Oakland, Florida · West Orange County
Oakland, Florida real estate and new construction guide
Oakland is a small historic town on the south shore of Lake Apopka, minutes from downtown Winter Garden. It has become one of the places in Central Florida where people come to build. Matthew Burks works on site at Briley Farm, the town's 111 acre custom home community.
Updated October 10, 2026
The short answer
Why Oakland. Small town streets, Lake Apopka, the West Orange Trail and downtown Winter Garden a few minutes away, with room to build a custom home.
What is for sale. At Briley Farm, 312 Briley Avenue is listed at $3,295,000 and 402 N Pollard Street is in contract at $3,495,000 as of October 10, 2026. Homesites and other builders' homes are also available.
Who to call. Matthew Burks of Corcoran Premier Realty, on site at the Briley Farm model, at (407) 257-5347.
The town
Why people are building in Oakland.
- It is still a small town. Historic homes and tree lined streets, in west Orange County on the south shore of Lake Apopka.
- The West Orange Trail runs through it. You can ride or walk to downtown Winter Garden.
- Downtown Winter Garden is minutes away. Restaurants, the farmers market and quick highway access to greater Orlando.
- There is protected land next door. Briley Farm borders the 128 acre Oakland Nature Preserve.
- There is land to build on. Estate lots and custom homes are still available.
The community
Briley Farm, the custom home community in Oakland.
Briley Farm is 111 acres of historic farm land near Lake Apopka that the Briley family settled in 1890. It is now a custom home community. The community's site names five builders: Element Home Builders, Pioneer Builders, FG Schaub Custom Homes, J&J Building and Davila Homes.
| Address | Status | Home | MLS | Price |
|---|---|---|---|---|
| 312 Briley Avenue | For sale | 6 bd · 6 full + 1 half · 5,144 sq ft | O6429415 | $3,295,000 |
| 402 N Pollard Street | In contract | 5 bd · 5 full + 1 half · 5,001 sq ft | O6405707 | $3,495,000 |
| 511 Briley Avenue | Sold 2026 | Element Home Builders spec. We represented the seller | $1,949,000 |
Active and in contract listings verified against Corcoran.com listing data on October 10, 2026. Builder list from brileyfarm.com, read October 10, 2026. Briley Farm is an independent community; builders, pricing and availability change. Call for the current list.
How building at Briley Farm works
There is no fixed base price with everything included. The builders start from a per square foot basis and build the budget around what you want. Briley Farm luxury homes generally list from roughly $1.95M into the $4M range. You choose a homesite, a builder and a plan, and we walk the lots with you.
Nearby in our record
Oakland and Winter Garden sales.
| Address | Area | Price | Record |
|---|---|---|---|
| 15255 E Oakland Avenue | Oakland Park, Winter Garden | $1,950,000 | Closed Jul 19, 2024 · 5,754 sq ft · MLS O6191774 |
| 511 Briley Avenue | Briley Farm, Oakland | $1,949,000 | Sold 2026 · Represented seller |
| 13252 Lakeshore Grove Drive | Wintermere Harbor, Winter Garden | $875,000 | Closed Aug 29, 2022 · 3,201 sq ft · MLS O6042560 |
Properties connected to Matthew or Chocky Burks' work. Closed prices, dates and MLS numbers verified against Stellar MLS distributed records on August 25, 2026; other prices reflect the latest verified MLS or public record. Individual representation details are available on request.
The 34787 market in numbers
Oakland shares the 34787 ZIP code with Winter Garden, so these readings cover both. They are context for the area. A custom home on an estate lot is priced against other custom homes.
| Measure | Reading | Source and period |
|---|---|---|
| Median sale price, three months | $606,000 | Redfin, through August 2026, up 3.6% year over year |
| Median sale price per square foot | $254 | Redfin, through August 2026, down 0.39% year over year |
| Homes sold in the month | 546 | Redfin, August 2026, up from 493 a year earlier |
| Median days on market | 42 days | Redfin, August 2026, against 43 a year earlier |
| Sale to list price | 97.8% | Redfin, August 2026 |
| Homes sold above list price | 9.9% | Redfin, August 2026 |
| Listings with a price drop | 38.7% | Redfin, August 2026 |
Source: Redfin housing market page for ZIP code 34787, read October 11, 2026. Redfin calculates these from MLS and public records.
Questions
Oakland, Florida real estate, answered.
Why is Oakland, Florida real estate in demand?
Oakland is a small historic town on the south shore of Lake Apopka with the West Orange Trail running through it and downtown Winter Garden minutes away. It also has custom home communities such as Briley Farm, which is why buyers come here to build.
What kind of homes are in Oakland, Florida?
A mix of historic homes and new custom homes, including estate homesites at Briley Farm near Lake Apopka.
Is there new construction in Oakland and Winter Garden?
Yes. Briley Farm in Oakland is a 111 acre custom home community. As of October 10, 2026, 312 Briley Avenue was listed at $3,295,000 and 402 N Pollard Street was in contract at $3,495,000.
Who builds homes at Briley Farm in Oakland?
The community's site names five builders: Element Home Builders, Pioneer Builders, FG Schaub Custom Homes, J&J Building and Davila Homes.
Who is a real estate agent for Oakland, Florida?
Matthew Burks of Corcoran Premier Realty works on site at the Briley Farm model in Oakland. The Burks team represented the seller of 511 Briley Avenue, which sold for $1,949,000 in 2026. Call or text (407) 257-5347.
What do homes cost in Oakland, Florida?
It depends on the home. At Briley Farm, recent homes run from $1,949,000 (511 Briley Avenue, sold 2026) to $3,495,000 (402 N Pollard Street, in contract October 2026). Nearby, 15255 E Oakland Avenue closed for $1,950,000 in July 2024. Across the whole 34787 ZIP code, which Oakland shares with Winter Garden, Redfin reports a median sale price of $606,000 for the three months ending August 2026, up 3.6% from a year earlier.
Come walk it.
The best way to understand Oakland is to drive in under the oaks and stand on a homesite. Matthew is at the Briley Farm model every week; call ahead for a tour.