Raintree
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 31 closed sales in Raintree in Kissimmee, FL since 2014, the most recent in February 2024. Recorded prices across those 31 sales ran from $165,950 to $442,500 (median $234,000), on homes of 1,541 to 2,508 sq ft. 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 $3,560 ($2,960 with the full homestead exemption).
The snapshot for Raintree is thin right now, so I'm not going to pretend I have price trends I don't. What I can tell you is that in a Kissimmee community like this, what sets one home apart from another is usually condition, updates, and lot position rather than any single headline number. Buyers should be underwriting each listing on its own merits, not on a community-wide average.
Without a current median or days-on-market figure in hand, the honest posture is to treat this as a market you shop deal-by-deal. Sellers should price to recent comparable sales and be ready to justify condition; buyers should expect to do the same homework rather than lean on a broad Osceola County narrative.
Nearby homes for sale
No active listings inside Raintree 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
Raintree sits in Kissimmee, within Osceola County, and reads as a place where individual home condition and location within the community matter more than any single market statistic.
Stellar MLS sales records identify 49 homes in Raintree that have changed hands since 2014, built between 2009 and 2012 (median 2010), with a median living area of about 1,770 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 Raintree is best for.
Best for
- Buyers who want a Kissimmee location and will judge value home-by-home
- Buyers comfortable underwriting a purchase off recent comparable sales
- Sellers prepared to price to condition and back it with local comps
Probably not for
- Buyers who need a clear community-wide price trend before acting
- Buyers wanting a turnkey guarantee without inspecting condition
- Sellers expecting a premium unsupported by comparable sales
The market around Raintree
Raintree is too small for its own price trend, so here is the market around it.
In ZIP 34744, 419 homes are on the market and 21% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,430 homes are active and 1,110 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 Raintree specifically. Momentum Research analysis of MLS records.
The Raintree buying strategy.
If we were buying in Raintree 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 Raintree.
The location and the amenities are priced into every listing in Raintree. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
We work Osceola County on the ground and won't hand you a canned narrative. In a community where the public data is limited, our value is comparing homes one at a time, pulling the recent local sales that actually apply, and telling you plainly when a specific listing doesn't hold up.
Raintree 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 Raintree 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 Raintree sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Raintree, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Raintree home worth?
Get a no-obligation home value based on real comparable sales in Raintree, 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 Raintree on the map →
Should you buy in Raintree?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-08-30 |
| Historical depth | Closed-sale records back to 2014 (31 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.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Raintree fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Raintree
Where is Raintree?
Raintree is a community in Kissimmee, Osceola County, Florida, ZIP 34744.
Are there homes for sale in Raintree right now?
No active listings inside Raintree at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Raintree have an HOA or CDD?
No HOA is on record for Raintree 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 Raintree with Momentum Realty’s local guides.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.