Neighborhood · Kissimmee, Florida
Oak Hollow
Central Kissimmee living within reach of the theme parks
1
Homes for sale
$359,900
Median list price
$256
Avg price / sqft
355
Median days on market
Oak Hollow is a compact residential pocket in central Kissimmee, the kind of established neighborhood where modest single-family homes sit close to everyday errands rather than resort gates. It's zoned to a strong school lineup that includes the Kissimmee magnet Osceola County School for the Arts, and the location keeps you well-connected — Orlando International Airport is about 22 minutes out, Universal roughly 26, and Walt Disney World around 31.
The market here is small and slow-moving, which cuts both ways for a buyer. There's just one active listing at $359,900, and homes recently sold at a median of $365,000 with sellers collecting about 99% of asking. If you want more selection or a resort-style setup, nearby communities like Storey Lake and Solara give you room to compare.
Oak Hollow is a community in Kissimmee, Florida.
Quick facts
$359,900 – $360K price range
1,406 sqft median home
8 sold in 12 months
Drive times
On the market now
Homes for sale in Oak Hollow
Every active listing inside the Oak Hollow boundary
Open full map search →The numbers that matter
The Oak Hollow market
8
Sold, last 12 months
$365,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
48 days
Median time to sell
Oak Hollow vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 14.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Oak Hollow boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Oak Hollow is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Oak Hollow home
≈ $2,177/mo
$359,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
681
Median age
40
Median income
$59,652
Median home value
$280,223
Beyond the listings
Living in Oak Hollow
Food & Drink
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
Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Lifestyles
Daily Grind
Whether throwing punches at the boxing club or punching the clock at work, this population likes to talk about their hard work.
Relationships
Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Entertainment
Competitive Nature
These folks have their head in the game. Whether it's creating a card game tournament with friends or cheering on the home team, these people want to win.
Entertainment
Late-night Leisure
Ready to turn up when the sun goes down, this population is looking for nighttime entertainment at home or out on the town.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Oak Hollow FAQs
Is Oak Hollow a good place to live?+
It's a good fit if you want an established central Kissimmee location over a resort-community feel. You're zoned to Osceola County School for the Arts and Mill Creek Elementary, and the commute picture is strong with Orlando International Airport about 22 minutes away and downtown Orlando roughly 28. For more resort-style options nearby, Windsor at Westside is worth a look.
Is Oak Hollow expensive?+
It sits in the mid-range for the area, with the current active listing priced at $359,900 and recent sales landing at a median of $365,000. At roughly $256 per square foot, pricing tracks with modest single-family homes rather than luxury product — there are no active listings above $1M here.
What do homes cost in Oak Hollow?+
The one home on the market is listed at $359,900, and over the past 12 months eight homes sold at a median of $365,000. Median home size is around 1,406 square feet, so you're generally looking at right-sized single-family houses.
How is the market in Oak Hollow?+
It's a slow, steady market with very limited supply — just one active listing and eight sales in the past year. Homes can sit a while, with a median 272 days on market, but sellers still average about 99% of asking when they close, so pricing holds firm.
What about HOA and taxes in Oak Hollow?+
Property taxes are a highlight here, with a median of roughly $846 per year. HOA data isn't currently reported for the neighborhood, so confirm any dues directly on a specific listing before you write an offer.
Keep exploring
More Kissimmee 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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