Homes for sale in
Oakland, Florida
A West Orange County town built for trail life
27
Homes for sale
$796,000
Median list price
$325
Avg price / sqft
54
Median days on market
Oakland sits at the western edge of Orange County, a small town wrapped in oak canopy near Lake Apopka with the West Orange Trail running through its heart. It's the kind of place where you can be at your front door and 24 minutes from downtown Orlando, yet still feel a world away from the theme-park sprawl — single-family homes on generous lots dominate, and neighborhoods like Johns Landing and Johns Cove lean toward space and water access.
For buyers, the market here is thin and priced up: just 27 active listings with a median list price of $796,000, and 10 of those homes ask over $1M. Inventory moves at a measured pace — a median of 54 days on market — so there's room to negotiate, especially among the just reduced listings. If your budget is tighter, the low end of the range starts around $360,000, and it's worth watching the new construction coming online.
Oakland is in Orange County, Florida.
Within a 30-minute drive
Quick facts
$360,000 – $2.7M price range
2,999 sqft median home
$2,700/mo median rent
Leans seller right now
Drive times
Fresh on the market
Newest homes in Oakland
View all 27 homes →
$639,000
529 JOHNS LANDING WAY, OAKLAND
4 bd · 3 ba · 2,650 sqft
$799,999
16 OAKLAND POINTE CIRCLE, OAKLAND
5 bd · 3 ba · 3,413 sqft
$850,000$870,000
1603 JOHNS COVE LN, OAKLAND
6 bd · 4 ba · 4,001 sqft
$874,900
1231 FOLTZ LOOP, OAKLAND
4 bd · 4.5 ba · 3,134 sqft
$499,000$515,000
1937 STANDING ROCK CIRCLE, OAKLAND
3 bd · 2.5 ba · 2,069 sqft
$669,900
710 REGINA CIRCLE, OAKLAND
5 bd · 4 ba · 3,285 sqft
$457,900
2247 WHITE FEATHER LOOP, OAKLAND
3 bd · 2.5 ba · 1,838 sqft
$825,000$845,000
14001 RUGBY STREET, OAKLAND
5 bd · 4 ba · 4,240 sqft
$1,025,000$1,059,000
219 LARGOVISTA DRIVE, OAKLAND
5 bd · 4 ba · 3,951 sqft
$699,900$724,900
2017 BOSS HEWETT STREET, OAKLAND
4 bd · 4 ba · 2,852 sqft
$525,000$545,000
2259 WHITE FEATHER LOOP, OAKLAND
4 bd · 2.5 ba · 2,204 sqft
$1,145,000$1,195,000
250 N WALKER STREET, OAKLAND
4 bd · 2.5 ba · 2,469 sqft
24 of 27 active listings shown
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Most popular Oakland searches
Popular searches
Property features
The numbers that matter
The Oakland market
Leans seller
3.8 months of inventory
Demand still outpaces supply, but buyers have a little more room.
93
Sold, last 12 months
$649,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
36 days
Median time to sell
Oakland vs Orange County
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 23.6% yr/yr
Homes on the market
▼ 13.2% yr/yr
Homes sold per month
Live Stellar MLS data — listings and closed sales in Oakland, FL. Rolling medians smooth single-month swings in thin markets.
Where to look
Oakland neighborhoods
Johns Cove
4 homes · $1.7M median
Johns Landing
3 homes · $670K median
Trailside Station
1 home · $519K median
Oakland Pointe
1 home · $800K median
Show all 13 Oakland neighborhoods A–ZHide the full neighborhood list+
Neighborhood boundaries by edgeAI — listings matched to the actual polygon, not agent-entered subdivision names.
For the school run
School zones with homes for sale
Assigned schools as reported on active MLS listings — always verify zoning with the district.
Beyond the listings
Living in Oakland
Trail-town character
Oakland is defined by the West Orange Trail and its shaded, low-density streets near Lake Apopka.
Pools are the norm
Twelve of the 27 active listings include a pool, so [homes with a pool](/area/oakland-fl/homes-with-pool) are easy to find here.
A real luxury tier
Ten active listings ask $1M or more, with the top end reaching $2,699,000 among the [luxury homes ($1m+)](/area/oakland-fl/luxury-homes).
Space over density
The median home spans 2,999 sqft at about $325 per square foot, reflecting larger single-family floor plans.
Quick commute to Orlando
Downtown Orlando is roughly 24 minutes away, with MCO about 33 minutes and Disney around 38.
Population
3,566
Median age
40.2
Median income
$142,917
Median home value
$487,900
What people here are into
Hobbies & Interests
Top 2% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Active
Top 7% in the U.S.Yoga Advocates
Improving flexibility, strength, and overall well-being is the yogi's aim. This population is looking for the right community, instruction, and accessories.
Hobbies & Interests
Top 7% in the U.S.Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
Hobbies & Interests
Top 8% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Beliefs
Top 10% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Beliefs
Top 11% in the U.S.Mindfulness & Spirituality
Seeking peace and well-being through meditation, gratitude and spirituality.
On the calendar
Near Oakland
Jul
17
Fri
Ride the Cyclone
19:30
Ride the Cyclone is a musical about a Canadian chamber choir whose members die in a roller coaster accident and find themselves in limbo. A mechanical fortune teller invi…
Jul
24
Fri
Adam Ray
8:00pm
Adam Ray is an American comedian and actor who has appeared in many movies and TV shows including "Ghostbusters," "Spy," "Arrested Development," and "American Vandal." No…
Jul
25
Sat
Kaliente Fest
1:00 PM
The First Annual Kaliente 103.1 FM Fest, presented by Norsan Media and Sunwave Energy, promises a vibrant celebration of Latin culture, complete with live performances fr…
Jul
25
Sat
B.E.L.A.C. Childhood Cancer 5K
8:00 AM
The B.E.L.A.C. Foundation's annual Childhood Cancer 5K is a community-driven event that combines physical activity with philanthropy, aiming to raise awareness and funds…
Jul
29
Wed
Mumford & Sons
Mumford & Sons are a Grammy Award-winning British band that brought a modern edge to folk rock. With their signature blend of soaring harmonies and acoustic instrumentati…
Aug
9
Sun
Mon Laferte
8:00pm
Mon Laferte is a singer, songwriter, and musician from Chile who composes songs combining many genres like pop, bolero, rock, salsa, and cumbia. She is the biggest Chilea…
What it really costs
Owning here
Owning the median Oakland home
≈ $5,049/mo
$796,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
0%
In a FEMA flood zone
Most homes here sit outside high-risk zones
$2,700/mo
Median rent
3 homes for rent right now
Straight answers
Oakland real estate FAQs
Is Oakland, FL a good place to live?+
It suits buyers who want a quiet, tree-lined town with trail access but still need an easy Orlando commute — downtown is about 24 minutes and the airport around 33. The housing is overwhelmingly single-family homes on larger lots, so it reads more residential than commercial.
Is Oakland an expensive place to buy?+
Yes, relative to the metro — the median list price is $796,000 and 10 of the 27 active listings are priced above $1M. That said, the range runs from $360,000 up to $2,699,000, so there's more entry-level room than the median suggests; you can browse by price to find the lower end.
What do homes cost in Oakland?+
Homes here average about $325 per square foot, and the median home is roughly 2,999 sqft, which is how you get to a $796,000 median list price. Most inventory is single-family, though a couple of townhomes & condos do come up.
How is the Oakland housing market right now?+
There are 27 active listings with a median of 54 days on market, which points to a measured, negotiable pace rather than a frenzy. Five listings are new construction and several have seen price cuts, so patient buyers have leverage.
What about HOA fees and property taxes?+
The median HOA runs about $150 per month, and median property tax is around $5,946 per year. Fees vary by community — gated and newer neighborhoods like the ones you'll find among Oakland's gated communities may carry different dues, so confirm on a per-listing basis.
Keep exploring
Nearby areas
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS. Market statistics are computed from listing and sold data and change as the market moves.
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