David Ramirez
Map of Oak Hollow
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Neighborhood · Kissimmee, Florida

Oak Hollow

Steady Kissimmee living within reach of everything

2

Homes for sale

$379,950

Median list price

$228

Avg price / sqft

246

Median days on market

Search Oak Hollow on the map

Oak Hollow is a small residential pocket of Kissimmee in Osceola County, the kind of place where homes sit on modest lots and the pace stays quiet. It's zoned to a strong local lineup that includes Osceola County School for the Arts and Mill Creek Elementary School, and the location does a lot of quiet work: Orlando International Airport is about 22 minutes out, Universal Orlando roughly 26, and Walt Disney World around 31. If you want to be near the Kissimmee homes for sale market without paying resort-community premiums, this is a practical corner of it.

The market here is thin and slow-moving, which cuts both ways for a buyer. Just two homes are active right now, with a median list price of $379,950 and a median 219 days on market — sellers aren't in a hurry, but neither is the demand pushing them. Over the past year seven homes sold at a median of $365,000, and sellers collected about 99% of asking, so there's little fat to negotiate away once a home is priced right. Nearby options like Lake Marion Village and Storey Lake are worth a look if you want more inventory to compare against.

Oak Hollow is a community in Kissimmee, Florida.

Quick facts

$359,900$400K price range

1,704 sqft median home

7 sold in 12 months

Drive times

Orlando Int’l Airport (MCO)22 min
Universal Orlando26 min
Downtown Orlando28 min
Walt Disney World31 min

On the market now

Homes for sale in Oak Hollow

Every active listing inside the Oak Hollow boundary

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Find your fit

Browse Oak Hollow

Where the market lives

1
1
$300K–$400K$400K–$500K

The numbers that matter

The Oak Hollow market

7

Sold, last 12 months

$365,000

Median sold price

99%

Sale-to-list ratio

What sellers actually get vs asking

31 days

Median time to sell

Oak Hollow vs Kissimmee

Median list price

Oak Hollow$380K
Kissimmee Co.$380K

Price per sqft

Oak Hollow$228
Kissimmee Co.$216

Days on market

Oak Hollow246d
Kissimmee Co.45d

Median sold price — 3-yr, 3-mo rolling

14.1% yr/yr

$300K$350K$400KJul ’23Mar ’26

Homes sold per month

023Jul ’23Mar ’26

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

$2,302/mo

Principal & interest $2,002
Property tax $90
Insurance (est.) $210

$379,950 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

Straight answers

Oak Hollow FAQs

Is Oak Hollow a good place to live?+

It's a quiet residential neighborhood in Kissimmee with an easy commute footprint — about 22 minutes to Orlando International Airport and 28 to downtown Orlando. Families often value the school zoning, which includes Osceola County School for the Arts and Mill Creek Elementary School. It suits buyers who want steady residential living rather than a resort or vacation-rental setting.

Is Oak Hollow expensive?+

Not by Central Florida standards — the median list price is $379,950 and recent sales landed at a median of $365,000. Property taxes are light too, at roughly $1,082 a year. Compared with resort-style communities like Solara, it reads as an affordable, no-frills residential choice.

What do homes cost in Oak Hollow?+

Active listings currently range from $359,900 to $400,000, with a median of $379,950 and an average of about $228 per square foot. Homes here run around 1,704 square feet at the median, so you're generally looking at right-sized single-family properties rather than large estates.

How is the market in Oak Hollow right now?+

It's small and slow — just two homes are active and the median time on market is 219 days. That said, the seven homes sold over the past year fetched about 99% of asking, so well-priced homes still trade close to list. Buyers get time to think, but there's limited room to lowball once a seller has priced correctly.

What about HOA fees and taxes in Oak Hollow?+

Property taxes are the main recurring cost, with a median of about $1,082 per year. HOA data isn't available for this neighborhood in the current figures, so confirm any association dues directly on a specific listing. If HOA structure matters to you, communities like Windsor at Westside publish clearer fee schedules for comparison.

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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