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$430,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,251 Sq. Ft.
  • Updated 2 days ago
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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!

Full Property Details for 280 Santa Rosa Dr

General

  • Price: $430,000
  • HOA FEE: $42/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,002 (2026)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: L4964337
  • Updated: 8/18/2026
  • Added to Site: 3 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Wood Burning
  • Appliances: Built-In Oven, Convection Oven, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground, Salt Water, Tile

Exterior

  • Exterior Features: French Doors, Irrigation System, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors, Sprinkler Metered
  • Deck/Patio: Covered, Screened
  • Porch/Patio/Deck: Covered, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Garage Door Opener, Oversized

Location

  • Area: 33884 - Winter Haven / Cypress Gardens
  • County: Polk
  • Development Name: 33884 - Winter Haven / Cypress Gardens
  • Subdivision: OVERLOOK ESTATES
  • Driving 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.
  • Direction Faces: North

School Information

  • Elementary School: Elbert Elem
  • Middle School: Denison Middle
  • High School: Winter Haven Senior

Community

  • Community Name: 33884 - Winter Haven / Cypress Gardens
  • Association: Yes
  • Assoc. Name: Overlook Estates/ Mark Koski
  • Assoc. Fees Include: Common Area Taxes, Escrow Reserves Fund, Private Road
  • Pet Restrictions: Please see community documents regarding any pet restrictions.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Electricity Connected, Sprinkler Meter

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 2,251
  • Sq. Ft. Source: Public Records
  • Year Built: 1986

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 0.29
  • Lot Size (Sq. Ft.): 12,654
  • Lot Size: 12654
  • Lot Dimensions: 97 x 129
  • Frontage: Street Paved, Private Road
  • Street/Road Desc.: Paved
  • Fencing (Description): Wood

Financial Considerations

  • Association Fee: $500
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,002.64
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: Overlook Estates Phase One PB 79 PG 30 BLK A Lot 2
  • Flood Zone Info: X
  • APN: 262835662924001020
  • Property ID: 262835662924001020
  • Block/Lot/Section: A

Listed by Keller Williams Realty Smart 1

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— 280 Santa Rosa Dr —

  • Keller Williams Realty Smart 1

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 280 Santa Rosa Dr

School District:Polk County School District
NameGradesDistance
Elbert Elementary School
205 15th Street Northeast, Winter Haven, FL 33881
PK-51.4 mi
Denison Middle School
400 Avenue A Southeast, Winter Haven, FL 33880
6-82.2 mi
Winter Haven Senior High School
600 6th Street Southeast, Winter Haven, FL 33880
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 280 Santa Rosa Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/17/2026
Listed
$430,000
21.13%
MLS
1/31/2022
Sold
$355,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 280 Santa Rosa Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,258
-15%
$321,269
-2%
2024
$4,995
4%
$329,305
3%
2023
$4,785
10%
$319,599
12%
2022
$4,368
69%
$286,550
51%
2021
$2,590
—
$189,878
1%
2021
$2,590
3%
$187,256
2%
2019
$2,526
4%
$183,046
2%
2017
$2,419
—
$179,633
2%
2017
$2,419
2%
$175,938
2%
2016
$2,382
19%
$172,319
19%
2015
$1,998
2%
$144,631
1%
2014
$1,959
—
$143,483
1%
2013
$1,966
—
$141,363
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Keller Williams Realty Smart 1

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280 Santa Rosa Drive, Winter Haven, FL 33884 (MLS# L4964337) is a Single Family property with 3 bedrooms and 2 full bathrooms. 280 Santa Rosa Drive is currently listed for $430,000 and was received on August 17, 2026. Want to learn more about 280 Santa Rosa Drive? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.

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