Neighborhood · Winter Park, Florida
Sicilian Shores
Lakeside luxury living minutes from downtown Orlando
Sicilian Shores is one of Winter Park's quiet upper-tier enclaves, the kind of address where lakefront lots and mature landscaping set the tone. It sits within easy reach of downtown Orlando — about 17 minutes by car — while feeling a world removed from it, with Winter Park Pines and Lake Killarney among the familiar communities nearby. Families here are zoned to Winter Park High, Maitland Middle, and Dommerich Elementary, a school lineup that keeps demand steady.
This is a small, tightly held pocket, and the numbers reflect it: there are no active listings right now, so buyers should expect to move quickly and often quietly when a home does surface. Over the past 12 months, four homes changed hands at a median sold price of $4,536,250, with sellers collecting 98% of asking on average. If Sicilian Shores itself is dry, it's worth broadening the search to nearby Eastbrook, Cedarwood Village, or the wider pool of Winter Park homes for sale.
Sicilian Shores is a community in Winter Park, Florida.
Quick facts
3 sold in 12 months
Drive times
On the market now
Homes for sale in Sicilian Shores
Nothing active right now.
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Every active listing inside the Sicilian Shores boundary
Open full map search →The numbers that matter
The Sicilian Shores market
3
Sold, last 12 months
$4,300,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
5 days
Median time to sell
Sicilian Shores vs Winter Park
Live Stellar MLS data — every listing and closed sale inside the Sicilian Shores boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Sicilian Shores is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
427
Median age
50
Median income
$250,001
Median home value
$1,634,600
Beyond the listings
Living in Sicilian Shores
Relationships
Top 2% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Relationships
Top 3% in the U.S.Connected Motherhood
Motherhood is a unique journey for every woman. There are highs, lows,and lots to celebrate. These moms seek to share their experiences and engage with a community of moms.
Hobbies & Interests
Top 8% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Beliefs
Top 15% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Relationships
Top 15% in the U.S.Dating Life
With dating comes highs, lows, and lots of questions. You can find this population talking about dating advice, breakups and how to express their feelings.
Relationships
Top 17% in the U.S.Love & Romance
Love is in the air when this population is present. Includes people expressing their feelings for significant others in special ways. Common activities include anniversaries and date nights.
People who close here
Our Winter Park experts
Straight answers
Sicilian Shores FAQs
Is Sicilian Shores a good place to live?+
It's a small, established Winter Park enclave with a quiet residential feel and quick access to downtown Orlando, roughly 17 minutes away. Families are drawn to the school assignments — Winter Park High, Maitland Middle, and Dommerich Elementary — and the proximity to established neighborhoods like Lake Killarney. It suits buyers who want luxury without the density of a big-city address.
Is Sicilian Shores expensive?+
Yes — this is one of Winter Park's premium pockets. The median sold price over the last 12 months was $4,536,250, so it sits at the top of the local market and appeals to buyers shopping in the multimillion-dollar range.
What do homes cost in Sicilian Shores?+
There are no active listings at the moment, so the clearest signal comes from recent sales: four homes closed in the past year at a median of $4,536,250. When inventory is this thin, it helps to also watch nearby options among Winter Park homes for sale.
How is the market in Sicilian Shores?+
It's a low-volume, seller-favored market — four homes sold in the last 12 months and nothing is currently listed. Sellers averaged 98% of asking, so when a home does come up, buyers should be prepared to act decisively; broadening to communities like Eastbrook can widen your options.
What about HOA fees and property taxes?+
We don't have current HOA or property tax figures on file for Sicilian Shores, which is typical for a small enclave with so few recent transactions. For an accurate picture on a specific home, we'll pull the exact assessment and any association dues before you make an offer.
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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