Kissimmee Highlands
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in KISSIMMEE, FL · median $373,400 · 173 homes for sale in 34741 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 1 closed sale in Kissimmee Highlands 1St Add in Kissimmee, FL, the most recent in July 2026. Across Kissimmee as a whole, 2,431 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,223 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
There is nothing on the market right now in Kissimmee Highlands, and that fact is the whole story at the moment. With zero active listings in the Stellar MLS feed, there is no live inventory to price against and no current asking-price signal to read. Anyone telling you what a home here is 'worth' today is guessing, not analyzing.
For a seller, this is a low-competition window if a home does come up, since there is nothing else to compare it to on the open market. For a buyer, it means patience and a standing search alert rather than an active hunt - you need to be positioned to move the moment something is listed, because right now there is simply nothing to see.
Nearby homes for sale
No active listings inside Kissimmee Highlands 1St Add right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Kissimmee Highlands is a small platted subdivision in Osceola County, and as of this snapshot it shows zero active listings in the MLS, with no community amenities identified from current listing data.
Stellar MLS sales records identify 58 homes in Kissimmee Highlands that have changed hands since 2004, built between 1959 and 1985 (median 1960), with a median living area of about 1,304 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Kissimmee Highlands is best for.
Best for
- A buyer specifically targeting this plat who is willing to set a standing alert and wait for inventory
- An investor or researcher comfortable pulling off-MLS county records to evaluate the area before anything is listed
- A seller who wants to test pricing in a community with essentially no active competition
Probably not for
- A buyer who wants to compare multiple active listings side by side before deciding
- Anyone relying on MLS-listed amenities to shape their decision, since none are currently identified
- A buyer on a tight timeline who cannot wait for a listing to surface
The market around Kissimmee Highlands
Kissimmee Highlands is too small for its own price trend, so here is the market around it.
In ZIP 34741, 299 homes are on the market and 15% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
In ZIP 34741 (KISSIMMEE), 745 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 2.2% year over year, with a median 44 days on market. Right now 201 active and 47 pending listings put supply at about 6.0 months - a balanced market. See the live ZIP 34741 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Kissimmee Highlands specifically. Momentum Research analysis of MLS records.
The Kissimmee Highlands buying strategy.
If we were buying in Kissimmee Highlands today, this is the order of operations we would run for our clients.
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.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
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 Kissimmee Highlands.
A community with no current footprint
The '1st Add' in the name tells you this plat is an original or early addition to a larger Kissimmee Highlands community, which is common in older Osceola County subdivisions that were platted in phases. Beyond that, the MLS record is quiet: no active listings to study for pricing, condition, or lot pattern, and no amenities have been identified from listing data one way or the other.
That absence of data is itself useful information. It suggests this is a small, low-turnover pocket rather than an actively marketed, amenity-driven community. There is no clubhouse, pool, or gated-entry claim to evaluate here - not because those things don't exist, but because nothing currently listed references them. Until a home hits the market, any read on this community has to come from off-MLS research: county records, recent closed sales pulled directly, or local knowledge of the immediate streets.
The location and the amenities are priced into every listing in Kissimmee Highlands. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with no active listings, the value of an agent shifts from 'showing you what's on the market' to 'knowing before it hits the market.' We track new listings the moment they load into the Stellar feed, and we can pull recent closed-sale history directly from county and MLS records rather than waiting on a live listing to tell the story. If something in Kissimmee Highlands is going to move, you want to hear about it the day it's entered, not a week later.
Kissimmee Highlands in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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.
Tools for a Kissimmee Highlands buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Kissimmee Highlands sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Kissimmee Highlands, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Kissimmee Highlands home worth?
Get a no-obligation home value based on real comparable sales in Kissimmee Highlands, 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 all homes for sale in Kissimmee →
Should you buy in Kissimmee Highlands?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2026 (1 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 local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Kissimmee Highlands 1St Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Kissimmee Highlands
Where is Kissimmee Highlands?
Kissimmee Highlands is a community in KISSIMMEE, Osceola County, Florida, ZIP 34741.
Are there homes for sale in Kissimmee Highlands right now?
No active listings inside Kissimmee Highlands at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Kissimmee Highlands have an HOA or CDD?
No HOA is on record for Kissimmee Highlands in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Kissimmee Highlands with Momentum Realty’s local guides.
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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
KISSIMMEE HIGHLANDS 1ST ADD Market Scorecard
KISSIMMEE HIGHLANDS 1ST ADD is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34741 ZIP is $286,616, about 14.2% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.