2287 PHILIPPINE DRIVE UNIT 29, CLEARWATER, FL, 33763
Active184 days on marketListed Feb 1, 2026MLS #TB8471259
About this home
2287 PHILIPPINE DRIVE UNIT 29
Step outside your door and enjoy resort-style living in one of Florida’s best-kept secrets. Fantastic 2BR/2BA condo available in the highly desirable On Top of the World 55+ gated community where everyday living feels like a vacation. This 2nd-floor unit with elevator access is offered as a yearly, unfurnished rental and features a comfortable and functional floor plan. Small pet ok under 25lbs with $25 monthly fee. The living and dining room combo flows seamlessly into the kitchen and family room, creating an open and inviting living space. The unit includes NEW inside washer/dryer for added convenience. The primary bedroom offers an en-suite bathroom with walk-in shower. Neutral colors throughout, ceiling fans, pantry storage, and tile flooring in the kitchen and baths complete the home. Enjoy resort-style living in one of Florida’s best-kept secrets, offering a secure, well-maintained community with outstanding amenities. Community Features: Assigned parking. The 55+ community features Assigned parking. The 55+ community has two golf courses, two heated swimming pools, pickle ball, two active community centers, fitness center, billiards, hobby studio, and many activity classes to participate in including fitness, wood shop, and dancing. Additionally, the community offers hiking trails and fishing, kayaking and canoeing with a launch on Lake Arbor, allowing enjoyment of a wide variety of options to meet any lifestyle. On site, Good Karma Cafe is great for stopping in for snacks or bringing home dinner. Vehicle Restrictions apply. Included: Cable TV, Community Pool, Internet, Maintenance Exterior, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities, Sewer, Trash, Water. This condo unit is available for Annual Lease, 55+ age community. one time HOA fee: $150 app fee each adult or couple. One assigned parking spot. Easy access to shops, fine dining, Countryside Mall, Clearwater Aquarium, Coachman Park, groceries, banks, hospitals/Morton Plant/Mease Countryside and only a short drive to Clearwater Beach.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,070
Sqft
0 ac
Lot size
1986
Year built
One
Levels
$1
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$170 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$170/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs ON TOP OF THE WORLD
$1 vs $149
Days on market
184 vs 55 typical
Where $1/sqft sits among the 243 homes for sale in ON TOP OF THE WORLD
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Clearwater
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Clearwater. See the full Clearwater guide →
CLEARWATER 33763 — neighborhood snapshot
Population
21,278
Median age
53.8
Median income
$53,552
Median home value
$215,900
Avg household
2.12
Households w/ children
1,898
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Clearwater market
$328K → $350K
Clearwater median sold, yr/yr
95.8%
Sale-to-list ratio (12 mo)
110 of 243
ON TOP OF THE WORLD have cut their price
Median sold price, Clearwater, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 99% below the CLEARWATER 33763 median. See the full Clearwater market guide →
Paper trail
This home's history
Reality check
What actually sold near 2287 PHILIPPINE DRIVE UNIT 29
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$140,000
2441 PERSIAN DRIVE UNIT 51 · same community
2 bd · 2 ba · 1,070 sqft · $131/sqft · 86 DOM
Sold · Dec ’25$118,000
2287 PHILIPPINE DRIVE UNIT 29 · same community
2 bd · 2 ba · 1,070 sqft · $110/sqft · 189 DOM
Sold · Dec ’25$108,000
2431 CANADIAN WAY UNIT 9 · same community
2 bd · 1 ba · 1,100 sqft · $98/sqft · 79 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Jessica Stickler
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 2287 PHILIPPINE DRIVE UNIT 29 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2287 PHILIPPINE DRIVE UNIT 29 — before you fall in love.
See it in person
Schedule a tour
Live availability from Jessica's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2287 PHILIPPINE DRIVE UNIT 29 FAQs
What would the monthly payment be for 2287 PHILIPPINE DRIVE UNIT 29?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $170/mo — principal and interest, estimated property taxes and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
Are pets allowed at 2287 PHILIPPINE DRIVE UNIT 29?+
The listing reports pets: Cats OK, Number Limit, Size Limit, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Clearwater?+
At $1,400, this home is listed about 99% below the Clearwater median of $275,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2287 PHILIPPINE DRIVE UNIT 29?+
McMullen-Booth Elementary School (elementary), Countryside High School (high), Safety Harbor Middle School (middle) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the CLEARWATER 33763 market on paper
$1,400 is 99% below the CLEARWATER 33763 median of $162,000, and at $1/sqft it sits under the Clearwater average of $276.
02Time on market is leverage
184 days on market against a Clearwater median of 55 — sellers in this position are usually ready to negotiate.
03The price has already moved
Listed at $1,800, now $1,400 — a $400 cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of RENT SOLUTIONS · Lisa Connors. MLS #TB8471259.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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