Rolling Hills Estates
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 5 closed sales in Rolling Hills Ests Unit 1 in Kissimmee, FL since 2011, the most recent in April 2022. 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 Hills Estates Unit 1 is a tightly built pocket of 189 homes, all raised within a narrow 1998 to 2001 window, so age and construction style stay consistent from block to block. With a median living area just over 2,089 square feet, most homes here land in a similar mid-size range, which keeps comparisons between listings fairly straightforward rather than the wide swings you see in communities with mixed lot sizes or decades of infill.
With homestead exemptions filed on roughly 31% of homes, a meaningful share of the community turns over as non-homestead or investment-held property, which is worth noting when you are gauging how a listing has been used and maintained. No community amenities are identified from current MLS listings, so buyers should treat this as a straightforward single-family subdivision rather than an amenity-driven purchase, and confirm any HOA scope directly rather than assuming a clubhouse or pool comes with it.
Nearby homes for sale
No active listings inside Rolling Hills Ests Unit 1 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
Built out over a compact three-year span in the late 1990s, Rolling Hills Estates Unit 1 offers a consistent housing stock in Kissimmee without a documented amenity package, so the appeal here is the home and lot themselves rather than shared community features.
Stellar MLS sales records identify 159 homes in Rolling Hills Estates that have changed hands since 2004, built between 1998 and 2025 (median 1999), with a median living area of about 1,822 sq ft and a typical 4-bedroom, 3-bath layout; 99% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
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 Hills Estates is best for.
Best for
- Buyers wanting a single-family home from a consistent late-1990s build era without amenity fees attached
- Buyers comfortable evaluating condition and updates on a home that is now over two decades old
- Investors comfortable with a subdivision that already has a meaningful non-homestead share in its resale mix
Probably not for
- Buyers who want a documented clubhouse, pool, or recreational amenity package as part of the purchase
- Buyers seeking new construction or a recently built home rather than a fixed 1998–2001 build era
- Buyers who need confirmation of school assignment or quality before considering the location, which this analysis does not address
The market around Rolling Hills Estates
Rolling Hills Estates 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 Hills Estates specifically. Momentum Research analysis of MLS records.
Rolling Hills Estates Unit 1 by the numbers
From county property records and closed MLS sales for the Rolling Hills Estates Unit 1 subdivision: 15 homes on record; built 1998–1999; typical size about 1,822 heated sq ft; 4 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2009 | 1 | $125,000 |
| 2010 | 1 | $195,000 |
| 2012 | 4 | $180,000 |
| 2013 | 5 | $194,900 |
| 2014 | 3 | $200,000 |
| 2020 | 1 | $295,500 |
Newest recorded sale: $295,500 on 2020-12-14.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
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.
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 Hills Estates.
A consistent build era, minimal shared infrastructure
The 1998–2001 build window means most structural systems, roof ages, and floor plans across the 189 homes are working from a similar starting point, which simplifies comparisons but also means clusters of homes may need similar-timed updates around the same window. Median living space just over 2,089 square feet points to a subdivision built for standard single-family living rather than oversized or compact product.
The homestead share sitting near 31% signals that a notable portion of the community is not owner-occupied under exemption, which can mean more rental or investment activity mixed in with owner-occupied resale. Since no community amenities are identified from current MLS listings, buyers should verify any HOA obligations, restrictions, or shared maintenance responsibilities directly rather than assuming pooled recreational infrastructure exists.
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.
Why work with Momentum here
In a subdivision with a narrow build era and no documented amenity package, the real diligence is in the individual home, not the community brochure. We help you read condition and update history against a build year that is now over two decades old, confirm what HOA terms actually apply, and price against comparable homes rather than assumptions.
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.
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Should you buy in Rolling Hills Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2011 (5 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 local comps.
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See how Rolling Hills Estates Unit 1 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Rolling Hills Estates
Where is Rolling Hills Estates?
Rolling Hills Estates is a community in Kissimmee, Osceola County, Florida, ZIP 34747.
How many homes are in Rolling Hills Estates?
County property records list 15 homes in Rolling Hills Estates, built between 1998 and 1999; the typical home is about 1,822 heated square feet.
What do homes in Rolling Hills Estates sell for?
Rolling Hills Estates has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2020 (1 sale, median $295,500). For context, ZIP 34747 has 1258 homes on the market with 12% under contract.
Are there homes for sale in Rolling Hills Estates right now?
No active listings inside Rolling Hills Estates 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 Hills Estates have an HOA or CDD?
No HOA is on record for Rolling Hills Estates 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.
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