Pleasant Hill Trails Unit 2
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
23 homesBuilt 1978–2023
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data13 years of closingsFL DOR public recordsUpdated twice daily
Live · Pleasant Hill Trails Unit 2 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
83%
Owner-occupied · Pleasant Hill Trails Unit 2
19 of 23 parcels homesteaded (FL DOR 2025)
17%
Non-owner-occupied · Pleasant Hill Trails Unit 2
incl. 17% trust or LLC-held · 4% out-of-state
23
Homes in the community
23 residential parcels (FL DOR 2025)
Track record · 13 years of records
Est. 1978
Community established
homes built 1978-2023, median 1993 (FL DOR 2025)
1
Failed listings · 2026
peaked at 3 in 2010
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Pleasant Hill Trails Unit 2 is a small inventory pool—23 homes—so any read on this community leans more on physical characteristics than on price trend lines. The most striking data point is size: a median living area of 4,265 square feet puts this well above typical resale stock, and that alone does more to set value here than age or condition.

With homestead exemptions filed on roughly 83% of homes, this is a community built around long-term occupancy rather than turnover or investor holding. Combined with a build era spanning 1978 to 2023 and a median year built of 1993, buyers should expect a mix of original systems and updated construction, and sellers should expect scrutiny on condition and mechanicals rather than location alone.

Best for

  • Buyers prioritizing large living space over community amenities
  • Buyers comfortable evaluating individual homes across a wide range of construction years
  • Buyers planning long-term occupancy in a low-turnover setting

Probably not for

  • Buyers wanting a smaller, more manageable footprint
  • Buyers who want organized community amenities as part of the purchase
  • Buyers seeking a uniform build era with predictable system age across the community

The market around Pleasant Hill Trails Unit 2

Pleasant Hill Trails Unit 2 is a small community — 8 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.

Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Pleasant Hill Trails Unit 2 specifically. Momentum Research analysis of MLS records.

If we were buying in Pleasant Hill Trails Unit 2 today, this is the order of operations we would run for our clients.

1

Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Pleasant Hill Trails Unit 2.

Best Buy
Buyers specifically looking for large-format homes rather than a standard-size resale.
Biggest Risk
Wide age spread means condition and system age vary significantly from home to home.
Sweet Spot
A buyer prioritizing space and willing to evaluate each home individually on condition.
Avoid If
You are seeking a smaller footprint or a community with organized amenities.

Size Over Everything Else

The defining fact about Pleasant Hill Trails Unit 2 is square footage. A median of 4,265 living square feet is large by almost any resale comparison, and it signals that whatever else varies from house to house—vintage, finish level, lot configuration—buyers here are shopping for space first. That changes the math on everything from carrying costs to renovation scope, and it means two homes in this community can differ substantially in feel even if they're a few doors apart.

Age spread compounds that variation. With construction ranging from 1978 through 2023 and a median year built of 1993, the neighborhood holds both older homes likely due for system updates and newer builds with contemporary construction standards. There is no identified community amenity package in current MLS data, so whatever draws a buyer here is the home itself and its size, not a shared clubhouse or recreational feature. The high homestead share—about 83%—also tells you this is not a community with heavy transient or investment-driven turnover; most owners are settled in for the long run, which tends to keep inventory tight and listings less frequent.

The location and the amenities are priced into every listing in Pleasant Hill Trails Unit 2. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

A 23-home community with wide variation in age and no shared amenity baseline is exactly the kind of market where generic comps mislead. We look at each home on its own physical merits—square footage, year built, condition—rather than assume the community label alone tells you what a property is worth.

Pleasant Hill Trails Unit 2 in 15 seconds.

Best forBuyers specifically looking for large-format homes rather than a standard-size resale.
Biggest advantageSubstantial square footage relative to typical Kissimmee resale inventory.
Biggest riskWide age spread means condition and system age vary significantly from home to home.
Sweet spotA buyer prioritizing space and willing to evaluate each home individually on condition.
Avoid ifYou are seeking a smaller footprint or a community with organized amenities.

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • Any club/amenity membership is billed separately

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Pleasant Hill Trails Unit 2 sales matched to your home.

What is your Pleasant Hill Trails Unit 2 home worth?

Get a no-obligation home value based on real comparable sales in Pleasant Hill Trails Unit 2, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

See homes for sale in Pleasant Hill Trails Unit 2 on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Pleasant Hill Trails Unit 2?
The Florida DOR 2025 assessment roll shows 23 homes in Pleasant Hill Trails Unit 2 (public records).
What share of Pleasant Hill Trails Unit 2 is owner-occupied?
83% of Pleasant Hill Trails Unit 2 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Pleasant Hill Trails Unit 2 built?
Homes in Pleasant Hill Trails Unit 2 were built between 1978 and 2023, with a median year built of 1993 (FL DOR 2025 roll).
Who is the best real estate agent for Pleasant Hill Trails Unit 2?
The best agent for Pleasant Hill Trails Unit 2 is one who actively works Kissimmee and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Pleasant Hill Trails Unit 2.
How do I find a top Kissimmee real estate agent who knows Pleasant Hill Trails Unit 2?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Pleasant Hill Trails Unit 2 and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Pleasant Hill Trails Unit 2?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Pleasant Hill Trails Unit 2 purchase or sale - no call center and no pressure.
Buyers prioritizing large living space over community amenitiesExcellent fit
Buyers comfortable evaluating individual homes across a wide range of construction yearsExcellent fit
Buyers planning long-term occupancy in a low-turnover settingExcellent fit
Buyers wanting a smaller, more manageable footprintProbably not
Buyers who want organized community amenities as part of the purchaseProbably not
Buyers seeking a uniform build era with predictable system age across the communityProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34746))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2013 (6 transactions analyzed)

Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.

Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.

Own a home here?

You just read the data. Now see what your home is worth.

The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.

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More Kissimmee & Kissimmee, St. Cloud & Osceola County guides

Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Kissimmee, St. Cloud & Osceola County or the full Neighborhood Finder.

Thinking of selling in PLEASANT HILL TRAILS UNIT 2? 3 recorded closings; median 99 days on market (window ending 2026-08-02). See the Osceola County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
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