Rolling Oaks Ph 5
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Price in Rolling Oaks Ph 5 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 Ph 5 right now
🟢 Still climbing. The trailing-12-month median ($545K) is up 17.3% from the prior 12 months ($464K). With about 18 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending July 13. Confidence: Medium (16 and 14 sales in the two windows).
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Updated July 13, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Rolling Oaks Ph 5 market snapshot (as of July 13, 2026): the median sale price is about $545K ($318 per sq ft over the trailing 12 months of closed sales), and a median 50 days on market for closed sales. The trailing-12-month median is up 17% from the prior 12 months, computed from record-level Stellar MLS closed sales (16 closings in the current window).
Rolling Oaks Ph 5 is a community of 379 homes in Kissimmee, Osceola County, built between 2018 and 2022 (median 2019), with a median living area of about 1,548 square feet. 5% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Rolling Oaks Ph 5 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 Ph 5 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 July 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($545K) IS the median in the snapshot above, and the move from 2025 ($464K) IS the +17.3% one-year change.
Windows contain 5 to 53 sales each (16 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Deemed reliable but not guaranteed.
The Rolling Oaks Ph 5 buying strategy.
If we were buying in Rolling Oaks Ph 5 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 Ph 5.
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 Ph 5. 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 Ph 5 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 (5.8). Basis: Recent Direction +17.3% year-over-year; Owner Commitment 5% owner-occupied; Pricing Power 95.4% 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 Ph 5 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 Ph 5 in 15 seconds.
HOA, CDD & Fees
- 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.
Tools for a Rolling Oaks Ph 5 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 Ph 5 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 Ph 5, 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 Ph 5 home worth?
Get a no-obligation home value based on real comparable sales in Rolling Oaks Ph 5, 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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Frequently Asked Questions
What is the median home price in Rolling Oaks Ph 5?
How long do homes in Rolling Oaks Ph 5 take to sell?
How many homes are in Rolling Oaks Ph 5?
What share of Rolling Oaks Ph 5 is owner-occupied?
When were the homes in Rolling Oaks Ph 5 built?
Do cash buyers compete in Rolling Oaks Ph 5?
Who is the best real estate agent for Rolling Oaks Ph 5?
How do I find a top Kissimmee real estate agent who knows Rolling Oaks Ph 5?
Can Momentum Realty connect me with an agent for Rolling Oaks Ph 5?
Should you buy in Rolling Oaks Ph 5?
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 July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (12 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2021 (106 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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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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