Homes zoned for
Dillard Street Elementary
Historic-district living close to downtown Winter Garden
40
Homes for sale
$730,000
Median list price
$338
Avg price / sqft
29
Median days on market
The Dillard Street Elementary zone puts you in the heart of Winter Garden, a pocket of Orange County known for its walkable historic downtown, brick-paved streets, and easy access to the West Orange Trail. It's the kind of community where you can bike to a Saturday farmers market and still be 22 minutes from downtown Orlando or 30 minutes from Walt Disney World. Families weigh the whole ladder of nearby schools here, from Water Spring Elementary up through West Orange High and Horizon High School.
For buyers today, this is an active but disciplined market. There are 40 active listings across a wide spread — from $255,000 to $2,190,000 — with a median list price of $730,000, and homes are moving in about 26 days with sellers collecting 98% of asking. Browse the full range of Winter Garden homes for sale or narrow the search on the live map to see what fits.
Dillard Street Elementary is an attendance zone in Winter Garden, Florida.
Quick facts
$255,000 – $2.2M price range
2,354 sqft median home
$72/mo median HOA
$2,800/mo median rent
139 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 40 →
$800,000
214 S WOODLAND STREET, WINTER GARDEN
4 bd · 2 ba · 2,868 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 · 2,652 sqft
$750,000
921 WESTCLIFFE DRIVE, WINTER GARDEN
4 bd · 2.5 ba · 2,189 sqft
$499,990
1815 AMERICUS MINOR DRIVE, WINTER GARDEN
4 bd · 2 ba · 2,199 sqft
$950,000
434 VALLEY VIEW DRIVE, WINTER GARDEN
3 bd · 2.5 ba · 2,765 sqft
$919,000
129 S PARK AVENUE UNIT 8E, WINTER GARDEN
3 bd · 3.5 ba · 2,030 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
$480,000
14501 GROVE # 3425, Winter Garden FL 34787, WINTER GARDEN
2 bd · 2 ba
Every active listing inside the Dillard Street Elementary attendance boundary
Open full map search →Find your fit
Browse the zone
By feature — on the live map
Where the market lives
The numbers that matter
The Dillard Street Elementary market
139
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
≈ $4,578/mo
$730,000 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
$2,800/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 zone a good place to live?+
It's a strong fit for buyers who want walkable historic Winter Garden charm with fast access to Orlando's job and entertainment centers — downtown is about 22 minutes and Disney around 30. Families also value the surrounding school options, which range from elementary through high school.
Is it expensive to buy here?+
It sits on the higher side for the region, with a median list price of $730,000 and an average of $339 per square foot. That said, the range is wide — active listings start at $255,000 and stretch to $2,190,000 — so there's genuine choice at different budgets.
What do homes cost in this area?+
The median list price is $730,000 on a median home size of about 2,354 square feet, while homes that actually sold over the past year had a median sold price of $560,000 across 139 sales. Eleven of the 40 current listings are priced above $1 million, which pulls the list-side median up.
How is the market right now?+
It's steady and competitive: the median days on market is just 26, and sellers are getting about 98% of asking on average. With 40 active listings against 139 sales in the past year, buyers should be ready to move on well-priced homes.
What about HOA fees and property taxes?+
The median HOA runs about $72 per month, which is modest, and the median property tax is roughly $5,406 per year. If you're weighing renting first, the median rent in the area is around $2,800 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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