280 Santa Rosa Drive, FL280 Santa Rosa Drive, FL280 Santa Rosa Drive, FL
Stellar MLS
1 / 44

$430,000

280 Santa Rosa Drive

Winter Haven, FL 33884

Listing updated: September 3, 2026 at 8:56 PM ET

Active
Stellar MLSListing courtesy of Keller Williams Realty Smart 1 · Ashley James · MLS #L4964337 · Active · 863-508-3000
3
Beds
2
Baths
2,251
Sq Ft
0.29
Acres
1986
Built
Private poolFireplace$191/sqft360° tour
Single Family Residence

Property type

1986

Year built

12,654 sqft

Lot size

$191

Price / sq ft

$42/mo

HOA dues

11

Days on market

2

Garage spaces

X

Flood zone

About this home

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!

Estimated monthly payment

Principal & interest$2,174
Property taxes$417
Home insurance (est.)$197
HOA dues$42

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history11 days on market

  1. Status: Active
    Sep 4, 2026
  2. Listed$430,000
    Aug 17, 2026
  3. Price increased$430,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
11
Subdivision
Overlook Estates
County
Polk
Year built
1986
Living area
2,251 sq ft
Price/sq ft
$191
Building area
3,531 sq ft (Public Records)
Lot size
12,654 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X
Garage
2 spaces
Pool
Private pool
Annual taxes
$5,003 (2026)
Parcel #
26-28-35-662924-001020
Zoning
R
MLS #
L4964337

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Interior Details

Bedrooms
3
Full bathrooms
2
Flooring
Carpet, Tile, Vinyl
Appliances
Built-In Oven, Convection Oven, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
Interior features
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
Laundry
Inside, Laundry Room
Stories / Levels
One
Direction faces
North
Fireplace
Yes

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Garage Door Opener, Oversized

HOA & Financial

HOA fee
$500 / Annually
Monthly HOA
$42/mo
Total monthly fees
$42/mo
Total annual fees
$500
HOA name
Overlook Estates/ Mark Koski
CDD
No
Min lease term
1-2 Years
Listing terms
Cash, Conventional, FHA, Other, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Please see community documents regarding any restrictions on rental.

Exterior & Construction

Exterior features
Private Mailbox, Rain Gutters, Sidewalk, Sprinkler Metered
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Pool
Private pool
Road surface
Paved

Utilities

Sewer
Septic Tank
Water source
Public
Utilities
Electricity Connected, Sprinkler Meter

Community

Pets allowed
Yes

Schools

ElementaryElbert ElemGreatSchools ↗
MiddleDenison MiddleGreatSchools ↗
High SchoolWinter Haven SeniorGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
KitchenFirst25x27
Living RoomFirst21x20
Primary BedroomFirst14x18
Primary BathroomFirst14x14
Bedroom 2First
Bedroom 3First13x14
DenFirst12x13
Balcony/Porch/LanaiFirst14x39

Listing Details

Listing date
2026-08-17
On market date
2026-08-17
Original list price
$430,000
Occupant type
Vacant
MLS area
33884 - Winter Haven / Cypress Gardens
Listing AOR
East Polk
Status changed
2026-09-04
Tax legal description
Overlook Estates Phase One PB 79 PG 30 BLK A Lot 2

Flood risk

Minimal riskFEMA Zone X

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From US-17 head north, turn right onto Cypress Gardens Blvd SW, in 2.5 miles turn left onto Overlook Dr. In .05 a mile turn left onto Wakulla Dr. SE and then take your immediate right turn into the Overlook Estates neighborhood.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

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.

Based on information submitted to the MLS GRID as of September 3, 2026 at 8:56 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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