OAK HOLLOW PH 04
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Oak Hollow Ph 04 is an established Kissimmee community of 198 homes built between 1983 and 1996, with the median home dating to 1989. At roughly 1,947 square feet at the median, these are substantial single-family footprints, and in a neighborhood of this vintage the price is driven far more by condition than by address. A renovated kitchen, updated systems, and a re-roof will separate two otherwise identical floor plans, so the spread here is wide and condition-dependent.
The homestead share sits at about 78%, which tells you this is a lived-in, owner-occupied community rather than an investor churn. That tends to mean fewer listings hitting the market at once and sellers who are not forced to move quickly. For a buyer, expect to compete on well-kept homes and to find your value in properties that need cosmetic or mechanical work. For a seller, the age of the housing stock means updates are the lever that moves your number.
OAK HOLLOW PH 04 right now
🟡 Still climbing. The trailing-12-month median ($365K) is up 3.5% from the prior 12 months ($352K). With about 6 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (6 and 10 sales in the two windows).
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Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
OAK HOLLOW PH 04 market snapshot (as of August 2, 2026): the median sale price is about $365K ($244 per sq ft over the trailing 12 months of closed sales), and a median 33 days on market for closed sales. The trailing-12-month median is up 4% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
OAK HOLLOW PH 04 is a community of 378 homes in KISSIMMEE, Osceola County, built between 1981 and 2009 (median 1987.0), with a median living area of about 1,742 square feet. 77% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a mature Osceola County neighborhood with mid-1980s-to-1990s construction and larger-than-starter floor plans. The dominant story is age and ownership: homes here have had decades to be updated or deferred, and that variance is where the pricing conversation lives.
Who OAK HOLLOW PH 04 is best for.
Best for
- Buyers wanting more square footage for the money and willing to renovate for equity
- Owner-occupants planning a longer hold in an established, low-turnover neighborhood
- Value hunters who can read an inspection and price condition accurately
Probably not for
- Buyers set on new-build layouts and finishes with no tolerance for updates
- Short-term investors expecting fast inventory turnover and quick flips
- Anyone who can't budget for potential roof or HVAC replacement on an older home
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($365K) IS the median in the snapshot above, and the move from 2025 ($352K) IS the +3.5% one-year change.
Windows contain 0 to 15 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 2005 through 2026. Deemed reliable but not guaranteed.
19% of homes for sale in ZIP 34744 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-01).
The OAK HOLLOW PH 04 buying strategy.
If we were buying in OAK HOLLOW PH 04 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 OAK HOLLOW PH 04.
Why condition is the whole ballgame
With a build window closing in 1996 and a median year of 1989, every home in Oak Hollow Ph 04 is well past the age where original roofs, HVAC, and water heaters have either been replaced once or are overdue. Two homes with the same square footage can carry very different price tags depending on whether those big-ticket systems have been addressed. Buyers should budget for inspection and put real weight on documented updates; sellers should know that deferred maintenance is the first thing a sharp buyer prices out.
The median living area near 1,947 square feet means these are not compact starter boxes — there is room to work with, and floor plans from this era tend toward defined rooms rather than open concept. That's an opportunity for a buyer willing to renovate and a consideration for anyone who wants move-in-ready without paying for someone else's finishes.
The location and the amenities are priced into every listing in OAK HOLLOW PH 04. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in OAK HOLLOW PH 04 buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (7.8). Basis: Recent Direction +3.5% year-over-year; Owner Commitment 77% owner-occupied; Pricing Power 98.0% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a condition-driven, owner-occupied market like this, the number that matters is not the median — it's what a specific home's updates and deferred work are actually worth. We walk the systems, weigh the roof and HVAC honestly, and price the gap between renovated and original so you're negotiating on facts, not on a headline figure.
OAK HOLLOW PH 04 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 OAK HOLLOW PH 04 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 OAK HOLLOW PH 04 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in OAK HOLLOW PH 04, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your OAK HOLLOW PH 04 home worth?
Get a no-obligation home value based on real comparable sales in OAK HOLLOW PH 04, 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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Frequently Asked Questions
What is the median home price in OAK HOLLOW PH 04?
How long do homes in OAK HOLLOW PH 04 take to sell?
How many homes are in OAK HOLLOW PH 04?
What share of OAK HOLLOW PH 04 is owner-occupied?
When were the homes in OAK HOLLOW PH 04 built?
Do cash buyers compete in OAK HOLLOW PH 04?
Who is the best real estate agent for OAK HOLLOW PH 04?
How do I find a top KISSIMMEE real estate agent who knows OAK HOLLOW PH 04?
Can Momentum Realty connect me with an agent for OAK HOLLOW PH 04?
Should you buy in OAK HOLLOW PH 04?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (14 streets, ZIP 34744)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2005 (116 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.
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