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 407-967-1435.

11 Results

Oakland Park Winter Garden Florida Homes For Sale

Oakland Park For Sale $2,199,000

Charming home with a welcoming front porch, featuring rocking chairs and lush landscaping at 907 Celadon St, Winter Garden, FL 34787
Spacious three-car garage showcasing white doors, a brick driveway, and meticulous landscaping at 907 Celadon St, Winter Garden, FL 34787
Bright foyer with wood floors, French doors leading to an office, and a view of the front yard at 907 Celadon St, Winter Garden, FL 34787
On Market For 4 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    5247

  • Year Built

    2020

  • $/SqFt

    $419

All this—just a short golf cart ride from historic downtown Winter Garden, where you can enjoy vibrant dining, shopping, and year-round events at Plant Street Market and much more!! ! THE REAL ESTATE COLLECTION LLC.

Oakland Park For Sale $975,000

Charming two-story home showcasing a double porch, columns, and swing at 908 Tilden Oaks Trl, Winter Garden, FL 34787
Stunning two-story home featuring a double porch, beautiful landscaping, and a cozy swing at 908 Tilden Oaks Trl, Winter Garden, FL 34787
Beautiful two-story home with a double porch, swing, chairs, and professionally landscaped yard at 908 Tilden Oaks Trl, Winter Garden, FL 34787
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2683

  • Year Built

    2022

  • $/SqFt

    $363

Welcome to a life where every detail is designed for harmony, at 908 Tilden Oaks Trail. COMPASS FLORIDA LLC.

Oakland Park For Sale $1,650,000

Charming two-story home with a screened-in porch, landscaped yard, and inviting curb appeal at 921 Bradenville Ln, Winter Garden, FL 34787
Charming two-story home with a screened-in porch, landscaped yard, and inviting curb appeal at 921 Bradenville Ln, Winter Garden, FL 34787
Charming two-story home with a screened-in porch, landscaped yard, and inviting curb appeal at 921 Bradenville Ln, Winter Garden, FL 34787
On Market For 27 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3468

  • Year Built

    2022

  • $/SqFt

    $476

Tour this extraordinary estate and discover what it means to live without compromise. RE/MAX PRIME PROPERTIES.

Oakland Park For Sale $2,199,000

Reduced By $150,000

Beautiful two-story home with a paver driveway and lush landscaping offering an inviting curb appeal at 1224 Union Club Dr, Winter Garden, FL 34787
Eye-catching two-story home with paver driveway, manicured landscaping, and gray roof at 1224 Union Club Dr, Winter Garden, FL 34787
Expansive two-story home displaying a well-maintained yard and driveway with mature trees at 1224 Union Club Dr, Winter Garden, FL 34787
*POTENTIAL GREAT VALUE
On Market For 38 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5441

  • Year Built

    2016

  • $/SqFt

    $404

Don’t miss the chance to own a truly exceptional piece of LAKEFRONT PARADISE! BHHS FLORIDA REALTY.

Oakland Park For Sale $989,500

Charming two-story home featuring a covered front porch with stately white columns at 985 Huntspoint St, Winter Garden, FL 34787
Inviting front porch with blue door and seating area at 985 Huntspoint St, Winter Garden, FL 34787
Bright foyer with stylish decor, wood-look tile flooring, and ample natural light at 985 Huntspoint St, Winter Garden, FL 34787
On Market For 46 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3084

  • Year Built

    2018

  • $/SqFt

    $321

The Oakland Park community is one of the most sought-after in the area, making this an incredible opportunity to own a beautiful home in a prime location. EXP REALTY LLC.

Oakland Park Pended $785,000

Inviting two-story home with covered front porch, rocking chairs, and a beautifully landscaped entrance at 1118 Eagles Pass Way, Winter Garden, FL 34787
Attractive two-story home featuring a classic design, covered porch, and neatly maintained front yard at 1118 Eagles Pass Way, Winter Garden, FL 34787
Charming two-story home with a covered front porch and lush landscaping at 1118 Eagles Pass Way, Winter Garden, FL 34787
On Market For 53 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1982

  • Year Built

    2022

  • $/SqFt

    $396

Don’t miss this incredible opportunity to own a beautifully designed home in one of Central Florida’s most desirable communities! COLDWELL BANKER REALTY.

Oakland Park For Sale $1,049,000

Reduced By $100,000

Stylish single-Gathering home showcasing a lush green lawn and gray wood facade at 936 Allendale Ln, Winter Garden, FL 34787
Beautiful home with well-kept lawn and a welcoming porch with rocking chairs at 936 Allendale Ln, Winter Garden, FL 34787
Inviting front porch with rocking chairs, lanterns, and a vibrant orange front door at 936 Allendale Ln, Winter Garden, FL 34787
On Market For 60 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2711

  • Year Built

    2023

  • $/SqFt

    $387

Don’t miss out—schedule your private tour today! KELLER WILLIAMS ELITE PARTNERS III REALTY.

Oakland Park Pended $879,000

Bright living room with hardwood floors, neutral decor, and comfortable seating at 1024 Prosperity Dr, Winter Garden, FL 34787
Spacious living area with large TV, stylish furniture, and natural light at 1024 Prosperity Dr, Winter Garden, FL 34787
Modern kitchen features a large center island with seating, stainless steel appliances, and white cabinetry at 1024 Prosperity Dr, Winter Garden, FL 34787
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2260

  • Year Built

    2021

  • $/SqFt

    $389

Don’t miss the opportunity to make this your forever home- Schedule a showing today! OAK AVENUE REAL ESTATE LLC.

Oakland Park For Sale $1,675,000

Spacious backyard featuring a covered patio and a separate garage or guest house at 166 Hammock Preserve Loop, Winter Garden, FL 34787
View of the back of the house, highlighting its architectural design and yard at 166 Hammock Preserve Loop, Winter Garden, FL 34787
Attached two-car garage, providing ample parking and storage space at 166 Hammock Preserve Loop, Winter Garden, FL 34787
On Market For 73 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3186

  • Year Built

    2025

  • $/SqFt

    $526

Please note that the photos provided are of the Carrabelle design from another completed build and are used solely for demonstration purposes; contact us today for more details and customization options. CORCORAN PREMIER REALTY.

Oakland Park Pended $899,000

Reduced By $75,900

Charming two-story home with a welcoming front porch and well-manicured landscaping at 896 Tilden Oaks Trl, Winter Garden, FL 34787
A charming home with a covered front porch, set amidst a beautiful neighborhood and lush landscaping at 896 Tilden Oaks Trl, Winter Garden, FL 34787
Inviting front porch view with comfortable seating, showcasing the neighborhood ambiance at 896 Tilden Oaks Trl, Winter Garden, FL 34787
On Market For 87 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2268

  • Year Built

    2022

  • $/SqFt

    $396

Don’t miss your chance to own this move-in–ready home, where every detail has been designed for modern comfort and sophisticated living. Schedule your private tour today! CORCORAN PREMIER REALTY.

Oakland Park For Sale $999,900

Inviting front porch with seating, welcome sign, and potted plants at 931 Kylee Aly, Winter Garden, FL 34787
Charming two-story home with a welcoming front porch and lush landscaping at 931 Kylee Aly, Winter Garden, FL 34787
Community overview, showcasing homes and green spaces at 931 Kylee Aly, Winter Garden, FL 34787
On Market For 95 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2831

  • Year Built

    2022

  • $/SqFt

    $353

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. PREMIER SOTHEBYS INT'L REALTY.

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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 407-967-1435 and speak with one of our real estate consultants.

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