Winter Park Residential
Homes for Sale in Winter Park, FL

Winter Park Residential market snapshot (as of September 20, 2026): the median sale price is about $1.13M ($432 per sq ft over the trailing 12 months of closed sales), a median 4 days on market for closed sales, and 3.0 months of supply, a balanced market. The trailing-12-month median is up 3% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 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 16 homes in Winter Park Residential that have changed hands since 2019, built between 2008 and 2009 (median 2008), with a median living area of about 2,756 sq ft and a typical 3-bedroom, 3.5-bath layout; 94% 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 tightly held, amenity-secured residential community in Winter Park where inventory is thin enough that a single listing can define the current market for weeks at a time.

• Audubon Park K8 · Elementary
• Audubon Park K-8 · Middle
• Winter Park High · High

Zoned schools reflect the assignments reported on recent Winter Park Residential listings and can change; always confirm with Orange County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Winter Park Residential address.

The numbers here should be read with the sample size in mind: one active listing and a four-closing window behind the current median. That is not enough transactions to draw firm conclusions about a 'typical' unit, but it is enough to confirm the pattern - homes that do close here move at a median price north of a million dollars, at a price per square foot near $420, and they do not sit. A median of roughly three and a half days on market is close to an as-listed, pending-same-week pace.

The building amenities on file - key card entry, a manned or gated security layer, secured garage parking, elevators, on-site maintenance, and a restaurant - describe a full-service residence rather than a standard subdivision. Those features carry ongoing HOA and service costs that belong in any offer analysis, and they are worth confirming directly with the association since access and amenity details can change between MLS updates.

In a community running on a single active listing, the deal is often made before it hits general search - through standing buyer relationships, off-market conversations, and same-week response when something does surface. We track this address specifically so a serious buyer or seller does not lose a three-day window to a slow start.

Listings in this community report association dues of about $1,103 per month ($13,239 a year) - the median AssociationFee across 5 MLS records, normalised to a monthly figure; most are billed monthly. 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.