Rare find in prime Oakland: a completely remodeled turn-key home on an oversized 0.25-acre lot with no high 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 updated luxury, with major big-ticket items already completed, including a brand-new roof installed in December 2024, a new high-efficiency A/C installed in August 2023, and 4-Point-ready infrastructure for stress-free home insurance. Step inside to smooth, popcorn-free ceilings, fresh all-white interior paint, new fixtures and hardware throughout, and low-maintenance luxury vinyl plank flooring with no carpet anywhere. The bright kitchen features sparkling new quartz countertops, a classic white subway tile backsplash, a stainless steel range hood, a newly installed double oven, and spacious 42-inch upper white cabinets. Both bathrooms have been tastefully modernized, highlighted by a complete primary suite refresh. Outside, the quarter-acre grounds feature a brand-new 6-foot vinyl privacy fence, a massive 15×40 back patio perfect for outdoor dining, fresh sod and landscaping, an irrigation well for major utility savings, and ample room to build your dream custom 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.
Property Details
Price:
$525,000
MLS #:
O6440519
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
TRAILSIDE STATION REP 44/23
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 18, 2026
Finished Sq Ft:
2,028
Total Sq Ft:
2,484
Lot Size:
10,769 sqft / 0.25 acres (approx)
Year Built:
2003
See this Listing
Schools
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Luxury Vinyl
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
One
Exterior
Architectural Style
Florida, Ranch
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
Irrigation System, Lighting, Private Yard, Sidewalk
Fencing
Vinyl
Garage Spaces
2
Lot Features
Cleared, Corner Lot, Landscaped, Oversized Lot, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener
Patio And Porch Features
Patio
Roof
Shingle
Window Features
Aluminum Frames
Financial
HOA Fee
$350
HOA Fee Frequency
Annually
HOA Name
Trailside Station HOA
HOA Phone
3523660234
Tax Year
2025
Taxes
$2,334
Map
Community
- Address990 STATIONSIDE DRIVE OAKLAND FL
- SubdivisionTRAILSIDE STATION REP 44/23
- CityOAKLAND
- CountyOrange
- Zip Code34787
Subdivisions in OAKLAND
- BRILEY FARM
- GROVE AT THE HARVEST DISTRICT
- HULL ISLAND ESTATES FIRST ADD
- JOHNS COVE 43/104
- JOHNS LANDING
- JOHNS LANDING PH 01 44/47
- JOHNS LANDING PH 02 48 138
- JOHNS LANDING PHASE 1
- LONGLEAF
- LONGLEAF AT OAKLAND
- LONGLEAF/OAKLAND
- LONGLEAF/OAKLAND REP
- OAKLAND
- OAKLAND PARK
- OAKLAND PK UN 7 NORTH
- OAKLAND TOWN
- OAKLAND TRAILS
- OAKLAND TRAILS PH 1
- OAKLAND TRLS PH 1
- OAKLAND TRLS PH 2
- RYAN COURT
- THE GROVE AT OAKLAND
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in OAKLAND as of Sep 18, 2026
38
Single Family Listed
104
Avg DOM
372
Avg $ / SqFt
$1,372,013
Avg List Price
Property Summary
- Located in the TRAILSIDE STATION REP 44/23 subdivision, 990 STATIONSIDE DRIVE OAKLAND FL is a Single Family for sale in OAKLAND, FL, 34787. It is listed for $525,000 and features 4 beds, 2 baths, and has approximately 2,028 square feet of living space, and was originally constructed in 2003. The current price per square foot is $259. The average price per square foot for Single Family listings in OAKLAND is $372. The average listing price for Single Family in OAKLAND is $1,372,013. To schedule a showing of MLS#o6440519 at 990 STATIONSIDE DRIVE in OAKLAND, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of EXP REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 990 STATIONSIDE DRIVE
OAKLAND, FL
