Rolling Hills Estates
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Price here is driven by a fairly tight housing stock: 90 homes built between 1998 and 2001, with a median footprint around 2,089 square feet. That consistency means condition and updates do most of the work separating one sale from the next. The median sits at $459,900, or roughly $238.75 per square foot, and with year-over-year movement at just -1.1% this is a market holding roughly flat rather than swinging in either direction.
Median days on market is 41 — not fast, not stalled. Sellers should price to the condition of the home rather than to a headline number and expect a buyer who will compare against the rest of the community's older-2000s inventory. Buyers have some room to negotiate on homes that show deferred maintenance, but there is no fire sale here. The read is patience on both sides.
Rolling Hills Estates right now
🔴 Seller-leaning market. 1.5 months of supply and 50% of the inventory already under contract give sellers the pressure advantage.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 (2 active and pending listings, 8 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($440K) is down 5.0% from the prior 12 months ($462K). With about 5 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 (8 and 6 sales in the two windows).
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· Updated September 12, 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 Hills Estates market snapshot (as of September 12, 2026): the median sale price is about $440K ($247 per sq ft over the trailing 12 months of closed sales), a median 18 days on market for closed sales, and 1.5 months of supply, a seller-leaning market. The trailing-12-month median is down 5% from the prior 12 months, computed from record-level Stellar MLS closed sales (8 closings in the current window).
Rolling Hills Estates is a community of 100 homes in Kissimmee, Osceola County, built between 1998 and 2001 (median 1998.0), with a median living area of about 2,089 square feet. 33% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Rolling Hills Estates Unit 1 at Formosa Gardens is a small, era-consistent pocket in Kissimmee, Osceola County — 90 homes from a narrow late-1990s to 2001 build window, which keeps the housing stock predictable in size and layout.
The setting & the homes.
Aerial and on-site photos of Rolling Hills Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Rolling Hills EstatesPhotos from Stellar MLS listings in Rolling Hills Estates; content deemed reliable but not guaranteed.
Who Rolling Hills Estates is best for.
Best for
- Buyers targeting a roughly 2,000-square-foot home around the mid-$450s who value predictable layouts
- Owner-occupants who want a settled, built-out neighborhood rather than active new construction
- Investors who first confirm HOA and short-term-rental rules and want a tourist-corridor location
Probably not for
- Buyers who need newer construction or modern floor plans
- Anyone wanting a wide selection of price points and home sizes to compare
- Buyers who need a fast, competitive-bid market and can't wait out a roughly six-week median timeline
Housing distress & ownership in Rolling Hills Estates Unit 1 At Formosa Gardens, Kissimmee
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Rolling Hills Estates
Live MLS inventory for Rolling Hills Estates. 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 and pending Rolling Hills Estates listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2026. Tap any home to ask about it.
Rolling Hills Estates 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.
The Rolling Hills Estates buying strategy.
If we were buying in Rolling Hills Estates 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 Hills Estates.
A uniform vintage, priced by condition
With every home built within a three-year span and a median living area near 2,089 square feet, differences in value come down to what an owner has done since. Two homes of the same size can sit well apart on price depending on roof age, systems, kitchens, and finishes. That makes the median of $459,900 a starting reference, not a ceiling or floor — the spread is condition-driven.
The homestead share sits at 34.4%, which tells you a meaningful portion of the stock is not owner-occupied primary residence. Formosa Gardens' location in the Kissimmee tourist corridor is part of that story. Buyers should confirm HOA rules and any short-term rental restrictions before assuming a use case, because the mix here is not purely primary-residence.
The location and the amenities are priced into every listing in Rolling Hills Estates. 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 Hills Estates 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 (6.2). Basis: Recent Direction -5.0% year-over-year; Liquidity & Demand 1.5 months of supply; Owner Commitment 33% owner-occupied; Pricing Power 97.2% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a community this uniform, the money is in reading condition against condition — knowing which updates the last comparable sales actually paid for and which they didn't. With only a handful of recent closings to reference, we lean on the full picture: what sold, what stalled, and why. We will price a listing to its true condition and steer a buyer away from a home whose asking price assumes work that was never done.
Rolling Hills Estates 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 Hills Estates 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 Hills Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Rolling Hills Estates, 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 Hills Estates home worth?
Get a no-obligation home value based on real comparable sales in Rolling Hills Estates, 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 Hills Estates on the map →
Frequently Asked Questions
What is the median home price in Rolling Hills Estates?
How long do homes in Rolling Hills Estates take to sell?
Is Rolling Hills Estates a buyer's or seller's market right now?
How many homes are in Rolling Hills Estates?
What share of Rolling Hills Estates is owner-occupied?
When were the homes in Rolling Hills Estates built?
Who is the best real estate agent for Rolling Hills Estates?
How do I find a top Kissimmee real estate agent who knows Rolling Hills Estates?
Can Momentum Realty connect me with an agent for Rolling Hills Estates?
Should you buy in Rolling Hills Estates?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Rolling Hills Estates with Momentum Realty’s local guides.
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 (3 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2024 (14 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.
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See how Rolling Hills Estates Unit 1 At Formosa Gardens fits the bigger picture — live prices, inventory, and Momentum Scores: