Rolling Oaks / Margaritaville
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 1 closed sale in Rolling Oaks / Margaritaville in Kissimmee, FL, 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).
Rolling Oaks / Margaritaville sits in Kissimmee, Osceola County, an area shaped heavily by the short-term rental and resort-adjacent housing stock that surrounds the theme park corridor. Pricing in communities like this tends to be driven less by square footage alone and more by how a home is positioned for use — primary residence, seasonal stay, or investment rental — and that mix affects how listings compare to one another even within the same community.
Current MLS data for this community does not surface a confirmed amenities package, which is worth noting rather than glossing over. Before writing an offer or listing here, we verify the actual amenity access, HOA structure, and any rental restrictions directly against the listing and association documents rather than assuming based on the community's name or reputation.
Nearby homes for sale
No active listings inside Rolling Oaks / Margaritaville 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 / Margaritaville is a Kissimmee community in Osceola County where the current MLS feed does not identify a specific set of shared amenities, so buyers should treat amenity claims as something to confirm listing-by-listing rather than assume community-wide.
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 Rolling Oaks / Margaritaville is best for.
Best for
- Buyers who want a Kissimmee, Osceola County address near the resort corridor and are comfortable verifying HOA and amenity terms directly
- Investors evaluating short-term or seasonal rental use who plan to confirm rental rules against the specific listing before purchase
- Sellers who can document their unit's actual amenity access and HOA terms clearly to differentiate from other listings in the community
Probably not for
- Buyers assuming a fixed resort-style amenity package is included based on the community name alone
- Buyers who want amenity details fully confirmed before they start shopping rather than verified during the offer process
- Anyone unwilling to review HOA and rental-restriction documents directly before committing to a purchase here
The market around Rolling Oaks / Margaritaville
Rolling Oaks / Margaritaville is too small for its own price trend, so here is the market around it.
In ZIP 34747, 1,258 homes are on the market and 12% 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 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.
ZIP and county figures describe the wider market, not Rolling Oaks / Margaritaville specifically. Momentum Research analysis of MLS records.
The Rolling Oaks / Margaritaville buying strategy.
If we were buying in Rolling Oaks / Margaritaville 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 / Margaritaville.
What the data actually shows
The name Rolling Oaks / Margaritaville carries associations for a lot of buyers searching in the Kissimmee market, but our job is to separate reputation from what the current listing data confirms. As of this snapshot, no community amenities are identified from active MLS listings, which does not necessarily mean none exist — it means the listings themselves are not documenting them, and that gap needs to be closed before anyone budgets for a pool, clubhouse, or resort-style access as part of the purchase.
For a buyer or seller working in this community, the practical move is to pull the specific HOA documents and any resort or club membership terms tied to the individual address, rather than relying on the community name to imply a fixed amenity set. Osceola County's Kissimmee submarket includes a wide range of product types under similar-sounding community names, and terms can vary meaningfully from one section or phase to the next.
The location and the amenities are priced into every listing in Rolling Oaks / Margaritaville. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
When a community's amenity picture is not clearly documented in the MLS feed, the value we add is in verification — confirming HOA terms, rental rules, and any resort or club access directly with the association before you are under contract, not after. In a market like Kissimmee where naming and marketing can outpace what is actually recorded in the listing, that due diligence step is the difference between a clean transaction and a surprise at closing.
Rolling Oaks / Margaritaville in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $370/month (about $4,440/yr) · median of 4 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $370 per month ($4,440 a year) — the median AssociationFee across 4 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
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 / Margaritaville 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 / Margaritaville 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 / Margaritaville, 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 / Margaritaville home worth?
Get a no-obligation home value based on real comparable sales in Rolling Oaks / Margaritaville, 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 all homes for sale in Kissimmee →
Should you buy in Rolling Oaks / Margaritaville?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2026 (1 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 local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Rolling Oaks / Margaritaville fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Rolling Oaks / Margaritaville
Where is Rolling Oaks / Margaritaville?
Rolling Oaks / Margaritaville is a community in Kissimmee, Osceola County, Florida, ZIP 34747.
Are there homes for sale in Rolling Oaks / Margaritaville right now?
No active listings inside Rolling Oaks / Margaritaville at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Rolling Oaks / Margaritaville have an HOA or CDD?
No HOA is on record for Rolling Oaks / Margaritaville 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.
Nearby Communities
Explore more neighborhoods near Rolling Oaks / Margaritaville with Momentum Realty’s local guides.
Rolling Oaks Margaritaville Market Scorecard
Rolling Oaks Margaritaville is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34747 ZIP is $400,438, about 3.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.