ROLLING HILLS ESTATES in KISSIMMEE

ROLLING HILLS ESTATES
Homes for Sale in KISSIMMEE, FL

Community in KISSIMMEE · Osceola County · ZIP 34747
189 homesBuilt 1998–2001
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data21 years of closingsFL DOR public recordsUpdated twice daily
Live · ROLLING HILLS ESTATES Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
1
Sold · last 12 mo
10-yr average: about 4 a year
Ownership and context
31%
Owner-occupied · ROLLING HILLS ESTATES
59 of 190 parcels homesteaded (FL DOR 2025)
69%
Non-owner-occupied · ROLLING HILLS ESTATES
incl. 17% trust or LLC-held · 46% out-of-state
30%
Cash buyers · ROLLING HILLS ESTATES
3 of 10 sales, 12 mo ending June 2024
189
Homes in the community
plus 1 vacant residential lots · 190 residential parcels (FL DOR 2025)
Track record · 21 years of records
Est. 1998
Community established
homes built 1998-2001, median 1999 (FL DOR 2025)
3
Failed listings · 2026
peaked at 10 in 2015
0.5%/yr
Turnover rate
about 1 of 189 homes trade a year

The market around ROLLING HILLS ESTATES

ROLLING HILLS ESTATES is a small community — 58 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.

In ZIP 34747, 1,240 homes are on the market and 12% are under contract — a slower corner of KISSIMMEE.

Across Osceola County, 4,437 homes are active and 1,149 pending (21% under contract).

The housing mix here is 99% single family residence, 1% villa.

ZIP and county figures describe the wider market, not ROLLING HILLS ESTATES specifically. Momentum Research analysis of MLS records.

If we were buying in ROLLING HILLS ESTATES today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 closer look at the ROLLING HILLS ESTATES market

The housing stock is 189 homes built between 1998 and 2001, and 31% 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 ROLLING HILLS ESTATES. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

In short
  • Mandatory HOA. Confirm current dues
  • 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.

The takeaway

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.

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 →

Real comps, not an automated estimate.

ROLLING HILLS ESTATES Market Scorecard

No active listings

ROLLING HILLS ESTATES is currently a no active listings market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
$460,000
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/1
Active/Pend/Sold

Go deeper: 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.

Frequently Asked Questions

How many homes are in ROLLING HILLS ESTATES?
The Florida DOR 2025 assessment roll shows 189 homes plus 1 vacant residential lots in ROLLING HILLS ESTATES (public records).
What share of ROLLING HILLS ESTATES is owner-occupied?
31% of ROLLING HILLS ESTATES parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in ROLLING HILLS ESTATES built?
Homes in ROLLING HILLS ESTATES were built between 1998 and 2001, with a median year built of 1999 (FL DOR 2025 roll).
Do cash buyers compete in ROLLING HILLS ESTATES?
Cash buyers took 30% of ROLLING HILLS ESTATES sales in the 12 months ending June 2024 (3 of 10 closings, Stellar MLS).
Who is the best real estate agent for ROLLING HILLS ESTATES?
The best agent for ROLLING HILLS ESTATES is one who actively works KISSIMMEE and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for ROLLING HILLS ESTATES.
How do I find a top KISSIMMEE real estate agent who knows ROLLING HILLS ESTATES?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows ROLLING HILLS ESTATES and the wider KISSIMMEE area.
Can Momentum Realty connect me with an agent for ROLLING HILLS ESTATES?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your ROLLING HILLS ESTATES purchase or sale - no call center and no pressure.

Nearby Communities

Explore more neighborhoods near ROLLING HILLS ESTATES with Momentum Realty’s local guides.

Formosa Gardens Kissimmee0.3 mi awayFormosa Valley Kissimmee0.3 mi awayIndian Creek Kissimmee0.5 mi awayWindsor Hills Phase Three Kissimmee0.5 mi awayWyndham Pointe Acadia Estates Kissimmee0.6 mi awayWyndham Pointe Kissimmee0.6 mi awayWindsor Hills P1 Kissimmee0.7 mi awayVentura Windsor Hls P6 Kissimmee0.7 mi away

Browse all Florida neighborhood guides →

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: August 2, 2026)
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (6 streets, ZIP 34747))
Under-contract sharesStellar MLS records, as of 2026-08-01
Historical depthClosed-sale records back to 2005 (66 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 your area 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.

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CallFree valuation →
Thinking of selling in ROLLING HILLS ESTATES? 1 recorded closings (window ending 2026-08-02). See the Osceola County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
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