WESTSIDE CAY
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
WESTSIDE CAY right now
🔴 Seller-leaning market. 2.0 months of supply and 0% of the inventory already under contract give sellers the pressure advantage.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 August 2, 2026. Confidence: Medium (1 active and pending listings, 7 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 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
WESTSIDE CAY market snapshot (as of August 2, 2026): the median sale price is about $630K ($295 per sq ft over the trailing 12 months of closed sales), a median 6 days on market for closed sales, and 2.0 months of supply, a seller-leaning market.
WESTSIDE CAY is a community of 9 homes in KISSIMMEE, Osceola County, built between 2024 and 2024 (median 2024.0), with a median living area of about 2,160 square feet. 0% 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 WESTSIDE CAY. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WESTSIDE CAYHousing distress & ownership in WESTSIDE CAY, 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 August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in WESTSIDE CAY
Live MLS inventory for WESTSIDE CAY. 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 WESTSIDE CAY listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2025 through 2026. Tap any home to ask about it.
WESTSIDE CAY 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 WESTSIDE CAY
- Clubhouse · reported on 6 of 7 listings
- Fitness Center · reported on 5 of 7 listings
- Gated Community - No Guard · reported on 5 of 7 listings
- Playground · reported on 5 of 7 listings
- Restaurant · reported on 5 of 7 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 WESTSIDE CAY buying strategy.
If we were buying in WESTSIDE CAY 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 WESTSIDE CAY.
A closer look at the WESTSIDE CAY market
At a median of $295 per square foot, WESTSIDE CAY 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 2.0 months of supply, a seller-leaning market. Homes that do trade take a median 6 days on market, useful leverage on any listing that has lingered.
The housing stock is 9 homes built around 2024, and 0% 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 WESTSIDE CAY. 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 WESTSIDE CAY 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 (6.0). Basis: Liquidity & Demand 2.0 months of supply; Owner Commitment 0% owner-occupied; Pricing Power 100.0% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- 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 WESTSIDE CAY 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 WESTSIDE CAY sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WESTSIDE CAY, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your WESTSIDE CAY home worth?
Get a no-obligation home value based on real comparable sales in WESTSIDE CAY, 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 homes for sale in WESTSIDE CAY on the map →
WESTSIDE CAY Market Scorecard
WESTSIDE CAY is currently a no active listings market. Limited supply, a median asking price of n/a.
Go deeper: 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
What is the median home price in WESTSIDE CAY?
How long do homes in WESTSIDE CAY take to sell?
Is WESTSIDE CAY a buyer's or seller's market right now?
How many homes are in WESTSIDE CAY?
What share of WESTSIDE CAY is owner-occupied?
When were the homes in WESTSIDE CAY built?
Do cash buyers compete in WESTSIDE CAY?
Who is the best real estate agent for WESTSIDE CAY?
How do I find a top KISSIMMEE real estate agent who knows WESTSIDE CAY?
Can Momentum Realty connect me with an agent for WESTSIDE CAY?
Nearby Communities
Explore more neighborhoods near WESTSIDE CAY with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2025 (7 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 your area comps.
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