Ventura At Windsor Hills Condo Ph 2
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
40 homesBuilt 2005–2005
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Built fromLive Stellar MLS data1 years of closingsFL DOR public recordsUpdated twice daily
Live · Ventura At Windsor Hills Condo Ph 2 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
0%
Owner-occupied · Ventura At Windsor Hills Condo Ph 2
0 of 40 parcels homesteaded (FL DOR 2025)
100%
Non-owner-occupied · Ventura At Windsor Hills Condo Ph 2
incl. 22% trust or LLC-held · 65% out-of-state
40
Homes in the community
40 residential parcels (FL DOR 2025)
Track record · 1 years of records
Est. 2005
Community established
homes built 2005-2005, median 2005 (FL DOR 2025)
3
Failed listings · 2026
peaked at 5 in 2007
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Ventura At Windsor Hills Condo Ph 2 is a small, single-vintage condo community in Kissimmee: all 40 units were built in 2005, and the typical unit runs around 1,450 square feet. With no price data currently anchoring the snapshot, valuation here comes down almost entirely to unit condition, floor, and how the HOA and rental restrictions are structured — not to any broad range of build eras or footprints.

The notable data point is homestead share at zero: none of the recorded units carry a homestead exemption, which points to a community used predominantly as non-primary-residence property — likely short-term rental or investment holdings rather than owner-occupied living. Buyers and sellers should treat this as an income-property market first and a personal-residence market second, and underwrite accordingly.

Best for

  • Investors seeking a 2005-built condo suited to rental or income-property use
  • Buyers comfortable with a single, consistent unit size and layout across the complex
  • Purchasers who will independently verify HOA terms, rental rules, and any amenities before committing

Probably not for

  • Buyers specifically seeking a primary, owner-occupied residence with an established homestead pattern nearby
  • Buyers who want documented on-site amenities as a deciding factor, since current listings identify none
  • Anyone wanting a mix of build years or floor plans to choose from

The market around Ventura At Windsor Hills Condo Ph 2

Ventura At Windsor Hills Condo Ph 2 is a small community — 31 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.

Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).

The housing mix here is 93% condominium, 7% condo - hotel.

ZIP and county figures describe the wider market, not Ventura At Windsor Hills Condo Ph 2 specifically. Momentum Research analysis of MLS records.

If we were buying in Ventura At Windsor Hills Condo Ph 2 today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Condo Ph 2.

Best Buy
Buyers targeting a 2005-built condo for investment or rental use rather than a primary residence.
Biggest Risk
A zero homestead share signals this market is not structured around long-term owner-occupancy.
Sweet Spot
Investors comfortable underwriting a single-vintage condo with unconfirmed community amenities.
Avoid If
You want a primary residence in a community with established resident-occupancy patterns.

One Vintage, One Use Case

Because every unit in Ventura At Windsor Hills Condo Ph 2 was built in the same year, there is no era-to-era spread to sort through — the variable that matters is how well an individual unit has been maintained and updated since 2005, not when it was constructed. At roughly 1,450 square feet as the typical size, floor plans across the community are consistent, which simplifies comparison but also means differentiation comes down to interior condition, view, and proximity within the complex rather than layout options.

The zero-percent homestead share is the community's defining characteristic. It tells you this is not a market built around long-term owner-occupants; it behaves like an income-property or vacation-rental pool. Current MLS listings do not identify community amenities, so anyone evaluating a unit here should confirm directly what — if anything — is included at the complex level and what the HOA governs, rather than assuming resort-style features.

The location and the amenities are priced into every listing in Ventura At Windsor Hills Condo Ph 2. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

A single-vintage, investment-leaning condo community like this one requires reading HOA financials, rental restrictions, and unit-level condition carefully rather than leaning on broad market trends. We walk buyers and sellers through what the near-zero homestead share means for financing, insurance, and resale, and we verify amenity and rental-use questions directly rather than assuming.

Ventura At Windsor Hills Condo Ph 2 in 15 seconds.

Best forBuyers targeting a 2005-built condo for investment or rental use rather than a primary residence.
Biggest advantageA consistent unit size around 1,450 square feet simplifies comparison shopping within the complex.
Biggest riskA zero homestead share signals this market is not structured around long-term owner-occupancy.
Sweet spotInvestors comfortable underwriting a single-vintage condo with unconfirmed community amenities.
Avoid ifYou want a primary residence in a community with established resident-occupancy patterns.

HOA, CDD & Fees

In short
  • 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.

The takeaway

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 Condo Ph 2 sales matched to your home.

What is your Ventura At Windsor Hills Condo Ph 2 home worth?

Get a no-obligation home value based on real comparable sales in Ventura At Windsor Hills Condo Ph 2, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

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Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Ventura At Windsor Hills Condo Ph 2?
The Florida DOR 2025 assessment roll shows 40 homes in Ventura At Windsor Hills Condo Ph 2 (public records).
What share of Ventura At Windsor Hills Condo Ph 2 is owner-occupied?
0% of Ventura At Windsor Hills Condo Ph 2 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Ventura At Windsor Hills Condo Ph 2 built?
Homes in Ventura At Windsor Hills Condo Ph 2 were built between 2005 and 2005, with a median year built of 2005.0 (FL DOR 2025 roll).
Who is the best real estate agent for Ventura At Windsor Hills Condo Ph 2?
The best agent for Ventura At Windsor Hills Condo Ph 2 is one who actively works Kissimmee and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Ventura At Windsor Hills Condo Ph 2.
How do I find a top Kissimmee real estate agent who knows Ventura At Windsor Hills Condo Ph 2?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Ventura At Windsor Hills Condo Ph 2 and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Ventura At Windsor Hills Condo Ph 2?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Ventura At Windsor Hills Condo Ph 2 purchase or sale - no call center and no pressure.
Investors seeking a 2005-built condo suited to rental or income-property useExcellent fit
Buyers comfortable with a single, consistent unit size and layout across the complexExcellent fit
Purchasers who will independently verify HOA terms, rental rules, and any amenities before committingExcellent fit
Buyers specifically seeking a primary, owner-occupied residence with an established homestead pattern nearbyProbably not
Buyers who want documented on-site amenities as a deciding factor, since current listings identify noneProbably not
Anyone wanting a mix of build years or floor plans to choose fromProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (4 streets, ZIP 34747))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2025 (3 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.

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