Rolling Oaks
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 950 homes for sale in 34747 · Osceola County homes for sale
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.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 24, 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), 2,599 homes closed in the last 12 months at a median of $460K ($220/sq ft), down 3.8% year over year, with a median 75 days on market. Right now 581 active and 101 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 →
| Location | Kissimmee, Osceola County, FL · ZIP 34747 |
|---|---|
| Homes in the community | 666 (FL DOR 2025 assessment roll) |
| Years built | 2018–2023 (median 2019.0) |
| Typical living area | 1,557 sq ft (median) |
| Sale prices, last 12 months | $414,000 median across 42 closed sales · $293 per sq ft · -3.7% vs the prior 12 months |
| Days on market (closed sales) | 128 median |
| Owner-occupied (homestead) share | 4% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Rolling Oaks key facts,” movewithmomentum.com/neighborhoods/rolling-oaks-ph-5, data as of August 2, 2026.
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Kissimmee guides & data
- Market data
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- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
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Florida buyer guides
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- Florida property tax calculator
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- The 4-point inspection, explained
- Florida flood insurance calculator
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Caribbean Soul Drive (32 homes on record)
- Surf Street (29 homes on record)
- Dreamsicle Drive (23 homes on record)
- Knee Deep Road (18 homes on record)
- Lost Shaker Lane (16 homes on record)
- Salted Rim Road (13 homes on record)
- On The Rocks Point (12 homes on record)
- Knee Deep Road (10 homes on record)
- Surf Street (9 homes on record)
- Salted Rim Road (8 homes on record)
- Salted Rim Road (8 homes on record)
- Surf Street (7 homes on record)
Email me new listings in Rolling OaksHomes for Sale
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Rolling OaksHomes for Sale
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Recent Developments in Rolling Oaks Ph 5
Development, infrastructure, retail, and school activity affecting Rolling Oaks Ph 5, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 6 miles northwest of Rolling Oaks Ph 5.
Source: Spectrum News 13 - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The project is about 14 miles east of Rolling Oaks Ph 5, elsewhere in Osceola County.
Source: Spectrum News 13 - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 9 miles northwest of Rolling Oaks Ph 5.
Source: FOX 35 Orlando - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The project is about 9 miles southeast of Rolling Oaks Ph 5, elsewhere in Osceola County.
Source: Spectrum News 13 - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 9 miles northeast of Rolling Oaks Ph 5.
Source: ClickOrlando
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
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?
Where is Rolling Oaks, and what county is it in?
Is Rolling Oaks a good place to live?
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.
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More Kissimmee & Kissimmee, St. Cloud & Osceola County guides
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