Neighborhood · Orlando, Florida
Winter Run Crossing
Compact Orlando living close to everything that matters
1
Homes for sale
$398,000
Median list price
$362
Avg price / sqft
43
Median days on market
Winter Run Crossing sits in the heart of Orlando's southwest quadrant, where a quick drive puts you at Universal Orlando or Downtown in about 14 minutes and Orlando International Airport in roughly 23. It's the kind of everyday-practical location that appeals to buyers who want short commutes without paying for a headline address, with neighboring communities like Metro West and the newer energy of Laureate Park shaping the wider area's character. Homes here tend to run smaller and efficient, a fit for first-time buyers, right-sizers, and investors alike.
The market is tight and fast-moving. There's currently just one active listing at $398,000, and over the past year six homes sold at a median of $301,750, with sellers collecting about 98% of asking. With a median of only four days on market, well-priced homes don't linger here — so if you're shopping this pocket, come ready to move alongside the broader Orlando homes for sale picture.
Winter Run Crossing is a community in Orlando, Florida.
Quick facts
$398,000 – $398K price range
1,100 sqft median home
7 sold in 12 months
Drive times
On the market now
Homes for sale in Winter Run Crossing
Every active listing inside the Winter Run Crossing boundary
Open full map search →The numbers that matter
The Winter Run Crossing market
7
Sold, last 12 months
$300,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
16 days
Median time to sell
Winter Run Crossing vs Orlando
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 13.0% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winter Run Crossing boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winter Run Crossing is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winter Run Crossing home
≈ $2,400/mo
$398,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
927
Median age
54
Median income
$64,233
Median home value
$256,600
Beyond the listings
Living in Winter Run Crossing
Appearance oriented
Top 1% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Appearance oriented
Top 2% in the U.S.Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Appearance oriented
Top 3% in the U.S.Men's Style
This population is all about finding the latest in men's style - from fashion to grooming. Captures guys looking to stay on trend and significant others assisting with shopping.
Relationships
Top 4% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Lifestyles
Top 5% in the U.S.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.
Attitudes
Top 6% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
People who close here
Our Orlando experts
Straight answers
Winter Run Crossing FAQs
Is Winter Run Crossing a good place to live?+
It's a solid fit for buyers who prioritize location and value over square footage, with Downtown Orlando and Universal both about 14 minutes away and the airport around 23. Assigned schools include Millennia Gardens Elementary, Westridge Middle, and Oak Ridge High. The area sits near established communities like College Park, giving you plenty of nearby amenities.
Is Winter Run Crossing expensive?+
It's relatively affordable for Orlando. The single active listing is priced at $398,000, but sold homes over the past year came in at a median of $301,750, which lands below many comparable Orlando homes for sale.
What do homes cost in Winter Run Crossing?+
Recent sales had a median price of $301,750, while the current listing is at $398,000 and averages about $362 per square foot. With a typical home size near 1,100 square feet, this is a compact, value-oriented pocket of the market.
How is the market in Winter Run Crossing?+
It's fast and competitive, with a median of just four days on market and sellers averaging 98% of asking. Inventory is thin — there's only one active listing right now against six sales in the past year — so serious buyers should be prepared to act quickly.
What about HOA fees and property taxes?+
Median property tax runs about $1,112 per year, which is light for the area. HOA data isn't available for the current inventory, so confirm any association dues on a specific property before you write an offer.
Keep exploring
More Orlando 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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