Headsail Drive, New Port Richey, FL
Everything we know about Headsail Drive in New Port Richey: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.
76 homes sit on Headsail Drive in New Port Richey, FL (ZIP 34652), built 1962–2003, a typical 1,463 sq ft with 3 bedrooms. 6 are for sale right now from $200,000 to $650,000. Homes that sold since 2023 went for a median $322,500.
For sale on Headsail Drive now
The homes on Headsail Drive
76 single-family. Built by decade: 1960s 44, 1970s 29, 1980s 2, 2000s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 4003 Headsail Drive | $630,000 | 2026-06-05 | 1970 | 1,742 |
| 3849 Headsail Drive | $299,999 | 2026-04-30 | 1972 | 1,148 |
| 3915 Headsail Drive | $233,500 | 2026-03-05 | 1969 | 1,492 |
| 3961 Headsail Drive | $231,000 | 2026-02-20 | 1968 | 1,310 |
| 4153 Headsail Drive | $450,000 | 2025-12-29 | 1971 | 1,232 |
| 4210 Headsail Drive | $275,000 | 2025-10-28 | 1969 | 2,426 |
| 3960 Headsail Drive | $220,000 | 2025-06-30 | 1969 | 2,920 |
| 3944 Headsail Drive | $180,000 | 2025-03-20 | 1969 | 2,158 |
| 4110 Headsail Drive | $150,000 | 2024-11-26 | 1964 | 1,125 |
| 4012 Headsail Drive | $195,000 | 2024-11-21 | 1976 | 1,654 |
| 3837 Headsail Drive | $382,500 | 2024-05-31 | 1970 | 1,193 |
| 4160 Headsail Drive | $320,000 | 2024-03-29 | 1967 | 1,355 |
| 4044 Headsail Drive | $340,000 | 2024-03-21 | 1968 | 1,232 |
| 4211 Headsail Drive | $410,000 | 2024-01-12 | 1967 | 1,167 |
| 4227 Headsail Drive | $500,000 | 2023-08-31 | 1969 | 1,979 |
| 4055 Headsail Drive | $700,000 | 2023-08-28 | 1972 | 1,994 |
| 4124 Headsail Drive | $325,000 | 2023-07-26 | 1969 | 1,219 |
| 3924 Headsail Drive | $245,000 | 2023-07-01 | 1967 | 1,098 |
| 3925 Headsail Drive | $595,000 | 2023-06-13 | 1969 | 1,763 |
| 4217 Headsail Drive | $630,000 | 2023-03-27 | 1963 | 1,438 |
Communities along Headsail Drive
- Flor A Mar · 48 homes on the street
- Flor A Mar · 8 homes on the street
- Flor A Mar · 3 homes on the street
- Flor A Mar · 3 homes on the street
- Flor A Mar · 3 homes on the street
- Flor A Mar · 2 homes on the street
- Flor A Mar · 2 homes on the street
- Flor A Mar · 1 homes on the street
- Flor A Mar · 1 homes on the street
- Flor A Mar · 1 homes on the street
How to read this
Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 1,040 homes for sale in New Port Richey, homes for sale in 34652.