Westside
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in KISSIMMEE, FL · median $373,400 · 617 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 6 recorded sales closed at a median of $412,000, $240 per square foot, a median 110 days on market, sellers accepting 93% of original asking. Homes listed or recently sold were built 2007 - 2008; 8 of 8 report an HOA (median $142/mo); 5 of the 8 geocoded homes sit in a FEMA special flood hazard zone (median elevation 115 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $6,280 ($5,670 with the full homestead exemption).
Westside in Kissimmee is a small, tightly built pocket of 68 homes, all constructed within a narrow window between 2007 and 2013, with a median year built of 2008. That consistency means buyers are largely comparing homes of similar age and construction era rather than a mix of decades, which keeps condition and updates as the main price differentiator rather than structural vintage.
With zero active listings in this snapshot, there is nothing currently on the market to benchmark against in real time. The most recent closings over the trailing six-month window show a median price of $412,000 and a median days-on-market of just over 110 days - a slower absorption pace that suggests sellers here should price with patience in mind, and buyers who do find something listed may have more room to negotiate on timeline than on price.
The 60-Second Overview
Westside market snapshot (as of September 12, 2026): the median sale price is about $412K ($240 per sq ft over the trailing 12 months of closed sales), and a median 111 days on market for closed sales.
In ZIP 34747 (KISSIMMEE), 2,598 homes closed in the last 12 months at a median of $458K ($220/sq ft), down 3.9% year over year, with a median 74 days on market. Right now 552 active and 96 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.
Westside is a community of 68 homes in Kissimmee, Osceola County, built between 2007 and 2013 (median 2008.0), with a median living area of about 2,405 square feet. 31% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a compact, single-era community where nearly all homes share a similar age and general size profile, making it a straightforward comparison set once inventory appears.
The setting & the homes.
Aerial and on-site photos of Westside. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WestsidePhotos from Stellar MLS listings in Westside; content deemed reliable but not guaranteed.
Who Westside is best for.
Best for
- Buyers who want a larger, similarly built home and are comfortable waiting for the right listing to surface
- Owner-occupant buyers planning to stay long term in a deed-restricted, single-era community
- Buyers focused on square footage per dollar rather than the newest possible construction
Probably not for
- Buyers who need to close quickly and cannot wait out a market with no current inventory
- Buyers who want a wide range of floor plans, ages, or price points to choose from
- Investors seeking a fast-turnover rental market, given the higher share of owner-occupied homes
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 ($412K) IS the median in the snapshot above.
Windows contain 0 to 6 sales each (6 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 2016 through 2026. Deemed reliable but not guaranteed.
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 PRCL E TUSCANY Market Scorecard
WESTSIDE PRCL E TUSCANY is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34747 ZIP is $400,438, about 3.4% 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 WESTSIDE PRCL E TUSCANY, 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 Westside
Live MLS inventory for Westside. 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 listings as of 2026-09-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2016 through 2026. Tap any home to ask about it.
Westside 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
- Deed Restrictions · reported on 2 of 4 listings
- Cable TV · reported on 1 of 4 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.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Westside K-8 · Elementary
- Horizon Middle · Middle
- Celebration High · High
Zoned schools reflect the assignments reported on recent Westside listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Westside address.
Shop the zone: Homes zoned for Celebration High High School
The Westside buying strategy.
If we were buying in Westside 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 Westside.
A Narrow Build Window, A Narrow Market
The homes here run larger, with a median living area of 2,405 square feet, and the median price per square foot sits at $239.72 - figures that point to homes with more livable space per household than a typical starter product. Roughly 31% of homes carry a homestead exemption, indicating a meaningful share of owner-occupied ownership rather than a market dominated by short-term rental or investor churn.
The deed-restricted structure here comes with cable TV included among the reported community amenities, though as with any HOA-governed community, buyers should confirm current dues, rules, and access specifics directly with the association rather than relying on listing history. With no active listings in this snapshot, current opportunity depends entirely on watching for new inventory as it comes to market.
The location and the amenities are priced into every listing in Westside. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this small, with no current listings and a build history confined to a single window, pricing a home correctly means understanding exactly how the last handful of closings compared on size, condition, and time on market. We track that closing history in Osceola County closely so sellers do not underprice a larger-than-typical home, and buyers do not overpay for a listing that has not yet reflected the slower current pace.
Westside in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $142/month (about $1,704/yr) · median of 18 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $142 per month ($1,704 a year) - the median AssociationFee across 18 MLS records, normalised to a monthly figure; most are billed quarterly. 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 Westside 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 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Westside, 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 home worth?
Get a no-obligation home value based on real comparable sales in Westside, 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 →
Frequently Asked Questions
What is the median home price in Westside?
How long do homes in Westside take to sell?
How many homes are in Westside?
What share of Westside is owner-occupied?
When were the homes in Westside built?
Who is the best real estate agent for Westside?
How do I find a top Kissimmee real estate agent who knows Westside?
Can Momentum Realty connect me with an agent for Westside?
Should you buy in Westside?
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: 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 2016 (13 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 →
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See how Westside fits the bigger picture — live prices, inventory, and Momentum Scores:
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