216 HEMINGWAY DRIVE, OLDSMAR, FL, 34677
Active33 days on marketListed Aug 20, 2026MLS #TB8539671
About this home
216 HEMINGWAY DRIVE
WOW!!! Done home, move in ready in a great location!!! Welcome home to this beautifully updated pond front three-bedroom, 2½-bath townhome with a one-car garage in the desirable Sun Ketch community of Oldsmar! Best of all, the low $265/month HOA fee covers exterior maintenance, grounds care, the roof, and offering truly low-maintenance living. Residents also enjoy a community pool just steps from the home, making it easy to relax and enjoy the Florida lifestyle. Step inside to a welcoming foyer with a convenient half bath for guests. Continue into the bright, open-concept main living area, which boasts Travertine tile flooring, and where the beautifully updated kitchen features white cabinetry, quartz countertops, a breakfast bar, ample storage, and a fantastic corner pantry with built-in shelving. The kitchen flows seamlessly into the living and dining room, creating an ideal space for everyday living and entertaining. Pocket sliding doors lead to the screened-in lanai and brick-paver patio, where you can enjoy peaceful pond views and a private, fenced outdoor space. Upstairs, the spacious primary suite is positioned at the front of the home and features vaulted ceilings, an oversized wall closet, and a private en-suite bath with a step-in shower. Down the hall, the beautifully updated guest bath offers a tub/shower combination, while a linen closet provides additional storage. The two secondary bedrooms are located at the rear of the home, with one featuring a sizable walk-in closet and the other offering a generous wall closet. The entire second floor is light and bright with high-volume ceilings and attractive wood-look luxury vinyl plank flooring. Thoughtful storage continues throughout the home, including great under-stair storage, a laundry room with cabinetry, and direct access to the one-car garage. Recent updates in 2023 include quartz kitchen countertops, luxury vinyl plank flooring upstairs, carpeting on the staircase, reglazing of the guest bathtub, four new PGT hurricane rated windows (two double hung in the primary and sliding windows in the rear bedrooms), and a vinyl-coated chain-link fence enclosing the rear patio area overlooking the water. With these improvements already completed, there is truly nothing left to do but move in and start enjoying your new home. Located in a convenient Oldsmar location near Tampa Road, approximately 20 minutes to Tampa International Airport (TPA), St. Pete-Clearwater International Airport (PIE) and popular Honeymoon Island, you’ll also have easy access to restaurants, shopping, and so much more. Add in the community pool, peaceful pond setting, garage, and low-maintenance HOA lifestyle, and this wonderful townhome offers the perfect blend of comfort, convenience, and Florida living. Come see it for yourself!
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,452
Sqft
0.06 ac
Lot size
1
Garage
1997
Year built
Two
Levels
$272
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 and the real association fee — not generic estimates.
$3,295 /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
$3,295/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
+27.9%
$/sqft vs Oldsmar actives
$272 vs $228
Days on market
33 vs 56 typical
Where $272/sqft sits among the 157 Oldsmar 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.
The investor lens
Two ways this home pays
This home sits inside Cypress Lakes, a community zoned to allow true short-term rentals — so it can earn as a nightly rental or a traditional lease. Here’s how the two paths compare.
Short-term rental
Zoned & eligible
Projected nightly rate, occupancy and annual revenue for this exact home.
Long-term rental
$1,900/mo median
Live Oldsmar rental listing data — this home’s rate depends on size, condition and furnishing.
Where it sits
Inside Cypress Lakes
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Cypress Lakes is a short-term-rental community. See the full guide →
OLDSMAR 34677 — neighborhood snapshot
Population
22,337
Median age
47.3
Median income
$85,389
Median home value
$352,200
Avg household
2.49
Households w/ children
2,157
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Oldsmar market
$400K → $415K
Oldsmar median sold, yr/yr
96.5%
Sale-to-list ratio (12 mo)
78 of 157
Oldsmar actives have cut their price
Median sold price, Oldsmar, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 56% above the OLDSMAR 34677 median. See the full Oldsmar market guide →
Paper trail
This home's history
Reality check
What actually sold near 216 HEMINGWAY DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’26$350,000
271 HEMINGWAY DRIVE · same community
3 bd · 2.5 ba · 1,452 sqft · $241/sqft · 326 DOM
Sold · Jun ’26$300,000
208 HEMINGWAY DRIVE · same community
2 bd · 2 ba · 1,207 sqft · $249/sqft · 57 DOM
Sold · Mar ’26$276,000
248 HEMINGWAY DRIVE · same community
2 bd · 2 ba · 1,086 sqft · $254/sqft · 22 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
Nicholas Giaccone
Director of Agent Success · CENTURY 21 Edge
Tours, negotiation, and every question about 216 HEMINGWAY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 216 HEMINGWAY DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Nicholas's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
216 HEMINGWAY DRIVE FAQs
What would the monthly payment be for 216 HEMINGWAY DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,295/mo — principal and interest, the actual property-tax bill, the $265/mo association fee 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.
How much are the HOA fees at 216 HEMINGWAY DRIVE?+
The association fee works out to $265 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 216 HEMINGWAY DRIVE?+
The most recent tax bill on record (2025) was $4,435. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 216 HEMINGWAY DRIVE be rented short-term?+
Yes — this home sits inside Cypress Lakes, a community zoned to allow short-term rentals. Nightly-rental income could change the math on this purchase entirely; request a free rental income analysis and our team will prepare projections for this exact home.
Are pets allowed at 216 HEMINGWAY DRIVE?+
The listing reports pets: 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 Oldsmar?+
At $395,000, this home is listed about 22% above the Oldsmar median of $324,900. The market section on this page shows how the area is trending.
Which schools are assigned to 216 HEMINGWAY DRIVE?+
Oldsmar Elementary School (elementary), Joseph L. Carwise Middle School (middle), East Lake High School (high) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$395,000 runs 56% above the OLDSMAR 34677 median.
02Zoned for nightly rentals
Cypress Lakes is one of the communities zoned to allow true short-term rentals — nightly income could change the math on this purchase entirely. Ask for the free rental analysis below.
03Water views
The water view is part of what you're buying — views hold value independently of the structure.
04Strong assigned schools
Oldsmar Elementary School, Joseph L. Carwise Middle School, East Lake High School — Oldsmar Elementary School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY- PALM HARBOR · Vanessa Leonard. MLS #TB8539671.
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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