Neighborhood · Kissimmee, Florida
Oak Run
Established Kissimmee living close to everything Orlando
2
Homes for sale
$369,950
Median list price
$257
Avg price / sqft
4
Median days on market
Oak Run is a compact, settled corner of Kissimmee where homes sit on a comfortable scale — the median footprint here runs about 1,499 square feet — and daily life leans on easy access rather than resort flash. You're roughly 19 minutes from Orlando International, 25 to downtown Orlando, and 28 to Walt Disney World, which makes this a practical base whether you commute, travel often, or work in the theme-park corridor. It's a different feel from the vacation-rental communities nearby like Storey Lake and Solara — more neighborhood, less turnover.
For buyers, the market reality is tight and fast. There are just 2 active listings right now with a median list price of $369,950, and homes here have been moving in about 3.5 days, with sellers collecting an average of 99% of asking. Over the last 12 months 15 homes sold at a median of $360,000, so if Oak Run fits your search, expect to move decisively — and keep the broader Kissimmee homes for sale inventory in view as a backup.
Oak Run is a community in Kissimmee, Florida.
Quick facts
$349,900 – $390K price range
1,499 sqft median home
$2,295/mo median rent
15 sold in 12 months
Drive times
On the market now
Homes for sale in Oak Run
$349,900
2704 KENDALL AVENUE, KISSIMMEE
3 bd · 2 ba · 1,156 sqft
$390,000
1721 FREEMAN DRIVE, KISSIMMEE
3 bd · 2 ba · 1,842 sqft
Every active listing inside the Oak Run boundary
Open full map search →The numbers that matter
The Oak Run market
15
Sold, last 12 months
$360,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
20 days
Median time to sell
Oak Run vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 5.4% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Oak Run boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Oak Run is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Oak Run home
≈ $2,499/mo
$369,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$2,295/mo
Median rent
Homes for rent inside the boundary
Population
1,470
Median age
44
Median income
$63,930
Median home value
$284,523
Beyond the listings
Living in Oak Run
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 Run FAQs
Is Oak Run a good place to live?+
It's an established Kissimmee neighborhood built for everyday living rather than short-term rentals, which gives it a steadier, more residential feel than nearby resort communities. Commuting is easy, with Orlando International about 19 minutes out, downtown Orlando around 25, and Walt Disney World roughly 28 minutes away. Assigned schools include Osceola County School for the Arts, Gateway High School, Denn John Middle School, and Mill Creek Elementary School.
Is Oak Run expensive?+
It's moderately priced for the area, with a median list price of $369,950 and an average of $257 per square foot. That sits below many of the resort-oriented communities nearby, such as Windsor at Westside, making it a practical option for primary-residence buyers.
What do homes cost in Oak Run?+
Current active listings range from $349,900 to $390,000, with a median around $369,950 on a typical 1,499-square-foot home. Over the past 12 months, 15 homes sold at a median price of $360,000, so pricing has stayed consistent between what's listed and what's closing.
How is the market in Oak Run right now?+
It's tight and quick — just 2 active listings, a median of 3.5 days on market, and sellers averaging 99% of their asking price. If you find the right home here, be ready to act fast, and consider watching the wider Kissimmee homes for sale market for additional options.
What about HOA fees and property taxes?+
Median property taxes here run about $4,084 per year. HOA data isn't available for the current listings, so confirm any association dues on a home-by-home basis before you write an offer. For comparison, median rent in the area is around $2,295 a month.
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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