Crestwood
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Crestwood is a small, built-out pocket of larger early-2000s homes in Kissimmee, with a median living area just under 3,200 square feet and a median build year of 2003. At a median of $485,000 and roughly $175 per square foot, price here is driven less by location tiers and more by condition and how each home has been maintained or updated over the past two decades. Expect a wide spread from house to house rather than a tight, predictable band.
The market posture is patient. With a median of 62 days on market, well-priced homes still move but nothing sells itself, and the small pool of 97 homes means comparable sales are thin and lag real time. For sellers, that argues for pricing to condition and being ready to wait past a month. For buyers, the pace leaves room to inspect carefully and negotiate rather than rush.
CRESTWOOD right now
🟡 Still climbing. The trailing-12-month median ($465K) is up 5.8% from the prior 12 months ($439K) and up 335% since 2012. With about 5 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Low (5 and 5 sales in the two windows).
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Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Crestwood market snapshot (as of July 13, 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.
Crestwood is a community of 97 homes in Kissimmee, Osceola County, built between 2002 and 2006 (median 2003), with a median living area of about 3,197 square feet. 84% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Crestwood is a compact community of about 97 sizable homes built between 2002 and 2006 in Osceola County. A high homestead share — roughly 85% — points to a settled, owner-occupied character rather than heavy investor turnover.
Who Crestwood is best for.
Best for
- Buyers targeting a mid-$500s-and-under budget who want maximum square footage per dollar
- Owner-occupants planning to stay several years and willing to wait for the right listing
- Buyers comfortable budgeting for updates on a home built around 2003
Probably not for
- Buyers who need to close fast in a market that runs past a month on average
- Investors seeking high rental turnover in a heavily owner-occupied community
- Shoppers who want a wide selection of listings to compare side by side
Median sale price over the trailing 12 months ending July 13 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 3 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 %s through %s. Deemed reliable but not guaranteed.
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 condition-driven resale market
The homes here share a tight construction era — 2002 to 2006 — and generous square footage, so the questions that move price are about the individual property: roof, systems, kitchens, and baths that are now around twenty years old. Two homes of similar size can price very differently depending on what has been renovated. That is why the median matters more as an anchor than as a rule.
The high homestead share suggests most of these homes are lived in rather than rented, which tends to mean steadier upkeep but also fewer listings at any given moment. Combined with only 97 homes total, inventory is genuinely limited, so serious buyers should be ready to act when the right layout and condition appear rather than assume another will follow quickly.
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
In a small community where comps are thin and price hinges on condition, the work is in reading each home honestly against the median and the 62-day pace. We help sellers position to condition instead of chasing a number, and we help buyers judge which asking prices reflect real updates versus deferred maintenance on a twenty-year-old house.
Crestwood in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA — confirm current dues
- 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.
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Frequently Asked Questions
What is the median home price in Crestwood?
How long do homes in Crestwood take to sell?
How many homes are in Crestwood?
What share of Crestwood is owner-occupied?
When were the homes in Crestwood built?
Do cash buyers compete in Crestwood?
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 July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (4 streets, ZIP 34741)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2011 (17 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.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($465K) IS the median in the snapshot above, and the move from 2025 ($439K) IS the +5.8% one-year change.
Windows contain 1 to 16 sales each (5 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 2004 through 2026. Deemed reliable but not guaranteed.
27% of homes for sale in ZIP 33511 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 (2026-08-01).
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (12 streets, ZIP 33511/33703/33714/33880/33881/34471/34695/34741)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2004 (123 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.
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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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