INNOVATE Real Estate
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 2 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 3 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 4 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 5 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 6 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 7 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 8 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 9 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 10 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 11 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 12 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 13 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 14 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 15 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 16 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 17 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 18 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 19 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 20 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 21 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 22 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 23 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 24 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 25 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 26 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 27 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 28 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 29 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 30 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 31 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 32 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 33 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 34 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 35 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 36 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 37 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 38 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 39 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 40 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 41 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 42 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 43 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 44 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 45 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 46 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 47 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 48 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 49 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 50 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 51 of 52
Single Family Residence at 4237 HEADSAIL DR, NEW PORT RICHEY, photo 52 of 52
52 photos

$474,999

4237 HEADSAIL DR
NEW PORT RICHEY, FL 34652
Listed by Chad Karr · KELLER WILLIAMS REALTY
Bedrooms
3
Bathrooms
2.5
Living area
1,594 sqft
Year built
1969

About this home

Unlock an incredible opportunity to own your waterfront dream home in the highly sought-after Gulf Harbors community. This 3-bedroom, 2-bath block home sits on a double lot and offers Florida charm, water access, and coastal lifestyle that make this neighborhood so desirable. Enjoy a large open kitchen, a bright and airy layout, and a Florida room overlooking the water, perfect for morning coffee or sunset views. The home features a side-entry two-car garage, plus a breezeway with additional storage, giving you plenty of room for tools, toys, and gear. Boaters will love the floating dock, ready for you to tie up your boat and or cut ties and head straight to the big water in minutes. Whether you’re fishing, cruising, or island-hopping, this location delivers unmatched convenience. Gulf Harbors offers an exceptional coastal lifestyle with optional access to its private beach, known for its pristine sand, turquoise water, and unforgettable sunsets. This is your chance to secure a true waterfront gem and make it your own.

Highlights

Waterfront

Property details

MLS #
MFRL4961684
Property type
Single Family Residence
Subdivision
FLOR A MAR
Status
Active
Days on market
120
On market date
May 17, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.17 acres

Location

Get directions →
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
MITTYE P. LOCKE ELEMENTARY SCHOOL
1.31 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
533
Student:teacher ratio
13.7:1
District
PASCO
Middle
GULF MIDDLE SCHOOL
2.25 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
926
Student:teacher ratio
16.5:1
District
PASCO
High
GULF HIGH SCHOOL
1.63 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,468
Student:teacher ratio
17.7:1
District
PASCO

Walkability

Blended score for NEW PORT RICHEY's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

26
Car-dependent
out of 100
EPA National Walkability Index
6.5 / 20 -- Below average walkable
Google Places amenity density
15 / 100
Restaurants & cafes0
Grocery stores0
Parks5
Schools0
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in NEW PORT RICHEY, from live MLS data.

On the market 120 days -- 11 more days than NEW PORT RICHEY's current average of 109 days.
For reference, the median list price across 1,518 active listings in NEW PORT RICHEY right now is $229,900.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$3,011/mo
$95,000 down
$379,999 loan
Principal & interest$2,465
Property tax (est.)$396
Home insurance (est.)$150

Similar homes you might like

11730 LAKEVIEW DR
New
$525,000
11730 LAKEVIEW DR
NEW PORT RICHEY, 34654
3 bd·3 ba·2,053 sqft
1 day on market
Pool
Listed by Bobby Welbourn, KELLER WILLIAMS RLTY NEW TAMPA
4916 POMPANO DR
$519,000
4916 POMPANO DR
NEW PORT RICHEY, 34652
2 bd·2 ba·1,655 sqft
2 days on market
Listed by Vanessa Leonard, KELLER WILLIAMS REALTY- PALM HARBOR
4401 FORT SHAW DR
$499,500
4401 FORT SHAW DR
NEW PORT RICHEY, 34655
4 bd·2 ba·2,325 sqft
2 days on market
Pool
Listed by Jennifer Hatzistefanou, RE/MAX CHAMPIONS
8220 ROLLING TIDES DR
New
$464,000
8220 ROLLING TIDES DR
NEW PORT RICHEY, 34655
4 bd·2.5 ba·2,334 sqft
1 day on market
Listed by RE/MAX CHAMPIONS
11123 OYSTER BAY CIR
New
$459,900
11123 OYSTER BAY CIR
NEW PORT RICHEY, 34654
4 bd·3 ba·2,916 sqft
1 day on market
Listed by Summer Brady, MAINSTAY BROKERAGE LLC
7246 GABERIA RD
New
$449,000
7246 GABERIA RD
NEW PORT RICHEY, 34655
3 bd·2.5 ba·2,066 sqft
1 day on market
Listed by Bryan Packer, ABI ROAD REALTY LLC
10305 COPPERWOOD DR
New
$440,000
10305 COPPERWOOD DR
NEW PORT RICHEY, 34654
3 bd·2 ba·1,664 sqft
1 day on market
Pool
Listed by Amy Schmitzer, CHARLES RUTENBERG REALTY INC
8657 CYPRESS LAKES BLVD
New
$425,000
8657 CYPRESS LAKES BLVD
NEW PORT RICHEY, 34653
3 bd·2 ba·1,694 sqft
1 day on market
Pool
Listed by Douglas Clark, EXIT KING REALTY

Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 20 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.