Cypresswood Meadows
Homes for Sale in Winter Haven, FL

Cypresswood Meadows is a compact, established pocket of roughly 120 homes in Winter Haven, built out across the late 1970s through the early 1990s and defined by larger floor plans than much of the surrounding market.

Stellar MLS sales records identify 25 homes in CYPRESSWOOD Meadows that have changed hands since 2005, built between 1985 and 1993 (median 1986), with a median living area of about 1,773 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.

Cypresswood Meadows is a small community — 2 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.

In ZIP 33884, 457 homes are on the market and 25% are under contract — a steady corner of Winter Haven.

Across Polk County, 5,189 homes are active and 1,757 pending (25% under contract).

Homes here are single family residence.

In ZIP 33884 (Winter Haven), 651 homes closed in the last 12 months at a median of $308K ($163/sq ft), down 0.9% year over year, with a median 57 days on market. Right now 2 active and 2 pending listings. See the live ZIP 33884 housing market and the Polk County market.

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

• Polk County Public Schools (verify by address) · Public
• Confirm zoned elementary, middle, and high · By address
• Magnet and choice options may apply · Choice

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

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

With a median year built around 1981 and a build range running from 1975 to 1993, this is a mature neighborhood where the trees and lots have filled in. The median living area near 2,699 square feet is the headline feature: these are substantial houses, and much of the value question comes down to how a given home has been maintained and updated over four-plus decades.

About 71 percent of homes here carry a homestead exemption, which points to a largely owner-occupied street rather than a rental-heavy one. No community amenities surface from current MLS listings, so buyers should not expect an HOA amenity package; the appeal here is the house and the lot, not shared facilities.

With no active listings and only a handful of recent closings, pricing this neighborhood takes local judgment rather than a quick comp pull. We read condition and square footage against a thin sales record so sellers don't leave money on the table and buyers don't overpay for a home that needs work.