Neighborhood · Kissimmee, Florida
Pleasant Hill Trails
Larger homes on the quieter side of Kissimmee
3
Homes for sale
$985,000
Median list price
$310
Avg price / sqft
53
Median days on market
Pleasant Hill Trails sits in the southern reach of Kissimmee, in Osceola County, where lot sizes and floor plans run bigger than much of the surrounding market. Homes here average around 3,129 square feet, and pools show up on a good share of listings, giving the neighborhood a spread-out, settled feel. It's a practical base for families too, with assignments to Osceola County School for the Arts, Poinciana High School and Bellalago Charter Academy. Compared to the vacation-rental energy of nearby Storey Lake or Solara, this is a place built for people who actually live here.
The market is small and priced at the upper end for the area — just three active listings with a median list price of $985,000 and homes running about $310 per square foot. Buyers should expect a measured pace: the median home sits 53 days before going under contract, and over the last year sellers collected about 91% of asking. If your budget is more flexible, it's worth comparing against Kissimmee homes for sale more broadly, including value-driven communities like Lake Marion Village, before committing here.
Pleasant Hill Trails is a community in Kissimmee, Florida.
Quick facts
$833,000 – $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
$833,000$838,900
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
Open full map search →Find your fit
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.
Straight answers
Pleasant Hill Trails FAQs
Is Pleasant Hill Trails a good place to live?+
It suits buyers who want space and a full-time residential feel rather than the vacation-rental scene of communities like Solara. Homes are larger — around 3,129 square feet on average — and the area is assigned to well-regarded schools including Osceola County School for the Arts. Disney is about 40 minutes away and Orlando International Airport roughly 46 minutes, so it stays connected without feeling touristy.
Is Pleasant Hill Trails expensive?+
Yes, it sits at the upper end of the Kissimmee market, with a median list price of $985,000 and current listings ranging from $833,000 to $999,999. At about $310 per square foot, you're paying for size and pool-equipped homes. If that stretches your budget, it's worth browsing Kissimmee homes for sale more widely for lower entry points.
What do homes cost in Pleasant Hill Trails?+
Active listings currently run from $833,000 to $999,999, with a median list price of $985,000. Over the last 12 months, homes sold at a median of $900,000. Expect roughly $310 per square foot for the larger floor plans that define this neighborhood.
How is the market here?+
It's a small, slower-moving market — just three active listings and three sales in the past year. Homes take a median of 53 days to go under contract, and sellers are netting about 91% of their asking price. That leaves room for informed buyers to negotiate, unlike faster-turning communities such as Storey Lake.
What about HOA fees and property taxes?+
Property taxes here run a median of about $7,219 per year, in line with homes at this price point. HOA figures aren't currently available for the active listings, so confirm any dues and rules directly with the seller 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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