271 HEMINGWAY DRIVE, OLDSMAR, FL, 34677
Active312 days on marketListed Sep 15, 2025MLS #TB8426952
About this home
271 HEMINGWAY DRIVE
Virtually Staged. Welcome to this inviting 3-bedroom, 2.5-bath townhome with a private garage, perfectly set on a premier conservation lot, in the quaint Oldsmar community of Sun Ketch Townhomes of Cypress Lakes. Step inside to find brand-new luxury vinyl plank flooring and a bright, open layout. The spacious great room features sliding glass doors leading to a sunroom, expanding your living area while offering serene views of the conservation! The kitchen is both functional and stylish, with white cabinetry, solid-surface countertops, tile flooring, a breakfast bar and a closet pantry. For added convenience, the inside laundry room—complete with full-size Bosch washer and dryer—is located just off the kitchen. Upstairs, the primary suite impresses with vaulted ceilings, a walk-in closet and a private bath, while the additional bedrooms are well-sized for family, guests, or office space. Enjoy the saltwater, community pool, a low HOA fee of only $265 per month and the unbeatable location! Oldsmar is the gateway to Tampa, offering easy access to shopping, dining, parks, Tampa Skating Academy, and highly rated schools including Forest Lakes Elementary, Carwise Middle, and East Lake High. Plus, Tampa International Airport is less than 30 minutes away!
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,452
Sqft
0.06 ac
Lot size
1
Garage
1998
Year built
Two
Levels
$255
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.
$2,863 /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
$2,863/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
+15.7%
$/sqft vs Oldsmar actives
$255 vs $227
Days on market
312 vs 43 typical
Where $255/sqft sits among the 155 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
$2,000/mo median
Live Oldsmar rental listing data — this home’s rate depends on size, condition and furnishing.
The Buenaventura Lakes short-term market
▼ Softening54%
Occupancy
▼ 29% yr/yr
$175
Avg nightly rate
▲ 5% yr/yr
$26K/yr
Revenue per listing
$101
RevPAR
45 days
Booking lead time
4.9 nights
Avg stay
4
Typical min nights
134
Active rentals
▼ 31% supply
Seasonality — monthly occupancy
Peaks at 68% in Mar · bottoms at 39% in Sep
Last 12 months of data, January–December, bars scaled to the seasonal peak. Market-wide averages across all home sizes in Buenaventura Lakes — the projection above is specific to this home’s size.
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
$360K → $355K
Oldsmar median sold, yr/yr
96.3%
Sale-to-list ratio (12 mo)
93 of 155
Oldsmar actives have cut their price
Median sold price, Oldsmar, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 44% above the OLDSMAR 34677 median. See the full Oldsmar market guide →
Paper trail
This home's history
Reality check
What actually sold near 271 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 ’25$350,000
284 HEMINGWAY DRIVE · same community
3 bd · 2.5 ba · 1,604 sqft · $218/sqft · 165 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 271 HEMINGWAY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 271 HEMINGWAY DRIVE — 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
271 HEMINGWAY DRIVE FAQs
What would the monthly payment be for 271 HEMINGWAY DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,863/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 271 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 271 HEMINGWAY DRIVE?+
The most recent tax bill on record (2024) was $1,157. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 271 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 271 HEMINGWAY DRIVE?+
The listing reports pets: Number 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 Oldsmar?+
At $370,000, this home is listed about 8% above the Oldsmar median of $342,450. The market section on this page shows how the area is trending.
Which schools are assigned to 271 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
Five things that matter here
01Positioned at the premium end
$370,000 runs 44% 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.
03Park/Greenbelt & Trees/Woods views
The park/greenbelt and trees/woods view is part of what you're buying — views hold value independently of the structure.
04Time on market is leverage
312 days on market against a Oldsmar median of 43 — sellers in this position are usually ready to negotiate.
05Strong 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 COLDWELL BANKER REALTY · Marcy Daniels. MLS #TB8426952.
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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