Homes zoned for
Dillard Street Elementary
Historic downtown living with an easy Orlando commute
35
Homes for sale
$799,000
Median list price
$328
Avg price / sqft
19
Median days on market
The Dillard Street Elementary zone sits close to the heart of Winter Garden, a corner of Orange County where brick streets, the West Orange Trail, and a walkable downtown set the tone. It's the kind of pocket where you can grab a Saturday farmers-market coffee and still be at Winter Garden homes for sale that range from cottage-scale to newer builds. Downtown Orlando is about 22 minutes out, Universal roughly 25, and Walt Disney World around 30 — central to everything without living on top of it.
For buyers, this is a market with real spread. Active list prices run from just under $200,000 to $1.35 million, with a median around $800,000, while homes that actually closed over the past year did so at a median of $552,500 — a reminder to read the sold data, not just the asking prices. Homes move at a healthy clip (about 29.5 days on market) and sellers are collecting 98% of asking, so serious buyers should come prepared. You can watch inventory shift on the live map, and families weighing the long game often look ahead to West Orange High as part of the picture.
Dillard Street Elementary is an attendance zone in Winter Garden, Florida.
Quick facts
$199,999 – $1.5M price range
2,199 sqft median home
$82/mo median HOA
$2,750/mo median rent
133 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 35 →
$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
$750,000
301 VALENCIA COURT, WINTER GARDEN
4 bd · 2.5 ba · 2,029 sqft
$719,500
502 PALM DRIVE, WINTER GARDEN
4 bd · 2.5 ba · 3,009 sqft
$611,610
636 SIGLER DRIVE, WINTER GARDEN
3 bd · 2.5 ba · 1,634 sqft
$435,000
208 3RD STREET, WINTER GARDEN
8 bd · 3 ba · 1,750 sqft
$199,999
844 KLONDIKE STREET, WINTER GARDEN
1 bd · 1 ba · 1,300 sqft
$495,000$500,000
516 S HIGHLAND AVENUE, WINTER GARDEN
3 bd · 2 ba · 1,716 sqft
$469,900
113 W DIVISION STREET, WINTER GARDEN
4 bd · 2 ba · 1,487 sqft
$288,000
225 1ST STREET, WINTER GARDEN
3 bd · 1 ba · 1,020 sqft
$915,000
484 W PLANT STREET, WINTER GARDEN
3 bd · 3.5 ba · 2,242 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
133
Sold, last 12 months
$555,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
25 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
▲ 5.2% 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
≈ $4,900/mo
$799,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$82/mo
Median HOA
From current listings inside the boundary
$2,750/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 if you want proximity to downtown Winter Garden and easy access across Orlando — about 22 minutes to downtown and 30 to Disney. The area blends historic charm with newer construction, and families often factor in nearby schools like Horizon High School when planning ahead. With 138 homes sold in the past year, it's an active, established community.
Is it expensive to buy here?+
It depends on where you look — active listings range from $199,999 to $1,349,000, with a median list price of $800,000. The more grounded number is the median sold price of $552,500 over the last 12 months, which reflects what buyers actually paid. There are five homes currently listed above $1 million, so the top end is real but not the whole story.
What do homes cost per square foot?+
Average price is about $328 per square foot, and the median home runs around 2,285 square feet. That combination is why so many properties land in the mid-to-high five figures per year for closed sales, with newer builds and pool homes pushing higher.
How is the market right now?+
It's moving briskly — the median days on market is 29.5, and sellers are averaging 98% of their asking price. With 28 active listings including four new-construction options, buyers have choices but should expect competition on well-priced homes.
What about HOA fees and property taxes?+
Fees here are light on the HOA side, with a median of about $78 per month, and only one active listing is in a gated community. Property taxes run a median of roughly $6,073 per year. If you're weighing renting first, the median rent in the area is around $2,900 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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