Oakleigh
Homes for Sale in Maitland, FL
All 109 homes for sale in MAITLAND, FL · median $460,000 · 58 homes for sale in 32751 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Homes listed or recently sold were built 1971 - 1972; none of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 82 ft). As of September 2026, the MLS records 3 closed sales in Oakleigh Third Add in Maitland, FL since 2017, the most recent in April 2026. Across Maitland as a whole, 156 homes closed in the last 12 months at a median of $515,000, 29 median days on market, with 28 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,590 ($7,910 with the full homestead exemption).
With a single active listing, Oakleigh is not a market you can read from an inventory chart, it is a market defined by whatever that one home is doing. Months of supply sitting at 12.0 tells you demand is not pressing against what is available, which puts this squarely in buyer-leaning territory, but with this little on the market, that classification can flip the moment a second or third listing appears or disappears.
For a seller, thin inventory cuts two ways: less competition for eyeballs, but also fewer comparable sales to lean on when setting a price, so pricing has to be justified on the property itself, not on a pattern. For a buyer, the same thinness means less room to shop this specific pocket, if the one listing does not fit, there may not be an alternative here for a while.
The 60-Second Overview
Oakleigh is a small, established pocket of the Maitland market in Orange County, and current MLS activity here is limited enough that a single listing represents the entire visible market.
Stellar MLS sales records identify 11 homes in Oakleigh that have changed hands since 2005, built between 1963 and 1972 (median 1969), with a median living area of about 3,299 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Oakleigh. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Oakleigh
Oakleigh
OakleighPhotos from Stellar MLS listings in Oakleigh; content deemed reliable but not guaranteed.
Who Oakleigh is best for.
Best for
- A buyer focused on one specific home rather than shopping a range of comparable listings.
- A buyer comfortable negotiating without a deep pool of recent comps to benchmark against.
- A seller prepared to price based on the property's own condition and features rather than a competitive set.
Probably not for
- A buyer who wants to compare several active listings before committing to a community.
- A buyer prioritizing packaged community amenities, since none are identified here.
- A seller expecting a fast sale in a market currently running at 12 months of supply.
The market around Oakleigh
Oakleigh is too small for its own price trend, so here is the market around it.
In ZIP 32751, 137 homes are on the market and 35% are under contract — a fast-moving corner of Maitland.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32751 (MAITLAND), 295 homes closed in the last 12 months at a median of $480K ($261/sq ft), down 0.3% year over year, with a median 30 days on market. Right now 31 active and 17 pending listings put supply at about 3.2 months - a healthy market. See the live ZIP 32751 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Oakleigh specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in OAKLEIGH THIRD ADD, MAITLAND
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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
OAKLEIGH THIRD ADD Market Scorecard
OAKLEIGH THIRD ADD is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32751 ZIP is $463,203, 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.
Homes For Sale Right Now in Oakleigh
Live MLS inventory for Oakleigh. 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 Oakleigh listings as of 2026-09-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2017 through 2026. Tap any home to ask about it.
Oakleigh 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.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Lake Sybelia Elem · Elementary
- Maitland Middle · Middle
- Winter Park High · High
Zoned schools reflect the assignments reported on recent Oakleigh 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 Oakleigh address.
Shop the zone: Homes zoned for Winter Park High High School
The Oakleigh buying strategy.
If we were buying in Oakleigh 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 Oakleigh.
A market of one
There is not enough active or comparable inventory in Oakleigh right now to talk about pricing trends, absorption patterns, or typical days on market with any confidence. What we can say is that months of supply at 12.0 places the community in buyer-leaning conditions, meaning that, at the current pace, existing inventory would take roughly a year to clear if nothing new came on. That is a slow clock, and it usually favors buyers on negotiating terms once they find the right property.
No community amenities have been identified from current MLS listings, which is common for smaller, established residential pockets where the draw is the home and its immediate location rather than a packaged amenity set. Anyone evaluating this community should treat the listing itself, not neighborhood-wide data, as the primary source of truth.
The location and the amenities are priced into every listing in Oakleigh. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this thin, the value of an agent is not pulling comps, it is knowing how to evaluate a single property on its own terms and negotiate accordingly. We will walk the listing, verify condition against price rather than against a market average that does not really exist here, and tell you plainly whether this is the right opportunity or whether patience makes more sense.
Oakleigh in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
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 Oakleigh 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 Oakleigh sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oakleigh, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oakleigh home worth?
Get a no-obligation home value based on real comparable sales in Oakleigh, 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 Maitland →
Should you buy in Oakleigh?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2017 (3 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 →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Oakleigh fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Oakleigh
Where is Oakleigh?
Oakleigh is a community in MAITLAND, Orange County, Florida, ZIP 32751.
Are there homes for sale in Oakleigh right now?
Yes - 0 active and 2 pending listings as of the last feed refresh (twice daily). They are listed on this page.
Does Oakleigh have an HOA or CDD?
No HOA is on record for Oakleigh in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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