Oak Hollow Ph 1
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
89 homesBuilt 1981–2001
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Built fromLive Stellar MLS data17 years of closingsFL DOR public recordsUpdated twice daily
Live · Oak Hollow Ph 1 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
76%
Owner-occupied · Oak Hollow Ph 1
68 of 89 parcels homesteaded (FL DOR 2025)
24%
Non-owner-occupied · Oak Hollow Ph 1
incl. 6% trust or LLC-held · 9% out-of-state
89
Homes in the community
89 residential parcels (FL DOR 2025)
Track record · 17 years of records
Est. 1981
Community established
homes built 1981-2001, median 1984 (FL DOR 2025)
1
Failed listings · 2026
peaked at 4 in 2007
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Oak Hollow Ph 1 is a small, established pocket of 89 homes in Kissimmee, built between 1981 and 2001 with the median home dating to 1984. At a median living area of roughly 1,510 square feet, this is a modest-footprint community where price is driven far less by square footage than by condition and how much updating a given home has seen. Expect a wide spread between original-condition houses and those that have been renovated.

The owner-occupancy signal is meaningful: about 76% homestead. That points to a community held by long-term owners rather than churned by short-term flips, which typically means limited inventory and slower turnover. There were no closings in the current window, so buyers should treat individual listings on their own merits rather than expecting a deep set of recent comps to lean on.

Best for

  • Buyers comfortable with an early-1980s-era home who will budget for updates as needed
  • Owner-occupants seeking a compact, established home to hold long term
  • Value-focused buyers willing to be patient in a low-turnover market

Probably not for

  • Buyers wanting new construction or large square footage
  • Those who need a wide selection of listings to choose from right now
  • Buyers unwilling to inspect closely or budget for older-home maintenance

The market around Oak Hollow Ph 1

Oak Hollow Ph 1 is a small community — 26 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).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Oak Hollow Ph 1 specifically. Momentum Research analysis of MLS records.

If we were buying in Oak Hollow Ph 1 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 Oak Hollow Ph 1.

Best Buy
Buyers who want an established, owner-occupied Kissimmee neighborhood over a new-build subdivision.
Biggest Risk
With no recent closings, current comps are thin and each home must be judged on its own.
Sweet Spot
An updated home near the community's 1,510-square-foot median at a condition-appropriate price.
Avoid If
You need move-in-perfect and refuse to budget for any updating.

Condition, not size, sets the price

With homes clustered around a median build year of 1984 and a median footprint near 1,510 square feet, the value question here is almost entirely about what has been done to the house. Roof age, HVAC, windows, kitchens, and baths will separate a strong buy from a project. Two homes of similar size can sit far apart on price purely on the strength of updates, so an inspection and a clear-eyed renovation budget matter more here than in newer subdivisions.

The 76% homestead share tells you this is a neighborhood people stay in, which tends to keep resale supply thin. For sellers, that scarcity can work in your favor when a well-maintained home hits the market. For buyers, it means patience: the right house may not appear on your timeline, and when it does, being ready to move is worth more than waiting for a bigger menu of choices.

The location and the amenities are priced into every listing in Oak Hollow Ph 1. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a small, thinly traded community like Oak Hollow Ph 1, generic pricing tools fall short because condition drives so much of the value and recent sales are scarce. We underwrite each home on its own merits — build era, updates, and deferred maintenance — and we tell you plainly when a listing is priced for its condition and when it is not.

Oak Hollow Ph 1 in 15 seconds.

Best forBuyers who want an established, owner-occupied Kissimmee neighborhood over a new-build subdivision.
Biggest advantageA high homestead share signals stability and limited turnover.
Biggest riskWith no recent closings, current comps are thin and each home must be judged on its own.
Sweet spotAn updated home near the community's 1,510-square-foot median at a condition-appropriate price.
Avoid ifYou need move-in-perfect and refuse to budget for any updating.

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 Oak Hollow Ph 1 sales matched to your home.

What is your Oak Hollow Ph 1 home worth?

Get a no-obligation home value based on real comparable sales in Oak Hollow Ph 1, 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 Oak Hollow Ph 1 on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Oak Hollow Ph 1?
The Florida DOR 2025 assessment roll shows 89 homes in Oak Hollow Ph 1 (public records).
What share of Oak Hollow Ph 1 is owner-occupied?
76% of Oak Hollow Ph 1 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Oak Hollow Ph 1 built?
Homes in Oak Hollow Ph 1 were built between 1981 and 2001, with a median year built of 1984 (FL DOR 2025 roll).
Who is the best real estate agent for Oak Hollow Ph 1?
The best agent for Oak Hollow Ph 1 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 Oak Hollow Ph 1.
How do I find a top Kissimmee real estate agent who knows Oak Hollow Ph 1?
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 Oak Hollow Ph 1 and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Oak Hollow Ph 1?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Oak Hollow Ph 1 purchase or sale - no call center and no pressure.
Buyers comfortable with an early-1980s-era home who will budget for updates as neededExcellent fit
Owner-occupants seeking a compact, established home to hold long termExcellent fit
Value-focused buyers willing to be patient in a low-turnover marketExcellent fit
Buyers wanting new construction or large square footageProbably not
Those who need a wide selection of listings to choose from right nowProbably not
Buyers unwilling to inspect closely or budget for older-home maintenanceProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34744))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2009 (11 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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