Homes for sale in
Oakland, Florida
Small-town Orange County living near Lake Apopka
20
Homes for sale
$1,067,500
Median list price
$407
Avg price / sqft
95
Median days on market
Oakland is a compact town on the western edge of Orange County, tucked between Winter Garden and Lake Apopka with the West Orange Trail running through it. It leans quiet and residential, with larger lots and a mix of established neighborhoods like Johns Landing and Johns Cove — and it still keeps you within about 24 minutes of downtown Orlando and 38 of Walt Disney World.
For buyers, this is a higher-end market with limited supply: just 20 active listings and a median list price of $1,067,500, though 11 of those homes sit above $1M. There's real range here, from around $350,000 up to $3.295M, and a strong showing of new construction — 10 of the active homes are newly built. With homes taking a median 94.5 days to sell, patient buyers have room to negotiate.
Oakland is in Orange County, Florida.
Quick facts
$350,000 – $3.3M price range
3,774 sqft median home
Seller’s market right now
Drive times
Fresh on the market
Newest homes in Oakland
View all 20 homes →
$559,000
2471 SKY STONE COURT, OAKLAND
4 bd · 2.5 ba · 2,854 sqft
$3,295,000
312 BRILEY AVENUE, OAKLAND
6 bd · 6.5 ba · 5,144 sqft
$640,000
1750 STANDING ROCK CIRCLE, OAKLAND
4 bd · 2.5 ba · 2,614 sqft
$540,000
223 LARGOVISTA DR., OAKLAND
4 bd · 2.5 ba · 2,486 sqft
$199,000
320 W SADLER AVENUE, OAKLAND
2 bd · 1 ba · 722 sqft
$1,400,000
1112 HULL ISLAND DRIVE, OAKLAND
4 bd · 3.5 ba · 3,562 sqft
$435,000$455,000
521 W HERRIOTT AVENUE, OAKLAND
3 bd · 2 ba · 1,170 sqft
$2,615,320
1152 PRADO LANE, OAKLAND
6 bd · 6.5 ba · 4,658 sqft
$2,545,000$2,595,000
1134 PRADO LANE, OAKLAND
5 bd · 6.5 ba · 4,433 sqft
$2,575,000
1155 PRADO LANE, OAKLAND
5 bd · 6 ba · 4,210 sqft
$809,000$850,000
1603 JOHNS COVE LN, OAKLAND
6 bd · 4 ba · 4,001 sqft
$825,000$845,000
14001 RUGBY STREET, OAKLAND
5 bd · 4 ba · 4,240 sqft
20 of 20 active listings shown
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The numbers that matter
The Oakland market
Seller’s market
2.3 months of inventory
Homes sell fast and inventory is thin — buyers should come prepared.
91
Sold, last 12 months
$649,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
31 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
▲ 12.4% yr/yr
Homes on the market
▼ 20.0% 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 Landing
3 homes · $599K median
Johns Cove
2 homes · $1.7M median
Oak Park Of Winter Garden
1 home · $468K 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
Pool homes dominate the market
Eleven of the 20 active listings come with a pool, so outdoor Florida living is easy to find here.
Strong new-construction pipeline
Ten active listings are new construction, giving buyers a genuine choice between move-in-ready builds and established homes.
Spacious homes on larger lots
With a median home size of 3,774 sqft, floor plans here run bigger than the typical Orlando-area listing.
Central to the metro's big draws
Downtown Orlando is about 24 minutes out, Universal 26, MCO 33, and Walt Disney World roughly 38.
West Orange schools
Homes here are assigned to Tildenville Elementary, Lakeview Middle, and West Orange High.
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.
What it really costs
Owning here
Owning the median Oakland home
≈ $6,426/mo
$1,067,500 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
Straight answers
Oakland real estate FAQs
Is Oakland a good place to live?+
It's a small, residential town on the west side of Orange County with easy access to Winter Garden, the West Orange Trail, and Lake Apopka. Homes are assigned to Tildenville Elementary, Lakeview Middle, and West Orange High, and you're still about 24 minutes from downtown Orlando. Established communities like Oak Park Of Winter Garden give the area a settled, neighborhood feel.
Is Oakland expensive?+
It's a higher-end market — the median list price is $1,067,500 and 11 of the 20 active listings are priced above $1M. That said, the range runs from about $350,000 to $3.295M, so there are entry points well below the median if you browse by price.
What do homes cost in Oakland?+
Active listings average $407 per square foot against a median home size of 3,774 sqft, and the median list price is $1,067,500. Over the last 12 months, 91 homes sold at a median price of $649,000 — a reminder that closed prices skew lower than current asking prices. Many of the higher-priced homes are among the luxury homes ($1m+) currently listed.
How is the Oakland housing market?+
Supply is tight with just 20 active listings, and homes take a median 94.5 days to sell. Sellers are getting about 98% of asking on average, so well-priced homes still move — but the longer days on market give buyers room to negotiate, especially on anything just reduced.
What about HOA fees and property taxes?+
The median HOA runs about $150 per month, which is modest for the price point. Median annual property tax is around $5,306 — plan on both when budgeting, and check individual community rules since fees vary across neighborhoods like Oakland Pointe.
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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