Waterfront Square
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.
Photo via Stellar MLS
As of September 2026, Waterfront Square in Kissimmee, FL has 1 home for sale. Homes listed or recently sold were built 1985 - 1985; none of the 5 geocoded homes sit in a FEMA special flood hazard zone (median elevation 62 ft).
Waterfront Square is a six-home community, and right now exactly one of those homes is on the market - so any read on pricing or pace here is really a read on a single listing, not a trend. The median living area, just over 5,300 square feet, tells you these are large-format homes built in a tight window between 1985 and 1987, which points to a single development phase rather than ongoing infill.
None of the homes in this community currently carry a homestead exemption, which typically signals non-primary or investment ownership rather than owner-occupied use. Combined with the thin inventory, this is a market where a buyer or seller needs to negotiate on the specifics of the one home available rather than lean on community-wide comps.
Waterfront Square right now
🟡 Balanced market. 3.0 months of supply and 0% 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 July 15, 2026. Confidence: Low (1 active and pending listings, 0 closed sales in 12 months).
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
Waterfront Square Kissimmee is a small enclave of large, mid-1980s-built homes in Osceola County, with inventory so limited that the market functions more like a single-property negotiation than a traditional community trend.
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.
The setting & the homes.
Aerial and on-site photos of Waterfront Square. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Waterfront SquarePhotos from Stellar MLS listings in Waterfront Square; content deemed reliable but not guaranteed.
Who Waterfront Square is best for.
Best for
- A buyer seeking a large-format home and comfortable evaluating it on its own merits rather than by community trend
- A buyer or investor comfortable with a non-homestead ownership pattern typical of this small enclave
- Someone specifically targeting mid-1980s construction with substantial square footage in Osceola County
Probably not for
- A buyer who wants a defined set of community amenities, since none are identified from current MLS listings
- A buyer who relies on active comparable listings to benchmark price, given only one home is currently for sale
- A buyer looking for newer construction or a recently built home
The market around Waterfront Square
Waterfront Square is a small community — 6 recorded sales on file, most recently in 2025 — 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).
ZIP and county figures describe the wider market, not Waterfront Square specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Waterfront Square, 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 Waterfront Square
Live MLS inventory for Waterfront Square. 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 Waterfront Square listings as of 2026-06-22, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Tap any home to ask about it.
Waterfront Square 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.
The Waterfront Square buying strategy.
If we were buying in Waterfront Square 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 Waterfront Square.
A six-home market
With only six homes in the entire community and one currently active, months of supply sitting at 3.0 reflects a balanced posture on paper, but the sample size means it should be treated as informational rather than predictive. There is no listing history here that can reliably tell you how fast homes move or how much room there is on price - you are working with what is in front of you.
The homes themselves share a construction era, 1985 to 1987, and a scale, with median living space above 5,300 square feet. That combination - older build, large footprint - usually means updates and condition vary property to property, and it means the value story for any given home rests heavily on what has been maintained or renovated inside it, not on a community-wide standard finish.
The location and the amenities are priced into every listing in Waterfront Square. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this small, there is no substitute for looking closely at the one home that is actually for sale - its condition, its updates, its actual comparable sales - rather than relying on aggregate stats that a six-home dataset cannot reliably support. We do that work directly instead of pointing you to a market summary that does not really apply.
Waterfront Square 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 Waterfront Square 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 Waterfront Square sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Waterfront Square, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Waterfront Square home worth?
Get a no-obligation home value based on real comparable sales in Waterfront Square, 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 →
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.
WATERFRONT SQUARE Market Scorecard
WATERFRONT SQUARE is currently a seller's market. About 3.0 months of supply, a median asking price of $11,940, and homes go under contract in about 205 days.
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.
Frequently Asked Questions
Is Waterfront Square a buyer's or seller's market right now?
How many homes are in Waterfront Square?
What share of Waterfront Square is owner-occupied?
When were the homes in Waterfront Square built?
Who is the best real estate agent for Waterfront Square?
How do I find a top Kissimmee real estate agent who knows Waterfront Square?
Can Momentum Realty connect me with an agent for Waterfront Square?
Should you buy in Waterfront Square?
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: June 22, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
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 →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Waterfront Square fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
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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.