The Oaks
Homes for Sale in Kissimmee, FL
All 2,920 homes for sale in Kissimmee, FL · median $374,990 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 22 closed sales in The Oaks Plat No 2 in Kissimmee, FL since 2015, the most recent in May 2026. 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).
Pricing here tracks the home itself more than anything communal. With a twenty-year build span (1987 to 2007) and a median living area of 2,584 square feet, condition and vintage do the heavy lifting — a well-updated 2002-era home and an original 1987 build can sit at very different price points despite similar square footage.
The homestead share sitting at 66.3% points to a base of owner-occupied homes rather than a heavy rental turnover, which tends to support steadier upkeep and fewer distressed listings hitting the market at once. For a buyer, that means patience pays off — inventory here doesn't churn fast, so the right floor plan may take some waiting on.
Nearby homes for sale
No active listings inside The Oaks Plat No 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
The Oaks No 2 is a 576-home section of Kissimmee built out mostly across the 1990s and early 2000s, with a median home landing around 2,584 square feet — sizeable for the era and area.
Stellar MLS sales records identify 38 homes in The Oaks that have changed hands since 2004, built between 1996 and 2022 (median 2002), with a median living area of about 2,538 sq ft and a typical 4-bedroom, 2.5-bath layout; 97% 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.
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 The Oaks is best for.
Best for
- Buyers prioritizing living space, given the 2,584 sqft median, over community perks
- Buyers comfortable evaluating each home on its own condition rather than leaning on a uniform build era
- Buyers who want an established Kissimmee section with a majority owner-occupied base
Probably not for
- Buyers who want a confirmed clubhouse, pool, or gated amenity package as part of the purchase
- Buyers who want single-era construction with consistent finishes across the section
- Buyers unwilling to budget for condition variance across a 1987-to-2007 build range
The market around The Oaks
The Oaks is too small for its own price trend, so here is the market around it.
In ZIP 34746, 975 homes are on the market and 17% 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 34746 (Kissimmee), 1,615 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.5% year over year, with a median 67 days on market. Right now 421 active and 72 pending listings put supply at about 6.7 months — a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not The Oaks specifically. Momentum Research analysis of MLS records.
The The Oaks buying strategy.
If we were buying in The Oaks 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 The Oaks.
Size and Vintage Over Amenities
Current MLS listings show no confirmed community amenities tied to this section — no clubhouse, pool, or gate referenced in active data. That's worth knowing going in: whatever draws a buyer here is the house and the lot, not a shared recreation package. Buyers should verify any HOA structure and amenity access directly rather than assume a standard suburban package.
The build range of 1987 to 2007, with a median year built of 2002, means the neighborhood is not a single-era subdivision — it's a mix of older and newer construction under one plat name. That spread shows up in finishes, roof ages, and system conditions, so a showing-by-showing comparison matters more here than in a tract built in a single wave.
The location and the amenities are priced into every listing in The Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a plat this size with a two-decade build range and no standardized amenity package to anchor comps, pricing requires a house-by-house read rather than a community-wide shortcut. We pull recent closings by vintage and condition, not just square footage, so a seller isn't left guessing what their specific build year is actually worth, and a buyer isn't overpaying for a listing priced off the wrong comp.
The Oaks 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 The Oaks 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 The Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in The Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your The Oaks home worth?
Get a no-obligation home value based on real comparable sales in The Oaks, 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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Should you buy in The Oaks?
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 2015 (22 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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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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See how The Oaks No 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about The Oaks
Where is The Oaks?
The Oaks is a community in Kissimmee, Osceola County, Florida, ZIP 34746 / 34758 / 34771.
Are there homes for sale in The Oaks right now?
No active listings inside The Oaks at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does The Oaks have an HOA or CDD?
No HOA is on record for The Oaks 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.
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