Margaritaville Rolling Oaks
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in KISSIMMEE, FL · median $373,400 · 734 townhomes for sale in KISSIMMEE · 617 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Margaritaville Rolling Oaks in Kissimmee, FL has 4 homes for sale, asking from $299,999 to $575,000 (median $372,000). Over the 12 months ending 2026-09-12, 6 recorded sales closed at a median of $434,500, $268 per square foot, a median 179 days on market, sellers accepting 90% of original asking (+17% versus the prior year). Homes listed or recently sold were built 2018 - 2023; 11 of 11 report an HOA (median $583/mo); none of the 11 geocoded homes sit in a FEMA special flood hazard zone (median elevation 108 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $6,620 ($6,020 with the full homestead exemption).
Homes For Sale Right Now in Margaritaville Rolling Oaks
Live MLS inventory for Margaritaville Rolling Oaks. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 63 daysTop listing
Active · 1 days
Active · 45 days
Active · 1 daysActive and pending Margaritaville Rolling Oaks listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2022 through 2026. Tap any home to ask about it.
Margaritaville Rolling Oaks right now
🟢 Buyer-leaning market. 6.9 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 12, 2026. Confidence: Medium (4 active and pending listings, 6 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($434K) is up 17.4% from the prior 12 months ($370K). With about 4 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 September 12. Confidence: Medium (6 and 12 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 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
Margaritaville Rolling Oaks market snapshot (as of September 12, 2026): the median sale price is about $434K ($268 per sq ft over the trailing 12 months of closed sales), a median 180 days on market for closed sales, and 6.9 months of supply, a buyer-leaning market. The trailing-12-month median is up 17% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 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.
Flood zones in Margaritaville Rolling Oaks: of 11 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Kissimmee.
Margaritaville Rolling Oaks is a community of 141 homes in Kissimmee, Osceola County, built between 2019 and 2023 (median 2022), with a median living area of about 1,557 square feet. 2% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Margaritaville Rolling Oaks. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Margaritaville Rolling OaksPhotos from Stellar MLS listings in Margaritaville Rolling Oaks; content deemed reliable but not guaranteed.
Margaritaville Rolling Oaks on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Margaritaville Rolling Oaks
- Fitness Center · reported on 12 of 12 listings
- Pool · reported on 12 of 12 listings
- Restaurant · reported on 9 of 12 listings
- Gated Community - Guard · reported on 6 of 12 listings
- Dog Park · reported on 3 of 12 listings
- Gated Community - No Guard · reported on 2 of 12 listings
- Gated · reported on 1 of 12 listings
- Park · reported on 1 of 12 listings
- Playground · reported on 1 of 12 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
The Margaritaville Rolling Oaks buying strategy.
If we were buying in Margaritaville 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Margaritaville Rolling Oaks.
A closer look at the Margaritaville Rolling Oaks market
At a median of $268 per square foot, Margaritaville Rolling Oaks prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 6.9 months of supply, a buyer-leaning market and the trailing-12-month median up 17% year over year. Homes that do trade take a median 180 days on market, useful leverage on any listing that has lingered.
The housing stock is 141 homes built between 2019 and 2023, and 2% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Margaritaville 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 Margaritaville 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 4 factors (4.2). Basis: Recent Direction +17.4% year-over-year; Liquidity & Demand 6.9 months of supply; Owner Commitment 2% owner-occupied; Pricing Power 90.4% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $583/month (about $6,996/yr) · median of 33 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $583 per month ($6,996 a year) - the median AssociationFee across 33 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 Margaritaville 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 Margaritaville 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 Margaritaville 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 Margaritaville Rolling Oaks home worth?
Get a no-obligation home value based on real comparable sales in Margaritaville 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.
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MARGARITAVILLE, ROLLING OAKS Market Scorecard
MARGARITAVILLE, ROLLING OAKS is currently a buyer's market. About 6.9 months of supply, a median asking price of $372,000, and homes go under contract in about 23 days.
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: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
What is the median home price in Margaritaville Rolling Oaks?
How long do homes in Margaritaville Rolling Oaks take to sell?
Is Margaritaville Rolling Oaks a buyer's or seller's market right now?
How many homes are in Margaritaville Rolling Oaks?
What share of Margaritaville Rolling Oaks is owner-occupied?
When were the homes in Margaritaville Rolling Oaks built?
Who is the best real estate agent for Margaritaville Rolling Oaks?
How do I find a top Kissimmee real estate agent who knows Margaritaville Rolling Oaks?
Can Momentum Realty connect me with an agent for Margaritaville Rolling Oaks?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2022 (19 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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