Windsor Hills Ph 02
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Windsor Hills Ph 02 is a mid-2000s community in Kissimmee, with homes built between 2004 and 2006 and a median living area right around 1,451 square feet. The homestead share here is under 2%, which tells you almost everything about how this market behaves: this is not a primary-residence enclave. Pricing is driven by rental and second-home demand far more than by owner-occupant turnover, so condition, furnishings, and rental performance move value more than square footage alone.
With so little owner-occupancy, expect a wide spread between a tired, turnkey-in-name-only unit and a well-kept, rental-ready one. The single median price is your anchor; treat everything above and below it as a condition-and-performance story, not a size story. For sellers, presentation and documented rental history carry weight. For buyers, underwrite the numbers, not the photos.
Who Windsor Hills Ph 02 is best for.
Best for
- Investors seeking a short-term-rental or vacation-use property in an established mid-2000s community
- Buyers who will underwrite a purchase on condition and operating numbers rather than square footage
- Second-home buyers comfortable with HOA rules and rental-market dynamics
Probably not for
- Buyers wanting a primary residence in an owner-occupant-dominated neighborhood
- Buyers who need a large or highly customized floor plan beyond the compact norm here
- Buyers unwilling to scrutinize condition, HOA terms, and rental performance before offering
The market around Windsor Hills Ph 02
Windsor Hills Ph 02 is a small community — 61 recorded sales on file, most recently in 2025 — 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 75% townhouse, 22% single family residence, 2% ?.
ZIP and county figures describe the wider market, not Windsor Hills Ph 02 specifically. Momentum Research analysis of MLS records.
The Windsor Hills Ph 02 buying strategy.
If we were buying in Windsor Hills Ph 02 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 Windsor Hills Ph 02.
A rental-market community, not an owner-occupant one
With 258 homes and a homestead share below 2%, Windsor Hills Ph 02 functions as an investment and vacation-use market. The build window of 2004 to 2006 means the housing stock is broadly consistent in age and layout, so differentiation comes down to upkeep, updates, and how the unit has been operated. Two homes of nearly identical size can trade very differently depending on condition and rental readiness.
The median living area near 1,451 square feet keeps these homes in a compact, manageable footprint. Because owner-occupancy is minimal, the practical questions are operational: HOA rules, rental permissions, management costs, and the state of the interior. Those factors, not raw dimensions, are what separate a strong buy from a money pit here.
The location and the amenities are priced into every listing in Windsor Hills Ph 02. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community this investment-driven rewards analysts, not optimists. We read condition against the median, dig into HOA and rental parameters, and help you separate a turnkey performer from a cosmetic listing. Whether you are buying to operate or selling and need to position against near-identical inventory, we work the numbers before the narrative.
Windsor Hills Ph 02 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 Windsor Hills Ph 02 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 Windsor Hills Ph 02 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor Hills Ph 02, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windsor Hills Ph 02 home worth?
Get a no-obligation home value based on real comparable sales in Windsor Hills Ph 02, 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 Windsor Hills Ph 02 on the map →
Frequently Asked Questions
How many homes are in Windsor Hills Ph 02?
What share of Windsor Hills Ph 02 is owner-occupied?
When were the homes in Windsor Hills Ph 02 built?
Do cash buyers compete in Windsor Hills Ph 02?
Who is the best real estate agent for Windsor Hills Ph 02?
How do I find a top Kissimmee real estate agent who knows Windsor Hills Ph 02?
Can Momentum Realty connect me with an agent for Windsor Hills Ph 02?
Should you buy in Windsor Hills Ph 02?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (6 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2014 (63 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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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.
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