Neighborhood · Kissimmee, Florida
Pleasant Hill Trails
Quiet South Kissimmee living with Orlando within reach
3
Homes for sale
$985,000
Median list price
$311
Avg price / sqft
23
Median days on market
Pleasant Hill Trails sits in the south end of Kissimmee, in Osceola County, where the pace slows down and the lots tend to run larger than the resort-style subdivisions closer to the parks. It's the kind of pocket that draws buyers who want space and a residential feel while staying connected to the wider Kissimmee area, with communities like Lake Marion Village and Solara shaping the broader neighborhood character. Walt Disney World is about 40 minutes out, and Orlando International Airport sits roughly 46 minutes away, so you're close to the action without living in it.
The market here is thin right now, which is worth understanding before you shop. There are just 3 active listings with a median list price of $985,000, and no homes have sold in the past 12 months, so pricing signals are limited and every property really needs to be judged on its own merits. Buyers who like this area often widen their search to nearby options like Storey Lake or Windsor at Westside to compare value.
Pleasant Hill Trails is a community in Kissimmee, Florida.
Quick facts
$838,900 – $1000K price range
3,129 sqft median home
3 sold in 12 months
Drive times
On the market now
Homes for sale in Pleasant Hill Trails
$999,999
3150 APPALOOSA COURT, KISSIMMEE
5 bd · 2.5 ba · 3,796 sqft
$838,900$849,000
3180 CANTER LANE, KISSIMMEE
3 bd · 2 ba · 2,360 sqft
$985,000
4261 TWILIGHT TRAIL, KISSIMMEE
3 bd · 2.5 ba · 3,129 sqft
Every active listing inside the Pleasant Hill Trails boundary
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Browse Pleasant Hill Trails
By feature — on the live map
The numbers that matter
The Pleasant Hill Trails market
3
Sold, last 12 months
$900,000
Median sold price
91%
Sale-to-list ratio
What sellers actually get vs asking
99 days
Median time to sell
Pleasant Hill Trails vs Kissimmee
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Pleasant Hill Trails boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Pleasant Hill Trails 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 Trails home
≈ $6,002/mo
$985,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
610
Median age
39
Median income
$74,135
Median home value
$356,400
Beyond the listings
Living in Pleasant Hill Trails
Attitudes
Top 5% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
Beliefs
Top 7% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Hobbies & Interests
Top 12% in the U.S.Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
Emotional
Top 14% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Entertainment
Top 14% in the U.S.Party Life
The party don't stop until the sun comes up. Loud music, crowds, and shots are a recipe for a great night out for these people.
Lifestyles
Top 15% 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.
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 Trails FAQs
Is Pleasant Hill Trails a good place to live?+
It appeals to buyers who want a residential, lower-key setting in south Kissimmee while staying connected to the Orlando metro. Downtown Orlando is about 53 minutes away and the major theme parks are closer, so you get space without being cut off. Assigned schools include Osceola County School for the Arts and Poinciana High School.
Is Pleasant Hill Trails expensive?+
It sits at the higher end of the Kissimmee market, with a current median list price of $985,000 across the active listings. That's well above the entry-level resort communities in the area, so it's geared toward buyers with a larger budget. For comparison shopping, it's worth also looking at nearby Solara.
What do homes cost in Pleasant Hill Trails?+
Right now there are 3 active listings with a median list price of $985,000. Detailed price-per-square-foot and size data isn't available for the current inventory, so each home is best evaluated individually. Given how few listings there are, pricing can move quickly when something new comes on.
How is the market in Pleasant Hill Trails?+
Inventory is very limited, with just 3 homes active and no recorded sales in the past 12 months. That makes it a thin market where comparable data is scarce, so working with an agent who tracks the broader Kissimmee area matters. Many buyers cast a wider net into communities like Lake Marion Village to find the right fit.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available in the current data for this neighborhood, which is common when there's little active inventory and no recent sales. We'd recommend confirming these numbers directly on any listing you're considering, since they vary by property. Your agent can pull the exact figures during your search.
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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