Pleasant Oaks
Homes for Sale in Orlando, FL
All 4,319 homes for sale in Orlando, FL · median $379,900 · 156 homes for sale in 32808 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside Pleasant Oaks right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
As of October 2026, the MLS records 34 closed sales in Pleasant Oaks in Orlando, FL since 2006, the most recent in March 2026. Recorded prices since 2024 ran from $270,000 to $365,000 (median $340,000), on homes of 1,628 to 1,740 sq ft. Across Orlando as a whole, 6,171 homes closed in the last 12 months at a median of $415,000, 42 median days on market, with 3,923 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $5,670 ($5,000 with the full homestead exemption).
The market around Pleasant Oaks
Pleasant Oaks is too small for its own price trend, so here is the market around it.
In ZIP 32808, 216 homes are on the market and 28% are under contract — a steady corner of Orlando.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
ZIP and county figures describe the wider market, not Pleasant Oaks specifically. Momentum Research analysis of MLS records.
Pleasant Oaks 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 contributors.
The Pleasant Oaks buying strategy.
If we were buying in Pleasant Oaks 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 Pleasant Oaks.
A closer look at the Pleasant Oaks market
The housing stock is 62 homes built between 1940 and 1990, and 66% 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 Pleasant Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Tools for a Pleasant Oaks 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 Pleasant Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Pleasant Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Pleasant Oaks home worth?
Get a no-obligation home value based on real comparable sales in Pleasant Oaks, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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| Location | Orlando, Orange County, FL · ZIP 32808 |
|---|---|
| Homes in the community | 62 (FL DOR 2025 assessment roll) |
| Years built | 1940–1990 (median 1989.0) |
| Typical living area | 1,398 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 66% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Pleasant Oaks key facts,” movewithmomentum.com/neighborhoods/pleasant-oaks-orlando, data as of September 20, 2026.
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Orlando guides & data
- Market data
- Cost of living
- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Old Oak Tree Drive (24 homes on record)
What it really costs to own in Pleasant Oaks
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | MLS listings here mostly enter dues as billed annually, but the median entry is only $270/year across 3 listings (2026-10-24), which usually means a quarterly or monthly amount was entered as annual. Ask the association for the current dues. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Orange County is $1,409/yr (4,204 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
Email me new listings in Pleasant Oaks
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Pleasant Oaks
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Pleasant Oaks will answer, and the answer is published on this page for the next buyer.
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.
Price History: What Homes Here Have Actually Sold For
Median sale prices in Pleasant Oaks Orlando year by year since 2013, from closed MLS sales. Long-run history beats any single estimate: it shows what this community has actually done through rate cycles, not what a model guesses.
Frequently Asked Questions
How many homes are in Pleasant Oaks?
What share of Pleasant Oaks is owner-occupied?
When were the homes in Pleasant Oaks built?
Who is the best real estate agent for Pleasant Oaks?
How do I find a top Orlando real estate agent who knows Pleasant Oaks?
Can Momentum Realty connect me with an agent for Pleasant Oaks?
Where is Pleasant Oaks, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 23, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 32808)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (34 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 Pleasant Oaks fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
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