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 3 closed sales in Kissimmee Highlands 2Nd Add in Kissimmee, FL since 2024, the most recent in June 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 active in Kissimmee Highlands 2Nd Add right now, so there is no live pricing signal to read. That is not unusual for a small, established section of Kissimmee - inventory here tends to move in small batches rather than a steady stream, and a quiet stretch simply means owners are not listing at the moment.
For a buyer, that means patience and a standing search rather than browsing an active list. For a seller, it means less direct in-community competition when something does come up, but also less comparable data to lean on when setting a price - an agent will need to pull from nearby areas and recent history to build the case.
Nearby homes for sale
No active listings inside Kissimmee Highlands 2Nd 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 2Nd Add is a small, established residential section in Kissimmee, Osceola County, with a neighborhood park among its noted amenities.
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
- Buyers with flexible timing who want to be first in line when a home here lists
- Buyers prioritizing a park amenity and an established Kissimmee location over move-in-ready selection today
- Sellers comfortable pricing with limited direct in-community comparables, using broader Kissimmee data instead
Probably not for
- Buyers who need to choose from active listings right now
- Buyers wanting a resort-style amenity package beyond a neighborhood park
- Sellers who need fast, community-specific comparable sales to set a price
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.
Life at Kissimmee Highlands
- Park · reported on 1 of 1 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
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 Quiet Section of Kissimmee
With zero active listings as of this snapshot, Kissimmee Highlands 2Nd Add is not a community where you can currently browse options - it is one where you wait for something to surface or work a targeted search with an agent who will flag it the moment it hits the market.
The one amenity consistently reported across this community's MLS listings is a park, which speaks to a neighborhood built around basic residential infrastructure rather than a resort-style or heavily amenitized layout. Confirm current access and any HOA rules directly, since MLS-reported amenities are not a substitute for verifying with the association.
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 current inventory, the value of an agent is watching the market for you - setting up alerts, knowing when a listing is about to come on, and pulling accurate comparables from the wider Kissimmee area since there is nothing active locally to compare against.
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 2024 (3 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 2Nd 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 2ND ADD Market Scorecard
KISSIMMEE HIGHLANDS 2ND 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.