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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 386-801-4854.

13 Results

Oakland Park Winter Garden Florida Homes For Sale

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
View Details 78 Photos
Beautiful aerial view of a home in a residential neighborhood with well-maintained lawns 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 4 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 $2,349,000

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
On Market For 16 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5441

  • Year Built

    2016

  • $/SqFt

    $432

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 24 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 For Sale $785,000

Charming two-story home with a welcoming front porch and a well-manicured lawn at 1118 Eagles Pass Way, Winter Garden, FL 34787
View Details 59 Photos
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 32 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 $1,099,999

Reduced By $49,001

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 62 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 38 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2711

  • Year Built

    2023

  • $/SqFt

    $406

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

Oakland Park Pended $725,000

Charming two-story home with white siding, landscaped yard, and a welcoming front porch at 932 Kylee Aly, Winter Garden, FL 34787
View Details 60 Photos
Attractive two-story home with a welcoming front porch, manicured landscaping, and a black metal fence at 932 Kylee Aly, Winter Garden, FL 34787
Inviting two-story home featuring a landscaped front yard, a black fence, and a charming covered porch at 932 Kylee Aly, Winter Garden, FL 34787
Cozy front porch with rocking chairs, potted plants, a welcome mat, and a painted ceiling at 932 Kylee Aly, Winter Garden, FL 34787
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1936

  • Year Built

    2022

  • $/SqFt

    $374

This location is just 20 minutes from downtown Orlando and major attractions, with easy access to Florida’s Turnpike and SR-429 less than a mile away. Schedule your private showing today! CORCORAN PREMIER REALTY.

Oakland Park Pended $879,000

Charming two-story home featuring blue shutters and a well-manicured lawn with a white picket fence at 1024 Prosperity Dr, Winter Garden, FL 34787
View Details 43 Photos
Bright living room featuring hardwood floors, large TV, and a comfortable sofa at 1024 Prosperity Dr, Winter Garden, FL 34787
Bright living room featuring hardwood floors, large TV, and a comfortable sofa at 1024 Prosperity Dr, Winter Garden, FL 34787
Spacious kitchen with white cabinetry, stainless steel appliances, large island, and pendant lighting at 1024 Prosperity Dr, Winter Garden, FL 34787
On Market For 44 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 30 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 51 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3186

  • Year Built

    2025

  • $/SqFt

    $526

Please note that photos provided are of the Carrabelle design from another completed build and are used for demonstration purposes. CORCORAN PREMIER REALTY.

Oakland Park For Sale $959,000

Charming two-story home with a covered front porch and manicured landscaping creating a welcoming curb appeal at 1041 Linehart Dr, Winter Garden, FL 34787
View Details 52 Photos
Inviting entryway view showcasing the hardwood floors, light colored walls and access to the home at 1041 Linehart Dr, Winter Garden, FL 34787
Hardwood floors fill the room, brightened by natural light from the windows, and a ceiling fan overhead at 1041 Linehart Dr, Winter Garden, FL 34787
Well-lit home office featuring hardwood floors, a spacious desk area, and a large window overlooking the backyard at 1041 Linehart Dr, Winter Garden, FL 34787
On Market For 53 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3084

  • Year Built

    2018

  • $/SqFt

    $311

Experience the best of Oakland Park living! OLYMPUS EXECUTIVE REALTY INC.

Oakland Park Pended $899,000

Reduced By $75,900

An inviting exterior view of a two-story home with a covered front porch and charming curb appeal at 896 Tilden Oaks Trl, Winter Garden, FL 34787
View Details 67 Photos
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 65 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

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 73 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.

Oakland Park Pended $1,049,000

Reduced By $150,000

Two-story white house with a front porch and landscaped yard at 210 Hammock Preserve Loop, Winter Garden, FL 34787
View Details 61 Photos
Two-story house with a front porch, landscaping, and sidewalk at 210 Hammock Preserve Loop, Winter Garden, FL 34787
Front porch with rocking chairs and view into the house at 210 Hammock Preserve Loop, Winter Garden, FL 34787
Light hallway with dark wainscoting and hardwood floors at 210 Hammock Preserve Loop, Winter Garden, FL 34787
On Market For 91 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3070

  • Year Built

    2023

  • $/SqFt

    $342

Discover why this is the one you’ve been waiting for! BERGER REALTY & INVESTMENTS.

Oakland Park Pended $980,000

Charming two-story home with a welcoming front porch and manicured landscaping at 1338 Union Club Dr, Winter Garden, FL 34787
View Details 28 Photos
Inviting front porch featuring stylish chairs and a swing, perfect for relaxing outdoors at 1338 Union Club Dr, Winter Garden, FL 34787
Elegant foyer with gleaming hardwood floors and an open layout at 1338 Union Club Dr, Winter Garden, FL 34787
Warm entryway boasting hardwood floors, a stylish door, and built-in shelving at 1338 Union Club Dr, Winter Garden, FL 34787
On Market For 68 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2637

  • Year Built

    2014

  • $/SqFt

    $372

Call to see this house today. EOLA 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 386-801-4854 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$515,840
$439,950
136
2.2%
51.5%
84

Apopka
$526,296
$470,000
545
1.3%
47.9%
90

Belle Isle
$838,602
$630,000
23
0.0%
56.5%
72

Casselberry
$446,494
$429,450
102
2.0%
47.1%
63

Celebration
$1,353,791
$1,059,362
50
0.0%
46.0%
101

Champions Gate
$682,426
$687,495
22
0.0%
50.0%
264

Chuluota
$877,584
$689,000
25
0.0%
28.0%
38

Clermont
$578,870
$499,000
710
0.7%
49.6%
80

Gotha
$1,020,229
$649,990
15
0.0%
46.7%
59

Groveland
$481,190
$405,500
264
1.1%
51.9%
84

Harmony
$447,824
$421,650
70
0.0%
34.3%
89

Kissimmee
$518,604
$445,000
2396
1.5%
47.2%
100

Longwood
$749,935
$570,000
213
1.4%
46.5%
72

Maitland
$847,906
$657,500
78
2.6%
52.6%
79

Minneola
$559,225
$538,995
144
0.7%
38.2%
83

Montverde
$1,464,596
$1,090,370
58
0.0%
36.2%
115

Ocoee
$533,270
$489,450
188
1.6%
51.1%
75

Orlando
$682,457
$498,700
2941
1.6%
47.9%
78

Oviedo
$727,415
$648,750
196
1.0%
41.3%
73

Poinciana
$328,195
$314,900
273
0.4%
54.2%
120

Reunion
$1,814,038
$1,125,000
110
0.9%
50.0%
148

Saint Cloud
$558,479
$467,444
384
1.0%
72.1%
178

Sanford
$532,974
$415,990
371
0.8%
53.6%
99

Sorrento
$615,159
$470,000
107
0.9%
53.3%
84

Windermere
$2,150,589
$1,300,000
285
0.4%
45.6%
98

Winter Park
$1,234,494
$695,000
301
0.3%
46.2%
78

Winter Springs
$647,268
$494,000
130
0.0%
45.4%
74

EasyStreet

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