Osceola Court
Homes for Sale in Winter Park, FL
All 337 homes for sale in Winter Park, FL · median $664,900 · 150 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 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, 494 homes closed in the last 12 months at a median of $459,450, 34 median days on market, with 124 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,660 ($6,990 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.
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.
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, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32789 (Winter Park), 394 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.4% year over year, with a median 40 days on market. Right now 88 active and 21 pending listings put supply at about 4.9 months — a balanced 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.
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 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 →
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: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| 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. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Osceola Court fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Osceola Court
Where is Osceola Court?
Osceola Court is a community in Winter Park, Orange County, Florida, ZIP 32789.
Are there homes for sale in Osceola Court right now?
No active listings inside Osceola Court at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Osceola Court have an HOA or CDD?
No HOA is on record for Osceola Court 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.
Nearby Communities
Explore more neighborhoods near Osceola Court with Momentum Realty’s local guides.
Osceola Court Market Scorecard
Osceola Court is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32789 ZIP is $809,773, about 61.9% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.