Below you can view all the homes for sale in the Oakland Park subdivision located in Winter Garden Florida. Listings in Oakland Park are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Oakland Park, give us a call at 407-278-2057.

14 Results

Oakland Park Winter Garden Florida Homes For Sale

Oakland Park Pended $1,350,000

View 914 Tilden Oaks Trl Winter Garden FL
View 914 Tilden Oaks Trl Winter Garden FL
View 914 Tilden Oaks Trl Winter Garden FL
On Market For 6 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3803

  • Year Built

    2022

  • $/SqFt

    $355

Schedule a showing today and experience the epitome of refined living. MLS#O6224418. COMPASS FLORIDA, LLC.

Oakland Park For Sale $975,000

View 967 Prosperity Dr Winter Garden FL
View 967 Prosperity Dr Winter Garden FL
View 967 Prosperity Dr Winter Garden FL
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2585

  • Year Built

    2014

  • $/SqFt

    $377

Easy access to major highways for a seamless commute to Orlando and surrounding areas. MLS#O6214760. EXP REALTY LLC.

Oakland Park For Sale $959,000

Reduced By $11,000

View 1041 Linehart Dr Winter Garden FL
View 1041 Linehart Dr Winter Garden FL
View 1041 Linehart Dr Winter Garden FL
On Market For 25 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3084

  • Year Built

    2018

  • $/SqFt

    $311

West Orange Trail runs through the community connecting to downtown Winter Garden and short distance away in this golf cart friendly community. MLS#O6219373. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Oakland Park For Sale $1,100,000

Reduced By $50,000

View 931 Kylee Aly Winter Garden FL
View 931 Kylee Aly Winter Garden FL
View 931 Kylee Aly Winter Garden FL
On Market For 31 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2831

  • Year Built

    2022

  • $/SqFt

    $389

A well-appointed kitchen with plenty of storage, quality finishes including plantation shutters, and a luxurious owner's retreat with a spacious customized walk-in closet. MLS#O6218297. PREMIER SOTHEBYS INT'L REALTY.

Oakland Park Pended $999,900

On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2822

  • Year Built

    2014

  • $/SqFt

    $354

Embrace a lifestyle of elegance and environmental stewardship in this beautifully appointed residence MLS#A4615176. JOSEPH WALTER REALTY LLC.

Oakland Park For Sale $865,000

Reduced By $10,000

On Market For 31 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2260

  • Year Built

    2019

  • $/SqFt

    $383

Schedule your showing today and experience the luxurious lifestyle that awaits you in Oakland Park! MLS#O6217570. LAKESIDE REALTY WINDERMERE INC.

Oakland Park For Sale $1,250,000

On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3012

  • Year Built

    2013

  • $/SqFt

    $415

Call to see this home before it's SOLD! MLS#O6216860. CENTURY 21 PROFESSIONAL GROUP.

Oakland Park For Sale $861,900

On Market For 46 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2240

  • Year Built

    2024

  • $/SqFt

    $385

In addition this new home features a large loft entertaining area, vaulted ceilings, garage door opener, energy efficient construction, new home warranty, full landscaping package, dual pane energy efficient windows, 8 foot doors, garage door opener and more! MLS#O6213614. OLYMPUS EXECUTIVE REALTY INC.

Oakland Park Pended $780,000

On Market For 47 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1963

  • Year Built

    2018

  • $/SqFt

    $397

Enjoy resort-style amenities just steps away, convenient Winter Garden location, and an elevated lifestyle. Schedule your private tour today! MLS#O6212842. NESTA REAL ESTATE CONSULTANTS.

Oakland Park For Sale $825,000

Reduced By $25,000

On Market For 50 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2219

  • Year Built

    2019

  • $/SqFt

    $372

Don’t miss the opportunity to own this stunning home in the highly sought-after Oakland Park community. MLS#O6207877. COMPASS FLORIDA, LLC.

Oakland Park Pended $749,900

Reduced By $16,000

On Market For 57 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1990

  • Year Built

    2013

  • $/SqFt

    $377

It is also steps from the west Orange bike/walking trail, and just a short bike or golf cart ride to historic downtown with all the restaurants and brewery available for your enjoyment. Come see this home today!! ! MLS#O6209331. CORCORAN PREMIER REALTY.

Oakland Park For Sale $850,000

Reduced By $49,000

On Market For 85 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2509

  • Year Built

    2015

  • $/SqFt

    $339

Just a short GOLF-CART ride to HISTORIC DOWNTOWN WINTER GARDEN where you can enjoy the West Orange Trail, Plant Street Market, Splash Pad, Restaurants, Shopping, and the many social events that take place throughout the year. MLS#O6201286. THE REAL ESTATE COLLECTION LLC.

Oakland Park Pended $829,900

On Market For 139 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2254

  • Year Built

    2024

  • $/SqFt

    $368

Room Feature: Linen Closet In Bath (Bedroom 2). MLS#O6178611. KELLER WILLIAMS ELITE PARTNERS III REALTY.

Oakland Park For Sale $1,649,900

On Market For 163 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3186

  • Year Built

    2024

  • $/SqFt

    $518

Optional in-law or guest-suite added on top of garage available at an additional cost. MLS#V4934605. EXP REALTY LLC.

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Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-278-2057 and speak with one of our real estate consultants.

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