4 Bedroom Homes for Sale in Oakland, FL
Four bedrooms is the most-searched size in most Florida and Georgia markets. This page tracks every Oakland listing whose MLS record reports four or more bedrooms, by community, with live counts and asking prices, and how the price compares with smaller homes in the same city.
33 homes with four or more bedrooms are for sale or pending in Oakland, FL today across 21 communities. The median asking price is $890,000, from $515,000 to $3,495,000. Listings in Oakland without that feature have a median of $504,950. Most listings right now: Grove/Oakland (4), Grove At The Harvest District (3), Oakland Trls Ph 1 (3). Updated October 2, 2026 from the MLS.
Live 4-bedroom homes in Oakland: the listings
23 active listings match today (72% of Oakland inventory), median asking $995,900, $393/sq ft, median 49 days on market. Photo cards link to the listing; refreshed nightly.
Newest 4-bedroom homes in Oakland
The most expensive 4-bedroom homes in Oakland
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 312 Briley Avenue | $3,295,000 | 5,144 | briley farm |
| 1152 Prado Lane | $2,615,320 | 4,658 | Grove/Oakland |
| 1155 Prado Lane | $2,575,000 | 4,210 | Grove/Oakland |
| 812 Johns Point Drive | $2,550,000 | 4,373 | Johns Cove 43 104 Oakland |
| 1134 Prado Lane | $2,495,000 | 4,433 | Grove/Oakland |
| 1173 Prado Lane | $2,380,160 | 4,204 | Grove At The Harvest District |
| 1146 Prado Lane | $2,310,600 | 3,992 | Grove At The Harvest District |
| 1106 Sarah Mathews Drive | $1,975,000 | 3,596 | Grove At The Harvest District |
| 137 Petris Avenue | $1,495,000 | 3,620 | — |
| 1112 Hull Island Drive | $1,400,000 | 3,562 | Hull Island At Oakland |
4-Bedroom Homes by price
| Band | For sale | Share |
|---|---|---|
| $500K–$750K | 6 | 26% |
| $750K–$1M | 7 | 30% |
| $1M+ | 10 | 43% |
Oakland 4-bedroom homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | 4-Bedroom Homes | New build | Median list | From |
|---|---|---|---|---|
| Grove/Oakland | 4 | 4 | $2,595,160 | $2,495,000 |
| Grove At The Harvest District | 3 | 3 | $2,310,600 | $1,975,000 |
| Oakland Trls Ph 1 | 3 | 0 | $559,000 | $515,000 |
| Briley Farm | 2 | 2 | $3,395,000 | $3,295,000 |
| Oakland Parkb-3 | 2 | 1 | $869,950 | $850,000 |
| Johns Landing | 2 | 0 | $835,900 | $675,900 |
| Oakland Town | 2 | 1 | $809,000 | $619,000 |
| Hull Island/Oakland Ph 2 | 2 | 0 | $737,450 | $649,900 |
| Briley Farm Ph 1A | 1 | 1 | $3,399,000 | $3,399,000 |
| Johns Cove 43/104 | 1 | 0 | $2,550,000 | $2,550,000 |
| Town/Oakland | 1 | 0 | $1,495,000 | $1,495,000 |
| Hull Island At Oakland | 1 | 0 | $1,400,000 | $1,400,000 |
| Oakland | 1 | 0 | $1,250,000 | $1,250,000 |
| Oakland Park | 1 | 0 | $890,000 | $890,000 |
| Verde Park Ph 1 | 1 | 0 | $825,000 | $825,000 |
| Oakland Pointe | 1 | 0 | $799,999 | $799,999 |
| Oakland Trls Ph 2 | 1 | 0 | $796,000 | $796,000 |
| Johns Cove | 1 | 0 | $795,000 | $795,000 |
| Oakland Trails | 1 | 0 | $730,000 | $730,000 |
| Johns Landing Ph 2 | 1 | 0 | $540,000 | $540,000 |
| Trailside Station Rep 44/23 | 1 | 0 | $525,000 | $525,000 |
What the fourth bedroom costs
The answer block above compares the median asking price of four-plus-bedroom homes with the median of everything else listed in the city; the gap is what the extra room, and usually the extra square footage and lot, is priced at today. Compare on price per square foot, not price alone: a four-bedroom home at 2,000 square feet and one at 2,800 are different purchases, and the MLS square footage on each listing page makes that comparison in seconds. Newer subdivisions tend to deliver four bedrooms in less square footage than older ones; the community pages show year-built ranges so you can see which is which.
Questions to ask about any four-bedroom listing
Is the fourth bedroom a true bedroom with a closet and window, or a converted den, garage bay or bonus room? Are the bedrooms split (owner’s suite away from the others) or all on one side? Is there a second full bath near the secondary bedrooms? What does the seller pay for insurance and, in an HOA community, what do the dues cover? A local agent who works the area will know which builders’ four-bedroom plans hold their value.
Common questions
How many homes with four or more bedrooms are for sale in Oakland?
What do 4-bedroom homes cost in Oakland?
Which Oakland community has the most 4-bedroom homes for sale?
How much more does a 4-bedroom home cost?
Keep exploring Oakland
- All homes for sale in Oakland
- Oakland ZIP codes with prices
- Oakland pool homes
- 4-Bedroom Homes in every city
4-Bedroom Homes in nearby Orange County cities
- Orlando 4-bedroom homes (1645 for sale)
- Winter Garden 4-bedroom homes (499 for sale)
- Apopka 4-bedroom homes (341 for sale)
- Windermere 4-bedroom homes (225 for sale)
- Winter Park 4-bedroom homes (166 for sale)
- Ocoee 4-bedroom homes (100 for sale)
- Maitland 4-bedroom homes (39 for sale)
- Belle Isle 4-bedroom homes (13 for sale)
Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Oakland, FL whose MLS record reports four or more bedrooms. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.