Osceola Acres 2Nd Add
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
55 homesBuilt 1959–2022
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Built fromLive Stellar MLS data17 years of closingsFL DOR public recordsUpdated twice daily
Live · Osceola Acres 2Nd Add Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
70%
Owner-occupied · Osceola Acres 2Nd Add
40 of 57 parcels homesteaded (FL DOR 2025)
30%
Non-owner-occupied · Osceola Acres 2Nd Add
incl. 7% trust or LLC-held · 7% out-of-state
55
Homes in the community
plus 2 vacant residential lots · 57 residential parcels (FL DOR 2025)
Track record · 17 years of records
Est. 1959
Community established
homes built 1959-2022, median 1980 (FL DOR 2025)
0
Failed listings · 2024
peaked at 2 in 2024
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Osceola Acres 2nd Add is a small, established pocket of Kissimmee with only 55 homes on record, built across a wide span from 1959 to 2022. That range means the neighborhood is not defined by a single architectural era or construction style — it is defined by individual homes, and each one needs to be evaluated on its own merits rather than assumed to match a community norm.

With a median year built of 1980 and a median living area of 1,589 square feet, this reads as a working, mid-size housing stock rather than a new-construction or luxury enclave. Roughly seven in ten homes here carry a homestead exemption, pointing to a base of owner-occupied properties rather than a market dominated by investor turnover or short-term rentals.

Best for

  • A buyer prioritizing owner-occupancy in an established Kissimmee location over shared community features.
  • Someone comfortable evaluating homes individually given the wide range of build years present.
  • A buyer targeting a mid-size home footprint near the community's median living area.

Probably not for

  • A buyer who wants HOA-managed amenities such as a pool, clubhouse, or gated access.
  • Someone who wants a large inventory of directly comparable homes to shop against.
  • A buyer seeking a single, consistent architectural era across the community.

The market around Osceola Acres 2Nd Add

Osceola Acres 2Nd Add is a small community — 5 recorded sales on file, most recently in 2024 — too few for its own price trend. Here is the market around it.

Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Osceola Acres 2Nd Add specifically. Momentum Research analysis of MLS records.

If we were buying in Osceola Acres 2Nd Add 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 Osceola Acres 2Nd Add.

Best Buy
Buyers looking for an individual home in Kissimmee rather than a packaged community with shared amenities.
Biggest Risk
With only 55 homes and no listed community amenities, each property has to be evaluated strictly on its own condition and updates.
Sweet Spot
Owner-occupant buyers comfortable researching a specific home's construction era rather than relying on neighborhood-wide norms.
Avoid If
You are seeking a community with organized amenities, a consistent architectural style, or a large pool of directly comparable homes.

A neighborhood defined by range, not uniformity

The defining fact about Osceola Acres 2nd Add is its build-year spread: homes here date from 1959 through 2022. That is unusual for a community of only 55 properties, and it means shoppers should not expect matching lot layouts, consistent square footage, or a single generation of finishes. Each listing has to be judged on its own construction era, condition, and update history.

No community amenities are identified from current MLS listings, which tells buyers this is a straightforward residential area without HOA-run recreational features baked into the value proposition. Value here is driven by the individual home and lot, not by shared clubhouse, pool, or gate infrastructure — so due diligence should center on the property itself.

The location and the amenities are priced into every listing in Osceola Acres 2Nd Add. 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 small, mixed-vintage community like this, comparables are harder to pull cleanly — a 1960s home and a 2020s home sitting a few doors apart do not compete on the same basis. We walk buyers and sellers through what is actually driving a given listing's value: age, square footage, and condition, not neighborhood-wide assumptions.

Osceola Acres 2Nd Add in 15 seconds.

Best forBuyers looking for an individual home in Kissimmee rather than a packaged community with shared amenities.
Biggest advantageThe wide build-year range means there is genuine variety in home age and style within a very small footprint.
Biggest riskWith only 55 homes and no listed community amenities, each property has to be evaluated strictly on its own condition and updates.
Sweet spotOwner-occupant buyers comfortable researching a specific home's construction era rather than relying on neighborhood-wide norms.
Avoid ifYou are seeking a community with organized amenities, a consistent architectural style, or a large pool of directly comparable homes.

HOA, CDD & Fees

In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Osceola Acres 2Nd Add sales matched to your home.

What is your Osceola Acres 2Nd Add home worth?

Get a no-obligation home value based on real comparable sales in Osceola Acres 2Nd Add, 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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Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Osceola Acres 2Nd Add?
The Florida DOR 2025 assessment roll shows 55 homes plus 2 vacant residential lots in Osceola Acres 2Nd Add (public records).
What share of Osceola Acres 2Nd Add is owner-occupied?
70% of Osceola Acres 2Nd Add parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Osceola Acres 2Nd Add built?
Homes in Osceola Acres 2Nd Add were built between 1959 and 2022, with a median year built of 1980 (FL DOR 2025 roll).
Who is the best real estate agent for Osceola Acres 2Nd Add?
The best agent for Osceola Acres 2Nd Add 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 Osceola Acres 2Nd Add.
How do I find a top Kissimmee real estate agent who knows Osceola Acres 2Nd Add?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Osceola Acres 2Nd Add and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Osceola Acres 2Nd Add?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Osceola Acres 2Nd Add purchase or sale - no call center and no pressure.
A buyer prioritizing owner-occupancy in an established Kissimmee location over shared community features.Excellent fit
Someone comfortable evaluating homes individually given the wide range of build years present.Excellent fit
A buyer targeting a mid-size home footprint near the community's median living area.Excellent fit
A buyer who wants HOA-managed amenities such as a pool, clubhouse, or gated access.Probably not
Someone who wants a large inventory of directly comparable homes to shop against.Probably not
A buyer seeking a single, consistent architectural era across the community.Probably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34744))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2009 (9 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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