Country Crossing
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 49 closed sales in Country Crossing Unit 01 in Kissimmee, FL since 2005, the most recent in April 2026. Recorded prices since 2024 ran from $330,000 to $365,000 (median $350,000), on homes of 970 to 2,018 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 $5,330 ($4,730 with the full homestead exemption).
The honest starting point on Country Crossing is that we have no closings inside the current window as of mid-July 2026. That means there is no active median, no clean spread, and no recent comparable set to lean on here. What sets price in a situation like this is the individual listing: condition, updates, lot, and how a seller reads a market that hasn't printed a local number recently.
For a buyer, that lack of recent data is leverage — it forces both sides back to fundamentals rather than a momentum narrative. For a seller, it means pricing has to be built from the ground up off the broader Kissimmee and Osceola market rather than a fresh in-community comp. Neither party should anchor to a figure this snapshot cannot support.
Nearby homes for sale
No active listings inside COUNTRY CROSSING UNIT 01 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
Country Crossing is a small pocket community in Kissimmee, Osceola County, and right now it is quiet on the transaction side — worth watching, but not a place where recent sales are doing the talking for you.
Stellar MLS sales records identify 101 homes in COUNTRY CROSSING that have changed hands since 2005, built between 1990 and 1994 (median 1991), with a median living area of about 1,304 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 Country Crossing is best for.
Best for
- Buyers who want a Kissimmee address and are willing to value a home on condition and location rather than recent sales
- Patient shoppers who can move when the right specific listing appears rather than tracking a monthly trend
- Long-hold owners focused on the property itself, not short-term local pricing signals
Probably not for
- Buyers who need a fresh in-community comp to feel confident on price
- Anyone wanting a fast, data-driven decision off recent local closings
- Sellers expecting a ready-made local median to price against
The market around Country Crossing
Country Crossing is a small community — 118 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.
In ZIP 34744, 405 homes are on the market and 19% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,437 homes are active and 1,149 pending (21% under contract).
Homes here are single family residence.
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 Country Crossing specifically. Momentum Research analysis of MLS records.
The Country Crossing buying strategy.
If we were buying in Country Crossing 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 Country Crossing.
Pricing without a recent comp
With no closings recorded in the current window, the usual tools — median trend, days-on-market read, a tight comp grid — aren't available for this community as of this snapshot. That doesn't make the neighborhood a bad bet; it makes it a manual one. Every valuation conversation here should start from the specific home and widen out to the surrounding Kissimmee and Osceola market for context.
Practically, this rewards patience and discipline. Buyers should underwrite the property on its own merits and location within Osceola County rather than chasing a story. Sellers should expect to justify price with condition and broader-market evidence, and to accept that the first well-priced sale in the community effectively resets what everyone else points to.
The location and the amenities are priced into every listing in Country Crossing. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with no recent closings, the value we add isn't reciting a number — it's building the pricing case honestly from the property up and the surrounding Osceola market in. We'll tell you plainly where the data ends and judgment begins, and we won't hand you a figure this snapshot can't back.
Country Crossing 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 Country Crossing 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 Country Crossing sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Country Crossing, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Country Crossing home worth?
Get a no-obligation home value based on real comparable sales in Country Crossing, 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 Country Crossing on the map →
Frequently Asked Questions
How many homes are in Country Crossing?
What share of Country Crossing is owner-occupied?
When were the homes in Country Crossing built?
Do cash buyers compete in Country Crossing?
Who is the best real estate agent for Country Crossing?
How do I find a top Kissimmee real estate agent who knows Country Crossing?
Can Momentum Realty connect me with an agent for Country Crossing?
Should you buy in Country Crossing?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 34744)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2005 (49 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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More Kissimmee & Kissimmee, St. Cloud & Osceola County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Kissimmee, St. Cloud & Osceola County or the full Neighborhood Finder.
See how COUNTRY CROSSING UNIT 01 fits the bigger picture — live prices, inventory, and Momentum Scores:
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