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$599,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,860 Sq. Ft.
  • Updated 2 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 7/11 11:00 AM - 1:00 PM

1808 Western Trailway Drive,Winter Garden, FL 34787

1808 Western Trailway DriveWinter GardenFL34787

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Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,800 square feet of thoughtfully designed living space in the highly sought-after Hull Island community of Oakland. Tasteful décor and stylish finishes create a warm, inviting atmosphere, while the open-concept floor plan features a spacious kitchen with stainless steel appliances, a large center island with counter seating, and seamless flow into the living and dining areas-perfect for everyday living and entertaining. Step outside to your private backyard featuring maintenance-free turf, providing a lush, green outdoor space you can enjoy year-round without the upkeep. Residents also enjoy access to the community pool, scenic walking trails, and direct access to the West Orange Trail, with beautiful Lake Apopka just a couple of blocks away. Best of all, you'll enjoy all these incredible amenities while benefiting from a LOW HOA FEE! Whether you're purchasing your first home, growing your family, or right-sizing after the kids have moved out, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Hull Island is a welcoming, family-oriented community for all ages, conveniently located near charming downtown Winter Garden, shopping, dining, parks, and major roadways. Don't miss your opportunity to make this move-in-ready home your own!

Full Property Details for 1808 Western Trailway Dr

General

  • Price: $599,000
  • HOA FEE: $165/month
  • Taxes: $8,388 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5152973
  • Updated: 7/8/2026
  • Added to Site: 3 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 4
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination, Open Floorplan, Thermostat, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater
  • Furnishings: Unfurnished
  • Flooring: Luxury Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Park, Playground, Pool

Exterior

  • Exterior Features: Irrigation System, Sidewalk
  • Deck/Patio: Covered, Rear Porch
  • Porch/Patio/Deck: Covered, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Off Street, On Street

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: HULL ISLAND/OAKLAND
  • Driving Directions: * Take FL-429 North to Exit 19 for FL-50/Colonial Drive. * Head west on FL-50 toward Oakland. * Turn left onto W. Oakland Avenue (SR-438). * Continue through the traffic circle, staying on W. Oakland Avenue. * Turn left onto Hull Island Drive. * Turn left onto Western Trailway Drive. * 1808 Western Trailway Drive will be on the right.
  • Direction Faces: West

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Dock, Fishing, Lake, Water Access, Dog Park, Park, Playground, Pool
  • Optional Amenities: Park, Playground, Pool
  • Association: Yes
  • Assoc. Name: Amaan Lakhani
  • Number of Pets: 2
  • Pet Restrictions: Buyer’s agent and Buyer to confirm pet restrictions with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Craftsman
  • Architectural Style: Craftsman
  • Exterior Const.: Block
  • Roof: Shake
  • Windows: Window Treatments
  • Stories/Levels: One
  • Square Feet: 1,860
  • Sq. Ft. Source: Public Records
  • Year Built: 2019

Lot Features

  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,000
  • Lot Size: 6000
  • Street/Road Desc.: Asphalt
  • Fencing (Description): Vinyl

Water Features

  • Water Front Desc.: Lake

Financial Considerations

  • Association Fee: $165
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $8,388.74
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: HULL ISLAND AT OAKLAND 99/91 LOT 16
  • Flood Zone Info: X
  • APN: 192227377500160
  • Property ID: 192227377500160

Listed by Florida in Motion Realty Inc

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Listing agents

— 1808 Western Trailway Dr —

  • Florida in Motion Realty Inc

  • Florida in Motion Realty Inc

Get Pre-Approved Today

Be ready to buy your new home!

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 1808 Western Trailway Dr

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-52.4 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-82.7 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-125 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 1808 Western Trailway Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/07/2026
Listed
$599,000
3.63%
MLS
2/02/2026
Sold
$578,000
—
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 1808 Western Trailway Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,389
—
$458,000
-1%
2025
$8,389
67%
$462,500
43%
2024
$5,022
6%
$322,765
3%
2023
$4,736
4%
$313,364
6%
2021
$4,535
-1%
$295,376
-3%
2022
$4,590
1%
$304,237
4%
2021
$4,535
—
$291,298
—
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 Florida in Motion Realty Inc

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1808 Western Trailway Drive, Winter Garden, FL 34787 (MLS# S5152973) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1808 Western Trailway Drive is currently listed for $599,000 and was received on July 07, 2026. Want to learn more about 1808 Western Trailway 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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