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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 386 801 5417.

10 Results

Oakland Park Winter Garden Florida Homes For Sale

Oakland Park For Sale $1,210,000

Charming two-story home with a welcoming front porch and beautifully landscaped yard at 1071 Kershaw Dr, Winter Garden, FL 34787
View Details 59 Photos
Attractive two-story home with a covered porch and manicured landscaping at 1071 Kershaw Dr, Winter Garden, FL 34787
Inviting front porch featuring comfortable seating and stylish decor at 1071 Kershaw Dr, Winter Garden, FL 34787
Cozy porch with a swing, plants, and a welcoming entrance at 1071 Kershaw Dr, Winter Garden, FL 34787
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2822

  • Year Built

    2021

  • $/SqFt

    $429

This home is priced to sell and won't last long! OAK AVENUE REAL ESTATE LLC.

Oakland Park Pended $2,199,000

Beautiful white home featuring a brick driveway, front porch with rocking chairs, and a three-car garage at 907 Celadon St, Winter Garden, FL 34787
View Details 72 Photos
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 25 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 featuring a double porch, columns, and landscaped yard at 908 Tilden Oaks Trl, Winter Garden, FL 34787
View Details 92 Photos
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 28 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 $1,565,000

Reduced By $85,000

Charming two-story home featuring a screened porch, a welcoming front porch, and well-manicured landscaping at 921 Bradenville Ln, Winter Garden, FL 34787
View Details 78 Photos
Charming two-story home with a screened-in porch and well-maintained landscaping in a desirable neighborhood 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 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3468

  • Year Built

    2022

  • $/SqFt

    $451

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

Oakland Park For Sale $2,100,000

Reduced By $249,000

Stunning two-story home showcasing impeccable landscaping and an inviting paver driveway leading to a spacious three-car garage at 1224 Union Club Dr, Winter Garden, FL 34787
View Details 99 Photos
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 59 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5441

  • Year Built

    2016

  • $/SqFt

    $386

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 with a welcoming front porch and manicured lawn at 985 Huntspoint St, Winter Garden, FL 34787
View Details 49 Photos
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 66 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 $1,049,000

Reduced By $100,000

Charming single-Gathering home featuring a well-manicured lawn and an inviting orange front door at 936 Allendale Ln, Winter Garden, FL 34787
View Details 67 Photos
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 81 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

Charming two-story home features a manicured lawn, picket fence, and inviting front porch at 1024 Prosperity Dr, Winter Garden, FL 34787
View Details 42 Photos
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 37 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

Charming two-story home with a welcoming front porch and beautiful landscaping at 166 Hammock Preserve Loop, Winter Garden, FL 34787
View Details 27 Photos
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 94 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 For Sale $999,900

Two-story craftsman home with front porch, landscaping, and palm trees at 931 Kylee Aly, Winter Garden, FL 34787
View Details 53 Photos
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 116 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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Viewing HOMES 1 to 10 of 10

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 386 801 5417 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$491,591
$437,700
146
2.1%
55.5%
82

Apopka
$527,569
$470,000
562
1.6%
47.3%
88

Belle Isle
$866,169
$654,946
20
0.0%
35.0%
66

Casselberry
$435,319
$420,000
101
2.0%
55.4%
68

Celebration
$1,331,938
$1,015,000
49
0.0%
53.1%
103

Champions Gate
$724,328
$719,000
17
0.0%
47.1%
300

Chuluota
$804,438
$684,900
29
0.0%
44.8%
48

Clermont
$574,445
$490,410
753
0.7%
49.7%
76

Gotha
$1,055,980
$629,945
12
0.0%
66.7%
81

Groveland
$483,033
$409,990
279
1.1%
57.7%
88

Harmony
$439,332
$419,900
76
0.0%
42.1%
98

Kissimmee
$519,931
$445,000
2425
1.8%
49.4%
102

Longwood
$750,529
$547,000
226
1.3%
52.2%
71

Maitland
$1,018,271
$596,950
96
2.1%
51.0%
79

Minneola
$560,496
$541,050
135
0.7%
39.3%
79

Montverde
$1,551,170
$1,090,942
49
0.0%
46.9%
120

Ocoee
$535,829
$489,999
179
1.1%
52.0%
77

Orlando
$692,834
$500,000
3083
1.7%
49.9%
79

Oviedo
$710,896
$615,000
227
0.4%
51.5%
68

Poinciana
$325,200
$314,900
291
1.4%
52.2%
122

Reunion
$1,870,834
$1,100,000
107
2.8%
57.0%
165

Saint Cloud
$649,306
$503,363
66
3.0%
57.6%
254

Sanford
$527,241
$427,000
392
0.8%
49.7%
96

Sorrento
$597,440
$450,920
108
0.9%
50.9%
83

Windermere
$2,108,888
$1,280,000
286
0.3%
46.9%
100

Winter Park
$1,260,532
$749,000
325
0.3%
51.1%
87

Winter Springs
$639,430
$496,700
156
0.6%
48.7%
70

EasyStreet

Call to Schedule a Showing

(386) 801-5417

(386) 801-5417