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(561) 379-5536 ddills@comcast.net
  • Seawinds Investment Realty, LLC
    14852 68th Drive North
    Palm Beach Gardens, FL 33418
    561-379-5536
    ddills@comcast.net
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Miami Association of REALTORS®

MIAMI ASSOCIATION OF REALTORS® All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than Marjo Realty Co. may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS.

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West Orange Trail Town on Lake Apopka

Townhouses & Duplexes 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.

Population 3,000
County Orange County
Active Listings 43
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homeHouses apartmentCondos & Apartments holiday_villageTownhouses & Duplexes crop_landscapeLots & Land parkFarms & Ranches

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.

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 $742,500 +15.1%
square_foot Price per Sq Ft $11,146
schedule Avg Days on Market 52
sell Homes Sold 19
percent Sale-to-List Ratio 99.0%
inventory_2 Months of Inventory 5.3

Price & Sales History

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

BROWSE BY ZIP

Zip Codes

Browse listings by postal code in this area.

010 homes for saleMedian sale$295K1 sale in the last 90 days
003 homes for saleMedian sale$295K
0001 home for saleMedian sale$295K
00006 homes for saleMedian sale$295K
0000026 homes for saleMedian sale$370KPer sq ft$199 sales in the last 90 days
006034 homes for saleMedian sale$235KPer sq ft$7273 sales in the last 90 days
006231 home for saleMedian sale$240KPer sq ft$19214 sales in the last 90 days
006462 homes for saleMedian sale$1.5MPer sq ft$59625 sales in the last 90 days
006921 home for saleMedian sale$345KPer sq ft$20613 sales in the last 90 days
007292 homes for saleMedian sale$170KPer sq ft$1653 sales in the last 90 days
007731 home for saleMedian sale$318KPer sq ft$60312 sales in the last 90 days
080301 home for saleMedian sale$235KPer sq ft$19625 sales in the last 90 days
View All Zip Codes
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  • List
3102 NW 24th Way For Sale
$399,900
3102 NW 24th WayOakland Park, FL 33309
  • 2 bd
  • 2.5 ba
  • 1487 sqft
  • Built 2007
  • A12069486
405 NE 35TH COURT #2 For Rent
$2,700
405 NE 35TH COURT #2Oakland Park, FL 33334
  • 2 bd
  • 2.5 ba
  • 1225 sqft
  • Built 2021
  • B26069520
2900 NE 12th Terrace #22 For Sale
$1,160,000
2900 NE 12th Terrace #22Oakland Park, FL 33334
  • 4 bd
  • 3 ba
  • 2152 sqft
  • Built 2017
  • B26068476
3275 NW 44TH STREET #2 For Rent
$3,200
3275 NW 44TH STREET #2Oakland Park, FL 33309
  • 3 bd
  • 3.5 ba
  • 1273 sqft
  • Built 1994
  • B26067996
1488 NE 34TH STREET For Sale
$675,000
1488 NE 34TH STREETOakland Park, FL 33334
  • 2 bd
  • 2.5 ba
  • 1551 sqft
  • Built 2021
  • B26067625
3016 NW 30TH AVENUE For Rent
$2,800
3016 NW 30TH AVENUEOakland Park, FL 33311
  • 3 bd
  • 2.5 ba
  • 1504 sqft
  • Built 2007
  • B26067568
2138 S Appleton Cir S For Sale
$619,000
2138 S Appleton Cir SOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1774 sqft
  • Built 2022
  • A12072088
3434 NE 13TH AVENUE For Sale
$598,000
3434 NE 13TH AVENUEOakland Park, FL 33334
  • 3 bd
  • 2.5 ba
  • 1888 sqft
  • Built 2005
  • B26065183
3105 NW 25TH TERRACE For Sale
$425,000
3105 NW 25TH TERRACEOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1459 sqft
  • Built 2007
  • B26065071
3251 NW 32nd Ter For Sale
$425,000
3251 NW 32nd TerOakland Park, FL 33309
  • 3 bd
  • 3 ba
  • 1514 sqft
  • Built 2008
  • A12070663
4208 NE 7TH TERRACE For Sale
$500,000
4208 NE 7TH TERRACEOakland Park, FL 33334
  • 3 bd
  • 2.5 ba
  • 1770 sqft
  • Built 2024
  • B26063894
4486 Appleton Circle W For Sale
$640,000
4486 Appleton Circle WOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1774 sqft
  • Built 2021
  • B26062562
4204 Dixie Hwy #1 For Sale
$480,000
4204 Dixie Hwy #1Oakland Park, FL 33334
  • 3 bd
  • 2.5 ba
  • 1251 sqft
  • Built 2017
  • A12068129
444 NW 41ST STREET For Rent
$3,400
444 NW 41ST STREETOakland Park, FL 33309
  • 3 bd
  • 3 ba
  • 1149 sqft
  • Built 2021
  • B26059824
3032 S Oakland Forest Dr #2804 For Rent
$2,600
3032 S Oakland Forest Dr #2804Oakland Park, FL 33309
  • 3 bd
  • 2 ba
  • 1359 sqft
  • Built 1986
  • A12063566
3227 NW 32nd Ter For Rent
$3,200
3227 NW 32nd TerOakland Park, FL 33309
  • 3 bd
  • 3 ba
  • 1514 sqft
  • Built 2007
  • A12061243
3037 NE 13th Ave For Sale
$399,900
3037 NE 13th AveOakland Park, FL 33334
  • 2 bd
  • 2.5 ba
  • 1540 sqft
  • Built 1982
  • A12063131
809 W Oakland Park Boulevard #K2 For Sale
$219,900
809 W Oakland Park Boulevard #K2Oakland Park, FL 33311
  • 2 bd
  • 1.5 ba
  • 1000 sqft
  • Built 1973
  • B26058541
3247 NW 31st Ter Active With Contract
$430,000
3247 NW 31st TerOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1514 sqft
  • Built 2010
  • A12056456
1066 NE 35th St For Sale
$715,000
1066 NE 35th StOakland Park, FL 33334
  • 3 bd
  • 2.5 ba
  • 1787 sqft
  • Built 2021
  • A12057359
3011 NW 30th Ave #3011 For Sale
$330,000
3011 NW 30th Ave #3011Oakland Park, FL 33311
  • 2 bd
  • 2.5 ba
  • 1424 sqft
  • Built 2007
  • A12041608
405 NE 35th Ct #5 Active With Contract
$450,000
405 NE 35th Ct #5Oakland Park, FL 33334
  • 2 bd
  • 2.5 ba
  • 1225 sqft
  • Built 2021
  • A12050418
1001 NE 58th St #A For Rent
$3,186
1001 NE 58th St #AOakland Park, FL 33334
  • 1 bd
  • 1 ba
  • 1473 sqft
  • Built 2024
  • A11952939
3050 S Oakland Forest Dr #2008 For Sale
$309,000
3050 S Oakland Forest Dr #2008Oakland Park, FL 33309
  • 2 bd
  • 2.5 ba
  • 1098 sqft
  • Built 1986
  • A12046868
1951 Coral Heights Boulevard #402 For Sale
$589,000
1951 Coral Heights Boulevard #402Oakland Park, FL 33308
  • 3 bd
  • 3.5 ba
  • 1914 sqft
  • Built 2005
  • F10527008
4480 W Appleton Cir W For Sale
$610,000
4480 W Appleton Cir WOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1774 sqft
  • Built 2021
  • B26037442
3432 NE 16th Avenue For Sale
$625,000
3432 NE 16th AvenueOakland Park, FL 33334
  • 2 bd
  • 2 ba
  • 1594 sqft
  • Built 1982
  • B26020955
2293 S Appleton Circle For Sale
$625,000
2293 S Appleton CircleOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1754 sqft
  • Built 2023
  • F10554665
803 W Oakland Park Boulevard #A7 For Sale
$175,000
803 W Oakland Park Boulevard #A7Oakland Park, FL 33311
  • 2 bd
  • 1.5 ba
  • 1000 sqft
  • Built 1972
  • R11132807
2900 NE 12th Terrace #25 For Sale
$948,500
2900 NE 12th Terrace #25Oakland Park, FL 33334
  • 3 bd
  • 3 ba
  • 2152 sqft
  • Built 2017
  • B26043831
2543 NW 31st Court #2543 For Sale
$370,000
2543 NW 31st Court #2543Oakland Park, FL 33309
  • 2 bd
  • 2.5 ba
  • 1459 sqft
  • Built 2007
  • B26019359
3000 NE 8th Terrace #B4 For Sale
$668,900
3000 NE 8th Terrace #B4Oakland Park, FL 33334
  • 3 bd
  • 2.5 ba
  • 2132 sqft
  • Built 1982
  • B26039670
3291 NW 44th Street #2 Active With Contract
$355,000
3291 NW 44th Street #2Oakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1273 sqft
  • Built 1995
  • B26039290
3932 Coral Heights Way For Sale
$635,000
3932 Coral Heights WayOakland Park, FL 33308
  • 3 bd
  • 3.5 ba
  • 1933 sqft
  • Built 2005
  • B26014443
2700 S Oakland Forest Drive #305 Active With Contract
$260,000
2700 S Oakland Forest Drive #305Oakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 978 sqft
  • Built 1984
  • B26034420
3062 S Oakland Forest Drive #203 For Sale
$259,900
3062 S Oakland Forest Drive #203Oakland Park, FL 33309
  • 2 bd
  • 2 ba
  • 978 sqft
  • Built 1986
  • B26032676
3024 NW 30th Way For Sale
$365,000
3024 NW 30th WayOakland Park, FL 33311
  • 3 bd
  • 2.5 ba
  • 1504 sqft
  • Built 2010
  • B26030519
3263 NW 44th St #2 For Rent
$2,750
3263 NW 44th St #2Oakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • Built 1995
  • A12028363
3082 S Oakland Forest Dr #1301 For Rent
$1,975
3082 S Oakland Forest Dr #1301Oakland Park, FL 33309
  • 2 bd
  • 2.5 ba
  • 1098 sqft
  • Built 1988
  • A12025780
2163 Appleton Cir S For Rent
$3,900
2163 Appleton Cir SOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1754 sqft
  • Built 2022
  • A12025238
4488 E Appleton Cir E For Sale
$598,500
4488 E Appleton Cir EOakland Park, FL 33309
  • 3 bd
  • 2.5 ba
  • 1754 sqft
  • Built 2022
  • A12020915
807 W Oakland Park Blvd #G2 For Rent
$2,150
807 W Oakland Park Blvd #G2Oakland Park, FL 33311
  • 2 bd
  • 1.5 ba
  • 1000 sqft
  • Built 1972
  • A12013932
1302 NE 32nd St #2 For Sale
$926,160
1302 NE 32nd St #2Oakland Park, FL 33334
  • 3 bd
  • 4 ba
  • Built 2026
  • A11979795
1001 NE 58th St #B For Rent
$3,451
1001 NE 58th St #BOakland Park, FL 33334
  • 3 bd
  • 2.5 ba
  • 1585 sqft
  • Built 2024
  • A11952957
1001 NE 58th St #A1 For Rent
$3,906
1001 NE 58th St #A1Oakland Park, FL 33334
  • 1 bd
  • 1 ba
  • 1499 sqft
  • Built 2024
  • A11952920
45

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