Neighborhood · Winter Park, Florida
Osceola Shores
Lakeside living minutes from downtown Winter Park
1
Homes for sale
$2,500,000
Median list price
$547
Avg price / sqft
78
Median days on market
Osceola Shores sits in one of Winter Park's most established pockets, where large lots and mature tree canopy set the tone for a quiet, upscale everyday. You're a short hop from Lake Killarney, the shops and restaurants of Hannibal Square, and the broader mix of Winter Park homes for sale — all while keeping downtown Orlando about 20 minutes away. Families are drawn to the assigned schools here, with Lakemont Elementary, Maitland Middle, and Winter Park High rounding out the lineup.
This is a small, high-end market, so inventory moves in a trickle rather than a wave. There's currently one active listing at $2,500,000, and just two homes sold over the past year at a median of $2,743,750. Buyers should expect to negotiate — sellers here landed about 89% of asking on average, and homes have taken a median of 74 days to sell. If you're comparing options, nearby Winter Park Pines and Eastbrook offer more frequent turnover.
Osceola Shores is a community in Winter Park, Florida.
Quick facts
$2,500,000 – $2.5M price range
4,572 sqft median home
2 sold in 12 months
Drive times
On the market now
Homes for sale in Osceola Shores
Every active listing inside the Osceola Shores boundary
Open full map search →Find your fit
Browse Osceola Shores
By feature — on the live map
The numbers that matter
The Osceola Shores market
2
Sold, last 12 months
$2,743,750
Median sold price
89%
Sale-to-list ratio
What sellers actually get vs asking
220 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
≈ $14,331/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, established Winter Park neighborhood with large homes, mature trees, and strong school assignments including Winter Park High and Lakemont Elementary. You're close to Lake Killarney and about 20 minutes from downtown Orlando, which makes it convenient without feeling busy. It suits buyers who want space and privacy over walkable density.
Is Osceola Shores expensive?+
Yes — this is a high-end pocket of Winter Park. The single active listing is priced at $2,500,000, and the two homes sold over the past year had a median price of $2,743,750, with an average $/sqft around $547.
What do homes cost in Osceola Shores?+
Expect to be in the multi-million-dollar range here, with the current listing at $2,500,000 and recent sales at a median of $2,743,750. The typical home is large at roughly 4,572 square feet. For more attainable options nearby, it's worth looking at Winter Park Pines.
How is the market in Osceola Shores?+
It's a small, slow-moving market — only two homes sold in the past 12 months and one is active now. Homes have taken a median of 74 days to sell, and sellers received about 89% of asking on average, so there's usually room to negotiate.
What about HOA fees and property taxes?+
There's no HOA data reported for the neighborhood, so buyers should confirm any dues on a per-home basis. Property taxes run around $11,393 per year at the median, in line with the area's higher home values.
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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