Homes zoned for
Dillard Street Elementary
Historic downtown living with room to grow
34
Homes for sale
$707,250
Median list price
$312
Avg price / sqft
27
Median days on market
The Dillard Street Elementary zone sits close to the heart of Winter Garden, where a walkable historic downtown, brick-lined streets and the West Orange Trail set the pace of daily life. It's a spot that trades theme-park hustle for something more rooted, yet you're roughly 22 minutes from downtown Orlando, 30 from Walt Disney World and 37 from MCO — close enough to the region's jobs and attractions without living on top of them. Families here have options beyond the elementary school too, with feeder paths toward West Orange High and nearby campuses like Horizon High School.
For buyers, the current market is active but not frantic: 35 homes are listed with a median asking price of $719,500, and the range runs from an entry-level $199,999 all the way to $1.49M. Homes are moving in a median of 25 days and sellers are collecting about 98% of asking, so well-priced listings don't linger. Browse the live map to see how the inventory breaks down before you tour.
Dillard Street Elementary is an attendance zone in Winter Garden, Florida.
Quick facts
$199,999 – $1.5M price range
2,185 sqft median home
$72/mo median HOA
$2,566/mo median rent
132 sold in 12 months
Drive times
On the market now
Homes for sale in this zone
View all 34 →
$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
$435,000
208 3RD STREET, WINTER GARDEN
8 bd · 3 ba · 1,750 sqft
$475,000
1553 SPRING RIDGE CIRCLE, WINTER GARDEN
3 bd · 2 ba · 1,729 sqft
$199,999
844 KLONDIKE STREET, WINTER GARDEN
1 bd · 1 ba · 1,300 sqft
$839,000
1707 FULLERS OAK LOOP, WINTER GARDEN
6 bd · 4 ba · 4,181 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
$475,000
1009 SPRING LOOP WAY, WINTER GARDEN
3 bd · 2 ba · 1,497 sqft
$849,988
427 TIERRA VERDE LANE, WINTER GARDEN
4 bd · 3 ba · 2,368 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
132
Sold, last 12 months
$560,000
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
≈ $4,409/mo
$707,250 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
$2,566/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 one of the more grounded pockets of Winter Garden, close to a walkable historic downtown and the West Orange Trail while still connected to the wider region. Families also value the school options nearby, including feeder paths toward campuses like Water Spring Elementary. The 22-minute drive to downtown Orlando makes commuting realistic without giving up the small-town feel.
Is it expensive to buy here?+
It sits at the mid-to-upper end for the area, with a median list price of $719,500 and homes selling around $308 per square foot. That said, the active range spans from $199,999 to $1.49M, so there's genuine room for both entry-level buyers and those shopping the four listings above $1M.
What do homes actually cost?+
Over the last 12 months, 133 homes sold at a median of $560,000, while current asking prices sit higher at a $719,500 median. A typical home here runs about 2,199 square feet, and you can compare live options among Winter Garden homes for sale.
How is the market right now?+
It's steady and competitive but not overheated — homes are going under contract in a median of 25 days, and sellers are averaging 98% of their asking price. With 35 active listings against 133 sales in the past year, well-priced homes tend to move quickly.
What about HOA fees and property taxes?+
Costs here are relatively easy on the wallet, with a median HOA of $72 per month and median property taxes around $4,850 a year. If you're weighing renting versus buying, the median rent in the area runs about $2,567 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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