Ventura at Windsor Hills Windsor Hills
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.
As of September 2026, the MLS records 1 closed sale in Ventura At Windsor Hills Windsor Hills in Kissimmee, FL, the most recent in July 2026. Across Kissimmee as a whole, 2,431 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,223 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
Part of the Windsor Hills master-planned community in Kissimmee, FL — see all Windsor Hills homes for sale (34 listings across 4 villages and sections in the MLS).
There is no active inventory in Ventura at Windsor Hills as of this snapshot, so there is no current asking-price signal to read. That is a data point in itself: this is a small, gated section within Windsor Hills, and it does not turn over listings constantly.
For a buyer, that means patience and a standing search rather than a browse-and-buy approach. For an owner considering a sale, it means testing the market with a clear-eyed look at recent comparable closings in the broader Windsor Hills area rather than assuming a quick, easy comp exists inside this specific pocket.
Nearby homes for sale
No active listings inside Ventura At Windsor Hills Windsor Hills right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Ventura at Windsor Hills is a gated enclave within the larger Windsor Hills community in Kissimmee, Osceola County, built around shared clubhouse, pool, and court amenities rather than a large standalone product line.
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.
Who Ventura at Windsor Hills Windsor Hills is best for.
Best for
- Buyers set on Windsor Hills who want the extra layer of a guarded, gated section
- Buyers who value clubhouse, pool, and tennis-court access as part of daily use
- Buyers comfortable running a patient, alert-driven search rather than shopping active listings
Probably not for
- Buyers who need to close quickly and cannot wait on a gated section with no current inventory
- Buyers who want a large pool of homes to compare before deciding
- Buyers focused purely on price who are not drawn to the amenity package here
The market around Ventura at Windsor Hills Windsor Hills
Ventura at Windsor Hills Windsor Hills is too small for its own price trend, so here is the market around it.
In ZIP 34747, 1,258 homes are on the market and 12% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
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.
ZIP and county figures describe the wider market, not Ventura at Windsor Hills Windsor Hills specifically. Momentum Research analysis of MLS records.
Life at Ventura at Windsor Hills Windsor Hills
- Clubhouse · reported on 1 of 1 listings
- Dog Park · reported on 1 of 1 listings
- Gated Community - Guard · reported on 1 of 1 listings
- Pool · reported on 1 of 1 listings
- Tennis Court(s) · reported on 1 of 1 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 Ventura at Windsor Hills Windsor Hills buying strategy.
If we were buying in Ventura at Windsor Hills Windsor Hills 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 Ventura at Windsor Hills Windsor Hills.
A gated pocket, not a volume market
Windsor Hills is a known name in this part of Osceola County, and Ventura is one of its guarded, gated sections. The amenity set reported across MLS listings here - clubhouse, pool, tennis courts, dog park, guarded gate - points to a community built for a resort-style lifestyle package rather than a single price tier or home style.
With zero active listings at this snapshot, there is nothing to compare against inside Ventura itself right now. Anyone serious about this address should widen the lens to recent Windsor Hills activity for pricing context and set up alerts for the next listing to hit, because inventory here does not sit long once it appears.
The location and the amenities are priced into every listing in Ventura at Windsor Hills Windsor Hills. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a section this tight on inventory, timing is the whole game. We track Windsor Hills and its gated pockets closely enough to flag a Ventura listing the moment it appears, and to help you weigh it honestly against what has actually closed nearby rather than guessing at value.
Ventura at Windsor Hills Windsor Hills in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $354/month (about $4,248/yr) · median of 3 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $354 per month ($4,248 a year) - the median AssociationFee across 3 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 Ventura at Windsor Hills Windsor Hills 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 Ventura at Windsor Hills Windsor Hills sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Ventura at Windsor Hills Windsor Hills, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Ventura at Windsor Hills Windsor Hills home worth?
Get a no-obligation home value based on real comparable sales in Ventura at Windsor Hills Windsor Hills, 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 →
Should you buy in Ventura at Windsor Hills Windsor Hills?
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) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2026 (1 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 Ventura At Windsor Hills Windsor Hills fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Ventura at Windsor Hills Windsor Hills
Where is Ventura at Windsor Hills Windsor Hills?
Ventura at Windsor Hills Windsor Hills is a community in KISSIMMEE, Osceola County, Florida, ZIP 34747.
Are there homes for sale in Ventura at Windsor Hills Windsor Hills right now?
No active listings inside Ventura at Windsor Hills Windsor Hills at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Ventura at Windsor Hills Windsor Hills have an HOA or CDD?
No HOA is on record for Ventura at Windsor Hills Windsor Hills in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Ventura at Windsor Hills Windsor Hills with Momentum Realty’s local guides.
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.
VENTURA AT WINDSOR HILLS, WINDSOR HILLS Market Scorecard
VENTURA AT WINDSOR HILLS, WINDSOR HILLS 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.