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Single family home for sale at 14253 Country Est Dr, Winter Garden, FL 34787 | MLS# O6453112 | Listing updated on 2026-11-06
Photo 1 of Single family home for sale at 14253 Country Est Dr, Winter Garden, FL 34787 | MLS# O6453112 | Listing updated on 2026-11-06
Photo 2 of Single family home for sale at 14253 Country Est Dr, Winter Garden, FL 34787 | MLS# O6453112 | Listing updated on 2026-11-06
Photo 3 of Single family home for sale at 14253 Country Est Dr, Winter Garden, FL 34787 | MLS# O6453112 | Listing updated on 2026-11-06
Photo 4 of Single family home for sale at 14253 Country Est Dr, Winter Garden, FL 34787 | MLS# O6453112 | Listing updated on 2026-11-06
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$1,675,000

Monthly Est:$8,337

  • Beds Icon5 Beds
  • Beds Icon
    5 Baths
  • Beds Icon5,504sqft

14253 Country Est Dr, Winter Garden, FL 34787

$8,337/moEst:

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  • Single Family Residence

  • Built in 1990

  • $70.83/mo HOA

  • 2.8 acres lot

  • $304/sq.ft

Description

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.

  • Houzeo last checked: 6 minutes ago
  • Listing updated: November 6, 2026 at 11:15 pm
  • Listing Provided by: Desmond Garcia LLC (407) 202-5104 , Christopher Christensen | ONE LUXURY INTERNATIONAL LLC (407) 312-8003
  • Source: Stellar MLS-FL as distributed by MLS GRID | MLS#: O6453112 Stellar MLS-FL as distributed by MLS GRID

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Winter Garden

  • Neighborhood

    --

  • Year Built

    1990

  • HOA Fees

    $70.83/mo

  • Finished Area

    5,504 sqft

  • Lot Size

    2.8 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6453112

  • MLS Status

    Active

  • Days on Market

    1

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Location

HOA Management

Country Lakes Community Assoc / Sherry Shackelford

HOA Fees

$850/ Annually

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 5

  • Great Room

    Level: First

    Area: 425.00 Square Feet

    Dimensions: 25x17

  • Kitchen

    Level: First

    Area: 234.00 Square Feet

    Dimensions: 18x13

  • Dining Room

    Level: First

    Area: 208.00 Square Feet

    Dimensions: 16x13

  • Dinette

    Level: First

    Area: 272.00 Square Feet

    Dimensions: 17x16

  • Bonus Room

    Level: First

    Area: 378.00 Square Feet

    Dimensions: 27x14

  • Bathroom 2

    Level: Second

    Area: 182.00 Square Feet

    Dimensions: 14x13

  • Primary Bedroom

    Level: First

    Area: 400.00 Square Feet

    Dimensions: 20x20

  • Bathroom 3

    Level: Second

    Area: 252.00 Square Feet

    Dimensions: 18x14

  • Bedroom 4

    Level: Second

    Area: 195.00 Square Feet

    Dimensions: 15x13

  • Bedroom 5

    Level: Second

    Area: 210.00 Square Feet

    Dimensions: 15x14

Interior

  • Exterior Features

    Lighting, Outdoor Grill, Outdoor Kitchen, Private Yard

  • Sewer

    Septic Tank

  • Interior Features

    Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, Solid Wood Cabinets, Vaulted Ceiling(s), Walk In Closet(s)

  • Flooring

    Carpet, Ceramic Tile

  • Heating

    Central, Electric, Zoned

  • Appliances

    Built In Oven, Dishwasher, Disposal, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Water Softener

  • Cooling

    Central Air, Zoned

Construction

  • Year Built

    Year Built: 1990

  • Home type

    Single Family Residence

  • Construction Materials

    Brick, Frame

  • Foundation Details

    Slab

  • Roof

    Shingle

Utilities & Energy

  • Pool Features

    In Ground, Outside Bath Access, Screen Enclosure, Tile

  • Laundry Features

    Laundry Room

  • Parking Features

    Circular Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side, Oversized, Parking Pad

  • Fireplace Features

    Family Room, Wood Burning

  • Water Source

    Canal/lake For Irrigation, Well

  • Utilities

    Bb/hs Internet Available, Cable Available, Electricity Connected

Other Features

  • Subdivision Name

    Country Lakes

  • Community Features

    Street Lights

Price History

DateEventPrice

11/06/2026

Source: mls_logoStellar MLS-FL #MFRO6453112

Listed for Sale

$1,675,000 +123.33%

$304/sqft

12/02/2013

Source: mls_logoStellar MLS-FL as distributed by MLS GRID #MFRO5128120

Listing Removed

$750,000

$136/sqft

Nearby Homes

Based on information from Stellar MLS® through Nov 07, 2026, 08:30AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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