Stepping Stone
Homes for Sale in Kissimmee, FL
All 2,959 homes for sale in KISSIMMEE, FL · median $374,000 · 202 homes for sale in 34758 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Stepping Stone in Kissimmee, FL has 1 home for sale. Over the 12 months ending 2026-09-20, 4 recorded sales closed at a median of $343,500, $162 per square foot, a median 21 days on market, sellers accepting 100% of original asking (-8% versus the prior year). Homes listed or recently sold were built 2019 - 2023; 7 of 7 report an HOA (median $83/mo); none of the 7 geocoded homes sit in a FEMA special flood hazard zone (median elevation 76 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,230 ($4,630 with the full homestead exemption).
| Location | KISSIMMEE, Osceola County, FL · ZIP 34758 |
|---|---|
| Homes in the community | 470 (FL DOR 2025 assessment roll) |
| Years built | 2018–2024 (median 2022) |
| Typical living area | 2,405 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Playground, Dog Park, Fitness Center, Pool, Clubhouse, Deed Restrictions |
| Sale prices, last 12 months | $343,500 median across 4 closed sales · $162 per sq ft · -8.4% vs the prior 12 months |
| Days on market (closed sales) | 21 median |
| For sale right now | 1 active, 1 pending · median asking $370,000 · 2.4 months of supply |
| Owner-occupied (homestead) share | 64% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Stepping Stone key facts,” movewithmomentum.com/neighborhoods/stepping-stone-kissimmee, data as of September 20, 2026.
Last 30 days in Stepping Stone: 1 new listing (median asking $370,000), 1 under contract right now. As of September 28, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Stepping Stone right now
🟡 Balanced market. 2.4 months of supply and 50% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Medium (2 active and pending listings, 4 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($344K) is down 8.4% from the prior 12 months ($375K). With about 17 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Low (4 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 28, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Stepping Stone market snapshot (as of September 20, 2026): the median sale price is about $344K ($162 per sq ft over the trailing 12 months of closed sales), a median 22 days on market for closed sales, and 2.4 months of supply, a balanced market. The trailing-12-month median is down 8% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
In ZIP 34758 (KISSIMMEE), 725 homes closed in the last 12 months at a median of $305K ($169/sq ft), down 3.7% year over year, with a median 48 days on market. Right now 176 active and 81 pending listings put supply at about 4.7 months - a balanced market. See the live ZIP 34758 housing market and the Osceola County market.
County records show 46 qualified sales in Stepping Stone across 2024 - 2025 (36 in 2024, 10 in 2025), median $400,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Stepping Stone is a community of 470 homes in Kissimmee, Osceola County, built between 2018 and 2024 (median 2022), with a median living area of about 2,405 square feet. 64% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Stepping Stone. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Stepping Stone; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($344K) IS the median in the snapshot above, and the move from 2025 ($375K) IS the -8.4% one-year change.
Windows contain 0 to 47 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Deemed reliable but not guaranteed.
29% of homes for sale in ZIP 34758 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-26).
Stepping Stone Market Scorecard
Stepping Stone is currently a balanced market. About 2.4 months of supply, a median asking price of $370,000, and homes go under contract in about 3 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Stepping Stone, KISSIMMEE
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Stepping Stone
Live MLS inventory for Stepping Stone. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Stepping Stone listings as of 2026-09-26, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Tap any home to ask about it.
Every Home for Sale in Stepping Stone Kissimmee Right Now (2)
All 2 active and pending Stepping Stone Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 370 Quarry Rock Circle · $370,000 · 4 bd / 2.5 ba · listed Sep 7, 2026 · listed by La Rosa Realty Internacional L
- 124 Citrine Loop · $334,500 · 4 bd / 2 ba · pending · listed Aug 11, 2026 · listed by Preferred Real Estate Brokers Ii
Stepping Stone on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Stepping Stone
- Playground · reported on 4 of 6 listings
- Park · reported on 2 of 6 listings
- Deed Restrictions · reported on 2 of 6 listings
- Dog Park · reported on 2 of 6 listings
- Fitness Center · reported on 2 of 6 listings
- Pool · reported on 2 of 6 listings
- Recreation Facilities · reported on 1 of 6 listings
- Clubhouse · reported on 1 of 6 listings
- Tennis Court(s) · reported on 1 of 6 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 Stepping Stone buying strategy.
If we were buying in Stepping Stone 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 Stepping Stone.
A closer look at the Stepping Stone market
At a median of $162 per square foot, Stepping Stone prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 2.4 months of supply, a balanced market and the trailing-12-month median down 8% year over year. Homes that do trade take a median 22 days on market, useful leverage on any listing that has lingered.
The housing stock is 470 homes built between 2018 and 2024, and 64% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Stepping Stone. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Stepping Stone buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (6.9). Basis: Recent Direction -8.4% year-over-year; Liquidity & Demand 2.4 months of supply; Owner Commitment 64% owner-occupied; Pricing Power 99.6% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $79/month (about $948/yr) · median of 96 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $79 per month ($948 a year) - the median AssociationFee across 96 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
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 Stepping Stone 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 Stepping Stone sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Stepping Stone, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Stepping Stone home worth?
Get a no-obligation home value based on real comparable sales in Stepping Stone, 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 →
Recently off market in Stepping Stone
Homes in Stepping Stone that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 404 Quarry Rock Circle · off market
Frequently Asked Questions
What is the median home price in Stepping Stone?
How long do homes in Stepping Stone take to sell?
Is Stepping Stone a buyer's or seller's market right now?
How many homes are in Stepping Stone?
What share of Stepping Stone is owner-occupied?
When were the homes in Stepping Stone built?
Who is the best real estate agent for Stepping Stone?
How do I find a top Kissimmee real estate agent who knows Stepping Stone?
Can Momentum Realty connect me with an agent for Stepping Stone?
Where is Stepping Stone, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 26, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (9 streets, ZIP 34758)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2021 (102 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.
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See how Stepping Stone fits the bigger picture — live prices, inventory, and Momentum Scores:
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