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$599,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,857 Sq. Ft.
  • Updated 13 days ago
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Welcome to this stunning, like-new 3-bedroom, 2-bath home in the charming Hull Island community of Oakland, just 0.5 miles from the West Orange Trail, 1.5 miles to Costco, and only 10 minutes from historic downtown Winter Garden. Recently updated and truly move-in ready, this split-plan residence shines with beautiful wood-look tile flooring throughout (no carpet anywhere!), fresh backyard turf just one year old, a brand-new dishwasher, and thoughtful upgrades in every room. Step inside to an inviting open layout where natural light abounds. The gourmet L-shaped kitchen is a chef's dream, featuring abundant 42" maple cabinetry, quartz countertops, a tiled backsplash with sleek LED under-cabinet lighting, a gas range, a large center island with breakfast bar, an oversized walk-in pantry, and a built-in tech desk perfect for daily organization, charging devices, or remote work. Tucked at the rear for ultimate privacy, the serene primary suite offers a tray ceiling, expansive windows, and a spa-like ensuite bath with dual quartz vanities, an oversized shower showcasing upgraded subway tile and river rock flooring, semi-frameless glass enclosure, private water closet, and a huge walk-in closet. Two bright secondary bedrooms share a stylish hall bath at the front of the home. Relax or entertain on the covered lanai overlooking the fully fenced backyard with fresh turf and an extended paver patio. The custom backyard playhouse conveys, along with the washer, dryer, and security system. Additional upgrades include a tankless gas water heater, interior laundry room with utility sink, blinds on all windows, and all appliances included. Hull Island residents enjoy a resort-style pool with cabana, playground, bark park, scenic walking trails, and a peaceful dock on Lake Apopka, plus easy access to the Florida Turnpike. Impeccably maintained and turnkey in every way, schedule your private showing today and fall in love!

Full Property Details for 1808 Western Trailway Dr

General

  • Price: $599,000
  • HOA FEE: $165/month
  • Taxes: $5,022 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6362053
  • Updated: 1/5/2026
  • Added to Site: 60 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s)
  • Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Tankless Water Heater, Washer
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup

Additional Information

  • Shared Amenities: Park, Playground, Pool
  • Security/Safety: Closed Circuit Camera(s), Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Playground, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Front Porch, Rear Porch
  • Porch/Patio/Deck: Covered, Front Porch, Rear Porch

Parking

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

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: HULL ISLAND AT OAKLAND
  • Driving Directions: From SR 50 E, turn left on W Oakland Ave, turn right on Oakland Ave, turn left on Hull Island Dr, turn left on Western Trailway Dr, home will be on the right.
  • Direction Faces: South

School Information

  • Elementary School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Dock, Community Mailbox, Deed Restrictions, Dog Park, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Park, Playground, Pool
  • Association: Yes
  • Assoc. Name: Sentry Management Group - Amaan Lakhani
  • Assoc. Fees Include: Community Pool, Maintenance Grounds, Maintenance Repairs, Pool Maintenance
  • 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: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Available, Natural Gas Available, Phone Available, Public, Street Lights, Water Available

Structural Information

  • Architectural Info: Craftsman, Mediterranean, Traditional
  • Architectural Style: Craftsman, Mediterranean, Traditional
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: One
  • Square Feet: 1,857
  • Sq. Ft. Source: Public Records
  • Year Built: 2019

Lot Features

  • Property View: Park/Greenbelt
  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,000
  • Lot Size: 6000
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced

Financial Considerations

  • Association Fee: $165
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,022.29
  • Tax Year: 2024

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 1St Class Real Est Premier Grp

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— 1808 Western Trailway Dr —

  • 1St Class Real Est Premier Grp

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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 Pitney Bowes 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
12/22/2025
Price Reduced
$599,000
-1.8%
MLS
12/08/2025
Price Reduced
$610,000
-0.81%
MLS
11/20/2025
Listed
$615,000
14.95%
MLS
3/08/2024
Sold
$535,000
—
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
2024
$5,022
—
$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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by 1St Class Real Est Premier Grp

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1808 Western Trailway Drive, Oakland, FL 34787 (MLS# O6362053) 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 November 20, 2025. Want to learn more about 1808 Western Trailway Drive? Do you have questions about finding other Single Family real estate for sale in Oakland? You can browse all Oakland real estate or contact a Coldwell Banker agent to request more information.

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