Raintree
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 329 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 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, 4,246 homes closed in the last 12 months at a median of $360,000, 64 median days on market, with 2,907 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), 271 homes closed in the last 12 months at a median of $390K ($212/sq ft), up 5.3% year over year, with a median 36 days on 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.
Recent Developments in Raintree
Development, infrastructure, retail, and school activity affecting Raintree, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Parks & Amenities
145,000 sq ft All Sports Dome planned on Gus Road in Kissimmee
All Sports Dome Southeast plans a climate-controlled indoor inflatable dome at 3070 Gus Road with multi-sport courts, turf fields and training areas. It would be the brand's first Greater Orlando location, with an opening expected in 2027 and no exact date given.
What it may mean for the marketAn indoor sports venue would add year-round recreation and event space on Kissimmee's Gus Road area. The project is about 13 miles west of Raintree, elsewhere in Osceola County.
Source: What Now Orlando - October 2026Infrastructure
Turnpike widening in Osceola County runs ahead of schedule at Fortune Road Bridge
Steel beams for the new westbound Fortune Road Bridge are in place a month early as Florida's Turnpike is widened from two to four lanes each way between Partin Settlement Road and Osceola Parkway. Westbound bridge traffic is expected at the start of 2027, and the broader project targets 2031. The bridge adds bike lanes and sidewalks.
What it may mean for the marketDoubling Turnpike capacity through this stretch should ease regional commutes between Kissimmee and the Orlando area once complete. The project is about 9 miles west of Raintree, elsewhere in Osceola County.
Source: WFTV - October 2026Development
Experience Kissimmee launches Film Kissimmee commission to recruit productions
The new film commission markets Osceola County to production companies through an online database of more than 100 filming locations and has hired a location manager. Leaders say productions could become a new economic driver, citing spending on hotels, vehicles, food and crew services.
What it may mean for the marketFilm work could add temporary jobs and visitor spending for hospitality and service businesses across Osceola County. The site is about 10 miles west of Raintree.
Source: WFTV - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The site is about 7 miles north of Raintree.
Source: Spectrum News 13 - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The site is about 4 miles southwest of Raintree.
Source: Spectrum News 13 - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 7 miles north of Raintree.
Source: ClickOrlando
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in the Orlando Metro.
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Ask an agent about Raintree
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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.
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