Neighborhood · Oakland, Florida
Winter's Landing
Small-town Oakland living near the West Orange Trail
Winter's Landing sits in the town of Oakland, on the western edge of Orange County where the pace slows down but Orlando stays close. It's the kind of pocket where neighbors know each other and the surrounding Oakland homes for sale lean toward larger lots and established streets, with nearby communities like Johns Cove, Johns Landing, and Trailside Station rounding out the area. Downtown Orlando is about 25 minutes away, Universal roughly 26, and MCO around 33 — you get the quiet without giving up the commute.
For buyers, this is a low-inventory, high-value corner of the market. There are currently no active listings, so you're watching for something to come available rather than picking from a shelf — keep an eye on the live map. Over the last 12 months just 4 homes sold here, at a median of $850,000, and sellers collected about 97% of asking, which tells you demand holds firm when a home does hit the market.
Winter's Landing is a community in Oakland, Florida.
Quick facts
4 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
4
Sold, last 12 months
$850,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
55 days
Median time to sell
Winter's Landing vs Oakland
Median sold price — 3-yr, 3-mo rolling
▲ 13.3% yr/yr
Homes sold per month
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?+
If you want a quieter, established slice of Orange County with an easy line into Orlando, it fits. Downtown Orlando is roughly 25 minutes and MCO about 33, and the area feeds into West Orange High. It's residential and settled rather than flashy — a good match for buyers who value space and calm.
Is it expensive to buy here?+
It sits at the higher end of the Oakland market — the median sold price over the last 12 months was $850,000. There's no current active inventory, so pricing on the next listing will depend on the home, but recent sales point to a $800K-plus range.
What do homes cost in Winter's Landing?+
With no active listings right now, the clearest signal is the sold data: 4 homes closed in the past year at a median of $850,000. Check the live map for anything new that comes on.
How is the market here?+
It's thin and steady — just 4 sales over the last 12 months, with sellers averaging 97% of their asking price. That combination of low supply and near-full-price sales means well-positioned homes tend to move, so buyers should be ready to act.
What about HOA fees and property taxes?+
We don't have current HOA or tax figures on file for Winter's Landing specifically, so those are worth confirming per property. Nearby communities such as Trailside Station can give a sense of how the area is structured, but always verify the numbers on the exact home before you write an offer.
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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