Oaks At Cypress Woods
Homes for Sale in Kissimmee, FL

Oaks At Cypress Woods sits in Kissimmee within Osceola County as a gated-feel, amenity-supported community, but current MLS activity here is minimal, which limits how much the numbers alone can tell a buyer or seller.

Stellar MLS sales records identify 68 homes in Oaks At Cypress Woods that have changed hands since 2005, built between 1995 and 1999 (median 1997), with a median living area of about 1,734 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Oaks At Cypress Woods is too small for its own price trend, so here is the market around it.

In ZIP 34758, 389 homes are on the market and 30% are under contract — a fast-moving corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34758 (KISSIMMEE), 723 homes closed in the last 12 months at a median of $300K ($171/sq ft), down 2.0% year over year, with a median 49 days on market. Right now 171 active and 77 pending listings put supply at about 4.8 months - a balanced market. See the live ZIP 34758 housing market and the Osceola County market.

ZIP and county figures describe the wider market, not Oaks At Cypress Woods specifically. Momentum Research analysis of MLS records.

• Floral Ridge Elementary · Elementary
• Harmony Middle · Middle
• Poinciana High School · High

Zoned schools reflect the assignments reported on recent Oaks At Cypress Woods listings and can change; always confirm with Osceola County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Oaks At Cypress Woods address.

With one active listing and a single closing feeding the supply calculation, this community's 12-month supply figure is a mathematical artifact of low volume, not a market forecast. It would be a mistake to read it the way you would a 12-month supply number in a high-volume subdivision with dozens of recent sales.

The amenity package reported across this community's listings includes a clubhouse, both leased and owned recreation facilities, community mailbox service, and security fencing, lighting, and alarm infrastructure. Access and current condition of any of these should be verified directly with the HOA before a buyer treats them as settled facts.

In a community this thin on active listings, pricing and timing decisions can't rely on the community's own data alone. We pull comparable closings from the broader Kissimmee market, confirm HOA amenity details directly rather than taking listing notes at face value, and help you build a realistic offer or list strategy when the subject community itself isn't giving you enough to go on.

Listings in this community report association dues of about $90 per month ($1,080 a year) - the median AssociationFee across 12 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, 2026-09.

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