A town of about 3,500 people on the south shore of Lake Apopka, wedged between Winter Garden and Clermont. Brick streets, a trail through the middle of town, and fast access to SR 429, the Turnpike and the parks.
Most of West Orange County turned into master-planned communities over the last twenty years. Oakland kept its bones. The town hall still sits in the old 1911 bank building, the live oaks still hang over the brick streets, and neighbors still run into each other at the post office.
Oakland was once the headquarters of the Orange Belt Railroad. That rail line is now the West Orange Trail, and it runs straight through town. Weekend mornings here look like bikes, strollers, coffee from a trailer, and a walk to the lake.
🌳 Tree City USA community nicknamed “Among the Oaks”
🚲 West Orange Trail runs through the town center
🌊 Between Lake Apopka (north) and Johns Lake (south)
🛣 SR 50, Florida’s Turnpike and SR 429 within minutes
🏛 Own town government and police department, inside Orange County
Convenience and efficiency is the whole point of living near Disney along SR 429. Here is the reality, not the brochure version.
Approximate off-peak drive times. Rush hour on SR 50 and the 408 adds real time. Ask me to map your actual work route before you pick a street.
Oakland is small, but the housing is not one thing. Historic cottages, newer trail communities, acreage, and gated lakefront all sit within a few minutes of each other. Each link opens that community’s guide with live listings and its own market card.
Brick streets, older Florida homes and character houses on mature lots, steps from the trail, Speer Park and the Arts & Heritage Center. Inventory is thin and turns over slowly.
Best for: downsizers who want walkability and charm over square footage.
Historic Town of Oakland Oakland Heights Oakland Pointe Ryan Court Starr Gardens of Oakland
Mostly built 2017 to 2019 by Meritage Homes, with a community pool and playground and quick access to the West Orange Trail. Mandatory HOA.
Best for: upsizers who want a newer home without leaving the small-town feel.
West side of town toward Lake Apopka. Older estate homes on larger lots, some on well and septic, plus newer phases with larger new construction.
Best for: buyers who want room to breathe and fewer neighbors.
Hull Island at Oakland Hull Island Estates Hull Island Reserve Trailside Station Lake Apopka Sound
Gated community on the south side of town with two-story homes and larger yards, minutes from the Turnpike and downtown Winter Garden.
Best for: relocators who want a gate and a short drive to everything.
Exclusive gated enclave on Johns Lake with custom and estate homes. This is the top of the Oakland market.
Best for: move-up buyers who want water and privacy.
Award-winning front-porch community straddling the Oakland and Winter Garden line, with pools, a clubhouse, parks and direct trail access. Addresses read Winter Garden 34787.
Best for: buyers who want to golf cart to downtown Winter Garden.
Pulte homes built 2019 to 2021 between the Oakland Nature Preserve and the Turnpike, with a waterfront pool and a playground. The entry point for newer construction in town.
Best for: first-time buyers and downsizers who want newer and lower maintenance.
Custom estate homes from three builders on homesites from a third of an acre to over an acre, with a clubhouse, a resort pool, pickleball and golf cart access to the trail.
Best for: upsizers who want a custom estate home in a small town.
Forty-four custom homesites in the Harvest District near the town center, with member access to the Briley Farm clubhouse, pool and courts.
Best for: buyers who want new luxury construction and a walkable address.
About 55 homes from 2005 to 2007 on the east side of town, mostly 2,400 to 3,450 square feet on homesites of about a third of an acre.
Best for: upsizers who want square footage at a resale price.
The town’s own K to 5 public charter school, with about 520 students and roughly a 14 to 1 student-teacher ratio. Every class visits the Oakland Nature Preserve as part of its science curriculum, and its 5th graders ranked fourth in Orange County on the state science assessment for 2022-23.
Middle and high school assignments come from Orange County Public Schools and depend on the exact address. Always confirm zoning for a specific home before you write an offer.
Grades: K to 5, public charter
Address: 456 E Oakland Ave, Oakland, FL 34760
Enrollment: about 520 students
Ratings: see Niche and GreatSchools for current scores
School data from SchoolDigger and the West Orange Chamber. Charter enrollment rules apply. Verify with the school.
About 150 acres of trails and wetlands with a shaded, wheelchair-accessible boardwalk that ends at a covered pavilion on Lake Apopka. Free and open sunrise to sunset. 747 Machete Trail.
The old rail line turned paved trail, running right through town and on to downtown Winter Garden, Apopka and beyond. Bike to breakfast, walk to the farmers market.
The Healthy West Orange Arts & Heritage Center sits on the trail at 126 W Petris Ave, with rotating art and history exhibits and porch music during town events.
Local vendors along the West Orange Trail on the 2nd and 4th Thursdays of the month.
Heritage Day at Speer Park in January, Celebration Among the Oaks in spring, Music Under the Oaks in October, and Santa’s Lane in the historic town center in December.
Prairie House Coffee on Tubb Street, the Village Lantern Coffee Co. trailer on Oakland Ave, and DG Doughnuts on McKey St. Downtown Winter Garden’s restaurants are 7 minutes away.
Oakland is almost all single-family homes: 94 of the 98 sales inside town limits were houses. Within that, it is really two markets. Resale homes in Oakland Trails, Longleaf, Johns Landing and Hull Island trade in the $500Ks and $600Ks. Brand-new luxury homes in Briley Farm and the Grove at the Harvest District trade in the $2 millions and $3 millions. Price your street, not the town.
76 sales at a median of $630,000, about $270 per square foot. Median time on market: 36 days. Resale buyers have room to negotiate here.
18 sales (homes built 2025 or later) at a median of $2,385,404, about $588 per square foot. Most sold before or at completion, so they never sat on the market.
September 2026: 6 single-family homes, 1 townhome and no condos closed inside town limits, too few for a monthly median by type. Property type is how the listing agent entered it in Stellar MLS. 98 closed sales in all over the 12 months ending Sept 30, 2026. Counts only homes inside Town of Oakland limits, confirmed parcel by parcel with the Orange County Property Appraiser. Homes with an Oakland or 34787 address that sit in Winter Garden, Lake County or unincorporated Orange County are not counted. Every community guide below has its own Stellar MLS market card. Stellar MLS figures as of the dates shown, deemed reliable but not guaranteed. For live comps on a specific home, book a 30 minute call and I will send a custom report.
Updated straight from the MLS. Save a search and get new Oakland listings the day they hit.
Tap any community for its guide, amenities and homes for sale today.
You want to be close to the parks without living in a tourist zone. Most people I help relocate are doing this alone with Google Maps and a lot of guesswork. I have walked these streets, and I can tell you which one fits before you fly in.
You have outgrown the starter home but want to keep the trail, the community events and a short drive to Winter Garden. Oakland Trails, Johns Landing and Hull Island give you that next step.
You want more life and less lawn. A walkable spot near the trail and the town center can be the best move you make.
Pick your guide, tell me where to send it, and it opens right away.
How buying in Oakland works, from historic homes versus newer communities to what to verify on HOA, well and septic, and school zoning.
Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.
If it did not open, use the buttons below. It is yours to keep.
Next step: book a 30 minute call and we will walk through it together for Oakland.
No. Oakland is its own incorporated town, founded in 1887, with its own town government and police department. It borders Winter Garden, and many newer Oakland-area homes carry a Winter Garden 34787 mailing address, which confuses a lot of buyers.
About 25 minutes by car off-peak, using SR 429. Downtown Orlando is about 25 to 30 minutes and Orlando International Airport about 35 to 40 minutes.
The historic town uses 34760. Several newer subdivisions in and around Oakland, such as Oakland Trails and Hull Island, use 34787.
It depends on the type of home, so I report each one separately. Per Stellar MLS, for the 12 months ending September 30, 2026, single-family homes inside the Town of Oakland sold at a $683,500 median across 94 sales, down 6.4% from $730,000 the year before, with a median of 26 days on market and 99% of list price. Single-family resales had a $630,000 median and new construction $2,385,404. Only 4 townhomes closed, all in Longleaf, too few for a median, and no condos closed inside town limits.
By property type, per Stellar MLS for the 12 months ending September 30, 2026, among communities with 5 or more sales of one type: single-family medians ranged from $505,000 in Oakland Trails to $3,387,000 in Briley Farm. Oakland Trails was the busiest, with 17 single-family sales. Longleaf had 9 single-family sales at a $519,000 median; its 4 townhome sales were too few for a median. No condos closed inside town limits. Every Oakland community guide has its own Stellar MLS market card.
Oakland Avenue Charter School is the town's K to 5 public charter school. Middle and high school assignments come from Orange County Public Schools based on the specific address, so verify zoning before you buy.
The Oakland Nature Preserve boardwalk to Lake Apopka, the West Orange Trail, the Arts & Heritage Center, a twice-monthly farmers market, and town events like Heritage Day and Music Under the Oaks.
Give me 30 minutes and tell me your timeline and what matters most. I will send back:
No pressure. If you are selling a home somewhere else first, we will plan both sides together.
Semper Fi to your real estate needs. Jorge Martinez, REALTOR®
Information deemed reliable but not guaranteed. Drive times are approximate. Market data from Stellar MLS as of the dates shown. School information from public sources; buyers should verify school assignments and all property details independently. JEM Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.
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