1655 S HIGHLAND AVENUE UNIT D238, CLEARWATER, FL, 33756
Active344 days on marketListed Aug 29, 2025MLS #TB8422801
About this home
1655 S HIGHLAND AVENUE UNIT D238
Virtually Staged. MAJOR PRICE REDUCTION!!! BRAND NEW CARPET, PAINT, and WINDOW COVERINGS THROUGHOUT! Turnkey and ready to move in!!! Welcome to your ideal retirement retreat in a fantastic location in Clearwater! This affordable 2-bedroom, 2-bathroom condo offers a rare opportunity to own in the highly sought-after Penthouse Groves community. The windows were replaced in 2020, bringing in more natural light and boosting energy efficiency. Nestled in a peaceful 55+ community, you’ll enjoy a low-maintenance lifestyle, with the monthly fee covering water, sewer, Wi-Fi, and common grounds maintenance. Take full advantage of the abundant amenities at Penthouse Groves, including a welcoming clubhouse, shuffleboard courts, a community pool, and a scenic dock. Stay active with access to a fitness center, sauna, and pool table room, or unwind in the cozy library. For those who love the beach, Clearwater Beach is just a quick 6-mile drive away, offering even more opportunities for relaxation and fun. This is an incredible opportunity to enjoy both comfort and convenience in one of Clearwater’s most desirable communities.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
1,270
Sqft
2.63 ac
Lot size
1971
Year built
One
Levels
$94
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.
$1,173 /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
$1,173/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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
−17.8%
$/sqft vs Clearwater actives
$94 vs $227
Days on market
344 vs 55 typical
Where $94/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 Penthouse Groves
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Clearwater. See the full Clearwater guide →
Penthouse Groves — neighborhood snapshot
Population
329
Median age
57
Median income
$50,190
Median home value
$290,500
Avg household
2
Households w/ children
48%
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 → $307K
Clearwater median sold, yr/yr
95.8%
Sale-to-list ratio (12 mo)
221 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 65% below the CLEARWATER 33756 median. See the full Clearwater market guide →
Paper trail
This home's history
Reality check
What actually sold near 1655 S HIGHLAND AVENUE UNIT D238
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$180,000
1655 S HIGHLAND AVENUE UNIT F126 · same community
2 bd · 2 ba · 1,270 sqft · $142/sqft · 106 DOM
Sold · Jan ’26$120,000
1655 S HIGHLAND AVENUE UNIT J390 · same community
2 bd · 2 ba · 1,270 sqft · $94/sqft · 6 DOM
Sold · Mar ’26$178,000
1655 S HIGHLAND AVENUE UNIT F125 · same community
2 bd · 2 ba · 1,270 sqft · $140/sqft · 0 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 1655 S HIGHLAND AVENUE UNIT D238 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1655 S HIGHLAND AVENUE UNIT D238 — 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
1655 S HIGHLAND AVENUE UNIT D238 FAQs
What would the monthly payment be for 1655 S HIGHLAND AVENUE UNIT D238?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,173/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 1655 S HIGHLAND AVENUE UNIT D238?+
The most recent tax bill on record (2024) was $3,040. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 1655 S HIGHLAND AVENUE UNIT D238?+
The listing reports pets: No. 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 $119,999, this home is listed about 56% below the Clearwater median of $275,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1655 S HIGHLAND AVENUE UNIT D238?+
Ponce De Leon Elementary School (elementary), Largo High School (high), Largo Middle School (middle) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Under the CLEARWATER 33756 market on paper
$119,999 is 65% below the CLEARWATER 33756 median of $339,000, and at $94/sqft it sits under the Clearwater average of $276.
02Time on market is leverage
344 days on market against a Clearwater median of 55 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Ponce De Leon Elementary School, Largo High School, Largo Middle School — Ponce De Leon Elementary School rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $135,000, now $119,999 — a $15K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of SERHANT · Kelli Azeman. MLS #TB8422801.
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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