Neighborhood · Winter Park, Florida
Osceola Shores
Lakeside luxury minutes from downtown Winter Park
3
Homes for sale
$2,500,000
Median list price
$617
Avg price / sqft
78
Median days on market
Osceola Shores is a small, luxury-scaled pocket of Winter Park where large lots and custom homes sit close to the water and just minutes from the city's core. It's the kind of address that feels private and settled, with easy reach to the shops and restaurants of nearby Hannibal Square and the calm of Lake Killarney. Families here are zoned for well-regarded schools including Winter Park High, and downtown Orlando is roughly 20 minutes away.
For buyers, this is a rarefied, low-inventory market. There are just three active listings, with a median list price of $2,500,000 ranging from $1,800,000 to $3,600,000, and homes here move quickly at a median of 14 days on market. If you want to compare, neighboring enclaves like Winter Park Pines and Eastbrook offer different price points within the same school reach.
Osceola Shores is a community in Winter Park, Florida.
Quick facts
$1,800,000 – $3.6M price range
4,202 sqft median home
2 sold in 12 months
Drive times
On the market now
Homes for sale in Osceola Shores
$3,600,000
276 DETMAR DRIVE, WINTER PARK
4 bd · 5 ba · 4,202 sqft
$1,800,000
281 BREWER AVENUE, WINTER PARK
5 bd · 4.5 ba · 4,029 sqft
$2,500,000
450 LAKEWOOD DRIVE, WINTER PARK
5 bd · 5 ba · 4,572 sqft
Every active listing inside the Osceola Shores boundary
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Browse Osceola Shores
By feature — on the live map
Where the market lives
The numbers that matter
The Osceola Shores market
2
Sold, last 12 months
$3,950,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
53 days
Median time to sell
Osceola Shores vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 36.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Osceola Shores boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Osceola Shores is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Osceola Shores home
≈ $15,624/mo
$2,500,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
221
Median age
59
Median income
$149,784
Median home value
$1,078,300
Beyond the listings
Living in Osceola Shores
Beliefs
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.
Lifestyles
Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Culture
Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Appearance oriented
Fitness Fashion
Workout clothes aren't just for working out anymore. This population enjoys wearing name-brand athletic apparel for fashion and functional purposes.
Hobbies & Interests
Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Active
Outdoor Adventures
Appreciating the outdoors, this population wants to actively engage with nature. Whether it's finding a new hiking trail or looking for the perfect spot to catch the sunset, they seek to explore the world around them.
People who close here
Our Winter Park experts
Straight answers
Osceola Shores FAQs
Is Osceola Shores a good place to live?+
It's a quiet, upscale neighborhood of large custom homes close to downtown Winter Park and its dining and shopping. Families value the school zoning for Lakemont Elementary, Maitland Middle, and Winter Park High, and the central location puts downtown Orlando about 20 minutes away.
Is Osceola Shores expensive?+
Yes, this is one of Winter Park's higher-priced pockets, with a median list price of $2,500,000 and active listings running from $1,800,000 to $3,600,000. Homes over $1M make up the entire active market here. Buyers wanting more accessible pricing nearby often look at Winter Park Pines.
What do homes cost in Osceola Shores?+
Current listings average about $617 per square foot, with a median home size of roughly 4,202 square feet. Over the past 12 months, the two homes that sold closed at a median price of $3,950,000, reflecting the neighborhood's larger, higher-end properties.
How is the market in Osceola Shores?+
Inventory is very tight, with just three active listings, and homes move quickly at a median of 14 days on market. Sellers have averaged 92% of asking price over the last year, so serious buyers should be ready to act when the right home comes up.
What about HOA fees and property taxes?+
HOA data isn't reported for the active listings here, so there may be little or no association structure. Property taxes reflect the high home values, with a median of about $26,908 per year.
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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