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Oakland, FL Condos for Rent

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  • /20

    $6,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,038 Sq Ft
    • Condo for Rent

    15075 Tea Tree Dr Unit 4/3, Oakland, FL 34787

    ? Brand New • High Ceilings • Prime Location ? CODE: RVRS 2614 ?? Tea Tree Drive, Winter Garden, FL 34787 ?? 4 Bedrooms | ?? 3 Bathrooms ?? 3,038 Sq. Ft. Imagine being the very first to live here ? Walking into soaring 20-ft ceilings, natural light everywhere, and a space that actually feels like yours from day one. ?? $6,000/month ?? 13-month lease ??

    15075 Tea Tree Dr Unit 4/3, Oakland, FL 34787
  • /62

    $3,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,181 Sq Ft
    • **Charming Upgraded 4-Bedroom Home for Rent in Waterleigh Community**

    16707 Oakboro St, Oakland, FL 34787

    Welcome to 16707 Oakboro Street, a beautifully maintained 4-bedroom, 3-bathroom single-family home located in the highly desirable Waterleigh community of Winter Garden. Built in 2021, this spacious one-story residence offers approximately 2,181 square feet of thoughtfully designed living space, combining modern finishes, an inviting open-concept layout, and the comfort and convenience today's

    16707 Oakboro St, Oakland, FL 34787

Frequently Asked Questions

How much does it cost to rent a condo in Oakland, FL?
The median rent for a condo in Oakland, FL is $3,000 per month, though prices vary by neighborhood, size, and property type. As of September 2026, townhouses tend to be the most affordable option while single-family homes are currently more expensive.
How much do you need to make to afford rent in Oakland, FL?
To comfortably afford the median rent in Oakland, FL, a household needs to earn roughly $120,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $3,000 per month in Oakland, FL, renters typically need to show $9,000 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Oakland, FL?
In Oakland, FL, the price-to-rent ratio is 19.0, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Oakland, FL are best for renting a condo?
The best neighborhood for renting in Oakland, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a condo include West Oaks, MetroWest, Dr. Phillips, Universal and Florida Center North, each with its own character and price range.
How to Rent a Home