Single Family Residence at 999 GILLESPIE DR, PALM HARBOR

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 2 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 3 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 4 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 5 of 37

+32 more

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 6 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 7 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 8 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 9 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 10 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 11 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 12 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 13 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 14 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 15 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 16 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 17 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 18 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 19 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 20 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 21 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 22 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 23 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 24 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 25 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 26 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 27 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 28 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 29 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 30 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 31 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 32 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 33 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 34 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 35 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 36 of 37

Single Family Residence at 999 GILLESPIE DR, PALM HARBOR, photo 37 of 37

37 photos

$449,000

999 GILLESPIE DR

PALM HARBOR, FL 34684

Listed by Diane Thompson · CHARLES RUTENBERG REALTY INC

Bedrooms

Bathrooms

Living area

1,732 sqft

Year built

1983

About this home

Virtually Staged. PRICE REDUCED — Charming brick home in Highland Lakes (55+) with LOW HOA. This 3-bed, 2-bath residence offers 1,732 sq ft of bright, open living with vaulted ceilings and flexible expanded space that enhances flow and functionality. The kitchen features solid maple cabinets, granite countertops, pantry storage, and an easy entertaining layout; both baths are updated with granite vanities. Major systems updated: hurricane-impact windows, 2023 A/C, 2022 water heater, and 200-amp electric. Enjoy rare backyard privacy with mature landscaping, a paver patio, and a motorized awning — plus an enclosed A/C lanai for extra living space. Additional highlights: 2-car garage with attic access and storage, irrigation well, security system, ceiling fans throughout, and all appliances included. Highland Lakes amenities: three golf courses, tennis and pickleball, heated Olympic pool, clubhouse and fitness programs, lake access, boat/RV storage, and an active social calendar. Great updates, awesome layout, desirable location — ready to move in.

Property details

MLS #: MFRTB8516714
Property type: Single Family Residence
Subdivision: HIGHLAND LAKES UNIT FIFTEEN PH 1
Status: Active
Days on market: 96
On market date: June 8, 2026
Stories: N/A
Total bathrooms: 2
Garage spaces: 2
Parking spaces: N/A
Lot size: 0.18 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

HIGHLAND LAKES ELEMENTARY SCHOOL

0.19 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: 518
Student:teacher ratio: 14.0:1
District: PINELLAS

Middle

JOSEPH L. CARWISE MIDDLE SCHOOL

0.87 mi away · Grades 6-8

Nearest school -- attendance-zone data not available here

2.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 1,155
Student:teacher ratio: 18.0:1
District: PINELLAS

High

PALM HARBOR UNIVERSITY HIGH

2.58 mi away · Grades 9-12

Nearest school -- attendance-zone data not available here

1.0

Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating

Enrollment: 2,480
Student:teacher ratio: 22.1:1
District: PINELLAS

Walkability

Blended score for PALM HARBOR'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).

Somewhat walkable

out of 100

EPA National Walkability Index

5.3 / 20 -- Least walkable

Google Places amenity density

78 / 100

Restaurants & cafes20

Grocery stores4

Parks0

Schools3

Transit stops1

Pharmacies3

Market position

How this listing compares to current activity in PALM HARBOR, from live MLS data.

On the market 96 days -- 4 fewer days than PALM HARBOR's current average of 100 days.

For reference, the median list price across 724 active listings in PALM HARBOR right now is $309,950.

Mortgage calculator

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

Home price

Down payment

Interest rate

Loan term

Adjust tax / insurance estimates

Property tax

% / yr

Home insurance

/mo

Est. monthly payment

$2,854/mo

$89,800 down

$359,200 loan

Principal & interest$2,330

Property tax (est.)$374

Home insurance (est.)$150

Similar homes you might like

Listed by Amanda Lebiszczak, CHARLES RUTENBERG REALTY INC

Listed by Katrina Jauregui, REDFIN CORPORATION

Listed by RE/MAX ACTION FIRST OF FLORIDA

Listed by Katie Ducharme Procissi, KATIE DUCHARME REALTY, LLC

Listed by Cyndi Olmstead

Listed by Karen Apa, PREMIER SOTHEBY'S INTL REALTY

Listed by Natalie Spencer, TAM BAY REALTY LLC

$435,000

504 OMAHA ST

PALM HARBOR, 34683

3 bd·2.5 ba·1,404 sqft

2 days on market

Listed by Christine Morcos, FUTURE HOME REALTY

Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 22 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.