Oakland Trails
Homes for Sale in Oakland, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Oakland Trails in Oakland, FL has 1 home for sale. Over the 12 months ending 2026-09-12, 6 recorded sales closed at a median of $492,500, $237 per square foot, a median 41 days on market, sellers accepting 96% of original asking (+10% versus the prior year). Homes listed or recently sold were built 2017 - 2020; 9 of 9 report an HOA (median $105/mo); none of the 8 geocoded homes sit in a FEMA special flood hazard zone (median elevation 105 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,210 ($7,540 with the full homestead exemption).
Oakland Trails right now
🔴 Seller-leaning market. 1.7 months of supply and 50% of the inventory already under contract give sellers the pressure advantage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 12, 2026. Confidence: Medium (2 active and pending listings, 6 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($492K) is up 10.4% from the prior 12 months ($446K). With about 4 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Low (6 and 3 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 14, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Oakland Trails market snapshot (as of September 12, 2026): the median sale price is about $492K ($237 per sq ft over the trailing 12 months of closed sales), a median 42 days on market for closed sales, and 1.7 months of supply, a seller-leaning market. The trailing-12-month median is up 10% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
In ZIP 34787 (OAKLAND), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.
Flood zones in Oakland Trails: of 8 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov.
Oakland Trails is a community of 293 homes in Oakland, Orange County, built between 2017 and 2020 (median 2018), with a median living area of about 2,082 square feet. 74% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Oakland Trails. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Oakland TrailsPhotos from Stellar MLS listings in Oakland Trails; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($492K) IS the median in the snapshot above, and the move from 2025 ($446K) IS the +10.4% one-year change.
Windows contain 0 to 10 sales each (6 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2019 through 2026. Deemed reliable but not guaranteed.
OAKLAND TRAILS Market Scorecard
OAKLAND TRAILS is currently a strong seller's market. About 1.7 months of supply, a median asking price of $640,000, and homes go under contract in about 15 days.
Typical home value in the 34787 ZIP is $574,696, right around the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Oakland Trails Oakland, OAKLAND
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Oakland Trails
Live MLS inventory for Oakland Trails. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Oakland Trails listings as of 2026-09-13, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2019 through 2026. Tap any home to ask about it.
Oakland Trails on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Oakland Trails
- Pool · reported on 6 of 6 listings
- Park · reported on 5 of 6 listings
- Playground · reported on 5 of 6 listings
- Dog Park · reported on 3 of 6 listings
- Clubhouse · reported on 2 of 6 listings
- Golf Carts OK · reported on 1 of 6 listings
- Handicap Modified · reported on 1 of 6 listings
- Trail(s) · reported on 1 of 6 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Tildenville Elem · Elementary
- Lakeview Middle · Middle
- West Orange High · High
Zoned schools reflect the assignments reported on recent Oakland Trails listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Oakland Trails address.
Shop the zone: Homes zoned for West Orange High High School
The Oakland Trails buying strategy.
If we were buying in Oakland Trails today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Oakland Trails.
A closer look at the Oakland Trails market
At a median of $237 per square foot, Oakland Trails prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 1.7 months of supply, a seller-leaning market and the trailing-12-month median up 10% year over year. Homes that do trade take a median 42 days on market, useful leverage on any listing that has lingered.
The housing stock is 293 homes built between 2017 and 2020, and 74% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Oakland Trails. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Oakland Trails buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (7.9). Basis: Recent Direction +10.4% year-over-year; Liquidity & Demand 1.7 months of supply; Owner Commitment 74% owner-occupied; Pricing Power 95.6% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $105/month (about $1,260/yr) · median of 16 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $105 per month ($1,260 a year) - the median AssociationFee across 16 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Oakland Trails buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Oakland Trails sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oakland Trails, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oakland Trails home worth?
Get a no-obligation home value based on real comparable sales in Oakland Trails, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Oakland →
Recently off market in Oakland Trails
Homes in Oakland Trails that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 1937 Standing Rock Circle · off market
Frequently Asked Questions
What is the median home price in Oakland Trails?
How long do homes in Oakland Trails take to sell?
Is Oakland Trails a buyer's or seller's market right now?
How many homes are in Oakland Trails?
What share of Oakland Trails is owner-occupied?
When were the homes in Oakland Trails built?
Who is the best real estate agent for Oakland Trails?
How do I find a top Oakland real estate agent who knows Oakland Trails?
Can Momentum Realty connect me with an agent for Oakland Trails?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 13, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2019 (33 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
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See how Oakland Trails fits the bigger picture — live prices, inventory, and Momentum Scores:
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