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    Tampa, FL 33606
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: Renaissance Realty Group

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West Orange Trail Town on Lake Apopka

Listings in Oakland, FL

Welcome to Oakland, a historic town on the southern shore of Lake Apopka in Orange County, Florida, home to the West Orange Trail and a quiet lakeside pace just west of Winter Garden.

Oakland is a small incorporated town in Orange County, Florida, on the southern shore of Lake Apopka, about two miles west of Winter Garden and roughly fifteen to twenty miles west of downtown Orlando. The town occupies a stretch of gently rolling terrain along one of central Florida's largest lakes, and its identity is tied to both the water and the rail corridor that once ran through its center. Oakland was incorporated in 1887, during a period of rapid growth across west Orange County. Its early promise as a railroad and citrus town was tempered by a destructive business-district fire and a series of hard freezes in the 1890s, which allowed nearby Winter Garden to eclipse it. The result is a community that has remained deliberately small, with a historic core along Oakland Avenue and a population of roughly 3,000 residents. Today the former railroad right-of-way through town has been converted to the West Orange Trail, a regional rail-trail that brings cyclists and walkers through the heart of Oakland. The Oakland Nature Preserve, on the town's lakeside edge, protects wetlands and uplands along Lake Apopka and provides environmental education and trails. Public school students attend Orange County Public Schools, and the town is home to Oakland Avenue Charter School, an elementary campus serving local families. Winter Garden, immediately to the east, supplies dining, retail, and entertainment, while State Road 50 and the region's expressway network connect Oakland to the wider Orlando area. Oakland tends to appeal to households seeking a quiet, lakeside small-town atmosphere with historic character, strong trail access, and convenient proximity to Winter Garden and the Orlando region's amenities.

Renaissance Realty Group
Renaissance Realty Group Renaissance Realty Group

Get more information about Oakland

Listings 50
Population 3,000
County Orange County
Oakland Listings Market Stats Subdivisions Zip Codes Neighborhood FAQs Nearby

Houses in Oakland, FL

homeMore houses
2696 BOBCAT CHASE BOULEVARD
$515,000
MFRS5158021
For Sale
2696 BOBCAT CHASE BOULEVARD Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 2547 sq ft
2470 STANDING ROCK CIRCLE
$730,000
MFRO6443027
For Sale
2470 STANDING ROCK CIRCLE Oakland, FL 34787
5 Beds bathtub 3 Baths straighten 4322 sq ft
81 MILLHOLLAND STREET
$1,275,000
MFRO6442710
For Sale
81 MILLHOLLAND STREET Oakland, FL 34760
3 Beds bathtub 3 Baths straighten 5069 sq ft
2273 STANDING ROCK CIRCLE
$479,900
MFRO6439158
For Sale
2273 STANDING ROCK CIRCLE Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 2859 sq ft
1016 CATORI ROAD
$825,000
MFRO6440957
For Sale
1016 CATORI ROAD Oakland, FL 34787
4 Beds bathtub 3.5 Baths straighten 3878 sq ft
137 PETRIS AVENUE
$1,445,000
MFRO6440357
For Sale
137 PETRIS AVENUE Oakland, FL 34760
4 Beds bathtub 3.5 Baths straighten 4121 sq ft
2140 STANDING ROCK CIRCLE
$2,900
MFRO6440495
For Rent
2140 STANDING ROCK CIRCLE Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 2630 sq ft
239 LARGOVISTA DRIVE
$675,900
MFRFC321273
For Sale
239 LARGOVISTA DRIVE Oakland, FL 34787
4 Beds bathtub 2.5 Baths straighten 4090 sq ft
166 HAMMOCK PRESERVE LOOP
$850,000
MFRO6439973
For Sale
166 HAMMOCK PRESERVE LOOP Oakland, FL 34787
4 Beds bathtub 4 Baths straighten 5331 sq ft
1511 SWEET APPLE STREET
$339,900
MFRO6439535
For Sale
1511 SWEET APPLE STREET Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 2275 sq ft
2471 SKY STONE COURT
$559,000
MFRS5156522
For Sale
2471 SKY STONE COURT Oakland, FL 34787
4 Beds bathtub 2.5 Baths straighten 3774 sq ft
320 W SADLER AVENUE
$199,000
MFRO6436879
For Sale
320 W SADLER AVENUE Oakland, FL 34760
2 Beds bathtub 1 Baths straighten 747 sq ft
1112 HULL ISLAND DRIVE
$1,400,000
MFRO6434371
For Sale
1112 HULL ISLAND DRIVE Oakland, FL 34787
4 Beds bathtub 3.5 Baths straighten 4715 sq ft
312 BRILEY AVENUE
$3,295,000
MFRO6429415
For Sale
312 BRILEY AVENUE Oakland, FL 34760
6 Beds bathtub 6.5 Baths straighten 6551 sq ft
223 LARGOVISTA DR.
$540,000
MFRO6425925
For Sale
223 LARGOVISTA DR. Oakland, FL 34787
4 Beds bathtub 2.5 Baths straighten 2965 sq ft
1603 JOHNS COVE LN
$779,000
MFRO6419418
For Sale
1603 JOHNS COVE LN Oakland, FL 34787
6 Beds bathtub 4 Baths straighten 4824 sq ft
1134 PRADO LANE
$2,495,000
MFRO6413035
For Sale
1134 PRADO LANE Oakland, FL 34787
5 Beds bathtub 6.5 Baths straighten 6597 sq ft
1152 PRADO LANE
$2,615,320
MFRO6413825
For Sale
1152 PRADO LANE Oakland, FL 34787
6 Beds bathtub 6.5 Baths straighten 6015 sq ft
1155 PRADO LANE
$2,575,000
MFRO6415007
For Sale
1155 PRADO LANE Oakland, FL 34787
5 Beds bathtub 6 Baths straighten 5914 sq ft
2241 WHITE FEATHER LOOP
$510,000
MFRO6411576
For Sale
2241 WHITE FEATHER LOOP Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 3035 sq ft
16 OAKLAND POINTE CIRCLE
$795,999
MFRTB8513260
For Sale
16 OAKLAND POINTE CIRCLE Oakland, FL 34760
5 Beds bathtub 3 Baths straighten 4190 sq ft
2017 BOSS HEWETT STREET
$649,900
MFRO6402045
For Sale
2017 BOSS HEWETT STREET Oakland, FL 34787
4 Beds bathtub 4 Baths straighten 3580 sq ft
219 LARGOVISTA DRIVE
$995,900
MFRO6401756
For Sale
219 LARGOVISTA DRIVE Oakland, FL 34787
5 Beds bathtub 4 Baths straighten 4944 sq ft
250 WALKER STREET
$999,000
MFRG5110973
For Sale
250 WALKER STREET Oakland, FL 34760
4 Beds bathtub 2.5 Baths straighten 3953 sq ft

Townhouses & Duplexes in Oakland, FL

holiday_villageMore townhouses
1511 SWEET APPLE STREET
$339,900
MFRO6439535
For Sale
1511 SWEET APPLE STREET Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 2275 sq ft

For Rent in Oakland, FL

editMore rentals
2140 STANDING ROCK CIRCLE
$2,900
MFRO6440495
For Rent
2140 STANDING ROCK CIRCLE Oakland, FL 34787
3 Beds bathtub 2.5 Baths straighten 2630 sq ft

Lots & Land in Oakland, FL

crop_landscapeMore land
552 WALKER STREET
$1,195,000
MFRO6430656
For Sale
552 WALKER STREET Oakland, FL 34787
523 WALKER STREET
$595,000
MFRO6430636
For Sale
523 WALKER STREET Oakland, FL 34787
514 POLLARD STREET
$575,000
MFRO6332783
For Sale
514 POLLARD STREET Oakland, FL 34787

MARKET SNAPSHOT

The Market at a Glance

How homes have been selling here over the last 90 days.

home_work New This Week 1
Went Under Contract 0
trending_down Price Reductions 0
payments Median Sale Price $570,000 -10.2%
square_foot Price per Sq Ft $211
schedule Avg Days on Market 70
sell Homes Sold 18
percent Sale-to-List Ratio 98.0%
inventory_2 Months of Inventory 7.4

Price & Sales History

Market data reflects closed sales over the last 90 days and is provided for informational purposes.

Renaissance Realty Group
Renaissance Realty Group Renaissance Realty Group info@rrgrouptampa.com

Zip Codes

BROWSE BY ZIP

Browse listings by postal code in this area.

011 homes for saleMedian sale$295K1 sale in the last 90 days
002 homes for saleMedian sale$295K
0002 homes for saleMedian sale$295K
00007 homes for saleMedian sale$295K
0000026 homes for saleMedian sale$85KPer sq ft$211 sale in the last 90 days
0060223 homes for saleMedian sale$560.3KPer sq ft$2282 sales in the last 90 days
0060333 homes for saleMedian sale$312.5KPer sq ft$1842 sales in the last 90 days
0061231 homes for saleMedian sale$231KPer sq ft$1539 sales in the last 90 days
0062359 homes for saleMedian sale$262.5KPer sq ft$22010 sales in the last 90 days
0064113 homes for saleMedian sale$399KPer sq ft$1601 sale in the last 90 days
00646129 homes for saleMedian sale$1.2MPer sq ft$51622 sales in the last 90 days
0066234 homes for saleMedian sale$410KPer sq ft$3196 sales in the last 90 days
View All Zip Codes
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401 NW 43rd Ct #4 For Rent
$2,500
401 NW 43rd Ct #4Oakland Park, FL 33309
  • 3 bd
  • 1 ba
  • 4683 sqft
  • Built 1961
  • A12101444
2880 Oakland Forest Dr #209 For Rent
$1,900
2880 Oakland Forest Dr #209Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 786 sqft
  • Built 1992
  • A12102243
251 NE 40th Street ##251 For Rent
$1,800
251 NE 40th Street ##251Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 880 sqft
  • Built 1969
  • B26085332
981 NE 36TH STREET #1 For Rent
$2,200
981 NE 36TH STREET #1Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 1100 sqft
  • Built 1972
Address Not Shown For Rent
$2,475
Address Not ShownOakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 1202 sqft
  • Built 1961
5162 NE 6th Ave #308 For Sale
$165,900
5162 NE 6th Ave #308Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 609 sqft
  • Built 1978
  • A12101627
108 Royal Park Dr #2H For Sale
$180,000
108 Royal Park Dr #2HOakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 975 sqft
  • Built 1976
  • A12101901
981 NE 36TH STREET #1 For Rent
$2,200
981 NE 36TH STREET #1Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 1100 sqft
  • Built 1972
  • B26085090
1840 NE 42nd St For Rent
$8,500
1840 NE 42nd StOakland Park, FL 33308
  • 3 bd
  • 2 ba
  • 1657 sqft
  • Built 1957
  • A12101614
1931 NW 38th Street For Sale
$535,000
1931 NW 38th StreetOakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 1272 sqft
  • Built 1966
  • B26084366
3119 Oakland Shores Dr #C204 For Sale
$133,000
3119 Oakland Shores Dr #C204Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 760 sqft
  • Built 1974
  • A12100971
1931 NW 38th Street For Sale
$535,000
1931 NW 38th StreetOakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 1272 sqft
  • Built 1966
3119 OAKLAND SHORES DRIVE #C211 For Rent
$1,650
3119 OAKLAND SHORES DRIVE #C211Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 760 sqft
  • Built 1974
121 NW 55th St #0 For Rent
$4,400
121 NW 55th St #0Oakland Park, FL 33309
  • 3 bd
  • 2 ba
  • 1016 sqft
  • Built 1957
  • A12101104
1271 NE 32nd St #1289 For Rent
$1,600
1271 NE 32nd St #1289Oakland Park, FL 33334
  • 1 bd
  • 1 ba
  • 5769 sqft
  • Built 1959
  • A12100450
112 Lake Emerald Dr #109 For Sale
$195,000
112 Lake Emerald Dr #109Oakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 920 sqft
  • Built 1981
  • A12099640
401 NW 43rd Ct #7 For Rent
$1,500
401 NW 43rd Ct #7Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 4683 sqft
  • Built 1961
  • A12100350
5456 NE 1ST AVENUE For Rent
$2,800
5456 NE 1ST AVENUEOakland Park, FL 33334
  • 3 bd
  • 2 ba
  • 1017 sqft
  • Built 1956
  • B26067569
5456 NE 1ST AVENUE For Rent
$2,800
5456 NE 1ST AVENUEOakland Park, FL 33334
  • 3 bd
  • 2 ba
  • 1017 sqft
  • Built 1956
220 NW 42ND STREET For Sale
$750,000
220 NW 42ND STREETOakland Park, FL 33309
  • 4 bd
  • 2 ba
  • 2442 sqft
  • Built 1958
345 NW 32nd St #345 For Rent
$1,599
345 NW 32nd St #345Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 3262 sqft
  • Built 1965
  • A12100017
3000 NE 16th Ave #203 For Rent
$1,600
3000 NE 16th Ave #203Oakland Park, FL 33334
  • 1 bd
  • 1 ba
  • 600 sqft
  • Built 1965
  • A12098635
5650 NE 8th Ave For Rent
$3,975
5650 NE 8th AveOakland Park, FL 33334
  • 4 bd
  • 2 ba
  • 1332 sqft
  • Built 1961
  • A12100084
411 NW 52ND STREET For Sale
$374,000
411 NW 52ND STREETOakland Park, FL 33309
  • 2 bd
  • 1 ba
  • 856 sqft
  • Built 1956
  • B26083679
3409 NW 44th St #101 For Sale
$215,000
3409 NW 44th St #101Oakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 1020 sqft
  • Built 1989
  • A12099563
411 NW 52ND STREET For Sale
$374,000
411 NW 52ND STREETOakland Park, FL 33309
  • 2 bd
  • 1 ba
  • 856 sqft
  • Built 1956
2126 Appleton Cir N #2126 For Rent
$3,850
2126 Appleton Cir N #2126Oakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1754 sqft
  • Built 2022
  • A12099373
230 NW 52nd St For Sale
$380,000
230 NW 52nd StOakland Park, FL 33309
  • 2 bd
  • 1 ba
  • 1084 sqft
  • Built 1956
  • A12094922
114 Royal Pk Drive #3A For Sale
$169,900
114 Royal Pk Drive #3AOakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 975 sqft
  • Built 1976
  • B26083117
1540 NE 40th Street For Sale
$749,950
1540 NE 40th StreetOakland Park, FL 33334
  • 3 bd
  • 2 ba
  • 1452 sqft
  • Built 1970
  • B26082880
211 NE 35th St For Sale
$400,000
211 NE 35th StOakland Park, FL 33334
  • 3 bd
  • 1.5 ba
  • 1290 sqft
  • Built 2014
  • A12098530
401 NW 43rd Ct #4 For Rent
$1,300
401 NW 43rd Ct #4Oakland Park, FL 33309
  • 1 ba
  • 4683 sqft
  • Built 1961
  • A12100300
401 NW 43rd Ct #3 For Rent
$1,500
401 NW 43rd Ct #3Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 4683 sqft
  • Built 1961
  • A12100312
3119 OAKLAND SHORES DRIVE #C211 For Rent
$1,650
3119 OAKLAND SHORES DRIVE #C211Oakland Park, FL 33309
  • 1 bd
  • 1 ba
  • 760 sqft
  • Built 1974
  • B26084294
210 Lake Pointe Dr #210 For Rent
$1,890
210 Lake Pointe Dr #210Oakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 890 sqft
  • Built 1984
  • A12101976
401 NW 43rd Ct #1 For Rent
$2,300
401 NW 43rd Ct #1Oakland Park, FL 33309
  • 2 bd
  • 1 ba
  • 4683 sqft
  • Built 1961
  • A12101443
114 Royal Pk Drive #3A For Sale
$169,900
114 Royal Pk Drive #3AOakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 975 sqft
  • Built 1976
1540 NE 40th Street For Sale
$749,950
1540 NE 40th StreetOakland Park, FL 33334
  • 3 bd
  • 2 ba
  • 1452 sqft
  • Built 1970
250 NE 40TH STREET #38 For Sale
$155,000
250 NE 40TH STREET #38Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 820 sqft
  • Built 1969
  • B26082683
5150 NE 6TH AVENUE #113 For Rent
$1,800
5150 NE 6TH AVENUE #113Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 609 sqft
  • Built 1978
  • B26082669
1028 NE 36TH STREET #Cottage For Rent
$2,600
1028 NE 36TH STREET #CottageOakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 825 sqft
  • Built 1932
  • B26082697
3040 NE 16TH AVENUE #406 Active With Contract
$1,499
3040 NE 16TH AVENUE #406Oakland Park, FL 33334
  • 1 bd
  • 1 ba
  • 600 sqft
  • Built 1963
  • B26082607
4450 NW 19th Avenue For Sale
$599,900
4450 NW 19th AvenueOakland Park, FL 33309
  • 3 bd
  • 2 ba
  • 1279 sqft
  • Built 1967
  • B26082612
1028 NE 36TH STREET #Cottage For Rent
$2,600
1028 NE 36TH STREET #CottageOakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 825 sqft
  • Built 1932
250 NE 40TH STREET #38 For Sale
$155,000
250 NE 40TH STREET #38Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 820 sqft
  • Built 1969
5150 NE 6TH AVENUE #113 For Rent
$1,800
5150 NE 6TH AVENUE #113Oakland Park, FL 33334
  • 2 bd
  • 1 ba
  • 609 sqft
  • Built 1978
4450 NW 19th Avenue For Sale
$599,900
4450 NW 19th AvenueOakland Park, FL 33309
  • 3 bd
  • 2 ba
  • 1279 sqft
  • Built 1967
3697 NE 16TH AVENUE For Sale
$634,999
3697 NE 16TH AVENUEOakland Park, FL 33334
  • 3 bd
  • 2 ba
  • 1560 sqft
  • Built 1956
  • B26082202
4566 Silverwood Lane For Sale
$1,550,000
4566 Silverwood LaneOakland Park, FL 33309
  • 4 bd
  • 4 ba
  • 2574 sqft
  • Built 2024
  • B26082529
3616 NE 11th Ave #6 For Rent
$1,650
3616 NE 11th Ave #6Oakland Park, FL 33334
  • 1 bd
  • 1 ba
  • Built 1971
  • A12098468
916
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City Guide

About Oakland

Real Estate & Housing

Housing in Oakland blends historic and small-scale stock with newer construction. The town retains older homes near its original core along Oakland Avenue, alongside more recent single-family development on the surrounding streets. Homesites tend to be more spacious than in denser Orlando suburbs, and the town's lakeside setting and trail access add to its appeal. The market is modest in scale, reflecting Oakland's identity as a compact, historic town rather than a large master-planned community.

Neighborhoods

Lifestyle in Oakland

Oakland offers a small-town, lakeside pace within the Orlando metro area. Residents enjoy the shade of old oaks, the West Orange Trail for walking and cycling, and access to Lake Apopka's shoreline and wetlands. The historic downtown along Oakland Avenue retains a compact, walkable feel, while Winter Garden's thriving restaurant and shopping scene sits just two miles east. The community's small size and preserved character appeal to those who want a quieter alternative to suburban Orlando while staying close to regional employment, attractions, and services.

Schools & Education

Oakland is served by Orange County Public Schools, the district covering the county including the Orlando metro area. The town is also home to Oakland Avenue Charter School, an elementary charter campus that serves local students. Beyond the elementary level, students attend zoned Orange County middle and high schools, and the nearby communities of Winter Garden and Clermont offer additional public and private school options within a short drive.

Getting Around

Oakland sits near State Road 50, the main east–west route through west Orange County, connecting the town to Winter Garden, Ocoee, and the Orlando area. Florida's Turnpike and the Western Beltway (State Road 429) are reachable within a short drive, providing access to the broader Orlando region, the attractions area, and points beyond. The West Orange Trail also provides a non-motorized route to Winter Garden and adjacent communities, making the town unusually walkable and bike-friendly for the region.

Parks & Recreation

The West Orange Trail is Oakland's signature recreational asset, running through town along a former rail corridor and linking it to Winter Garden and the wider trail network of west Orange County. The Oakland Nature Preserve offers boardwalks and trails through Lake Apopka wetlands, with wildlife viewing and environmental programming. Lake Apopka itself provides fishing and scenic shoreline, while Winter Garden's parks, downtown, and lakefront pavilion add to nearby recreation options. The town's compact, walkable streets and shaded canopy make everyday outdoor activity part of local life.

About Oakland

Frequently asked questions

What county is Oakland, Florida in?

Oakland is a town in Orange County, Florida, located on the southern shore of Lake Apopka about two miles west of Winter Garden. It sits at the western edge of the Orlando metropolitan area.

What school district serves Oakland, Florida?

Oakland is part of Orange County Public Schools, which operates schools across the county. The town is also home to Oakland Avenue Charter School, an elementary charter campus serving local students.

What is Oakland, Florida known for?

Oakland is known for the West Orange Trail, a rail-trail that runs through town along a former railroad corridor, and for the Oakland Nature Preserve, which protects wetlands along the Lake Apopka shoreline.

How far is Oakland, Florida from Orlando?

Oakland is about two miles west of Winter Garden and roughly 15 to 20 miles west of downtown Orlando. The town's location near State Road 50 and the region's expressways provides access to the wider Orlando area.

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