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Overview

3 bd2 ba2,251 sqft2 car garageSingle Family
TypeSingle Family
HOA$500/yr
Built1986
Lot12,654 sqft
Living area2,251 sqft
Price / sqft$184
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Ceiling Fans(s)Eat-in KitchenHigh CeilingsKitchen/Family Room ComboOpen FloorplanSolid Wood CabinetsSplit BedroomStone Counters

280 Santa Rosa Dr is a 1986-built home in Overlook Estates, Winter Haven. Inside you'll find 3 bedrooms, 2 bathrooms, and 2,251 square feet of living space. Listed at $415,000 (about $184/sqft), 56 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $500 annually.

From the listing

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!

The essentials

Built
1986
Price / sqft
$184
On market
56 days
Annual tax
$5,003
HOA
$500/yr
Flood zone
X · Low risk
Lot
12,654 sqft
Type
Single Family Residence

At a glance

Single family
Built 1986
Private pool
Heated
2 car garage
Garage Door Opener
0.29 acres
Lot size
2,251 sqft
Living area

Payment

Est. monthly payment
$2,830/mo
Down payment (20%)
$83,000
Property taxes
$417/mo
HOA
$500/yr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1986
Lot
12,654 sqft
Cooling
Central Air
Heating
Central
Parking
Garage Door Opener, Oversized
Pool
Heated, In Ground, Salt Water, Tile
Days on Market
56
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Open Floorplan
Solid Wood Cabinets
Split Bedroom
Stone Counters
Walk-in Closet(s)
Window Treatments
Private Mailbox
Rain Gutters
Sidewalk
Sprinkler Metered
Built-in Oven
Convection Oven
Dishwasher
Dryer
Electric Water Heater
Microwave
Refrigerator
Washer
Elementary
Elbert Elem
Middle
Denison Middle
High
Winter Haven Senior

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2026)
$5,003
Parcel #
26-28-35-662924-001020

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Overlook Estates
County
Polk
MLS Area
33884 - Winter Haven / Cypress Gardens
Lot Size
12,654 sqft
PavedPrivate
HOA
$500/yr
Overlook Estates/ Mark Koski

Price history

Date
Event
Price
9/29/2026
Price change
Source: Stellar MLS #L4964337
$415,000-3.5%
$184/sqft
8/17/2026
Listed for sale
Source: Stellar MLS #L4964337
$430,000
$191/sqft

Neighborhood

280 Santa Rosa Dr
Winter Haven, FL, 33884 · 33884 - Winter Haven / Cypress Gardens

Market insights

Offer Insights

Choose an offer strength

List price: $415,000
$412,500 – $415,000
99.5% – 100% of listTops out right at the list price
80% of listList price
221 of the last 351 home closings in 33884 landed at this number or higher (63%). The median one sat 38 days before it went under contract, and this one is on day 56 after a $15,000 cut.

Sample: 351 closed home sales in 33884 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$2,831/mo
Principal & interest$2,164
Property taxes$417
Insurance$208
HOA$42
Down payment20% · $83,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$415,000

$184 per sq ft

Beds and baths

3 beds, 2 baths

Size

2,251 sq ft

Time on market

56 days

Year built

1986

Monthly payment

About $2,830/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $5,003 annual tax bill, insurance, and the $500/yr HOA fee.

HOA fee

$500/yr

Managed by Overlook Estates/ Mark Koski.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

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Brokered byKELLER WILLIAMS REALTY SMART 1Listing agent: Ashley JamesListing data from Stellar MLS, MLS# L4964337.

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