Osceola Court
Homes for Sale in Winter Park, FL
All 394 homes for sale in Winter Park, FL · median $636,250 · 169 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of November 2026, the MLS records 7 closed sales in Osceola Court in Winter Park, FL since 2016, the most recent in April 2026. Across Winter Park as a whole, 887 homes closed in the last 12 months at a median of $499,000, 37 median days on market, with 326 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,320 ($7,650 with the full homestead exemption).
There isn't enough current MLS activity on Osceola Court to point to a median price or a typical days-on-market figure, and that absence is itself the read: this is a low-volume pocket of Winter Park where pricing gets set listing by listing rather than by a visible trend line.
For a buyer or seller, that means less reliance on comps pulled from the street itself and more on how the immediate Winter Park submarket and Orange County context are pricing similar product right now. Anyone transacting here should expect a negotiation grounded in the specific home's condition and positioning, not in a well-worn pattern of recent sales.
Figures in this note are as of July 22, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Osceola Court 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.
The 60-Second Overview
Osceola Court sits within Winter Park, in Orange County, an established Central Florida address with no material MLS-reported sales activity in the current snapshot to characterize typical pricing or turnover.
Stellar MLS sales records identify 9 homes in Osceola Court that have changed hands since 2007, built between 1912 and 1948 (median 1938), with a median living area of about 2,011 sq ft and a typical 4-bedroom, 2.5-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.
County records show 8 qualified sales in Osceola Court across 2024–2025 (3 in 2024, 5 in 2025), median $615,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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.
Who Osceola Court is best for.
Best for
- A buyer targeting the Winter Park address specifically and comfortable evaluating a home on its own merits rather than street comps
- A seller prepared to have their home priced against the wider Winter Park market given the lack of Osceola Court-specific data
- Someone working with an agent to source off-street comparables rather than relying on this address's own MLS history
Probably not for
- A buyer who wants to see a clear, established price trend for the exact street before writing an offer
- Someone relying on a documented list of community amenities as part of the decision
- A buyer or seller expecting a fast, high-volume comp set to benchmark against
The market around Osceola Court
Osceola Court is too small for its own price trend, so here is the market around it.
In ZIP 32789, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
In ZIP 32789 (Winter Park), 111 homes closed in the last 12 months at a median of $627K ($396/sq ft), down 21.6% year over year, with a median 42 days on market. Right now 34 active and 4 pending listings put supply at about 3.7 months — a buyer's market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Osceola Court specifically. Momentum Research analysis of MLS records.
The Osceola Court buying strategy.
If we were buying in Osceola Court 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 Osceola Court.
A Street Without a Track Record
Current MLS listings tied to Osceola Court do not surface a defined set of community amenities, and there isn't a pricing or pace-of-sale pattern to report from the available feed. That's not unusual for a short street or small enclave inside a larger, well-known city like Winter Park — the address carries the reputation of its surroundings more than a data footprint of its own.
What that means practically: due diligence here leans harder on the individual property and its immediate block context rather than on street-level statistics. Buyers and sellers should treat any specific home on Osceola Court as its own case, cross-referenced against broader Winter Park activity rather than isolated averages.
The location and the amenities are priced into every listing in Osceola Court. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
On a street with this little standalone MLS history, the value we add is pulling the right comparison set from the surrounding Winter Park market rather than relying on numbers that don't yet exist for Osceola Court itself, and pricing or offering accordingly.
Osceola Court in 15 seconds.
Tools for a Osceola Court 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 Osceola Court sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Osceola Court, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Osceola Court home worth?
Get a no-obligation home value based on real comparable sales in Osceola Court, 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 Winter Park →
| Location | Winter Park, Orange County, FL · ZIP 32789 |
|---|---|
| Homes in the community | 105 (FL DOR 2025 assessment roll) |
| Years built | 1901–2015 (median 1969.0) |
| Typical living area | 1,964 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 65% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2016 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Osceola Court key facts,” movewithmomentum.com/neighborhoods/osceola-court, data as of September 20, 2026.
More Winter Park home searches
- All homes for sale in Winter Park, FL
- Homes for sale in Orange County, FL
- Gated communities in Winter Park
- Homes under $300K in Winter Park
- 4-bedroom homes for sale in Winter Park
- Winter Park home values: what is my house worth?
- ZIP 32789 housing scorecard
Winter Park guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
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
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
Real estate agent in Winter Park? Join Momentum in Winter Park: 100% commission, one $12K cap.
Email me new listings in Osceola Court
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 Osceola Court
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Osceola Court will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
How many homes are in Osceola Court?
What share of Osceola Court is owner-occupied?
When were the homes in Osceola Court built?
Who is the best real estate agent for Osceola Court?
How do I find a top Winter Park real estate agent who knows Osceola Court?
Can Momentum Realty connect me with an agent for Osceola Court?
Where is Osceola Court, and what county is it in?
Should you buy in Osceola Court?
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: November 12, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 32789)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2016 (7 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. A Momentum agent can 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 Osceola Court fits the bigger picture — live prices, inventory, and Momentum Scores: