Neighborhood · Longwood, Florida
Sleepy Hollow
Established Longwood living with quick Orlando access
Sleepy Hollow sits in the heart of Longwood in Seminole County, a mature residential pocket surrounded by well-known communities like Sweetwater Oaks, The Springs, and Wildmere. It's the kind of place where you're 18 minutes from downtown Orlando and 37 minutes from MCO, but still tucked into a quieter, tree-lined stretch of Central Florida. Kids here are zoned for Altamonte Elementary, Rock Lake Middle, and Lyman High School.
The market reality is simple: this is a low-turnover neighborhood where homes don't come up often. There are currently zero active listings, and only 5 homes changed hands over the past 12 months. When they do sell, the numbers tell the story — a median sold price of $550,000, with sellers pulling in about 98% of asking. If you want in, you'll need to be ready to move when a listing hits, and it helps to keep an eye on nearby Longwood homes for sale too.
Sleepy Hollow is a community in Longwood, Florida.
Quick facts
6 sold in 12 months
Drive times
On the market now
Homes for sale in Sleepy Hollow
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Sleepy Hollow boundary
Open full map search →The numbers that matter
The Sleepy Hollow market
6
Sold, last 12 months
$567,500
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
14 days
Median time to sell
Sleepy Hollow vs Longwood
Median sold price — 3-yr, 3-mo rolling
▼ 35.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Sleepy Hollow boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Sleepy Hollow is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
309
Median age
44
Median income
$69,702
Median home value
$314,400
Beyond the listings
Living in Sleepy Hollow
Food & Drink
Top 2% 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.
Food & Drink
Top 2% 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.
Food & Drink
Top 5% 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.
Food & Drink
Top 7% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
Food & Drink
Top 8% in the U.S.Hops & Brews
Thirst isn't the only reason this population looks for a good brew. From beer drinkers on a budget to the millennial craft beer enthusiast, these men and women are passionate about different kinds of beer and how it's made.
Entertainment
Top 14% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Straight answers
Sleepy Hollow FAQs
Is Sleepy Hollow a good place to live?+
It's a mature, low-turnover Longwood neighborhood with easy access to downtown Orlando in about 18 minutes and MCO in roughly 37. Families are drawn to the Seminole County school zoning — Altamonte Elementary, Rock Lake Middle, and Lyman High. It sits among well-established communities like Sweetwater Oaks, which speaks to the area's steady residential character.
Is Sleepy Hollow expensive?+
Homes here trade at a median sold price of $550,000 based on the last 12 months, which puts it solidly in Longwood's move-up range. Sellers have been getting about 98% of their asking price, so there isn't much room to lowball. It's not entry-level, but it's reasonable for the location and lot sizes.
What do homes cost in Sleepy Hollow?+
Over the past year, the median sold price was $550,000 across 5 closed sales. There are no active listings at the moment, so pricing is best judged off those recent closings. If nothing is available here, it's worth scanning nearby Longwood homes for sale for comparable options.
How is the market in Sleepy Hollow?+
It's a tight, low-inventory market — currently zero active listings and just 5 homes sold in the last 12 months. Sellers are averaging 98% of asking, which signals healthy demand and little negotiating slack. Buyers should be pre-approved and ready to act quickly when something lists.
What about HOA fees and property taxes?+
We don't have current HOA or property tax figures published for Sleepy Hollow specifically, so those are worth confirming per property before you write an offer. Fees can vary depending on the exact section and community. A local agent can pull the exact assessments and tax history once you're targeting a home, or look at nearby Wildmere for a sense of the area.
Keep exploring
More Longwood neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. 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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