Crestwood
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in Kissimmee, FL · median $373,400 · 173 homes for sale in 34741 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $485,000, $175 per square foot, a median 62 days on market, sellers accepting 94% of original asking. At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $7,390 ($6,790 with the full homestead exemption).
Crestwood Ph 2 is a built-out enclave of 103 homes from the early 2000s, and the numbers tell a story of larger-footprint, single-generation construction rather than a churn-heavy market. With a median living area over 3,200 square feet and a median price near $485,000, price per square foot lands in the mid-$170s — a level driven more by condition and updates within a fairly consistent build era than by lot or location swings.
A median days-on-market just over 60 and a market heat score of 35 point to a measured pace here — this is not a community where offers are decided in a weekend. With only three closings in the recent window, pricing data is thin, so sellers and buyers alike should treat comparables from within the neighborhood as directional rather than definitive, and lean on a broker who can pull recent activity in context.
Nearby homes for sale
No active listings inside Crestwood Ph 2 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
Crestwood market snapshot (as of September 12, 2026): the median sale price is about $485K ($175 per sq ft over the trailing 12 months of closed sales), and a median 62 days on market for closed sales.
In ZIP 34741 (Kissimmee), 745 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 2.2% year over year, with a median 44 days on market. Right now 201 active and 47 pending listings put supply at about 6.0 months — a balanced market. See the live ZIP 34741 housing market and the Osceola County market.
Stellar MLS sales records identify 60 homes in Crestwood that have changed hands since 2006, built between 2002 and 2005 (median 2003), with a median living area of about 2,785 sq ft and a typical 4-bedroom, 3.5-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.
Crestwood Ph 2 in Kissimmee is a small, established section of Osceola County built out between 2002 and 2006, with a high homestead share suggesting most homes here are held as primary residences rather than turned over frequently.
Who Crestwood is best for.
Best for
- Buyers seeking a larger-square-footage home built in the early 2000s at a moderate, condition-driven price point
- Buyers planning a longer hold, comfortable with a slower listing pace and less frequent comparable sales
- Buyers who want an established, built-out community rather than one still under active development
Probably not for
- Buyers who need a large pool of recent comparable sales to feel confident in pricing
- Buyers wanting on-site community amenities, since none are currently identified in MLS listings
- Investors seeking rapid turnover, given the high homestead share and thin recent closing volume
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($485K) IS the median in the snapshot above.
Windows contain 0 to 4 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2011 through 2026. Deemed reliable but not guaranteed.
15% of homes for sale in ZIP 34741 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-08).
The Crestwood buying strategy.
If we were buying in Crestwood 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 Crestwood.
A Small, Settled Pocket
At 103 homes, Crestwood Ph 2 is not a large enough inventory pool to generate constant listing turnover, and the recent closings window of just three sales confirms that. What that means practically: pricing here moves in narrower, less frequent data points, and a home's condition and any updates since the early-2000s construction era carry real weight in what it ultimately sells for.
The homestead share of 85.4% is a meaningful signal — it suggests a community where most owners have filed for homestead exemption, which typically correlates with longer hold periods rather than quick resale or investment turnover. Combined with a median year built of 2003, this points to a neighborhood of original or long-term owners rather than one cycling through frequent renovation-and-flip activity.
The location and the amenities are priced into every listing in Crestwood. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
With only three closings in the recent window, generic automated estimates and broad-market comparisons will miss the mark in Crestwood Ph 2. We pull the actual recent activity, weigh it against the community's build era and homestead pattern, and give sellers a realistic number and buyers a clear read on what condition and updates are actually worth here before an offer goes in.
Crestwood 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 Crestwood 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 Crestwood sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Crestwood, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Crestwood home worth?
Get a no-obligation home value based on real comparable sales in Crestwood, 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 →
Frequently Asked Questions
What is the median home price in Crestwood?
How long do homes in Crestwood take to sell?
Who is the best real estate agent for Crestwood?
How do I find a top Kissimmee real estate agent who knows Crestwood?
Can Momentum Realty connect me with an agent for Crestwood?
Should you buy in Crestwood?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2011 (26 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.
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 Crestwood Ph 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near CrestwoodHomes for Sale in Kissimmee, FL with Momentum Realty’s local guides.
