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Seawinds Investment Realty, LLC
(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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The source of this real property information is the copyrighted and proprietary database compilation of the Naples MLS. Copyright 2026 Naples MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

Daytona Beach Area Association of Realtors

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.

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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.

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West Orange Trail Town on Lake Apopka

Farms & Ranches 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.

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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
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