Homes zoned for
Dillard Street Elementary
A Winter Garden zone close to everything Orlando
38
Homes for sale
$824,500
Median list price
$346
Avg price / sqft
28
Median days on market
The Dillard Street Elementary attendance zone sits in the heart of Winter Garden, one of West Orange County's most walkable and family-anchored communities. It's an easy launch pad to the rest of the region, with Downtown Orlando about 22 minutes away, Universal roughly 25, and Walt Disney World around 30. Buyers who want a real neighborhood — not just a subdivision — while staying tied into the wider Winter Garden homes for sale market gravitate here.
The market reality today is competitive but not frantic. There are 38 active listings with a median list price of $807,500, and homes are moving at a median of 29 days while sellers collect about 98% of asking. Over the past year 141 homes sold at a median of $560,000, so you'll see a wide spread between entry-level resale and the newer, larger product — worth tracking on the live map as inventory shifts.
Dillard Street Elementary is an attendance zone in Winter Garden, Florida.
Quick facts
$372,500 – $2.2M price range
2,354 sqft median home
$72/mo median HOA
$2,733/mo median rent
141 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 38 →
$850,000
64 E CREST AVENUE, WINTER GARDEN
4 bd · 2 ba · 2,248 sqft
$800,000
214 S WOODLAND STREET, WINTER GARDEN
4 bd · 2 ba · 2,868 sqft
$750,000
921 WESTCLIFFE DRIVE, WINTER GARDEN
4 bd · 2.5 ba · 2,189 sqft
$919,000
129 S PARK AVENUE UNIT 8E, WINTER GARDEN
3 bd · 3.5 ba · 2,030 sqft
$915,000
484 W PLANT STREET, WINTER GARDEN
3 bd · 3.5 ba · 2,242 sqft
$1,157,190
650 MEDORA WAY, WINTER GARDEN
4 bd · 3 ba · 2,902 sqft
$1,137,150
642 MEDORA WAY, WINTER GARDEN
4 bd · 3.5 ba · 2,995 sqft
$899,760
611 SIGLER DRIVE, WINTER GARDEN
4 bd · 3.5 ba · 2,432 sqft
$611,610
636 SIGLER DRIVE, WINTER GARDEN
3 bd · 2.5 ba · 1,634 sqft
$850,000
637 GRASSY STONE DRIVE, WINTER GARDEN
5 bd · 3 ba · 3,241 sqft
$1,390,000
1324 VIC KAY COURT, WINTER GARDEN
5 bd · 3.5 ba · 3,749 sqft
$1,099,000
215 S HIGHLAND AVENUE, WINTER GARDEN
3 bd · 2.5 ba · 2,700 sqft
Every active listing inside the Dillard Street Elementary attendance boundary
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Browse the zone
By feature — on the live map
Where the market lives
The numbers that matter
The Dillard Street Elementary market
141
Sold, last 12 months
$560,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
21 days
Median time to sell
Dillard Street Elementary vs Winter Garden
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 8.2% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Dillard Street Elementary boundary. Rolling medians smooth single-month swings in small communities.
What it really costs
Owning here
Owning the median Dillard Street Elementary home
≈ $5,120/mo
$824,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$72/mo
Median HOA
From current listings inside the boundary
$2,733/mo
Median rent
Homes for rent inside the boundary
Population
11,445
Median age
40
Median income
$85,584
Median home value
$337,602
Beyond the listings
Living in Dillard Street Elementary
Hobbies & Interests
Top 1% 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.
Food & Drink
Top 3% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Lifestyles
Top 6% 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.
Food & Drink
Top 9% in the U.S.Asian Food & Culture
Asian culture has a lot to offer, but the Asian cuisine tends to be the most frequently referenced. This population is talking about Asian dishes, holidays, and drinks.
Hobbies & Interests
Top 10% in the U.S.Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
Food & Drink
Top 10% in the U.S.Trendy Eats
Meals are a social experience, and these foodies take it to the next level. This population can't wait to snap a pic of their plate and share it before chowing down.
Straight answers
Dillard Street Elementary FAQs
Is the Dillard Street Elementary area a good place to live?+
It's a strong pick for buyers who want a connected Winter Garden lifestyle with quick access across the metro — about 22 minutes to Downtown Orlando and 30 to Disney. The area also sits near well-regarded schools like Horizon High School, which adds to its family appeal. With 141 homes sold in the last year, it's an established, active community rather than a quiet outlier.
Is it expensive to buy here?+
It leans toward the upper end of the Winter Garden market, with a median list price of $807,500 and 11 of the 38 active listings priced above $1M. That said, the recent median sold price was $560,000, so there's meaningful room below the headline list numbers if you shop the resale segment.
What do homes cost in this zone?+
Active listings span $372,500 to $2,190,000, averaging about $343 per square foot on a median home size of 2,354 sqft. The median list price is $807,500, while homes actually sold over the past year at a median of $560,000.
How is the market right now?+
It's competitive but measured — homes take a median of 29 days to sell and sellers get about 98% of asking on average. With 38 active listings against 141 sales in the past year, there's steady turnover without a glut of inventory, which you can watch in real time on the live map.
What about HOA fees and property taxes?+
HOA costs are light here, with a median of about $72 per month, and many resale homes carry little or no HOA at all. Median property tax runs around $5,925 per year, and if you're weighing a rental, the median rent is about $2,733 per month.
Keep exploring
Other Winter Garden school zones
Homes matched to the official attendance boundary — school zoning changes; always verify with the district. 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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