Sicilian Shores
Homes for Sale in Winter Park, FL
All 356 homes for sale in WINTER PARK, FL · median $697,000 · 167 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Homes listed or recently sold were built 1955 - 2019; 1 of the 4 geocoded homes sit in a FEMA special flood hazard zone (median elevation 72 ft). As of October 2026, the MLS records 30 closed sales in Sicilian Shores in Winter Park, FL since 2006, the most recent in May 2026. Recorded prices since 2024 ran from $2,200,000 to $7,164,000 (median $3,278,530), on homes of 3,897 to 5,006 sq ft. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $449,000, 33 median days on market, with 128 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $54,670 ($53,990 with the full homestead exemption).
| Location | WINTER PARK, Orange County, FL · ZIP 32789 |
|---|---|
| Homes in the community | 150 (FL DOR 2025 assessment roll) |
| Years built | 1919–2024 (median 1994.0) |
| Typical living area | 4,394 sq ft (median) |
| Amenities listed by sellers | Closed Circuit Camera(s), Irrigation-Reclaimed Water, Optional Additional Fees, Security System, Special Community Restrictions, Tennis Court(s) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 80% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Sicilian Shores key facts,” movewithmomentum.com/neighborhoods/sicilian-shores-winter-park, data as of September 20, 2026.
There is nothing on the market in Sicilian Shores right now, and that zero is the story. With 158 homes total and no active listings as of this snapshot, price discovery here happens off the last closings and off comparable inventory nearby, not off a live shelf of choices. A buyer who wants in has to wait for something to surface or work a pre-market lead.
The homes themselves skew large - median living area runs north of 4,300 square feet - and span a build era from 1919 up through 2024, with the typical home dating to the mid-1990s. That spread means condition and update level do more to set value than square footage alone. A seller here is pricing against a small, architecturally mixed pool, which argues for a considered, comp-specific approach rather than a formula.
Nearby homes for sale
No active listings inside Sicilian Shores right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
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.
The setting & the homes.
Aerial and on-site photos of Sicilian Shores. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Sicilian Shores; content deemed reliable but not guaranteed.
Who Sicilian Shores is best for.
Best for
- Buyers who want a larger home footprint and are comfortable waiting for the right listing to surface
- Sellers of an updated or newer-build home who want to price against a mixed, smaller inventory pool
- Buyers or owners who value tennis courts and reclaimed-water irrigation as part of a community's shared amenities
Probably not for
- Buyers who need to choose from active, on-market inventory right now
- Buyers focused on newer, uniformly built neighborhoods rather than a century-spanning mix of home ages
- Anyone unwilling to budget for condition or renovation work given the wide range of build years
The market around Sicilian Shores
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.
Sicilian Shores on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Sicilian Shores
- Optional Additional Fees · reported on 1 of 3 listings
- Tennis Court(s) · reported on 1 of 3 listings
- Irrigation-Reclaimed Water · reported on 1 of 3 listings
- Special Community Restrictions · reported on 1 of 3 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
The Sicilian Shores buying strategy.
If we were buying in Sicilian Shores today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Sicilian Shores.
A Small Pool, No Current Inventory
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.
The location and the amenities are priced into every listing in Sicilian Shores. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
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.
Sicilian Shores in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Sicilian Shores buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Sicilian Shores sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Sicilian Shores, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Sicilian Shores home worth?
Get a no-obligation home value based on real comparable sales in Sicilian Shores, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Park →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Frequently Asked Questions
How many homes are in Sicilian Shores?
What share of Sicilian Shores is owner-occupied?
When were the homes in Sicilian Shores built?
Who is the best real estate agent for Sicilian Shores?
How do I find a top Winter Park real estate agent who knows Sicilian Shores?
Can Momentum Realty connect me with an agent for Sicilian Shores?
Where is Sicilian Shores, and what county is it in?
Should you buy in Sicilian Shores?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (7 streets, ZIP 32789)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (30 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Sicilian Shores fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Sicilian Shores with Momentum Realty’s local guides.