Holiday Woods
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in Kissimmee, FL · median $373,400 · 247 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 3 closed sales in Holiday Woods in Kissimmee, FL since 2016, the most recent in May 2026. Across Kissimmee as a whole, 2,431 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,223 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
Holiday Woods doesn't have a headline number attached to it right now, and that's worth noting rather than glossing over. With no current MLS listings carrying pricing or amenity data, the honest read is that this is a quiet corner of Kissimmee where activity has to be tracked listing by listing rather than off a community-wide trend line.
For a buyer or seller here, that means doing the legwork on individual comps in the immediate area rather than leaning on a packaged narrative. It's a market that rewards someone willing to look closely at what's actually on the ground today.
Nearby homes for sale
No active listings inside Holiday Woods right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Holiday Woods sits in Kissimmee, Osceola County, without a distinct amenity package showing up in current MLS records — a straightforward, no-frills residential setting rather than an amenity-driven community.
Stellar MLS sales records identify 9 homes in Holiday Woods that have changed hands since 2009, built between 1973 and 2011 (median 1988), with a median living area of about 2,061 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
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.
Who Holiday Woods is best for.
Best for
- Buyers prioritizing a Kissimmee location over community amenity packages
- Buyers comfortable evaluating a home on its own merits without a built-in comp trend
- Buyers who want to avoid amenity-related fees tied to shared facilities
Probably not for
- Buyers who want a clubhouse, pool, or other on-site recreational amenities
- Buyers who prefer to lean on an established, well-documented community price trend
- Buyers who want a fully packaged, amenity-marketed community experience
The market around Holiday Woods
Holiday Woods is too small for its own price trend, so here is the market around it.
In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
In ZIP 34744 (Kissimmee), 785 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.8% year over year, with a median 34 days on market. Right now 126 active and 26 pending listings put supply at about 6.6 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Holiday Woods specifically. Momentum Research analysis of MLS records.
The Holiday Woods buying strategy.
If we were buying in Holiday Woods 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 Holiday Woods.
A community without a current data trail
There's nothing in the current MLS feed identifying clubhouse, pool, or recreational amenities tied to Holiday Woods, and no active pricing pattern to point to. That's not unusual for smaller or lower-turnover pockets of Osceola County — it just means the market picture here has to be built from individual listings as they surface rather than from a running set of comps.
Practically, that puts more weight on direct comparison to nearby streets and recent closings in the immediate area when a listing does come up, since there isn't a community-level baseline to lean on yet.
The location and the amenities are priced into every listing in Holiday Woods. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with a thin current data trail, the value of local, listing-by-listing knowledge goes up. We track Osceola County inventory closely enough to flag a Holiday Woods listing the moment it hits, and to price or evaluate it against real nearby activity rather than a generic area average.
Holiday Woods in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 Holiday Woods 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 Holiday Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Holiday Woods, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Holiday Woods home worth?
Get a no-obligation home value based on real comparable sales in Holiday Woods, 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 all homes for sale in Kissimmee →
Should you buy in Holiday Woods?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2016 (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.
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 local comps.
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See how Holiday Woods fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Holiday Woods
Where is Holiday Woods?
Holiday Woods is a community in Kissimmee, Osceola County, Florida, ZIP 34744.
Are there homes for sale in Holiday Woods right now?
No active listings inside Holiday Woods at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Holiday Woods have an HOA or CDD?
No HOA is on record for Holiday Woods in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Holiday Woods with Momentum Realty’s local guides.
Holiday Woods Market Scorecard
Holiday Woods is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34744 ZIP is $385,786, about 10.6% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · 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.