Neighborhood · Kissimmee, Florida
Pleasant Hill Heights
Space-minded living south of Orlando's theme parks
3
Homes for sale
$559,000
Median list price
$196
Avg price / sqft
59
Median days on market
Pleasant Hill Heights sits in the stretch of Osceola County where lots run larger and the pace settles down, yet Walt Disney World is still about 36 minutes away and Orlando International Airport roughly 42. It's a practical spot for families who want room to spread out — the median home here runs close to 2,901 square feet — while staying within reach of the region's work and play. Families drawn to arts education will note the assigned Osceola County School for the Arts, and nearby communities like Lake Marion Village and Storey Lake round out the broader Kissimmee picture.
The market here is genuinely small and worth reading carefully. There are just 3 active listings right now, with a median list price of $559,000 and homes spanning $499,000 to $699,900. Over the last 12 months only 4 homes sold, at a median of $489,500 — and sellers pulled in about 99% of asking, so there's little room to lowball. Compare that with higher-volume options like Solara if you need more inventory to choose from.
Pleasant Hill Heights is a community in Kissimmee, Florida.
Quick facts
$499,000 – $700K price range
2,901 sqft median home
4 sold in 12 months
Drive times
On the market now
Homes for sale in Pleasant Hill Heights
$499,000
2222 N STEWART STREET, KISSIMMEE
4 bd · 3 ba · 3,452 sqft
$559,000
2749 S STEWART STREET, KISSIMMEE
5 bd · 2 ba · 2,901 sqft
$699,900$719,900
2921 LAKE TOHOPEKALIGA BOULEVARD, KISSIMMEE
3 bd · 2 ba · 2,790 sqft
Every active listing inside the Pleasant Hill Heights boundary
Open full map search →Find your fit
Browse Pleasant Hill Heights
By feature — on the live map
Where the market lives
The numbers that matter
The Pleasant Hill Heights market
4
Sold, last 12 months
$489,500
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
48 days
Median time to sell
Pleasant Hill Heights vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 29.0% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Pleasant Hill Heights boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Pleasant Hill Heights is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Pleasant Hill Heights home
≈ $3,691/mo
$559,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
928
Median age
40
Median income
$87,718
Median home value
$388,400
Beyond the listings
Living in Pleasant Hill Heights
Lifestyles
Top 5% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Culture
Top 10% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Attitudes
Top 10% in the U.S.Home & Leisure
There's no place like home. This activity is highest when people are feeling relaxed, like sharing a meal with friends or enjoying their morning coffee in their own home.
Food & Drink
Top 13% 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.
Hobbies & Interests
Top 17% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
Appearance oriented
Top 17% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Pleasant Hill Heights FAQs
Is Pleasant Hill Heights a good place to live?+
It suits buyers who want space and a calmer setting while staying connected to the Orlando region — Walt Disney World is about 36 minutes out and MCO airport around 42. Homes run large, with a median around 2,901 square feet, and the area is assigned to Osceola County School for the Arts and Liberty High School. If you want a wider range of nearby options, communities like Windsor at Westside sit in the same orbit.
Is Pleasant Hill Heights expensive?+
It's a mid-to-upper price point for the area, with a median list price of $559,000 and active homes ranging from $499,000 to $699,900. Recent sales landed lower, at a median of $489,500, so there's some gap between asking and closing prices. At about $196 per square foot, you're largely paying for the larger floor plans.
What do homes cost in Pleasant Hill Heights?+
Current listings have a median list price of $559,000, spanning roughly $499,000 to $699,900. Homes sold over the past year closed at a median of $489,500, which works out to about $196 per square foot on a typical 2,901-square-foot home. None of the current listings cross the $1M mark.
How is the market right now?+
It's a small, slow-moving market — just 3 homes are active and only 4 sold in the past 12 months. Properties take a median of 59 days to sell, but sellers still collect about 99% of asking, which signals realistic pricing rather than deep negotiating room. Expect limited choice and firm sellers.
What about HOA fees and property taxes?+
Property taxes here run a median of about $6,434 per year, in line with the home values. HOA data isn't available for the current listings, so confirm any community fees on a property-by-property basis. Your agent can pull the exact figures before you make 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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