VENTURA AT WINDSOR HILLS, WINDSOR HILLS
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
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.
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.
The setting & the homes.
Aerial and on-site photos of VENTURA AT WINDSOR HILLS, WINDSOR HILLS. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
VENTURA AT WINDSOR HILLS, WINDSOR HILLS
VENTURA AT WINDSOR HILLS, WINDSOR HILLS
VENTURA AT WINDSOR HILLS, WINDSOR HILLS
VENTURA AT WINDSOR HILLS, WINDSOR HILLS
VENTURA AT WINDSOR HILLS, WINDSOR HILLS
VENTURA AT WINDSOR HILLS, WINDSOR HILLSWho 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, 1,240 homes are on the market and 12% are under contract — a slower corner of KISSIMMEE.
Across Osceola County, 4,437 homes are active and 1,149 pending (21% under contract).
Homes here are condominium.
ZIP and county figures describe the wider market, not VENTURA AT WINDSOR HILLS, WINDSOR HILLS specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in VENTURA AT WINDSOR HILLS, WINDSOR HILLS, 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.
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
- 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 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 homes for sale in VENTURA AT WINDSOR HILLS, WINDSOR HILLS on the map →
Should you buy in VENTURA AT WINDSOR HILLS, WINDSOR HILLS?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near VENTURA AT WINDSOR HILLS, WINDSOR HILLS with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| 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 your area 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.
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.
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.