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Overview

4 bd3 ba2,850 sqft2 car garageSingle Family
TypeSingle Family
HOA$550/yr
Built1988
Lot12,350 sqft
Living area2,850 sqft
Price / sqft$156
Garage2 car

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

About this home

Cathedral Ceiling(s)Ceiling Fans(s)Crown MoldingHigh CeilingsPrimarybedroom UpstairsSplit BedroomWalk-in Closet(s)Fire Pit

240 Santa Rosa Dr is a 1988-built home in Overlook Ests Ph 3, Winter Haven. Inside you'll find 4 bedrooms, 3 bathrooms, and 2,850 square feet of living space. Listed at $445,000 (about $156/sqft), 290 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $550 annually.

From the listing

Back on the market! Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.

The essentials

Built
1988
Price / sqft
$156
On market
290 days
Annual tax
$2,790
HOA
$550/yr
Flood zone
X · Low risk
Lot
12,350 sqft
Type
Single Family Residence

At a glance

Single family
Built 1988
Private pool
Gunite
2 car garage
Garage Door Opener
0.28 acres
Lot size
2,850 sqft
Living area

Payment

Est. monthly payment
$2,822/mo
Down payment (20%)
$89,000
Property taxes
$233/mo
HOA
$550/yr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1988
Lot
12,350 sqft
Cooling
Central Air
Heating
Central
Parking
Garage Door Opener
Pool
Gunite, In Ground, Salt Water
Days on Market
290
Cathedral Ceiling(s)
Ceiling Fans(s)
Crown Molding
High Ceilings
Primarybedroom Upstairs
Split Bedroom
Walk-in Closet(s)
Fire Pit
Outdoor Shower
Rain Gutters
Storage
Deed Restrictions
Gated Community - No Guard
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
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.

Homestead exemption on file Flood Zone X
Annual Tax (2023)
$2,790
Parcel #
26-28-35-662927-000220

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 Ests Ph 3
County
Polk
MLS Area
33884 - Winter Haven / Cypress Gardens
Lot Size
12,350 sqft
In CountyLandscapedPaved
HOA
$550/yr
Overlook Estates

Price history

Date
Event
Price
9/30/2026
Price change
Source: Stellar MLS #L4958092
$445,000+1.4%
$156/sqft
-
Price change
Source: Stellar MLS #L4958092
$439,000-5.2%
$154/sqft
12/24/2025
Listed for sale
Source: Stellar MLS #L4958092
$462,900
$162/sqft

Neighborhood

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

Market insights

Offer Insights

Choose an offer strength

List price: $445,000
$442,500 – $445,000
99.5% – 100% of listTops out right at the list price
80% of listList price
219 of the last 347 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 290 after a $17,900 cut.

Sample: 347 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
$2,822/mo
Principal & interest$2,321
Property taxes$233
Insurance$223
HOA$46
Down payment20% · $89,000
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 is the fee 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

$445,000

$156 per sq ft

Beds and baths

4 beds, 3 baths

Size

2,850 sq ft

Time on market

290 days

Year built

1988

Monthly payment

About $2,822/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $2,790 annual tax bill, insurance, and the $550/yr HOA fee.

HOA fee

$550/yr

Managed by Overlook Estates.

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?

Have another question?

Brokered byLIVE FLORIDA REALTYListing agent: Brian SurrencyListing data from Stellar MLS, MLS# L4958092.

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