Neighborhood · Winter Park, Florida
Osceola Shores
Lakefront-scale living minutes from downtown Winter Park
2
Homes for sale
$2,150,000
Median list price
$497
Avg price / sqft
40
Median days on market
Osceola Shores is a small, high-end pocket of Winter Park where lots run large and the houses match — the median home here measures 4,301 square feet. It sits near Lake Killarney and rounds out a neighborhood roster that includes Winter Park Pines, Hannibal Square, and Eastbrook. Downtown Orlando is roughly 20 minutes away, MCO about 35, and the assigned schools — Winter Park High, Maitland Middle, and Lakemont Elementary — are the ones buyers move here for.
This is a thin, luxury market, so timing and preparation matter. Right now there are just two active listings, both with pools, at a median list price of $2,150,000 spanning $1.8M to $2.5M. Homes have been taking a median of 39 days to sell, and over the past year sellers averaged 89% of asking — meaning there's real room to negotiate at this price point.
Osceola Shores is a community in Winter Park, Florida.
Quick facts
$1,800,000 – $2.5M price range
4,301 sqft median home
2 sold in 12 months
Drive times
On the market now
Homes for sale in Osceola Shores
$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
Open full map search →Find your fit
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
$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
≈ $13,134/mo
$2,150,000 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 one of the more established luxury corners of Winter Park, with large homes and an assignment to Winter Park High, Maitland Middle, and Lakemont Elementary. You're about 20 minutes from downtown Orlando and 35 from MCO, so it pairs quiet residential scale with easy access. It works best for buyers who want space and a strong school feeder without leaving the Winter Park orbit.
Is Osceola Shores expensive?+
Yes — this is a top-tier price point. The median list price is $2,150,000 and active homes range from $1,800,000 to $2,500,000, while homes that sold over the past year had a median price of $2,743,750. It sits well above the broader Winter Park average.
What do homes cost in Osceola Shores?+
Expect roughly $497 per square foot on a median home of 4,301 square feet, which puts most properties well into seven figures. The two active listings are priced between $1.8M and $2.5M, both with pools. This is a small inventory, so options are limited at any given time.
How is the market in Osceola Shores?+
It's a low-volume, high-value market — just two active listings and two sales in the past 12 months. Homes take a median of 39 days to sell, and sellers averaged 89% of their asking price, which signals meaningful negotiating room. Because so few properties trade here, a serious buyer should be ready to move when the right one lists.
What about HOA fees and property taxes?+
Property taxes run about $19,150 per year at this price level, reflecting the high assessed values. HOA data isn't available for the active listings, so verify any dues or requirements on a per-property basis. Your agent can confirm the specifics before you write 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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