Four Seasons Condo
Homes for Sale in Winter Park, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Four Seasons Condo is a condominium market in Winter Park, and price here is driven less by any single list figure than by unit condition, floor level, and view. The median sits at $177,500, or about $182 per square foot, but with a small closing count the median moves easily and says more about which units traded than about the whole community.
The posture right now favors buyers who are patient. Prices are down 19.3% year over year, days on market run around 33 and a half, and the heat score of 36 points to a market that is cool rather than competitive. Sellers should expect to price to condition and give showings time; buyers have room to negotiate but should read each unit on its own merits.
Four Seasons Condo right now
🔴 Off the recent peak. The trailing-12-month median ($178K) is down 19.3% from the prior 12 months ($220K). With about a dozen 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 July 15. Confidence: Medium (20 and 11 sales in the two windows).
What's unique here: the median sale price is about 59% below the typical Orange County sale ($178K vs $435K, trailing 12 months, Stellar MLS records).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated July 15, 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
Four Seasons Condo market snapshot (as of July 15, 2026): the median sale price is about $178K ($182 per sq ft over the trailing 12 months of closed sales), and a median 34 days on market for closed sales. The trailing-12-month median is down 19% from the prior 12 months, computed from record-level Stellar MLS closed sales (20 closings in the current window).
This is a condo-only market in Winter Park, Orange County, where a thin recent sales window means individual unit quality carries more weight than headline averages.
Who Four Seasons Condo is best for.
Best for
- Value-focused buyers targeting a Winter Park condo near the current median who are comfortable negotiating
- Buyers who want a lower-maintenance condominium and are not in a rush to close
- Long-hold owners willing to update a unit and hold through a soft stretch
Probably not for
- Buyers who need to resell quickly and want strong short-term price momentum
- Buyers seeking a detached single-family home rather than a condominium
- Buyers who want a fast, competitive market where deals close within days
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 15 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($178K) IS the median in the snapshot above, and the move from 2025 ($220K) IS the -19.3% one-year change.
Windows contain 0 to 23 sales each (20 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 %s through %s. Deemed reliable but not guaranteed.
The Four Seasons Condo buying strategy.
If we were buying in Four Seasons Condo 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 Four Seasons Condo.
Reading a thin, cooling condo market
With only 20 closings in the window, Four Seasons Condo is a small enough market that one renovated unit or one distressed sale can shift the median noticeably. Treat the $177,500 median as a reference point, not a ceiling or a floor, and compare any specific unit against its own square footage, condition, and placement in the building rather than against the community number alone.
The year-over-year decline of 19.3% alongside a heat score of 36 tells a consistent story: less urgency, more inventory sitting, and buyers with time on their side. Days on market near 33 and a half are neither alarming nor fast. For a seller, that means realistic pricing and clean presentation matter more than they would in a hot market; for a buyer, it means there is usually room to ask.
The location and the amenities are priced into every listing in Four Seasons Condo. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin, cooling condo market, the median tells you almost nothing about the unit you actually want to buy or sell. We underwrite each unit on condition, floor, view, and the specific comps that apply, then price and negotiate from that instead of from a headline number that a single sale can swing.
Four Seasons Condo in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA — confirm current dues
- 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 Four Seasons Condo 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 Four Seasons Condo sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Four Seasons Condo, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Four Seasons Condo home worth?
Get a no-obligation home value based on real comparable sales in Four Seasons Condo, 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 homes for sale in Four Seasons Condo on the map →
Frequently Asked Questions
What is the median home price in Four Seasons Condo?
How long do homes in Four Seasons Condo take to sell?
Do cash buyers compete in Four Seasons Condo?
Who is the best real estate agent for Four Seasons Condo?
How do I find a top Winter Park real estate agent who knows Four Seasons Condo?
Can Momentum Realty connect me with an agent for Four Seasons Condo?
Should you buy in Four Seasons Condo?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2010 (132 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 your area comps.
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