Cloisters Condo
Homes for Sale in Winter Park, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Cloisters Condo is a condo market in Winter Park where price is driven far more by the individual unit than by the address. At a median of $837,500 and roughly $636 per square foot, this is premium territory, and that per-foot figure tells you the spread here is about condition, floor, view, and layout rather than a single going rate. Expect a wide range unit to unit, and price each one on its own merits.
The posture right now is measured, not frantic. A median of 57 days on market and a heat score of 30 point to a market that rewards patience on both sides — sellers who price to condition rather than to the last comp, and buyers who have room to negotiate and inspect. The year-over-year figure of 41.9% is eye-catching, but with only six closings in the window it reflects a thin, volatile sample; treat it as directional, not a promise.
Cloisters Condo right now
🟢 Still climbing. The trailing-12-month median ($838K) is up 41.9% from the prior 12 months ($590K). With about 4 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 (6 and 7 sales in the two windows).
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
Cloisters Condo market snapshot (as of July 15, 2026): the median sale price is about $838K ($636 per sq ft over the trailing 12 months of closed sales), and a median 57 days on market for closed sales. The trailing-12-month median is up 42% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
This is a small, high-per-foot condo pocket in Winter Park where a handful of sales set the tone — meaning every listing and every comp carries outsized weight, and the numbers move sharply on low volume.
Who Cloisters Condo is best for.
Best for
- Buyers with a budget comfortable near the mid-$800s who value a specific Winter Park condo location
- Buyers who prefer a low-maintenance condo lifestyle over a single-family home
- Buyers willing to underwrite a unit on its own merits rather than a deep comp set
Probably not for
- Buyers needing a wide selection of active listings to compare
- Buyers who want firm, data-backed pricing certainty from a large sample of recent sales
- Buyers expecting a fast-moving market where correctly priced units sell in 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 ($838K) IS the median in the snapshot above, and the move from 2025 ($590K) IS the +41.9% one-year change.
Windows contain 0 to 11 sales each (6 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 Cloisters Condo buying strategy.
If we were buying in Cloisters 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 Cloisters Condo.
Reading a thin condo market
With just six closings in the measured window, Cloisters is a low-volume market, and low volume changes how you interpret every statistic. A single premium sale or a single distressed one can swing the median and the year-over-year number materially, which is why the 41.9% annual move should be read as a signal of direction and scarcity rather than a reliable growth rate. The honest takeaway: comps are sparse, so pricing leans heavily on the specific unit in front of you.
The $636 median per square foot is the more stable read here, and it frames what your money buys. Because condo values in a building like this hinge on floor, exposure, finish level, and interior updates, two units at similar sizes can justify very different prices. At 57 days to a typical sale, this is not a market where mispriced listings move quickly — condition and pricing discipline do the work.
The location and the amenities are priced into every listing in Cloisters Condo. 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 analysis matters more than the listing count. We price and negotiate off the specific unit — floor, view, finishes, association details — because the comp set is too small to lean on blindly. Whether you are buying or selling, we will tell you plainly where a given unit sits against a volatile median and a 57-day pace, and we will not talk you into a number the evidence does not support.
Cloisters 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 Cloisters 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 Cloisters Condo sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cloisters 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 Cloisters Condo home worth?
Get a no-obligation home value based on real comparable sales in Cloisters 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 Cloisters Condo on the map →
Frequently Asked Questions
What is the median home price in Cloisters Condo?
How long do homes in Cloisters Condo take to sell?
Do cash buyers compete in Cloisters Condo?
Who is the best real estate agent for Cloisters Condo?
How do I find a top Winter Park real estate agent who knows Cloisters Condo?
Can Momentum Realty connect me with an agent for Cloisters Condo?
Should you buy in Cloisters 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 2012 (53 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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See how CLOISTERS CONDO fits the bigger picture — live prices, inventory, and Momentum Scores:
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