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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 407-485-1814.

12 Results

Oakland Park Winter Garden Florida Homes For Sale

Oakland Park For Sale $625,000

Charming two-story home with inviting front porch and beautifully landscaped yard and black metal fence at 923 Colie Aly, Winter Garden, FL 34787
View Details 31 Photos
Inviting two-story home with rocking chairs on the porch and an outdoor seating area at 923 Colie Aly, Winter Garden, FL 34787
Charming two-story home with a spacious front yard and welcoming front porch at 923 Colie Aly, Winter Garden, FL 34787
Inviting two-story home with a cozy front porch and well-manicured landscaping and black metal fence at 923 Colie Aly, Winter Garden, FL 34787
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1786

  • Year Built

    2022

  • $/SqFt

    $350

This is a rare opportunity to own an amazing modern home in McKinnon Square in Oakland Park a Parade of Homes Award winning community. CHARLES RUTENBERG REALTY ORLANDO.

Oakland Park For Sale $1,098,900

Charming two-story home with a welcoming front porch, lush lawn and well-manicured landscaping at 859 Easley Ave, Winter Garden, FL 34787
View Details 60 Photos
Charming two-story home with a welcoming front porch, lush lawn and well-manicured landscaping at 859 Easley Ave, Winter Garden, FL 34787
Relaxing front porch seating with hanging plants and 'Welcome to our Porch' sign at 859 Easley Ave, Winter Garden, FL 34787
Bright living room with a fireplace, large windows and a comfortable sectional sofa at 859 Easley Ave, Winter Garden, FL 34787
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2442

  • Year Built

    2016

  • $/SqFt

    $450

Don't miss this rare opportunity to own a gorgeous customized pool home in Oakland Park! OAK AVENUE REAL ESTATE LLC.

Oakland Park Pended $999,000

Charming two-story home with a welcoming front porch, manicured landscaping, and a light gray exterior at 1206 Civitas Way, Winter Garden, FL 34787
View Details 45 Photos
Inviting two-story home with a well-manicured lawn, showcasing a charming exterior and welcoming entrance at 1206 Civitas Way, Winter Garden, FL 34787
Relaxing covered porch with comfortable seating, perfect for enjoying outdoor living and entertaining at 1206 Civitas Way, Winter Garden, FL 34787
Cozy front porch with rocking chairs, creating a charming and inviting outdoor space to relax and enjoy at 1206 Civitas Way, Winter Garden, FL 34787
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2765

  • Year Built

    2022

  • $/SqFt

    $361

The community features parks, playgrounds, two pools (one resort styled pool), and clubhouse. INDEPENDENCE REALTY GROUP LLC.

Oakland Park Pended $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 36 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 For Sale $949,900

Reduced By $25,100

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 54 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2683

  • Year Built

    2022

  • $/SqFt

    $354

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

Oakland Park Pended $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 74 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 $2,075,000

Reduced By $274,000

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 100 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 85 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5441

  • Year Built

    2016

  • $/SqFt

    $381

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 showcasing inviting front porch with classic architectural details and fresh landscaping at 985 Huntspoint St, Winter Garden, FL 34787
View Details 49 Photos
Inviting home featuring a covered porch, a well-maintained lawn, and classic design at 985 Huntspoint St, Winter Garden, FL 34787
Welcoming front porch with seating, a light blue front door, and crisp white trim at 985 Huntspoint St, Winter Garden, FL 34787
Bright foyer featuring stylish wood-look tile flooring and a decorative console table at 985 Huntspoint St, Winter Garden, FL 34787
On Market For 93 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 107 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 63 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

Two-story home exterior under construction with covered patio, with visible framing and siding at 166 Hammock Preserve Loop, Winter Garden, FL 34787
View Details 99 Photos
Charming two-story home boasting a covered front porch, manicured lawn, and beautiful landscaping at 166 Hammock Preserve Loop, Winter Garden, FL 34787
This is an image with the text 'Inspired Living Starts Here' in blue and black lettering at 166 Hammock Preserve Loop, Winter Garden, FL 34787
Second floor plan showing the layout of the bedrooms, bathrooms, and loft at 166 Hammock Preserve Loop, Winter Garden, FL 34787
On Market For 120 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 $950,000

Reduced By $49,900

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 142 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2831

  • Year Built

    2022

  • $/SqFt

    $336

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 407-485-1814 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$502,714
$437,500
149
1.3%
56.4%
87

Apopka
$532,789
$484,990
575
1.2%
49.7%
87

Belle Isle
$871,104
$674,450
22
4.5%
50.0%
70

Casselberry
$418,059
$402,500
100
2.0%
53.0%
68

Celebration
$1,276,982
$996,495
52
0.0%
46.2%
90

Champions Gate
$686,906
$675,000
16
0.0%
43.8%
318

Chuluota
$929,472
$800,000
25
0.0%
36.0%
41

Clermont
$579,051
$495,000
751
0.5%
53.9%
76

Gotha
$832,677
$644,000
13
0.0%
46.2%
57

Groveland
$476,891
$404,000
283
1.1%
62.2%
87

Harmony
$432,413
$419,900
80
0.0%
35.0%
92

Kissimmee
$514,927
$440,000
2429
1.8%
51.7%
106

Longwood
$756,558
$559,000
215
0.9%
55.3%
73

Maitland
$993,167
$629,900
106
1.9%
54.7%
79

Minneola
$563,183
$541,227
154
0.0%
44.2%
75

Montverde
$1,517,524
$1,100,000
51
0.0%
52.9%
118

Ocoee
$524,926
$480,000
175
1.1%
45.7%
74

Orlando
$678,370
$499,900
3147
1.7%
51.5%
80

Oviedo
$704,967
$600,000
236
0.8%
53.4%
72

Poinciana
$322,651
$310,840
278
1.8%
52.9%
127

Reunion
$1,784,785
$1,050,000
113
2.7%
52.2%
164

Saint Cloud
$707,524
$525,000
31
3.2%
58.1%
307

Sanford
$518,173
$420,000
407
1.0%
50.6%
91

Sorrento
$613,118
$464,900
105
1.0%
50.5%
92

Windermere
$2,116,576
$1,349,950
288
0.0%
44.1%
93

Winter Park
$1,232,945
$740,000
337
0.6%
57.0%
87

Winter Springs
$608,081
$494,900
147
0.7%
52.4%
73

EasyStreet

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