Rolling Oaks
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-08-02, 42 recorded sales closed at a median of $414,000, $293 per square foot, a median 128 days on market, sellers accepting 90% of original asking (-4% versus the prior year). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $6,310 ($5,700 with the full homestead exemption).
Price in Rolling Oaks is driven less by a wide spread of housing types and more by condition and finish. This is a newer-construction pocket, with homes built between 2018 and 2022 and a median build year of 2019, so the stock is consistent. At a median of $545,000 and roughly $318 per square foot against a median of about 1,548 living square feet, buyers are paying for recent construction on a compact footprint rather than square footage.
The posture right now is warm but not frantic. A market heat score of 56 and a median 50 days on market tell you homes are moving at a measured pace, not overnight. Year-over-year the median is up 17.3%, so sellers have had the wind at their backs, but 50 days means buyers still have room to inspect, negotiate, and walk if the numbers don't work. Price to the recent comps, not to last year's momentum.
Rolling Oaks right now
🟡 Off the recent peak. The trailing-12-month median ($414K) is down 3.7% from the prior 12 months ($430K).Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Very High (42 and 45 sales in the two windows).
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· Updated September 14, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside ROLLING OAKS PH 5 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
Rolling Oaks market snapshot (as of August 2, 2026): the median sale price is about $414K ($293 per sq ft over the trailing 12 months of closed sales), and a median 129 days on market for closed sales. The trailing-12-month median is down 4% from the prior 12 months, computed from record-level Stellar MLS closed sales (42 closings in the current window).
In ZIP 34747 (KISSIMMEE), 2,598 homes closed in the last 12 months at a median of $458K ($220/sq ft), down 3.9% year over year, with a median 74 days on market. Right now 552 active and 96 pending listings put supply at about 7.3 months — a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.
Rolling Oaks is a community of 666 homes in Kissimmee, Osceola County, built between 2018 and 2023 (median 2019.0), with a median living area of about 1,557 square feet. 4% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Rolling Oaks is a small, newer-construction community of 379 homes in Kissimmee, Osceola County, where uniform build years keep the housing stock predictable and condition-driven pricing is the norm.
Who Rolling Oaks is best for.
Best for
- Buyers targeting newer construction who can transact comfortably around the $545,000 median
- Owner-occupants who value low-maintenance, recently built systems over maximum floor space
- Investors comfortable in a community where most homes are not primary residences
Probably not for
- Buyers who need substantially more than about 1,548 square feet of living space
- Anyone wanting a high-volume, fast-turnover market with abundant comps
- Buyers expecting the 17.3% year-over-year gain to continue as a given
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($414K) IS the median in the snapshot above, and the move from 2025 ($430K) IS the -3.7% one-year change.
Windows contain 11 to 101 sales each (42 in the current window); every figure carries its sample size. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Deemed reliable but not guaranteed.
12% of homes for sale in ZIP 34747 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-01).
The Rolling Oaks buying strategy.
If we were buying in Rolling 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 Rolling Oaks.
A newer, compact Osceola pocket
The defining trait here is age of the stock. Everything was built in a tight window from 2018 to 2022, with a median year built of 2019, which means fewer surprises on major systems and roofs than you'd find in older Kissimmee neighborhoods. The tradeoff is a smaller footprint: a median of about 1,548 living square feet keeps these homes efficient rather than sprawling, and at roughly $318 per square foot the premium is on the newness and the layout, not on raw size.
One number worth flagging: a homestead share of just 5.3%. That points to a community where a large portion of homes are not owner-occupied primary residences. For a buyer that shapes the character of the block and the resale pool; for a seller it means your competition and your buyer may both skew toward non-primary use. It's not a reason to walk, but it is a reason to understand who you're buying next to and pricing against.
The location and the amenities are priced into every listing in Rolling Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Rolling Oaks buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (3.0). Basis: Recent Direction -3.7% year-over-year; Owner Commitment 4% owner-occupied; Pricing Power 90.1% sale-to-list. Refreshed with each data update.
Why work with Momentum here
With only 16 closings in the tracking window and a tight, uniform build era, comps in Rolling Oaks have to be read carefully — small sample sizes reward a broker who knows which sales are truly comparable. We'll help you separate condition and finish differences from real value, weigh the low homestead share against your goals, and price to the current 50-day pace rather than to a headline year-over-year figure.
Rolling 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 Rolling 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 Rolling Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Rolling 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 Rolling Oaks home worth?
Get a no-obligation home value based on real comparable sales in Rolling 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.
See homes for sale in Rolling Oaks on the map →
Frequently Asked Questions
What is the median home price in Rolling Oaks?
How long do homes in Rolling Oaks take to sell?
How many homes are in Rolling Oaks?
What share of Rolling Oaks is owner-occupied?
When were the homes in Rolling Oaks built?
Do cash buyers compete in Rolling Oaks?
Who is the best real estate agent for Rolling Oaks?
How do I find a top Kissimmee real estate agent who knows Rolling Oaks?
Can Momentum Realty connect me with an agent for Rolling Oaks?
Should you buy in Rolling Oaks?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (18 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2021 (257 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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More Kissimmee & Kissimmee, St. Cloud & Osceola County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Kissimmee, St. Cloud & Osceola County or the full Neighborhood Finder.
See how ROLLING OAKS PH 5 fits the bigger picture — live prices, inventory, and Momentum Scores:
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