280 SANTA ROSA DRIVE, WINTER HAVEN, FL, 33884
Active34 days on marketListed Aug 17, 2026MLS #L4964337
About this home
280 SANTA ROSA DRIVE
This property went under contract fast and it's back on the market, no fault of the owner. If you missed it the first time, here's your second chance! Welcome to the beautiful neighborhood of Overlook Estates. This 3 bedroom 2 bath + bonus room is waiting for its new owner/s to make it their own. This home is completely vacant which makes it that much easier to envision your own life here. When you first arrive you will notice the beautiful curb appeal this home offers. Upon entering you will be greeted by the stunning entrance. This home is bright and spacious with high ceilings and beautiful wood beams giving it character right off the bat. The kitchen was completely remodeled in 2022. It has floor to ceiling cabinets giving you plenty of space for storage. Use the large island with a built in cook top or move it over to a more formal dining room. Either way this home is the perfect place for entertaining. You can access the lanai/salt water pool from the primary bedroom, kitchen, living room, and even the full guest bath. The open floor plan allows for friends and family to gather while still having plenty of space to spread out. The primary bedroom with ensuite bath and walk in closet as well as that access to the lanai. The primary bathroom has a walk in shower, garden tub, dual vanity and also includes a walk in closet as well as a linen closet. The two additional bedrooms as well as a full bath are located on the opposite side of the house. A fourth room allows for the perfect office space or even a room to host your guests. This home has been wonderfully updated while still holding onto its charm and character. Schedule your showing today!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
2,251
Sqft
0.29 ac
Lot size
2
Garage
1986
Year built
One
Levels
$191
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.
$3,340 /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
$3,340/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
+6.1%
$/sqft vs Winter Haven actives
$191 vs $170
Days on market
34 vs 48 typical
Where $191/sqft sits among the 400 Winter Haven 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 Winter Haven
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Haven. See the full Winter Haven guide →
WINTER HAVEN 33884 — neighborhood snapshot
Population
36,395
Median age
45.3
Median income
$70,516
Median home value
$269,400
Avg household
2.58
Households w/ children
3,777
For the school run
Polk County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Haven market
$283K → $280K
Winter Haven median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
216 of 400
Winter Haven actives have cut their price
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 54% above the WINTER HAVEN 33884 median. See the full Winter Haven market guide →
Paper trail
This home's history
Reality check
What actually sold near 280 SANTA ROSA DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$480,000
205 SANTA ROSA DRIVE · same community
3 bd · 2 ba · 2,251 sqft · $213/sqft · 11 DOM
Sold · Jul ’26$280,000
262 SANTA ROSA DRIVE · same community
4 bd · 2 ba · 2,336 sqft · $120/sqft · 99 DOM
Sold · Dec ’25$430,000
728 SANTA MARIA DRIVE · same community
4 bd · 2.5 ba · 2,104 sqft · $204/sqft · 18 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
Kevin Johnson
CEO & Managing Broker · CENTURY 21 Edge
Tours, negotiation, and every question about 280 SANTA ROSA DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 280 SANTA ROSA DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Kevin's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
280 SANTA ROSA DRIVE FAQs
What would the monthly payment be for 280 SANTA ROSA DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,340/mo — principal and interest, the actual property-tax bill, the $42/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 280 SANTA ROSA DRIVE?+
The association fee works out to $42 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 280 SANTA ROSA DRIVE?+
The most recent tax bill on record (2026) was $5,003. 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 280 SANTA ROSA 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 Winter Haven?+
At $430,000, this home is listed about 51% above the Winter Haven median of $285,000. The market section on this page shows how the area is trending.
Which schools are assigned to 280 SANTA ROSA DRIVE?+
Chain Of Lakes Elementary School (elementary), Lake Region High School (high) — Polk County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY SMART 1 · Ashley James. MLS #L4964337.
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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