Stepping Stone
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in KISSIMMEE, FL · median $373,400 · 204 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 2026-09-12, 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).
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 12, 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 12. Confidence: Low (4 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 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 12, 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), 723 homes closed in the last 12 months at a median of $300K ($171/sq ft), down 2.0% year over year, with a median 49 days on market. Right now 171 active and 77 pending listings put supply at about 4.8 months - a balanced market. See the live ZIP 34758 housing market and the Osceola County market.
Stellar MLS sales records identify 168 homes in Stepping Stone that have changed hands since 2019, built between 2018 and 2024 (median 2022), with a median living area of about 2,106 sq ft and a typical 4-bedroom, 2.5-bath layout; 98% 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.
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
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Stepping StonePhotos 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 12 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.
STEPPING STONE Market Scorecard
STEPPING STONE is currently a strong seller's market. About 2.4 months of supply, a median asking price of $370,000, and homes go under contract in about 3 days.
Typical home value in the 34758 ZIP is $311,140, about 7.0% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Stepping Stone Kissimmee, 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 2026-09-14, 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.
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 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 3 factors (7.1). Basis: Recent Direction -8.4% year-over-year; Liquidity & Demand 2.4 months of supply; 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 18 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 18 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?
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?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| 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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