Cherub Homes in Kissimmee

Cherub Homes
Homes for Sale in Kissimmee, FL

All 2,887 homes for sale in KISSIMMEE, FL · median $374,999 · 255 homes for sale in 34741 · Osceola County homes for sale

Community in Kissimmee · Osceola County · ZIP 34741
44 homesBuilt 1958–2005
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Built fromLive Stellar MLS data21 years of closingsFL DOR public recordsUpdated twice daily

As of October 2026, the MLS records 16 closed sales in Cherub Homes in Kissimmee, FL since 2005, the most recent in July 2025. Across Kissimmee as a whole, 2,523 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,265 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).

Cherub Homes key facts
LocationKISSIMMEE, Osceola County, FL · ZIP 34741, 34758
Homes in the community44 (FL DOR 2025 assessment roll)
Years built1958–2005 (median 1982.0)
Typical living area1,472 sq ft (median)
For sale right now0 active, 0 pending
Owner-occupied (homestead) share61%

Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cherub Homes key facts,” movewithmomentum.com/neighborhoods/cherub-homes-kissimmee, data as of September 20, 2026.

Live · Cherub Homes Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Ownership and context
61%
Owner-occupied · Cherub Homes
27 of 44 parcels homesteaded (FL DOR 2025)
39%
Non-owner-occupied · Cherub Homes
incl. 11% trust or LLC-held · 9% out-of-state
44
Homes in the community
44 residential parcels (FL DOR 2025)
Track record · 21 years of records
3
Recorded sales · 2024-2025
median $230K · qualified sales on the county roll (FL DOR 2025)
Est. 1958
Community established
homes built 1958-2005, median 1982 (FL DOR 2025)
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Cherub Homes in Kissimmee is a small, older pocket of the Osceola market - 54 homes total, with construction spanning from 1958 to 2005 and a median build year of 1982. That range matters more than any single stat: buyers here are choosing between a mid-century home and something built decades later, and condition, not just square footage, is what separates one listing from the next.

With zero active listings at this snapshot and only a single closing in the most recent window, this is not a market where you browse a deep inventory and compare five similar homes side by side. Activity is thin enough that when something does list, it needs to be evaluated on its own terms - recent updates, lot specifics, and how the age of the home lines up with what you're willing to take on.

Nearby homes for sale

No active listings inside Cherub Homes 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.

5161 WORCHESTER DRIVE
$384K · 0.2 mi away
3 bd · 2 ba · 1,555 sqft
5161 WORCHESTER DRIVE
Listed by LENNAR REALTY
5131 WORCHESTER DRIVE
$461K · 0.2 mi away
5 bd · 2.5 ba · 2,896 sqft
5131 WORCHESTER DRIVE
Listed by LENNAR REALTY
5162 WORCHESTER DRIVE
$413K · 0.3 mi away
4 bd · 2 ba · 1,936 sqft
5162 WORCHESTER DRIVE
Listed by LENNAR REALTY
5174 WORCHESTER DRIVE
$456K · 0.3 mi away
5 bd · 2.5 ba · 2,896 sqft
5174 WORCHESTER DRIVE
Listed by LENNAR REALTY
5101 WORCHESTER DRIVE
$471K · 0.3 mi away
4 bd · 2.5 ba · 2,584 sqft
5101 WORCHESTER DRIVE
Listed by LENNAR REALTY
5204 WORCHESTER DRIVE
$370K · 0.3 mi away
3 bd · 2 ba · 1,555 sqft
5204 WORCHESTER DRIVE
Listed by LENNAR REALTY

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

A modest, older-vintage pocket of Kissimmee homes with a median living area of 1,511 square feet and roughly half of owners holding a homestead exemption - a sign this is largely a stay-put community rather than a fast-turnover one.

Stellar MLS sales records identify 21 homes in Cherub Homes that have changed hands since 2005, built between 1959 and 2004 (median 1982), with a median living area of about 1,294 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.

County records show 3 qualified sales in Cherub Homes across 2024 - 2025 (2 in 2024, 1 in 2025), median $230,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

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.

Best for

  • Buyers who want an established, non-amenity residential setting and are comfortable with a home's age driving its price rather than a neighborhood premium.
  • Buyers planning to occupy long-term, given that roughly half of current owners hold a homestead exemption here.
  • Buyers who don't need a wide current selection and are willing to act when one of a small number of homes comes to market.

Probably not for

  • Buyers who want on-site community amenities, since none were identified from current MLS listings.
  • Buyers who want to compare several similar active listings before deciding, given there are none at this snapshot.
  • Buyers who prefer newer construction exclusively and aren't open to homes built well before the 2000s.

The market around Cherub Homes

Cherub Homes is too small for its own price trend, so here is the market around it.

In ZIP 34741, 290 homes are on the market and 14% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).

In ZIP 34741 (KISSIMMEE), 754 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 0.8% year over year, with a median 44 days on market. Right now 207 active and 46 pending listings put supply at about 6.1 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 Cherub Homes specifically. Momentum Research analysis of MLS records.

Housing distress & ownership in Cherub Homes, KISSIMMEE

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 20 listings
Distress share trend - 0.0% now (2026-08-12 → 2026-10-04)

Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.

If we were buying in Cherub Homes today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Cherub Homes.

Best Buy
Buyers looking for an older, established home in Kissimmee rather than new construction.
Biggest Risk
With zero active listings at this snapshot, availability is the main constraint, not price.
Sweet Spot
Buyers comfortable evaluating a home built anywhere from 1958 to 2005 on its own condition.
Avoid If
Skip this one if you need built-in amenities or a large current inventory to choose from.

A community defined by age spread, not size

The defining fact about Cherub Homes is the gap between its oldest and newest construction - homes built as far back as 1958 sitting in the same small community as ones built up through 2005. With a median build year of 1982, the typical home here has decades on it, which means the condition of any given listing - roof, systems, updates - will do more to set its value than location within the community.

No community amenities were identified from current MLS listings, so this reads as a straightforward residential pocket rather than an amenity-driven development. At 54 total homes and no active listings in this snapshot, buyers should expect to move deliberately when something does come to market, and sellers should expect a limited, specific pool of comparable sales to lean on rather than a steady stream of them.

“

The location and the amenities are priced into every listing in Cherub Homes. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a community this small - 54 homes with no active listings and only one recent closing - pricing a home well or making a competitive offer depends on reading a thin data set correctly rather than skimming a big one. We track what does come to market here closely enough to tell you whether a listing is priced against its actual condition and age, not just against a neighborhood average that may not apply.

Cherub Homes in 15 seconds.

Best forBuyers looking for an older, established home in Kissimmee rather than new construction.
Biggest advantageA modest living-area footprint around 1,511 square feet keeps maintenance and scale manageable.
Biggest riskWith zero active listings at this snapshot, availability is the main constraint, not price.
Sweet spotBuyers comfortable evaluating a home built anywhere from 1958 to 2005 on its own condition.
Avoid ifSkip this one if you need built-in amenities or a large current inventory to choose from.

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Cherub Homes homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Cherub Homes.
In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Cherub Homes sales matched to your home.

What is your Cherub Homes home worth?

Get a no-obligation home value based on real comparable sales in Cherub Homes, 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 →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Cherub Homes?
The Florida DOR 2025 assessment roll shows 44 homes in Cherub Homes (public records).
What share of Cherub Homes is owner-occupied?
61% of Cherub Homes parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Cherub Homes built?
Homes in Cherub Homes were built between 1958 and 2005, with a median year built of 1982.0 (FL DOR 2025 roll).
Who is the best real estate agent for Cherub Homes?
The best agent for Cherub Homes is one who actively works Kissimmee and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Cherub Homes.
How do I find a top Kissimmee real estate agent who knows Cherub Homes?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Cherub Homes and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Cherub Homes?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Cherub Homes purchase or sale - no call center and no pressure.
Where is Cherub Homes, and what county is it in?
Cherub Homes is in KISSIMMEE, Osceola County, FL, ZIP codes 34741, 34758. The community's center is about 5 miles southwest of the center of KISSIMMEE (straight-line).
Buyers who want an established, non-amenity residential setting and are comfortable with a home's age driving its price rather than a neighborhood premium.Excellent fit
Buyers planning to occupy long-term, given that roughly half of current owners hold a homestead exemption here.Excellent fit
Buyers who don't need a wide current selection and are willing to act when one of a small number of homes comes to market.Excellent fit
Buyers who want on-site community amenities, since none were identified from current MLS listings.Probably not
Buyers who want to compare several similar active listings before deciding, given there are none at this snapshot.Probably not
Buyers who prefer newer construction exclusively and aren't open to homes built well before the 2000s.Probably not

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: August 10, 2026)
Housing stock & ownershipFlorida DOR assessment roll (street-list match (4 streets, ZIP 34741/34758))
Under-contract sharesStellar MLS records, as of 2026-09-20
Historical depthClosed-sale records back to 2005 (16 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.

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Nearby Communities

Explore more neighborhoods near Cherub Homes with Momentum Realty’s local guides.

Knightsbridge 50S0.4 mi away · median $427K, 54 sales/12 moPoinciana Commercenter 10.4 mi away · 3 for saleLCLittle Creek0.9 mi away · 215 homes, built 2004–06Brighton Landings0.9 mi away · 116 homes, built 2007–13, 3 for sale

Browse all neighborhood guides →

Thinking of selling in Cherub Homes? See the Osceola County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
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