Neighborhood · Oakland, Florida
Winter's Landing
Quiet West Orange living close to everything
Winter's Landing sits in the town of Oakland on the western edge of Orange County, a pocket of established neighborhoods where the pace slows down but Orlando stays within easy reach. Surrounding communities like Johns Landing, Johns Cove, and Oak Park Of Winter Garden give the area its residential, settled feel, and families here are zoned for West Orange High and Tildenville Elementary. Downtown Orlando is about 25 minutes away, Universal roughly 26, and Walt Disney World around 37 — close enough for work or a day out, far enough to feel like a retreat.
For buyers, this is a tightly held market. There are no active listings right now, but four homes sold over the past year at a median price of $850,000, with sellers collecting about 97% of asking on average. That combination tells you inventory moves quietly and holds its value, so watching the live map and being ready to act matters more here than in a high-turnover area.
Winter's Landing is a community in Oakland, Florida.
Quick facts
3 sold in 12 months
Drive times
On the market now
Homes for sale in Winter's Landing
Nothing active right now.
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Every active listing inside the Winter's Landing boundary
Open full map search →The numbers that matter
The Winter's Landing market
3
Sold, last 12 months
$850,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
44 days
Median time to sell
Winter's Landing vs Oakland
Live Stellar MLS data — every listing and closed sale inside the Winter's Landing boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter's Landing is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
171
Median age
46
Median income
$127,917
Median home value
$571,500
Beyond the listings
Living in Winter's Landing
Food & Drink
Top 2% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Hobbies & Interests
Top 2% 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 3% in the U.S.Spiritual Practices
Making it to church on Sunday, this population is drawn together by their devotion to, primarily Christian, religion. Common activities include worship services and bible studies.
Hobbies & Interests
Top 4% in the U.S.Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
Hobbies & Interests
Top 6% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Attitudes
Top 6% in the U.S.Volunteering & Giving
Expressing a desire to give back and do good for the community, this behavior emphasizes charity. Common activities include volunteering, fundraisers, and donations.
Straight answers
Winter's Landing FAQs
Is Winter's Landing a good place to live?+
It's a good fit if you want a settled, residential feel with quick access to the city — downtown Orlando is about 25 minutes away and MCO airport roughly 33. Families are drawn to the school zoning for West Orange High, Lakeview Middle, and Tildenville Elementary. The surrounding Oakland communities keep the area quiet without cutting you off from Orlando's job centers and attractions.
Is Winter's Landing expensive?+
It sits at the upper end of the local market: the four homes sold in the past year had a median sold price of $850,000. There are no active listings at the moment, so pricing on the next home to hit the market will help set the current benchmark. Browse nearby Oakland homes for sale to compare price points across the area.
What do homes cost in Winter's Landing?+
Recent sales point to a median around $850,000, based on four closings over the last 12 months. With no active listings right now, that sold figure is the clearest read on value. Keeping an eye on the live map is the best way to catch new inventory as it comes up.
How is the market here?+
It's a low-inventory, tightly held market — zero active listings currently, with just four homes changing hands over the past year. Sellers averaged about 97% of asking, which signals steady demand and little room for lowball offers. Buyers should be pre-approved and ready to move when something lists.
What about HOA fees and property taxes?+
We don't have current published HOA or property tax figures for Winter's Landing specifically, since active listings drive that data and there are none right now. HOA structures often vary by community, so it's worth checking details for neighbors like Oakland Pointe when comparing. Reach out and we can pull the exact carrying costs on any home you're considering.
Keep exploring
More Oakland 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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