLIAMS SUBURBAN TAMPA
2030 Gulfview Drive, waterfront for sale in Holiday
$774,900
2 bd · 2 ba · 2,280 sq ft · built 1981
2030 Gulfview Drive, 34691
Baileys Bluff Estates
Listing courtesy of RE/MAX ALLIANCE GROUP
2146 Society Drive, waterfront for sale in Holiday
$259,000
2 bd · 2 ba · 1,371 sq ft · built 1979
2146 Society Drive, 34691
Aloha Gardens
Listing courtesy of KELLER WILLIAMS REALTY PORTFOLIO COLLECTION
4318 Tahitian Gardens Circle #F, waterfront for sale in Holiday
$113,900
1 bd · 1 ba · 576 sq ft · built 1968
4318 Tahitian Gardens Circle #F, 34691
Tahitian Gardens
Listing courtesy of VERANDA REALTY GROUP
3806 Staysail Lane, waterfront for sale in Holiday
$114,900
1 bd · 1 ba · 880 sq ft · built 1981
3806 Staysail Lane, 34691
Holiday Lake Villas Condo
Listing courtesy of REALTY EXPERTS ASSOCIATES
3318 Pineview Drive, waterfront for sale in Holiday
$509,000
2 bd · 1.5 ba · 1,047 sq ft · built 1969
3318 Pineview Drive, 34691
Baileys Bluff Estates
Listing courtesy of RE/MAX ALLIANCE GROUP
3011 Shadow Oaks Drive, waterfront for sale in Holiday
$319,000
3 bd · 2 ba · 1,480 sq ft · built 1987
3011 Shadow Oaks Drive, 34690
Shadow Oaks
Listing courtesy of RE/MAX CHAMPIONS
3022 Jackson Drive, waterfront for sale in Holiday
$450,000
4 bd · 2 ba · 1,837 sq ft · built 1981
3022 Jackson Drive, 34691
Tahitian Dev
Listing courtesy of LPT REALTY, LLC
3332 Wilson Drive, waterfront for sale in Holiday
$284,990
3 bd · 2 ba · 1,444 sq ft · built 1978
3332 Wilson Drive, 34691
Tahitian Dev
Listing courtesy of KELLER WILLIAMS REALTY- PALM H
3141 Nantucket Drive, waterfront for sale in Holiday
$134,900
2 bd · 2 ba · 1,120 sq ft · built 1978
3141 Nantucket Drive, 34690
Tanglewood Mobile Village
Listing courtesy of CITY BREEZE ACTION REALTY
1817 Dartmouth Drive, waterfront for sale in Holiday
$248,000
3 bd · 2 ba · 1,457 sq ft · built 1974
1817 Dartmouth Drive, 34691
Holiday Lake Estates
Listing courtesy of HOMETRUST REALTY GROUP
2349 Hama Drive, waterfront for sale in Holiday
$235,000
3 bd · 2 ba · 1,470 sq ft · built 1978
2349 Hama Drive, 34691
Tahitian Homes
Listing courtesy of HOMAN REALTY GROUP INC
1034 Bowsprit Lane, waterfront for sale in Holiday
$115,000
2 bd · 2 ba · 1,114 sq ft · built 1985
1034 Bowsprit Lane, 34691
Holiday Lake Villas Condo
Listing courtesy of RE/MAX ELITE REALTY

The most expensive waterfront homes in Holiday

ListingAskingSq ftCommunity
1906 Gulfview Drive$1,859,9003,412pasco county
3143 Pineview Drive$1,369,9904,204pasco county
3143 Pineview Drive$1,299,9994,204Baileys Bluff Estates
3114 Bluff Boulevard$1,265,0003,234pasco county
2030 Gulfview Drive$774,9002,280Baileys Bluff Estates
1238 Flotilla Drive$549,9005,360—
3318 Pineview Drive$509,0001,047Baileys Bluff Estates
1125 Fernwood Drive$474,9001,900—
3022 Jackson Drive$450,0001,837Tahitian Dev
1324 Chancellor Drive$448,9001,762—

Waterfront Homes by price

BandFor saleShare
Under $300K2259%
$300K–$500K822%
$500K–$750K25%
$750K–$1M13%
$1M+411%

Holiday waterfront homes by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

CommunityWaterfront HomesNew buildMedian listFrom
Forest Hills50$399,000$289,000
Beacon Square50$249,999$141,000
Tanglewood Mobile Village50$149,900$134,900
Baileys Bluff Estates40$774,950$509,000
Aloha Gardens40$249,500$239,900
Holiday Lake Villas Condo40$137,500$114,900
Tahitian Dev Sub30$255,000$210,000
Tahitian Dev20$360,000$270,000
Forest Hills Un #2210$549,900$549,900
Park Place10$447,400$447,400
Forest Hills Unit 2210$350,000$350,000
Shadow Oaks10$319,000$319,000
Townes/Darlington10$255,000$255,000
Holiday Lake Estates10$248,000$248,000
Tahitian Development10$245,995$245,995
Tahitian Homes10$235,000$235,000
Crest Ridge Gardens10$225,000$225,000
Holiday Gardens10$219,900$219,900
Tahitian Gardens Condo10$113,900$113,900

What waterfront ownership really costs

Waterfront homes carry costs inland homes do not: flood insurance where the parcel sits in a FEMA special flood hazard area, higher windstorm premiums closer to open water, and upkeep for seawalls, docks and lifts. Before you offer, pull the FEMA flood zone for the specific parcel, ask for the seawall’s age and any inspection reports, and get an insurance quote in hand, not an estimate. Our flood insurance calculator and wind mitigation savings calculator show what the parcel will actually cost to insure.

Questions to ask about any waterfront listing

Is the water frontage deeded or association-owned? Is there a fixed bridge between the dock and open water, and what is the clearance? What did the seller pay for flood and wind coverage last year, and with which carriers? Has the seawall or dock been permitted and inspected? What is the finished-floor elevation? A local agent who works waterfront deals will know which canals hold depth at low tide and which carriers are writing in the area.

Common questions

How many waterfront homes are for sale in Holiday?
As of October 17, 2026, 44 Holiday, FL listings whose MLS record reports waterfront are active or pending, across 19 communities. The count updates with every MLS refresh.
What do waterfront homes cost in Holiday?
The median asking price today is $255,000, with listings from $113,900 to $1,299,999. Holiday listings without that feature have a median of $229,150.
Which Holiday community has the most waterfront homes for sale?
Forest Hills has the most right now (5), followed by Beacon Square (5), Tanglewood Mobile Village (5), Baileys Bluff Estates (4).
Is a waterfront home always in a flood zone?
Not always, but most direct-frontage parcels are in a FEMA special flood hazard area, which means a lender will require flood insurance. The elevation certificate and the exact zone for the parcel decide the premium; two homes on the same canal can differ by thousands a year.

Keep exploring Holiday

Waterfront Homes in nearby Pasco County cities

Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Holiday, FL whose MLS record reports waterfront. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listings courtesy of Stellar MLS as distributed by MLS GRID.

Hiring an agent in Holiday, FL?

Get matched with the right local expert.

Tell us your goal in Holiday, FL and we’ll connect you with the Momentum agent who knows it best — backed by a RealTrends 500 brokerage. No pressure, no obligation.

Prefer to talk now? Call (904) 351-6461.

Work with a local Holiday, FL expert

A real conversation with a local specialist, usually within one business day.

or call (904) 351-6461