Cypress Lakes
Homes for Sale in Kissimmee, FL

Cypress Lakes market snapshot (as of August 2, 2026): the median sale price is about $366K ($246 per sq ft over the trailing 12 months of closed sales), and a median 15 days on market for closed sales. The trailing-12-month median is down 7% from the prior 12 months and up 385% since 2012, computed from record-level Stellar MLS closed sales (11 closings in the current window).

In ZIP 34743 (KISSIMMEE), 364 homes closed in the last 12 months at a median of $347K ($239/sq ft), down 2.7% year over year, with a median 31 days on market. Right now 31 active and 4 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 34743 housing market and the Osceola County market.

Cypress Lakes is a community of 701 homes in Kissimmee, Osceola County, built between 1990 and 2016 (median 1991), with a median living area of about 1,791 square feet. 60% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

A small, established community in Kissimmee of just 211 homes, all built in the early 1990s around a median of roughly 1,651 square feet — a place where condition, not year or size, drives the number.

With a homestead share of about 67 percent, most of these homes are owner-occupied rather than held as rentals — a signal of a stable, lived-in community where maintenance tends to be ongoing rather than deferred. That share also tells you the inventory here turns over deliberately, not in waves, so a buyer should treat any listing on its own terms.

Because the homes cluster around a median of 1,651 living square feet and a median build year of 1990, the spread in value comes almost entirely from what has been done inside and to the envelope. Roofs, HVAC, and kitchens from the original build are now well into replacement territory, so read every disclosure closely and price accordingly. This is a market where a careful inspection pays for itself.

In a community this size and this uniform in vintage, the difference between a good buy and an overpay is condition, and that is exactly what we underwrite line by line. We will walk the roof age, the systems, and the updates against the median footprint here and tell you plainly whether a listing is priced for its true state — including when the honest answer is to pass.

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