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$339,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,535 Sq. Ft.
  • Updated 11 hours ago
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Clean, clean, clean. Welcome to 356 Sterling Drive - a meticulously maintained 3-bedroom, 2-bath pool home that truly shows like a model. Pride of ownership is evident from the moment you arrive, where outstanding curb appeal showcases fresh exterior paint, hurricane-rated double-pane windows and sliding doors, lush landscaping, and a welcoming front lawn. This move-in ready residence offers extensive recent updates, including a brand-new roof with Heritage Proline Titan XT shingles (2025), refinished pool, new stainless steel appliances (2023), water heater (2023), new double-hung hurricane rate double pane windows (2024), updated bathroom vanities, new interior and exterior paint (2023), upgraded door hardware and electrical faceplates (2023), and more. Inside, an open and airy layout features tile flooring throughout, elevated ceilings, and an inviting great room designed for both relaxed living and entertaining while capturing tranquil views of the screened pool. The eat-in kitchen provides generous workspace, ample cabinetry, newer stainless appliances, and a charming bay-window dinette ideal for everyday dining. A desirable split bedroom plan ensures privacy. The spacious primary suite offers generous closet space and a well-appointed en-suite bath with dual sinks, updated finishes, and a tiled walk-in shower. Secondary bedrooms are nicely sized and provide convenient access to the full guest bath. Outdoor living is where this home truly shines. The screened pool and fully fenced backyard create the perfect setting for enjoying Florida's year-round lifestyle, offering privacy, space for pets or play, and fruit trees that add beauty and a touch of nature. A two-car garage provides additional storage and everyday convenience. Located in the established Berryhill community of southeast Winter Haven, the home offers convenient access to shopping, dining, schools, medical facilities, and everyday essentials. Winter Haven's central location between Tampa and Orlando makes commuting and travel easy while still enjoying the relaxed lifestyle the area is known for - including the Chain of Lakes, boating, recreation, and a vibrant community atmosphere. A beautifully updated home, thoughtfully cared for, and ready for its next chapter.

Full Property Details for 356 Sterling Dr

General

  • Price: $339,900
  • HOA FEE: $24/month
  • HOA FEE FREQ.: Annually
  • Taxes: $3,462 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: L4959652
  • Updated: 2/27/2026
  • Added to Site: 1 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, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile

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: Gunite, Screen Enclosure

Exterior

  • Exterior Features: Irrigation System, Sliding Doors
  • Deck/Patio: Patio, Screened
  • Porch/Patio/Deck: Patio, Screened

Parking

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

Location

  • Area: 33884 - Winter Haven / Cypress Gardens
  • County: Polk
  • Development Name: 33884 - Winter Haven / Cypress Gardens
  • Subdivision: BERRYHILL
  • Driving Directions: Cypress Gardens Blvd to Cypress Gardens Rd - N on Cypress Gardens Rd - W on Cypress Gardens Rd - S on Sterling Dr - Make first left and take Sterling Dr to address
  • Direction Faces: West

School Information

  • Elementary School: Garden Grove Elem
  • Middle School: Denison Middle
  • High School: Winter Haven Senior

Community

  • Community Name: 33884 - Winter Haven / Cypress Gardens
  • Association: Yes
  • Assoc. Name: Garrison Property Services
  • Pet Restrictions: Must contact HOA directly to confirm pet rules and restrictions.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected

Structural Information

  • Architectural Info: Contemporary
  • Architectural Style: Contemporary
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Double Pane Windows, Thermal Windows
  • Stories/Levels: One
  • Square Feet: 1,535
  • Sq. Ft. Source: Public Records
  • Year Built: 2001

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 0.2
  • Lot Size (Sq. Ft.): 8,638
  • Lot Size: 8638
  • Lot Dimensions: 75 x 115
  • Frontage: Street Paved
  • Street/Road Desc.: Paved
  • Fencing (Description): Vinyl

Financial Considerations

  • Association Fee: $287
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $3,462
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BERRYHILL PB 88 PG 48 & 49 LOT 18
  • Flood Zone Info: X
  • APN: 262901663569000180
  • Property ID: 262901663569000180

Listed by The Stones Real Estate Firm

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Listing agents

— 356 Sterling Dr —

  • The Stones Real Estate Firm

  • The Stones Real Estate Firm

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 356 Sterling Dr

School District:Polk County School District
NameGradesDistance
Garden Grove Elementary School
4599 Cypress Gardens Road, Winter Haven, FL 33884
PK-50.6 mi
Denison Middle School
400 Avenue A Southeast, Winter Haven, FL 33880
6-83.9 mi
Winter Haven Senior High School
600 6th Street Southeast, Winter Haven, FL 33880
9-123.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 356 Sterling Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/27/2026
Listed
$339,900
12.92%
MLS
9/07/2023
Sold
$301,000
—
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 356 Sterling Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,656
-24%
$240,817
-3%
2024
$3,484
118%
$249,505
117%
2023
$1,597
7%
$114,985
3%
2022
$1,499
2%
$111,636
3%
2021
$1,472
—
$108,384
1%
2021
$1,472
10%
$106,888
4%
2017
$1,342
—
$102,537
2%
2017
$1,342
3%
$100,428
2%
2016
$1,303
-1%
$98,362
1%
2015
$1,317
-6%
$97,678
-7%
2019
$1,407
10%
$104,485
8%
2014
$1,279
—
$96,903
1%
2013
$1,281
—
$95,471
—
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 The Stones Real Estate Firm

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356 Sterling Drive, Winter Haven, FL 33884 (MLS# L4959652) is a Single Family property with 3 bedrooms and 2 full bathrooms. 356 Sterling Drive is currently listed for $339,900 and was received on February 27, 2026. Want to learn more about 356 Sterling 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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