Westside Cay
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 773 townhomes for sale in Kissimmee · 950 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Westside Cay in Kissimmee, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 7 recorded sales closed at a median of $630,000, $295 per square foot, a median 6 days on market, sellers accepting 100% of original asking. Homes listed or recently sold were built 2024 - 2025 with 8 new construction; 8 of 9 report an HOA (median $449/mo); none of the 9 geocoded homes sit in a FEMA special flood hazard zone (median elevation 118 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $9,600 ($8,990 with the full homestead exemption).
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 September 12, 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 October 24, 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 September 12, 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.
In ZIP 34747 (Kissimmee), 2,599 homes closed in the last 12 months at a median of $460K ($220/sq ft), down 3.8% year over year, with a median 75 days on market. Right now 581 active and 101 pending listings put supply at about 7.3 months - a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.
County records show 7 qualified sales in Westside Cay across 2025 - 2025, median $580,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Westside Cay: of 8 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Kissimmee.
Westside Cay is a community of 8 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
Westside Cay
Westside Cay
Westside Cay
Westside Cay
Westside Cay
Westside Cay
Westside CayPhotos from Stellar MLS listings in Westside Cay; content 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 2026-09-12, 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 contributors.
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 8 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.
What it really costs to own in Westside CayHomes for Sale
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $449/month across 8 MLS listings (most billed monthly; 2026-10-24). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Osceola County is $1,735/yr (2,188 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 8 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2025 across 9 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Westside CayHomes for Sale
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Westside CayHomes for Sale
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Westside CayHomes for Sale will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $449/month (about $5,388/yr) · median of 8 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $449 per month ($5,388 a year) - the median AssociationFee across 8 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, 2026-10.
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 all homes for sale in Kissimmee →
Housing 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Just listed in Westside Cay
The newest homes for sale in Westside Cay right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 2591 Santorini Divide $595,000 · 5 bd · 4.5 ba · 2,133 sq ft · listed Oct 9, 2026 Courtesy of EXP REALTY LLC
- 9058 Hayman Lane $595,000 · 5 bd · 4.5 ba · 2,133 sq ft · listed Sep 16, 2026 Courtesy of EXP REALTY LLC
- 9084 Boracay Court $580,000 · 5 bd · 4.5 ba · 2,134 sq ft · listed Jul 11, 2026 Courtesy of LA ROSA REALTY LLC
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Westside Cay Kissimmee Right Now (3)
All 3 active and pending Westside Cay Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2591 Santorini Divide · $595,000 · 5 bd / 4.5 ba · listed Oct 10, 2026 · listed by Exp Realty Llc
- 9058 Hayman Lane · $595,000 · 5 bd / 4.5 ba · listed Sep 16, 2026 · listed by Exp Realty Llc
- 9084 Boracay Court · $580,000 · 5 bd / 4.5 ba · listed Jul 25, 2026 · listed by La Rosa Realty Llc
More Kissimmee home searches
- All homes for sale in Kissimmee, FL
- Homes for sale in Osceola County, FL
- Kissimmee pool homes for sale
- Kissimmee waterfront homes for sale
- Gated communities in Kissimmee
- Kissimmee golf course homes
- Homes under $300K in Kissimmee
- Homes from $300K to $500K in Kissimmee
- 4-bedroom homes for sale in Kissimmee
- Kissimmee home values: what is my house worth?
Kissimmee guides & data
- Market data
- Cost of living
- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
- Home insurance cost
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
Real estate agent in Kissimmee? Join Momentum in Kissimmee: 100% commission, one $12K cap.
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.
WESTSIDE CAY Market Scorecard
WESTSIDE CAY is currently a buyer's market. About 6.0 months of supply, a median asking price of $595,000, and homes go under contract in about 38 days.
Typical home value in the 34747 ZIP is $399,304, about 3.0% below 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
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?
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?
Where is Westside Cay, and what county is it in?
Is Westside Cay a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| 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 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 Westside Cay fits the bigger picture — live prices, inventory, and Momentum Scores:
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.
Nearby Communities
Explore more neighborhoods near Westside Cay with Momentum Realty’s local guides.