Oakcrest At Stonefield
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
59 homesBuilt 1999–2001
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Built fromLive Stellar MLS data11 years of closingsFL DOR public recordsUpdated twice daily
Live · Oakcrest At Stonefield Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
2
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
66%
Owner-occupied · Oakcrest At Stonefield
39 of 59 parcels homesteaded (FL DOR 2025)
34%
Non-owner-occupied · Oakcrest At Stonefield
incl. 8% trust or LLC-held · 14% out-of-state
25%
Cash buyers · Oakcrest At Stonefield
1 of 4 sales, 12 mo ending June 2022
59
Homes in the community
59 residential parcels (FL DOR 2025)
Track record · 11 years of records
Est. 1999
Community established
homes built 1999-2001, median 2000 (FL DOR 2025)
0
Failed listings · 2024
peaked at 4 in 2006
3.4%/yr
Turnover rate
about 2 of 59 homes trade a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Oakcrest At Stonefield is a small, defined pocket in Kissimmee — 59 homes, all built in a tight window between 1999 and 2001. When the vintage is that uniform and the floor plans that consistent, price here is not driven by which model you buy; it is driven almost entirely by condition and updates. A home that has been renovated will command a premium over one still carrying its original finishes, and that spread is where most of the negotiation happens.

With a median living area right around 2,013 square feet, these are substantively sized homes, not starter boxes. The homestead share sits at about 66%, which tells you this leans owner-occupied rather than rental-heavy. For a seller, that generally means neighbors who maintain their properties; for a buyer, it means turnover is limited and you may wait for the right listing rather than choose from a wide shelf.

Best for

  • Buyers wanting a roughly 2,000-square-foot home and willing to budget for cosmetic or system updates
  • Owner-occupants who value a steady, low-turnover street over constant inventory churn
  • Value-minded buyers comfortable negotiating on condition rather than chasing a specific floor plan

Probably not for

  • Anyone needing to close fast from a wide pool of active listings
  • Buyers seeking new construction or contemporary open-concept layouts
  • Investors counting on high rental turnover, given the owner-occupied lean here

The market around Oakcrest At Stonefield

Oakcrest At Stonefield is a small community — 23 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 Oakcrest At Stonefield specifically. Momentum Research analysis of MLS records.

If we were buying in Oakcrest At Stonefield 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 Oakcrest At Stonefield.

Best Buy
Buyers who want a settled, owner-occupied pocket with room to add value through updates.
Biggest Risk
Homes built around 2000 carry aging systems — verify roof and HVAC before you commit.
Sweet Spot
A well-maintained home near the median 2,013 square feet with recent major-system work.
Avoid If
You need selection and cannot wait for the occasional right listing to appear.

A condition-driven market, not a size-driven one

Because everything here was built within a two-year span, the usual price levers — age, square footage, era of construction — are largely flat across the community. That makes Oakcrest At Stonefield unusually easy to read: the differences you will pay for are kitchens, baths, roofs, HVAC, and cosmetic condition. Ask directly about the age of the major systems on any home built around 2000, because a quarter-century-old roof or air handler is a real number in your offer.

The roughly two-thirds homestead share matters more than it looks. A higher owner-occupied ratio typically correlates with steadier upkeep and fewer distressed listings, but it also means fewer homes trade in any given window. Buyers should be prepared to move decisively when a well-kept property lists; sellers benefit from a limited comparable set, provided the home shows well.

The location and the amenities are priced into every listing in Oakcrest At Stonefield. 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 and this uniform, the edge is knowing which homes have been updated and which are still original — and pricing accordingly. We track the condition story behind each closing rather than treating them as interchangeable, so buyers do not overpay for deferred maintenance and sellers do not leave money on the table when their finishes are actually current.

Oakcrest At Stonefield in 15 seconds.

Best forBuyers who want a settled, owner-occupied pocket with room to add value through updates.
Biggest advantageUniform vintage and layout make pricing easy to read once you assess condition.
Biggest riskHomes built around 2000 carry aging systems — verify roof and HVAC before you commit.
Sweet spotA well-maintained home near the median 2,013 square feet with recent major-system work.
Avoid ifYou need selection and cannot wait for the occasional right listing to appear.

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 Oakcrest At Stonefield sales matched to your home.

What is your Oakcrest At Stonefield home worth?

Get a no-obligation home value based on real comparable sales in Oakcrest At Stonefield, 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 Oakcrest At Stonefield?
The Florida DOR 2025 assessment roll shows 59 homes in Oakcrest At Stonefield (public records).
What share of Oakcrest At Stonefield is owner-occupied?
66% of Oakcrest At Stonefield parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Oakcrest At Stonefield built?
Homes in Oakcrest At Stonefield were built between 1999 and 2001, with a median year built of 2000 (FL DOR 2025 roll).
Do cash buyers compete in Oakcrest At Stonefield?
Cash buyers took 25% of Oakcrest At Stonefield sales in the 12 months ending June 2022 (1 of 4 closings, Stellar MLS).
Who is the best real estate agent for Oakcrest At Stonefield?
The best agent for Oakcrest At Stonefield 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 Oakcrest At Stonefield.
How do I find a top Kissimmee real estate agent who knows Oakcrest At Stonefield?
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 Oakcrest At Stonefield and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Oakcrest At Stonefield?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Oakcrest At Stonefield purchase or sale - no call center and no pressure.
Buyers wanting a roughly 2,000-square-foot home and willing to budget for cosmetic or system updatesExcellent fit
Owner-occupants who value a steady, low-turnover street over constant inventory churnExcellent fit
Value-minded buyers comfortable negotiating on condition rather than chasing a specific floor planExcellent fit
Anyone needing to close fast from a wide pool of active listingsProbably not
Buyers seeking new construction or contemporary open-concept layoutsProbably not
Investors counting on high rental turnover, given the owner-occupied lean hereProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 32741/34741))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2015 (15 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?

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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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