Call 407-493-3464

Central Florida Neighborhoods

Living in Oakland, Florida

Oakland is a small, historic town on the shores of Lake Apopka with a quiet, close-knit feel, just minutes from the shopping and dining at Winter Garden Village at Fowler Groves and downtown Winter Garden.

See Oakland HomesCall 407-493-3464

Search Homes

Browse Oakland Homes for Sale

Live listings on ColdwellBankerHomes.com open in a new tab.

Get Oakland homes sent to meNew construction in OaklandCondos & townhomes in Oakland

Oakland Market Snapshot

Typical Home Value (Zillow)$570,276+2.2% vs. last yearOakland, FL (City)
Median List Price$1,049,000+84.1% vs. last yearZIP 34760 (Oakland)
Active Listings7+133.3% vs. last yearZIP 34760 (Oakland)
Median Days on Market79 days-29.8% vs. last yearZIP 34760 (Oakland)

Caution: Oakland had only 7 active listings, so the list-price and days-on-market figures come from a very small sample and can swing a lot month to month.

Source: Zillow Home Value Index & Realtor.com, September 2026. Read the full Oakland market update, or ask me for a custom report for your street.

Why People Love Oakland

  • Small-town charm with large lots, mature oaks, and a slower pace
  • Easy access to SR 429 and Florida's Turnpike for commuting
  • Close to Winter Garden's shops, restaurants, and farmers market
  • A mix of established homes and newer construction

Points of Interest

  • West Orange Trail
  • Oakland Nature Preserve
  • Lake Apopka and Johns Lake
  • Winter Garden Village at Fowler Groves
  • Historic downtown Winter Garden (Plant Street)

Around Oakland

Green space along the West Orange Trail in Oakland, Florida
West Orange Trail, Oakland
River otter in Lake Apopka, near Oakland, Florida
Wildlife on Lake Apopka
Plant Street gazebo in downtown Winter Garden, near Oakland FL
Downtown Winter Garden, minutes away

Oakland FAQs

Is Oakland, FL a good place to live?

For many buyers, yes. Oakland offers a quiet, small-town feel with larger lots and mature trees, while Winter Garden's shopping, dining, and farmers market are just minutes away.

How far is Oakland from Orlando?

Oakland sits in West Orange County with access to SR 429 and Florida's Turnpike, so many residents commute toward Orlando. Drive times vary with traffic; ask me about your specific route.

Are there new construction homes in Oakland?

Yes, Oakland has a mix of established homes and newer construction. I can walk you through current options and builder incentives.

What's the difference between Oakland and Winter Garden?

Oakland is smaller and quieter; Winter Garden is larger, with a busy historic downtown and many new communities. Many buyers look at both.

★★★★★
“We have worked with Brenda 2 times over the years. The first time was a new home purchase in 2003 / 2004. Moving fro another state, Brenda spent quite a bit of time with us to somewhat familiarize us with the areas. In 2013, she again assisted us with the sale of the same home. … We highly regard Brenda as a well versed, highly skilled and caring realtor!”
Michael & Ingrid PaglioccaRelocated, bought new, later sold in Oakland, FL · Dec 2013via Zillow

Explore More Near Oakland

Homes for sale in Winter Garden · Homes for sale in Hamlin · Homes for sale in Mount Dora · Homes for sale in Orange County · Homes for sale in Lake County · Homes for sale in Polk County

Buying here for the first time? Read my first-time home buyer guide. Looking at builders? See new construction homes in Winter Garden and Lake County. Moving from out of state? Start with my Orlando-area relocation guide. Already own here? Get a free Oakland home value estimate.

Thinking about Oakland? I'll show you homes that fit your lifestyle and budget.

See Oakland Homes