Oakland neighborhoods with the market data that actually moves a decision.
25 Oakland community guides, each with real pricing, HOA/CDD reality, and flood/insurance posture. Below: the Oakland market snapshot, then every community we cover.
Oakland market snapshot
$596,250Median sale price
$285.8Median $/sq ft
32Median days on market
12Communities with sales data
Aggregated from MLS closed-sale records across 12 Oakland communities; latest data 2025. Aggregate statistics only, deemed reliable but not guaranteed; not an appraisal. Refreshes with each MLS data update.
All Oakland communities (25)
Briley FarmBriley Farm in Oakland, FL: Median sale $3.38M (2026), 19 homes, built 1923-2018, median 0 days on market. Live Stellar MLS data and public records.Grove at the Harvest DistrictGrove at the Harvest District in Oakland, FL: Median sale $2.35M (2026), 7 homes, median 0 days on market. Live Stellar MLS data and public records.Grove Oakland Winter GardenGrove Oakland Winter Garden in Oakland, FL: 7,737 homes for sale in Orange County (25% under contract). Live Stellar MLS data and public records.Hull IslandHull Island in Oakland, FL: Recent sales median $645K (2025), $283/sq ft, 15 sales since 2021. Live Stellar MLS data and public records.Hull Island At OaklandHull Island At Oakland in Oakland, FL: Median sale $694K (2026), median 38 days on market. Live Stellar MLS data and public records.Hull Island ReserveHull Island Reserve in Oakland, FL: ZIP 34787 median $595K, 357 for sale. Schools, HOA & nearby homes for sale.Johns LandingJohns Landing in Oakland, FL: 162 homes built 2000–2020, ~3,182 sq ft, 4 bd/3 ba. ZIP 34787 median $595K, 357 for sale.Johns Landing Ph 01 44/47Johns Landing Ph 01 44/47 in Oakland, FL: Median sale $633K (2026), 59 homes, built 2001-2004, median 62 days on market.LongleafLongleaf in Oakland, FL: Median sale $472K (2026), 147 homes, built 2019-2021, median 49 days on market. Live Stellar MLS data and public records.Longleaf At OaklandLongleaf At Oakland in Oakland, FL: Median sale $565K (2026), median 4 days on market. Live Stellar MLS data and public records.Longleaf At Oakland, A Replat 99/107 Lot35Longleaf At Oakland, A Replat 99/107 Lot35 in Oakland, FL: 957 homes for sale in ZIP 34787 (30% under contract), 1 MLS sale on record since 2026.Oakland (291003127)Oakland (291003127) in Oakland, FL: ZIP 34760 median $694K, 9 for sale. Schools, HOA & nearby homes for sale.Oakland ParkOakland Park in Oakland, FL: 353 homes built 2008–2026, ~2,653 sq ft, 4 bd/3 ba. ZIP 34787 median $595K, 357 for sale.Oakland ParkOakland Park in Oakland, FL: 353 homes built 2008–2026, ~2,653 sq ft, 4 bd/3 ba. ZIP 34787 median $595K, 357 for sale.Oakland PointeOakland Pointe in Oakland, FL: Recent sales median $619K (2025), $266/sq ft, 11 sales since 2010. Live Stellar MLS data and public records.Oakland TownOakland Town in Oakland, FL: Median sale $360K (2026), 64 homes, built 1910-2022, median 50 days on market. Live Stellar MLS data and public records.Oakland TrailsOakland Trails in Oakland, FL: Median sale $537K (2026), median 112 days on market. Live Stellar MLS data and public records.Oakland TrailsOakland Trails in Oakland, FL: Median sale $492K (2026), 293 homes, built 2017-2020, median 42 days on market. Live Stellar MLS data and public…Ryan CourtRyan Court in Oakland, FL: ZIP 34760 median $694K, 9 for sale. Schools, HOA & nearby homes for sale.Southern Oaks At Oakland ShoresSouthern Oaks At Oakland Shores in Oakland, FL: Recent sales median $1.25M (2025), $371/sq ft, 20 sales since 2011.Town Of OaklandTown Of Oakland in Oakland, FL: ZIP 34760 median $694K, 9 for sale. Schools, HOA & nearby homes for sale.Trailside StationTrailside Station in Oakland, FL: 38 homes built 2000–2003, ~2,120 sq ft, 4 bd/2 ba. ZIP 34787 median $595K, 357 for sale.Trailside Station Replat 44/23Trailside Station Replat 44/23 in Oakland, FL: 957 homes for sale in ZIP 34787 (30% under contract), 1 MLS sale on record since 2026.Winters LandingWinters Landing in Oakland, FL: 55 homes built 2005–2007, ~3,133 sq ft, 4 bd/3 ba. ZIP 34787 median $595K, 357 for sale.Winters LandingWinters Landing in Oakland, FL: Median sale $850K (2026), median 44 days on market. Live Stellar MLS data and public records.