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$1,675,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 5,504 Sq. Ft.
  • Updated 5 days ago
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Lakefront living with room to spread out. Welcome to 14253 Country Estate Drive. Set on nearly three acres along Black Lake, this two-story brick pool home pairs timeless character with expansive water views in an established community of custom homes. Mature oaks frame the circular driveway, creating a welcoming arrival to a residence offering approximately 5,504 square feet, five bedrooms, four full baths, and one half bath. Lake views greet you from the foyer and draw you into the soaring great room, where a wood-burning stone fireplace, tall windows, and French doors create an inviting setting for everyday living and entertaining. The spacious kitchen features a generous center island, extensive cabinetry, and adjoining casual dining, while a separate formal dining room provides space for larger gatherings. The main-floor primary suite offers its own screened lanai, a quiet place to start the day overlooking the grounds. An office with a closet provides flexibility for a potential fifth bedroom, and two upstairs bonus rooms offer additional space for recreation, hobbies, or working from home. Outside, the pool, lanai, and expansive backyard make the waterfront setting the centerpiece of the home. Enjoy afternoons by the water, outdoor dining, or time on Black Lake boating, fishing, paddleboarding, and jet skiing. A side-entry three-car garage completes the property. Conveniently located near the shopping and dining at Winter Garden Village at Fowler Groves, with access to SR 429, SR 408, and Florida's Turnpike, this home brings together spacious interiors, generous grounds, and the Florida lakefront lifestyle.

Full Property Details for 14253 Country Estate Dr

General

  • Price: $1,675,000
  • HOA FEE: $71/month
  • HOA FEE FREQ.: Annually
  • Taxes: $11,665 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6453112
  • Updated: 11/6/2026
  • Added to Site: 6 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 10
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Wood Burning
  • Appliances: Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Water Softener
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Outside Bath Access, Screen Enclosure, Tile

Exterior

  • Exterior Features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Yard

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Circular Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side, Oversized, Parking Pad

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: COUNTRY LAKES
  • Driving Directions: From hwy 50 and Vineland Rd in Winter Garden, go South, past traffic circle to Country Lakes enterance on right. Continue straight to home on the right.
  • Direction Faces: Northeast

School Information

  • Elementary School: SunRidge Elementary
  • Middle School: SunRidge Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Association: Yes
  • Assoc. Name: Country Lakes Community Assoc / Sherry Shackelford

Heating & Cooling

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

Utilities

  • Sewer: Septic Tank
  • Water District: BLACK LAKE
  • Water: Canal/Lake For Irrigation, Well
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Street Lights

Structural Information

  • Exterior Const.: Brick, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 5,504
  • Sq. Ft. Source: Public Records
  • Year Built: 1990

Additional Structures

  • Other Structures: Outdoor Kitchen

Lot Features

  • Property View: Water
  • Lot Size (Acres): 2.8
  • Lot Size (Sq. Ft.): 121,839
  • Lot Size: 2.797
  • Lot Dimensions: 130 x 350
  • Street/Road Desc.: Asphalt
  • Fencing (Description): Fenced

Water Features

  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Extras: Yes
  • Water Front Name: BLACK LAKE

Financial Considerations

  • Association Fee: $850
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $11,665
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: COUNTRY LAKES 9/99 LOT 14
  • Flood Zone Info: AE
  • APN: 342227180700140
  • Property ID: 342227180700140

Listed by One Luxury International Llc

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Listing agents

— 14253 Country Estate Dr —

  • One Luxury International Llc

  • One Luxury International Llc

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 14253 Country Estate Dr

School District:Orange County School District
NameGradesDistance
Sunridge Elementary School
14455 Sunridge Boulevard, Winter Garden, FL 34787
PK-51 mi
SunRidge Middle School
14955 Sunridge Boulevard, Winter Garden, FL 34787
6-81 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.2 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 14253 Country Estate Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/06/2026
Listed
$1,675,000
123.33%
MLS
4/22/2014
Sold
$750,000
—
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 14253 Country Estate Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$11,665
4%
$745,225
6%
2024
$11,253
7%
$705,183
3%
2023
$10,507
4%
$684,644
6%
2021
$10,063
-1%
$645,343
-3%
2022
$10,191
1%
$664,703
4%
2021
$10,063
2%
$636,433
2%
2019
$9,891
1%
$622,124
2%
2018
$9,806
1%
$610,524
2%
2017
$9,687
—
$597,967
2%
2016
$9,660
-2%
$585,668
1%
2015
$9,821
10%
$581,597
26%
2014
$8,915
13%
$460,910
10%
2013
$7,855
—
$419,009
—
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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NMLS#: 1598647

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Listed by One Luxury International Llc

14253 Country Estate Drive, Winter Garden, FL 34787 (MLS# O6453112) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 14253 Country Estate Drive is currently listed for $1,675,000 and was received on November 06, 2026. Want to learn more about 14253 Country Estate Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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