Neighborhood · Winter Park, Florida
Sicilian Shores
Lakefront living at Winter Park's high end
Sicilian Shores is a small, waterfront-oriented enclave in Winter Park, the kind of address where sales are rare and prices run at the top of the market. It sits within easy reach of the broader Winter Park homes for sale scene, with well-regarded neighbors like Lake Killarney and Winter Park Pines nearby, plus the shops and restaurants of Hannibal Square a short drive away.
For a buyer today, this is a patience game — there are currently no active listings, and only four homes have changed hands here in the past year. Those sales landed at a median of $4,536,250, with sellers collecting about 98% of their asking price. If you want in, expect to move quickly and pay close to list when the right home surfaces.
Sicilian Shores is a community in Winter Park, Florida.
Quick facts
4 sold in 12 months
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
4
Sold, last 12 months
$4,536,250
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
3 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 one of Winter Park's premier waterfront-oriented enclaves, with a quiet, high-end residential character. Homes here feed into Dommerich Elementary, Maitland Middle, and Winter Park High, and you're within reach of neighborhoods like Lake Killarney and the shops of Hannibal Square.
Is Sicilian Shores expensive?+
Yes — it's at the very top of the Winter Park market. Homes here sold at a median of $4,536,250 over the past year, so this is a luxury address in every sense.
What do homes cost in Sicilian Shores?+
With no active listings right now, pricing comes from recent sales: the median sold price over the last 12 months was $4,536,250. When homes do come to market, expect them to reflect that premium tier.
How is the market in Sicilian Shores?+
It's tight and competitive. Only four homes sold in the past year and there are currently no active listings, and sellers averaged 98% of their asking price — a sign you'll need to act fast and offer strong when something opens up.
What about HOA fees and property taxes?+
We don't have current HOA or property tax figures on record for Sicilian Shores. Given the neighborhood's price point, it's worth confirming those details on any specific home with your agent 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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