Homes zoned for
Dillard Street Elementary
Historic downtown living with a family address
38
Homes for sale
$667,500
Median list price
$337
Avg price / sqft
26
Median days on market
The Dillard Street Elementary zone puts you in the heart of Winter Garden, one of the most walkable pockets in west Orange County, where downtown's brick streets and the West Orange Trail set the daily pace. It's a mix of established neighborhoods and newer builds, and its schools connect to strong nearby options like West Orange High and the newer Horizon High School corridor.
For buyers, this is a competitive but reachable market: there are currently 39 active listings across the zone, and homes are moving in about 25 days. If you're comparing against the broader picture of Winter Garden homes for sale, start with the live map to see exactly what's on the market before you tour.
Dillard Street Elementary is an attendance zone in Winter Garden, Florida.
Quick facts
$255,000 – $2.3M price range
2,319 sqft median home
$72/mo median HOA
$2,951/mo median rent
138 sold in 12 months
On the market now
Homes for sale in this zone
View all 38 →
$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
$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
$450,000
721 S WOODLAND STREET, WINTER GARDEN
2 bd · 1 ba · 1,034 sqft
$480,000
14501 GROVE # 3425, Winter Garden FL 34787, WINTER GARDEN
2 bd · 2 ba
$450,000
217 W STORY ROAD, WINTER GARDEN
3 bd · 2 ba · 1,120 sqft
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
138
Sold, last 12 months
$560,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
22 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
≈ $4,249/mo
$667,500 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
$2,951/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 a walkable, family-oriented slice of Winter Garden with access to schools like Water Spring Elementary. The area balances historic downtown character with newer construction, and 138 homes have sold here in the past year — a sign of steady, real demand.
Is it expensive to buy here?+
The median list price is $625,000, and homes average $333 per square foot on a median size of about 2,259 sqft. There's genuine range, though — active listings start at $165,000 and climb to nearly $2.35 million, with nine homes currently priced above $1 million.
What do homes cost in this zone?+
Right now the median asking price is $625,000, while the median sold price over the last 12 months came in at $560,000. Sellers are averaging 98% of asking, so buyers should expect to negotiate close to list on well-priced homes.
How is the market moving?+
It's active and fairly quick: the median days on market is 25, and 138 homes have closed in the past year. With 39 active listings today, you can compare available inventory against the neighboring Water Spring Middle School area to gauge pace.
What about HOA fees and property taxes?+
HOA costs are on the lower side here, with a median of $72 per month, and only one active listing is in a gated community. Median annual property tax runs about $4,920, and if you're weighing renting first, median rent in the zone is around $2,951 a 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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