Neighborhood · Longwood, Florida
Sleepy Hollow
Quiet Longwood living, minutes from downtown Orlando
1
Homes for sale
$499,000
Median list price
$261
Avg price / sqft
85
Median days on market
Sleepy Hollow lives up to its name — a low-key residential pocket of Longwood in Seminole County where the pace is calm and the commute is short. You're about 18 minutes from downtown Orlando and 37 from MCO, with neighbors like Sweetwater Oaks, Sweetwater Club and The Springs rounding out the area. Homes here feed into Lyman High School, Rock Lake Middle School, and Altamonte Elementary.
Inventory is genuinely thin — there's currently one active listing at $499,000, so buyers should be ready to move when the right home appears. Over the past year six homes sold at a median of $567,500, with sellers collecting about 99% of asking, which tells you well-priced homes hold their value here. If nothing in Sleepy Hollow fits, it's worth widening the search across Longwood homes for sale and nearby Wildmere.
Sleepy Hollow is a community in Longwood, Florida.
Quick facts
$499,000 – $499K price range
1,913 sqft median home
$25/mo median HOA
6 sold in 12 months
Drive times
On the market now
Homes for sale in Sleepy Hollow
Every active listing inside the Sleepy Hollow boundary
Open full map search →Find your fit
Browse Sleepy Hollow
By feature — on the live map
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 list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 9.9% 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.
What it really costs
Owning here
Owning the median Sleepy Hollow home
≈ $3,064/mo
$499,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$25/mo
Median HOA
From current listings inside the boundary
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 quiet, established Longwood neighborhood in Seminole County with an easy 18-minute drive to downtown Orlando. Homes feed into Lyman High, Rock Lake Middle, and Altamonte Elementary, and it sits alongside respected communities like Sweetwater Oaks. The low HOA and settled feel appeal to buyers who want calm without giving up access to the city.
Is Sleepy Hollow expensive?+
It sits in a comfortable mid-range for the Longwood market. The single active listing is priced at $499,000, and homes over the past year sold at a median of $567,500. At roughly $261 per square foot, you're paying for an established neighborhood rather than new construction.
What do homes cost in Sleepy Hollow?+
The current active listing is $499,000, and the median size across the area runs about 1,913 square feet. Over the last 12 months, six homes closed at a median of $567,500, so recent sales have run a bit higher than the current asking price.
How is the market in Sleepy Hollow?+
It's tight — just one home is active right now, and only six sold in the past year, so opportunities are limited. Homes take a median of 85 days on market, but sellers still collect about 99% of asking, meaning realistic pricing gets results. Buyers should watch Longwood homes for sale closely and be ready to act.
What about HOA and taxes in Sleepy Hollow?+
Carrying costs are light for the area, with a median HOA of about $25 per month. Property taxes run roughly $2,399 per year based on recent data, keeping the overall cost of ownership reasonable.
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.
Never miss a listing
New Sleepy Hollow homes, in your inbox
A daily digest of new Longwood listings — straight from the MLS. Unsubscribe anytime.