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Oakland Real Estate Search

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Oakland Homes for Sale

Over 130 years ago, Oakland, Florida was a bustling railroad town, as well as the industrial and social hub of Orange County. Some of the homes built for railroad officials still stand in parts of Oakland, the final remnants of the area’s industrial history. In 1860, residents who lived in the area chose to name their community “Oakland” for the many Oak trees in the region. In 1886, Orange County Judge and the founder of Oakland, James Speer, opened a way for the Orange Belt Line Railroad to bring its tracks through the town. The coming of the railroad sparked a boost in economic growth for Oakland. The area was officially incorporated as a town in 1891.

People are attracted to Oakland in Orange County, Florida, for a lot of reasons, and the beauty of nature is most likely at the top of their list. One of the places near Oakland that represents the wonder of Florida’s nature is Wekiwa Springs State Park located in Apopka, Florida. Boasting 7,000 acres of untamed natural green space, this Florida State Park features a few attractions, the main one being the spring which provides the Wekiva River approximately 42 million gallons of water every day. Swimming is allowed, with the water depths varying depending on the location. An array of camping facilities are available throughout the entire park, offering visitors areas for tent camping all the way to RVs. Other activities are available as well, such as hiking, bicycling, and horseback riding. Furthermore, with Orlando less than 15 miles away, you can visit key destinations such as Universal Orlando located at 6000 Universal Boulevard; or Magic Kingdom located at 1180 Seven Seas Drive in Lake Buena Vista; Epcot located at 200 Epcot Center Drive. This is only a small fraction of the things available for residents living in Oakland. In addition to that, you have The Florida Mall for your shopping and dining needs. This super regional mall is located at 8001 S Orange Blossom Trail, featuring Abercrombie & Fitch, A’Gaci, Apple, Armani Exchange, Banana Republic, Bath & Body Works, and much more.

Real estate for sale in Oakland is designed and built by the top home builder in the state of Florida. Many of the property listings boast big names such as Hibiscus Homes, CalAtlantic, as well as many custom built homes. You can find both single-story and two story single-family homes ranging in size from three bedrooms, two bathrooms, and around 1,980 square feet to five bedrooms, four bathrooms, and about 4,370 square feet. Some of the amenities found in these homes include split floor plans, engineered hardwood flooring, granite counter-tops, bright and open family rooms, large bedrooms, hydro-massage tubs, and more. Some of these homes for sale in Oakland have been built in secure gated communities and feature Georgetown, Cambridge, Arbordale, Seamist, and Summerfield plans. If by chance you weren’t able to find what you’re looking for in Oakland, we can assist you in finding a home you’ll love in one of our other communities in Clermont. Whether you’re interested in Oakland real estate or other properties in Clermont, contact us today for more information or to schedule a tour.

Newest Oakland Homes for Sale

409 E Gulley Avenue, Oakland image
409 E Gulley Avenue, Oakland $499,999

Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and...

  • 3 Beds
  • 2 Baths
  • Oakland SubDv.
  • 34760 Zip Code
1134 Prado Lane, Oakland image
1134 Prado Lane, Oakland $2,595,000

Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers a...

  • 5 Beds
  • 8 Baths
  • Grove/Oakland SubDv.
  • 34760 Zip Code
16 Oakland Pointe Circle, Oakland image
16 Oakland Pointe Circle, Oakland $799,999

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where ch...

  • 5 Beds
  • 3 Baths
  • Oakland Pointe SubDv.
  • 34760 Zip Code
250 N Walker Street, Oakland image
250 N Walker Street, Oakland $1,125,000 ▼

SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms an...

  • 4 Beds
  • 3 Baths
  • Oakland Town SubDv.
  • 34760 Zip Code
38 S Pollard Street, Oakland image
38 S Pollard Street, Oakland $629,999 ▼

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space...

  • 4 Beds
  • 3 Baths
  • Oakland Town SubDv.
  • 34760 Zip Code
1106 Sarah Mathews Drive, Oakland image
1106 Sarah Mathews Drive, Oakland $1,975,000

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that show...

  • 5 Beds
  • 6 Baths
  • Grove At The Harvest District SubDv.
  • 34760 Zip Code
620 N Tubb Street, Oakland image
620 N Tubb Street, Oakland $1,250,000 ▼

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would al...

  • 6 Beds
  • 8 Baths
  • Oakland SubDv.
  • 34760 Zip Code
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Central Florida Real Estate

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Clermont Florida Real Estate

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Leesburg Florida Real Estate

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  • The Glen
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Groveland Florida Real Estate

  • Blue Spring Reserve
  • Cherry Lake Landing
  • Crane’s Landing
  • Cypress Oaks
  • Eagle Point
  • Green Valley West
  • Groveland Farms
  • Lake Douglas Preserve
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  • Trilogy
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  • Waterside Estates at Cherry Lake
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Winter Garden Florida Real Estate

  • Avalon Reserve Village
  • Banana Bay
  • Belle Meade
  • Deer Island
  • Hickory Hammock
  • Isles Lake Hancock
  • Lakeshore Preserve
  • Latham Park North
  • Latham Park South
  • Oakland Park
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  • Stoneybrook
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Minneola Florida Real Estate

  • Ardmore Reserve
  • Chelsea Park
  • Country Ridge
  • Eastridge
  • Highland Oaks
  • Highland Ridge
  • Oak Valley
  • Overlook at Grassy Lake
  • Park Ridge on Lake Minneola
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55+ Communities

  • Arlington Ridge
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  • Legacy of Leesburg
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  • Pennbrooke Fairways
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  • Royal Highland
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  • Summit Greens
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