505 N HIGHLAND AVENUE, CLEARWATER, FL, 33755
Active245 days on marketListed Dec 5, 2025MLS #TB8453434
About this home
505 N HIGHLAND AVENUE
PRICE IMPROVEMENT NOW $649900!! BEAUTIFUL 4BR 2 & 1/2 BATH POOL HOME IN CLEARWATER!! THIS IS A GREAT FAMILY HOME WITH HUGE ROOMS AND LARGE LIVING SPACES!! THE GIGANTIC PRIMARY BEDROOM HAS A BIG WALK IN CLOSET THAT IS CURRENTLY CONVERTED TO A 5TH BEDROOM!! LIVING ROOM IS LARGE WITH COZY FIREPLACE AND OPENS WITH 12FT SLIDERS TO FANTASTIC RECREATION OASIS!! HEATED POOL, OUTDOOR KITCHEN AND TABLE THAT SEATS 12!! THE GARAGE HAS BEEN CONVERTED TO A MEDIA AND GAME ROOM WITH LOTS OF GAMES, AND CUSTOM LIGHTING!! THERE IS A LARGE CIRCULAR DRIVE THAT WILL ACCOMMODATE SEVERAL VEHICLES!! MAKE YOUR APPOINTMENT TO SEE THIS HOME SOON!! HOME HAS BEEN OPERATED AS A VACATION RENTAL, REPORTS AVAILABLE. ASKING PRICE $649900
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,361
Sqft
0.28 ac
Lot size
2
Garage
1961
Year built
One
Levels
$275
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$4,594 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$4,594/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. 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.
vs edgeAI estimate
−26.9%
$/sqft vs Clearwater actives
$275 vs $226
Days on market
245 vs 55 typical
Where $275/sqft sits among the 399 Clearwater actives
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 Glenwood
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Clearwater. See the full Clearwater guide →
Glenwood — neighborhood snapshot
Population
330
Median age
46
Median income
$65,000
Median home value
$406,100
Avg household
3
Households w/ children
34%
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)
220 of 399
Clearwater actives have cut their price
Median sold price, Clearwater, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 78% above the CLEARWATER 33755 median. See the full Clearwater market guide →
Paper trail
This home's history
Reality check
What actually sold near 505 N HIGHLAND AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$460,000
1029 GLENWOOD ROAD · same community
3 bd · 2 ba · 2,485 sqft · $185/sqft · 34 DOM
Sold · Jul ’26$425,000
615 N GLENWOOD AVENUE · same community
3 bd · 3.5 ba · 2,197 sqft · $193/sqft · 4 DOM
Sold · Dec ’25$420,000
2150 55TH STREET N · same community
3 bd · 2 ba · 2,172 sqft · $193/sqft · 49 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 505 N HIGHLAND AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 505 N HIGHLAND AVENUE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
505 N HIGHLAND AVENUE FAQs
What would the monthly payment be for 505 N HIGHLAND AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,594/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 505 N HIGHLAND AVENUE?+
The most recent tax bill on record (2024) was $8,202. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Clearwater?+
At $649,900, this home is listed about 136% above the Clearwater median of $275,000. The market section on this page shows how the area is trending.
Which schools are assigned to 505 N HIGHLAND AVENUE?+
Skycrest Elementary School (elementary), Clearwater High School (high), Dunedin Highland Middle School (middle) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$649,900 runs 78% above the CLEARWATER 33755 median — but at 2,361 sqft it's also nearly twice the size of the typical Clearwater listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Time on market is leverage
245 days on market against a Clearwater median of 55 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Skycrest Elementary School, Clearwater High School, Dunedin Highland Middle School — Dunedin Highland Middle School rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $745,000, now $649,900 — a $95K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY PORTFOLIO COLLECTION · Calvin Van Auken. MLS #TB8453434.
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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