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.

9 Results

Oakland Park Winter Garden Florida Homes For Sale

Oakland Park For Sale $840,000

Two-story craftsman home with gray siding, front porch, and landscaping at 932 Tilden Oaks Trl, Winter Garden, FL 34787
View Details 45 Photos
Row of charming two-story homes with gray and white exteriors at 932 Tilden Oaks Trl, Winter Garden, FL 34787
Spacious living room with leather sectional sofa and large TV at 932 Tilden Oaks Trl, Winter Garden, FL 34787
Open concept living room with leather sectional and kitchen island view at 932 Tilden Oaks Trl, Winter Garden, FL 34787
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2362

  • Year Built

    2021

  • $/SqFt

    $356

No wonder it is the No.1 community to live in! REAL LIVING R E SOLUTIONS.

Oakland Park For Sale $1,199,000

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 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3070

  • Year Built

    2023

  • $/SqFt

    $391

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

Oakland Park Pended $869,900

Two-story craftsman style home with gray siding, white trim, and a charming front porch at 1102 Eagles Pass Way, Winter Garden, FL 34787
View Details 49 Photos
Two-story craftsman style home with gray siding, white trim, and a charming front porch at 1102 Eagles Pass Way, Winter Garden, FL 34787
Two-story craftsman style home with gray siding, white trim, and a charming front porch at 1102 Eagles Pass Way, Winter Garden, FL 34787
Inviting front porch with rocking chairs, white columns, and lush landscaping at 1102 Eagles Pass Way, Winter Garden, FL 34787
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2260

  • Year Built

    2023

  • $/SqFt

    $385

Ideally located within the community, this home sits on an oversized corner lot and is just about one quarter of a mile to the WO trail, community pool, clubhouse, playground, ?re pit and pavilion. SAGE REALTY FLORIDA, INC..

Oakland Park Pended $650,000

Gray two-story home with a front porch and well-manicured landscaping at 1411 Eastover Loop, Winter Garden, FL 34787
View Details 81 Photos
Gray two-story home with a front porch, walkway, and lush hedges at 1411 Eastover Loop, Winter Garden, FL 34787
Gray two-story home with a front porch and walkway, surrounded by greenery at 1411 Eastover Loop, Winter Garden, FL 34787
Covered porch with seating area, ceiling fan, and a view of the neighborhood at 1411 Eastover Loop, Winter Garden, FL 34787
*POTENTIAL GREAT VALUE
On Market For 65 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1937

  • Year Built

    2008

  • $/SqFt

    $336

This gem is one of the LOWEST priced entry points into the community & is ready to be embraced by its new owner! BHHS FLORIDA REALTY.

Oakland Park Pended $799,900

Reduced By $25,100

Two-story home with a front porch and American flag at 934 Mckinnon Sq, Winter Garden, FL 34787
View Details 42 Photos
Two-story home with a front porch and American flag at 934 Mckinnon Sq, Winter Garden, FL 34787
Light and bright entryway with wood floors and pocket doors at 934 Mckinnon Sq, Winter Garden, FL 34787
Living room with hardwood floors and a modern aesthetic at 934 Mckinnon Sq, Winter Garden, FL 34787
On Market For 109 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2536

  • Year Built

    2022

  • $/SqFt

    $315

In the golf cart district and short distance to the West Orange Trail, The Mannington offers the best of Oakland Park living. PREMIER SOTHEBY'S INTL. REALTY.

Oakland Park Pended $1,098,544

Charming craftsman style home with brick accents and a welcoming front porch at 1056 Sadler Oaks Way, Winter Garden, FL 34787
View Details 8 Photos
Open floor plan featuring 3 bedrooms, 2 baths, and a 2-car garage at 1056 Sadler Oaks Way, Winter Garden, FL 34787
Upstairs floor plan with a large retreat, bedroom and bath at 1056 Sadler Oaks Way, Winter Garden, FL 34787
Modern kitchen design featuring neutral colors, marble countertops, and black cabinets at 1056 Sadler Oaks Way, Winter Garden, FL 34787
On Market For 144 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2711

  • Year Built

    2024

  • $/SqFt

    $405

Don't miss out—schedule your private tour today! WEEKLEY HOMES REALTY COMPANY.

Oakland Park Pended $625,000

Reduced By $25,000

Two-story farmhouse-style home with front porch and landscaping at 925 Mckinnon Sq, Winter Garden, FL 34787
View Details 57 Photos
Two-story farmhouse-style home with front porch and landscaping at 925 Mckinnon Sq, Winter Garden, FL 34787
Charming front porch with rocking chairs and landscaping at 925 Mckinnon Sq, Winter Garden, FL 34787
Front porch detail with white rocking chairs and side table at 925 Mckinnon Sq, Winter Garden, FL 34787
On Market For 134 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1654

  • Year Built

    2022

  • $/SqFt

    $378

Conveniently located near interstate travels, shops, restaurants, golf courses, and theme parks, this gem is a must-see! BHHS FLORIDA REALTY.

Oakland Park Pended $949,000

Reduced By $26,000

Two-story light blue house with a front porch, white picket fence, and landscaped yard at 967 Prosperity Dr, Winter Garden, FL 34787
View Details 97 Photos
Aerial view of a neighborhood with houses, a park, and a community pool at 967 Prosperity Dr, Winter Garden, FL 34787
Relaxing covered porch with outdoor seating and a fire pit, overlooking a park at 967 Prosperity Dr, Winter Garden, FL 34787
Bright entryway with hardwood floors, leading to the living room and kitchen at 967 Prosperity Dr, Winter Garden, FL 34787
On Market For 197 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2585

  • Year Built

    2014

  • $/SqFt

    $367

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

Oakland Park For Sale $1,649,900

Two-story farmhouse-style home with gray siding and a white front porch at 166 Hammock Preserve Loop, Winter Garden, FL 34787
View Details 6 Photos
Rear view of a two-story home showcasing a large backyard and attached guest house at 166 Hammock Preserve Loop, Winter Garden, FL 34787
Side view of a two-story home with a gray exterior and attached garage at 166 Hammock Preserve Loop, Winter Garden, FL 34787
Two-car attached garage with gray exterior and a driveway at 166 Hammock Preserve Loop, Winter Garden, FL 34787
On Market For 349 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. EXP REALTY LLC.

  • 1

Viewing HOMES 1 to 9 of 9

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.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$521,847
$437,000
126
0.8%
53.2%
94

Apopka
$533,970
$469,992
544
1.3%
47.2%
91

Belle Isle
$844,154
$675,000
26
0.0%
26.9%
71

Casselberry
$437,904
$425,000
86
1.2%
46.5%
85

Celebration
$1,351,194
$1,177,000
42
0.0%
52.4%
147

Champions Gate
$717,218
$724,995
21
0.0%
47.6%
235

Chuluota
$785,231
$585,000
16
0.0%
56.2%
80

Clermont
$567,399
$497,750
580
0.7%
49.8%
94

Gotha
$1,112,908
$687,000
12
0.0%
16.7%
81

Groveland
$483,147
$421,000
211
0.9%
52.1%
99

Harmony
$434,619
$413,700
60
0.0%
40.0%
103

Kissimmee
$519,201
$442,000
2134
1.5%
46.4%
109

Longwood
$757,262
$569,900
173
1.2%
59.5%
98

Maitland
$733,057
$612,000
70
0.0%
52.9%
104

Minneola
$574,145
$539,900
129
0.8%
31.8%
95

Montverde
$1,556,955
$1,103,738
51
0.0%
56.9%
163

Ocoee
$532,554
$469,000
169
0.6%
45.6%
76

Orlando
$678,757
$490,000
2442
1.6%
49.2%
88

Oviedo
$694,118
$585,000
173
2.3%
45.7%
83

Poinciana
$337,961
$325,000
253
0.8%
57.7%
145

Reunion
$1,742,766
$1,260,000
89
3.4%
41.6%
165

Saint Cloud
$539,008
$465,000
843
0.9%
59.2%
116

Sanford
$514,336
$413,245
380
1.3%
53.2%
98

Sorrento
$582,285
$450,740
109
1.8%
53.2%
79

Windermere
$2,213,721
$1,287,485
234
0.4%
41.9%
121

Winter Park
$1,299,573
$699,495
235
1.3%
43.0%
95

Winter Springs
$542,558
$465,000
113
0.9%
56.6%
90

EasyStreet

Call to Schedule a Showing

(407) 278-2057

(407) 278-2057