Winding Cypress
Homes for Sale in Naples, FL

Winding Cypress market snapshot (as of September 20, 2026): the median sale price is about $825K ($397 per sq ft over the trailing 12 months of closed sales), and a median 73 days on market for closed sales. The trailing-12-month median is up 2% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (46 closings in the current window).

In ZIP 34114 (Naples), 1,440 homes closed in the last 12 months at a median of $660K ($314/sq ft), up 4.8% year over year, with a median 67 days on market. Right now 561 active and 136 pending listings put supply at about 12.0 months — a buyer's market. See the live ZIP 34114 housing market and the Collier County market.

County records show 27 qualified sales in Winding Cypress across 2024–2025 (20 in 2024, 7 in 2025), median $775,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Winding Cypress is a community of 360 homes in Naples, Collier County, built between 2015 and 2022 (median 2019.0), with a median living area of about 2,520 square feet. 59% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Winding Cypress is a Naples community of newer construction, with roughly 61% of homes recorded as homesteaded, suggesting most owners here use the home as a primary residence rather than a seasonal or investment property.

With 755 homes and construction spanning 2015 to 2023, Winding Cypress is still a relatively young community by Naples standards, which means most inventory shares a similar construction era and building code vintage — a meaningful factor for insurance and maintenance planning even if it's not something we quote a number on. The $835,000 median price and $398.09 median price per square foot together suggest a market where larger, better-finished homes pull the average up, while the spread underneath is shaped by lot type and upgrade level.

The current pace — a 76-day median days-on-market and a market heat score of 23 — puts this on the calmer end of the spectrum, not a fast-turnover market. Combined with the 49 closings in the most recent window and a slight year-over-year pullback of 2.1%, the picture is one of a market that has cooled from its earlier build-out pace and is now trading at a more measured rhythm. No community amenities are currently identified from active MLS listings, so buyers should confirm any clubhouse, gate, or recreational features directly rather than assume them from general Naples-area marketing.

In a newer-build community like Winding Cypress, the real work is in comparing construction vintage, floor plan, and finish level home to home, since the neighborhood doesn't have decades of resale history to lean on. We track the day-to-day MLS data — pricing, days-on-market, and what's actually closing versus listing — so you're negotiating from the current market posture, not a stale comp or a listing agent's asking price.

Listings in this community report association dues of about $515 per month ($6,180 a year) — the median AssociationFee across 38 MLS records, normalised to a monthly figure; most are billed quarterly. 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.