Cloisters
Condos for Sale in Winter Park, FL

Cloisters Condo market snapshot (as of September 20, 2026): the median sale price is about $970K ($695 per sq ft over the trailing 12 months of closed sales), and a median 131 days on market for closed sales. The trailing-12-month median is up 53% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).

In ZIP 32789 (Winter Park), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 32789 housing market and the Orange County market.

Stellar MLS sales records identify 50 homes in Cloisters Condo that have changed hands since 2012, built between 1971 and 1971 (median 1971), with a median living area of about 1,267 sq ft and a typical 2-bedroom, 2-bath layout; 100% are condominiums. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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.

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.

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.

Listings in this community report association dues of about $957 per month ($11,484 a year) — the median AssociationFee across 64 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.