Sicilian Shores
Homes for Sale in Winter Park, FL

Sicilian Shores is a small, established Winter Park community of 158 homes with a wide build-year range and a footprint that skews toward larger living areas, set against tennis courts and reclaimed-water irrigation as the notable shared amenities.

Stellar MLS sales records identify 62 homes in Sicilian Shores that have changed hands since 2004, built between 1950 and 2023 (median 1993), with a median living area of about 4,176 sq ft and a typical 4-bedroom, 4.5-bath layout; 98% 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.

County records show 10 qualified sales in Sicilian Shores across 2024 - 2025 (8 in 2024, 2 in 2025), median $2.90M - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

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.

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

In ZIP 32789, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

In ZIP 32789 (Winter Park), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months - a balanced market. See the live ZIP 32789 housing market and the Orange County market.

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

At 158 homes, Sicilian Shores is not a high-volume market, and the current snapshot shows zero active listings - meaning anyone shopping this community today is either waiting on the next listing or working through an off-market or pre-list channel. That scarcity is worth naming plainly rather than dressing up: there is no current shelf of comparable choices to browse.

The building stock spans more than a century, from homes built in 1919 through new construction as recent as 2024, with a median year built around 1994-1995. Combined with a median living area over 4,300 square feet, this points to a community of larger-format homes where age, renovation history, and lot specifics will matter more to value than any single market-wide number. A high share of homes carry homestead status, which signals a base of owner-occupied primary residences rather than a transient rental-heavy footprint - relevant context for anyone weighing resale patterns or long-term hold behavior in the community.

In a community this small with zero listings currently active, the value is in the network, not the search portal. We track Sicilian Shores closings and owner activity so we can flag a listing before it goes wide, or help a seller price against the right slice of this era-mixed, large-format inventory instead of a generic Winter Park comp set.

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