Cypress Club
Homes for Sale in Winter Springs, FL

Cypress Club sits in Seminole County within Winter Springs and carries a deed-restricted HOA structure with a fuller-than-typical amenity package for a community this size, including tennis, pickleball, and basketball courts alongside a pool and clubhouse.

Stellar MLS sales records identify 46 homes in Cypress Club that have changed hands since 2006, built between 1986 and 1995 (median 1990), with a median living area of about 1,224 sq ft and a typical 3-bedroom, 2-bath layout; 100% are townhomes. 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.

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

In ZIP 32708, 150 homes are on the market and 33% are under contract — a fast-moving corner of Winter Springs.

Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).

In ZIP 32708 (WINTER SPRINGS), 668 homes closed in the last 12 months at a median of $412K ($242/sq ft), down 1.5% year over year, with a median 33 days on market. Right now 32 active and 21 pending listings put supply at about 1.9 months - a healthy market. See the live ZIP 32708 housing market and the Seminole County market.

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

• Highlands Elementary · Elementary
• South Seminole Middle · Middle
• Winter Springs High · High

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

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

The amenity list here - pool, clubhouse, tennis, pickleball, basketball, playground, trails, and a park - is more extensive than what most communities this size carry, and it points to an HOA that has invested in shared recreational space over time. Deed restrictions and vehicle restrictions are both in place, so buyers used to fewer rules on parking or exterior use should factor that into their comfort level before writing an offer.

With active listings in the single digits and only one recorded closing in the current window, price data here should be treated as directional rather than definitive. Anyone serious about buying or selling in Cypress Club needs a hyper-local pull of recent comparable sales rather than a reliance on community-wide averages, because the sample size right now is too small to support broad conclusions.

In a community with this few active listings and this little recent closing activity, the value of an agent who tracks Cypress Club specifically - rather than Winter Springs broadly - goes up substantially. We monitor the individual listings here as they move, verify HOA documents and amenity access directly rather than relying on generic MLS notes, and help buyers and sellers price against real, current context instead of a stale average.

Listings in this community report association dues of about $520 per month ($6,240 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.