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$525,000 Just Listed
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Property Description
RARE FIND in prime OAKLAND, Florida, only a 1/4 mile away from the WEST ORANGE TRAIL: a COMPLETELY REMODELED turn-key home on an OVERSIZED 0.25-ACRE LOT with VERY LOW HOA FEES! Why settle for tiny high-density lots when you can have true space, privacy, and full peace of mind? This FULLY MODERNIZED 4-bedroom, 2-bathroom residence offers over 2,000 square feet of luxury, with major big-ticket items already completed, including a NEW ROOF IN 2024 and a NEW AC IN 2023. Step inside to this inviting and fresh home with satin-white interior paint, NEW FIXTURES AND HARDWARE throughout, and low-maintenance LUXURY VINYL PLANK FLOORING with NO CARPET anywhere. The BRIGHT KITCHEN features SPARKLING QUARTZ COUNTERTOPS, a CLASSIC WHITE SUBWAY TILE BACKSPLASH, a STAINLESS STEEL HOOD, a DOUBLE-OVEN, and SPACIOUS 42-INCH UPPER CABINETS. Both bathrooms have been tastefully modernized, highlighted by a complete primary suite revamp. Outside, the QUARTER-ACRE PROPERTY features a NEW 6-FOOT VINYL PRIVACY FENCE, a MASSIVE 15x40 BACK PATIO perfect for outdoor dining, ALL-NEW SOD AND LANDSCAPE, a MATURE AND PRODUCING MANGO TREE, an IRRIGATION WELL for MAJOR UTILITY SAVINGS, and ample room to build a pool. Nestled in charming, canopy-lined Oakland, FL-prized for its quiet, Old-Florida feel and proximity to the West Orange Trail-you're minutes from historic Downtown Winter Garden's famous weekly farmers market, craft breweries, boutique shopping, and fine dining. Best of all, instant connectivity to SR-50, FL-429, and the Florida Turnpike puts Downtown Orlando, Walt Disney World, Universal Studios, and all major Central Florida attractions within an easy 20-minute drive. CALL TODAY TO SCHEDULE A VISIT!
Full Property Details
Full Property Details for 990 Stationside Dr
General
- Price: $525,000
- HOA FEE: $29/month
- HOA FEE FREQ.: Annually
- Taxes: $2,334 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6440519
- Updated: 9/19/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 13
- Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Range Hood, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Luxury Vinyl
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Exterior
- Exterior Features: Irrigation System, Lighting, Private Yard, Sidewalk
- Deck/Patio: Patio
- Porch/Patio/Deck: Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Electric Vehicle Charging Station(s), Garage Door Opener
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: TRAILSIDE STATION REP 44/23
- Driving Directions: To drive from Orlando to 990 Stationside Dr in Oakland, Florida, you will generally head west out of the city. The most direct route typically involves taking FL-408 West (the East-West Expressway) and then merging onto Florida's Turnpike North toward Ocala. From there, you will take the exit for FL-50 West (West Colonial Drive) toward Winter Garden and Oakland. Continue on FL-50 West for several miles until you reach Oakland, then turn onto Oakland Avenue and follow the local roads to Stationside Drive. The entire trip is roughly 18 to 25 miles depending on your starting point in Orlando and usually takes about 25 to 30 minutes under normal traffic conditions.
- Direction Faces: East
Community
- Community Name: 34787 - Winter Garden/Oakland
- Association: Yes
- Assoc. Name: Trailside Station HOA
- Number of Pets: 4
- Pet Restrictions: please communicate with HOA for rules or clarification
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public, Well
- Utility Description: Cable Connected, Electricity Connected, Sewer Connected, Water Connected
Structural Information
- Architectural Info: Florida, Ranch
- Architectural Style: Florida, Ranch
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Aluminum Frames
- Stories/Levels: One
- Square Feet: 2,028
- Sq. Ft. Source: Public Records
- Year Built: 2003
Lot Features
- Lot Size (Acres): 0.25
- Lot Size (Sq. Ft.): 10,769
- Lot Size: 10769
- Lot Dimensions: 132 x 80
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Vinyl
Financial Considerations
- Association Fee: $350
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Tax Amount: $2,334
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: TRAILSIDE STATION REPLAT 44/23 LOT 56
- Flood Zone Info: X
- APN: 192227868200560
- Property ID: 192227868200560
Listed by Exp Realty Llc
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Schools
Schools serving 990 Stationside Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Tildenville Elementary School 1221 Brick Road, Winter Garden, FL 34787 | PK-5 | 2.1 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 2.5 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 4.7 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 990 Stationside Dr
Date
Details
Price
Change
Source
9/18/2026
Listed
$525,000
—
MLS
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
Tax History for 990 Stationside Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,334
3%
$174,846
6%
2024
$2,257
6%
$165,451
3%
2023
$2,120
5%
$160,632
6%
2021
$2,011
-2%
$151,411
-3%
2022
$2,044
2%
$155,953
4%
2021
$2,011
2%
$149,321
2%
2019
$1,968
1%
$145,964
2%
2018
$1,955
1%
$143,242
2%
2017
$1,930
1%
$140,296
2%
2016
$1,914
-1%
$137,410
1%
2015
$1,941
—
$136,455
1%
2014
$1,949
3%
$135,372
2%
2013
$1,897
—
$133,371
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 990 Stationside Dr
990 Stationside Drive, Oakland, FL 34787 (MLS# O6440519) is a Single Family property with 4 bedrooms and 2 full bathrooms. 990 Stationside Drive is currently listed for $525,000 and was received on September 18, 2026. Want to learn more about 990 Stationside 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.

