81 Millholland Street, Oakland
Oakland FL Homes for Sale
There are 30 homes for sale in Oakland, Florida as of 2026-09-17, at a median list price of $869,950 and a median of 66 days on market. Every active Oakland listing is above, newest first. What follows is what those listings add up to.
Oakland market at a glance
| Active listings | 30 |
|---|---|
| Median list price | $869,950 |
| Median price per square foot | $299 |
| Median size | 3,545 square feet |
| Median year built | 2019 |
| Median days on market | 66 |
| On market 60+ days | 16 (53.33%) |
| Priced below original asking | 11 (36.67%) |
Source: Stellar MLS via the Bridge RESO feed, pulled 2026-09-17. Updated weekly.
What the numbers say for Oakland buyers
11 of the 30 Oakland homes on the market (37%) are asking less than they did on day one, and 16 (53%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 66 days in who has already cut once is a different negotiation than one of the 14 listings still inside its first 60 days.
Across the 11 Oakland listings that have already come down, the typical reduction is 7.27% off the original asking price. That is the size of a first concession, not a final one.
Oakland homes by price range
| Under $250,000 | 0 | 0.0% |
|---|---|---|
| $250,000 to $400,000 | 1 | 3.3% |
| $400,000 to $600,000 | 6 | 20.0% |
| $600,000 and up | 23 | 76.7% |
Property types in Oakland
| Single Family Residence | 29 |
|---|---|
| Townhouse | 1 |
Neighborhoods and subdivisions in Oakland
Every Oakland subdivision with an active listing or its own page here, ranked by inventory. A subdivision showing 0 still appears: this is a live MLS feed and inventory changes daily. The 30 homes in named subdivisions are 100% of the Oakland market; the rest are on unplatted land or were listed without a subdivision name.
Subdivision names come from the MLS as agents entered them. Active count and median list price as of 2026-09-17. * Medians on rows with fewer than 4 listings are indicative only. Open a subdivision for days on market, price per square foot and sales history.
About Oakland
Oakland is a town of 3,516 at the 2020 census, up 38.5 percent from 2,538 in 2010, on 2.10 square miles.
Its post office opened in 1860, closed in 1867 and reopened in 1877. During the Civil War it was the only post office operating inside what is now Orange County, because the Orlando office was closed from 1861 to 1866.
In the boom of the 1880s Oakland was the commercial center of west Orange County and incorporated in 1887. Then a fire in the business district, a run of freezes through the 1890s and the growth of neighbouring Winter Garden left it a village instead of a town.
Oakland zip codes
34787 (23 listings), 34760 (7 listings)
Oakland homes by property type
More Orange County searches
- Orange County FL Homes for Sale
- Orange County Price Reduced Homes
- Orange County Homes 90+ Days on Market
- Orlando Housing Market
Frequently asked questions
How many homes are for sale in Oakland, FL?
There were 30 active residential listings in Oakland as of 2026-09-17, at a median list price of $869,950. That count comes from the Stellar MLS feed and is refreshed weekly.
What is the median home price in Oakland, FL?
The median list price in Oakland was $869,950 as of 2026-09-17, or about $299 per square foot. The median home on the market is 3,545 square feet and was built in 2019.
How long do homes take to sell in Oakland?
Median days on market was 66 as of 2026-09-17. 16 of the 30 listings, 53% of the Oakland market, have been listed 60 days or longer, and that is where most of the negotiating room sits.
Are Oakland sellers reducing their prices?
11 Oakland listings, 36.67% of the market, are now asking less than they did originally, at a median reduction of 7.27%. That is the size of a typical first concession here, and it is usually not the last one.
What neighborhoods are in Oakland, FL?
16 named subdivisions had at least one active listing in Oakland as of 2026-09-17, and every one is listed above with its own median price and days on market. Oakland Trls led with 5 active listings at a median of $515,000.
What zip codes cover Oakland, FL?
Oakland listings sat in 2 zip codes as of 2026-09-17: 34787 with 23 active listings, 34760 with 7 active listings.
The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Oakland listing on this page.