Chelsea Square
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.
As of September 2026, the MLS records 2 closed sales in Chelsea Sq Plat 2 in Kissimmee, FL since 2014, the most recent in February 2017. 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 $5,910 ($5,310 with the full homestead exemption).
Chelsea Square 2 is a tight, single-era pocket in Kissimmee — every home here went up between 1983 and 1986, with a median build year of 1985. That kind of construction consistency means pricing is driven almost entirely by condition and updates rather than by lot size, floor plan variety, or age spread. Two homes on the same street can price very differently depending on whether systems and finishes have been touched since the mid-1980s.
The homestead share sits at 14.6%, which is low relative to a typical owner-occupied subdivision and points to meaningful investor or rental ownership across the 254 homes in the plat. For a buyer, that means more of the inventory you'll see may be turnover from non-owner-occupants, and for a seller, it means your comparables pool includes a mix of long-held owner units and recently-cycled investment units — worth sorting through carefully rather than averaging.
Nearby homes for sale
No active listings inside Chelsea Sq Plat 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
A compact, uniformly-built section of Kissimmee where every home dates to the same mid-1980s window, with living areas centered around 1,001 square feet — this is a starter-scale footprint community, not a move-up subdivision.
Stellar MLS sales records identify 86 homes in Chelsea Square that have changed hands since 2004, built between 1983 and 1992 (median 1984), with a median living area of about 992 sq ft and a typical 2-bedroom, 2-bath layout; 86% are townhomes. 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 Chelsea Square is best for.
Best for
- Buyers seeking a smaller-footprint, lower-maintenance home in Kissimmee at a manageable size
- Investors comfortable evaluating condition property-by-property in a plat with meaningful rental turnover
- Buyers prioritizing a consistent, known build era over amenity access
Probably not for
- Buyers who want a larger living area than the roughly 1,000 sq ft median here
- Buyers expecting a clubhouse, pool, or other shared community amenities
- Buyers wanting a wide range of home ages or architectural styles to choose from
The market around Chelsea Square
Chelsea Square is too small for its own price trend, so here is the market around it.
In ZIP 34741, 299 homes are on the market and 15% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
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.
ZIP and county figures describe the wider market, not Chelsea Square specifically. Momentum Research analysis of MLS records.
The Chelsea Square buying strategy.
If we were buying in Chelsea Square 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 Chelsea Square.
One build era, one size story
With a median living area of 1,001 square feet, Chelsea Square 2 reads as a compact-footprint community. Buyers should expect efficient floor plans rather than expansive layouts, and should size any comparison against actual square footage rather than assuming the neighborhood scales up. There is no community amenities package identified from current MLS listings, so whatever appeal a given home holds will come from the unit itself and its immediate lot, not from a shared clubhouse, pool, or recreational infrastructure.
The narrow 1983–1986 build window also simplifies due diligence in one respect — buyers largely know what era of systems, roofing, and construction standards they're dealing with going in. The open question on any specific home is how much has been replaced or renovated since. In a market like this, a pre-offer conversation about age of roof, HVAC, and electrical panel status is far more useful than the year-built figure alone.
The location and the amenities are priced into every listing in Chelsea Square. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, single-era plat like this, comparables require judgment, not just pulling recent sales — 254 homes built in a three-year window with a low homestead share means the sales mix includes both long-held owner properties and investor turnovers with very different condition profiles. We pull the actual comps, weigh which ones reflect genuine owner-occupied condition versus rental-grade turnkey work, and price or negotiate accordingly rather than taking a blended average at face value.
Chelsea Square 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 Chelsea Square 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 Chelsea Square sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chelsea Square, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chelsea Square home worth?
Get a no-obligation home value based on real comparable sales in Chelsea Square, 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 →
Should you buy in Chelsea Square?
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 2026-09-08 |
| Historical depth | Closed-sale records back to 2014 (2 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 Chelsea Square 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Chelsea Square
Where is Chelsea Square?
Chelsea Square is a community in Kissimmee, Osceola County, Florida, ZIP 34741.
Are there homes for sale in Chelsea Square right now?
No active listings inside Chelsea Square at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Chelsea Square have an HOA or CDD?
No HOA is on record for Chelsea Square 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 Chelsea Square with Momentum Realty’s local guides.