Rolling Hills Estates
Homes for Sale in Crestview, FL
All 415 homes for sale in Crestview, FL · median $329,800 · 155 homes for sale in 32536 · Okaloosa County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Emerald Coast MLS
As of October 2026, the MLS records 31 closed sales in Rolling Hills Estates in Crestview, FL since 2002, the most recent in July 2026. Across Crestview as a whole, 571 homes closed in the last 12 months at a median of $321,973, 71 median days on market, with 398 homes for sale today. At that median and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $4,150 ($3,640 with the full homestead exemption).
Rolling Hills Estates is a small, established pocket of Crestview where price is driven mostly by condition and square footage, not by amenities or new construction. With a median of $288,000 on roughly 2,045 square feet, and homes built between 1988 and 2005, what separates one closing from another here is how much updating the owner has done. Expect a wide spread around that median: a dated interior and an updated one in the same neighborhood will not price the same.
The market posture leans toward patience. A median of 82 days on market tells you homes here are not moving quickly, which gives a buyer real room to negotiate and inspect without pressure. For a seller, that same number is the warning: price to condition from day one, because this is not a market that rewards testing a high number and waiting.
Figures in this note are as of July 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside ROLLING HILLS ESTATES 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
A compact, mature subdivision of about 41 homes in Crestview with a median build year of 1996 and no identified community amenities — the value proposition here is space and an established location rather than pools or shared features.
Emerald Coast MLS sales records identify 17 homes in ROLLING HILLS ESTATES that have changed hands since 2002, built between 1988 and 2005 (median 1996), with a median living area of about 1,584 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Emerald Coast MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 7 qualified sales in ROLLING HILLS ESTATES across 2024–2025 (6 in 2024, 1 in 2025), median $285,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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 prioritizing living space around 2,045 square feet at a mid-$280s median in an established area
- Buyers who value a slower market and want time to inspect and negotiate
- Buyers comfortable taking on a home built between 1988 and 2005 and budgeting for updates
Probably not for
- Buyers who want community amenities like a pool or shared spaces
- Buyers set on new construction or turnkey, never-updated finishes
- Buyers who need to close fast in a fast-moving, competitive market
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 32536, 257 homes are on the market and 32% are under contract — a fast-moving corner of Crestview.
Across Okaloosa County, 1,890 homes are active and 551 pending (23% under contract).
In ZIP 32536 (Crestview), 425 homes closed in the last 12 months at a median of $322K, up 3.9% year over year, with a median 73 days on market. Right now 122 active and 57 pending listings put supply at about 3.9 months — a balanced market. See the live ZIP 32536 housing market and the Okaloosa County market.
ZIP and county figures describe the wider market, not Rolling Hills Estates specifically. Momentum Research analysis of MLS records.
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.
An established pocket where condition sets price
The housing stock is consistent in age but not in updates. Built across a roughly two-decade window ending in 2005, these are homes that have had time to be renovated well, renovated cheaply, or not at all. That is why the median price of $288,000 is best read as a midpoint, not a benchmark — the actual number on any given home depends heavily on roof, systems, and kitchen and bath condition.
A homestead share of 78% points to a neighborhood held largely by long-term owner-occupants rather than short-term turnover. Combined with only a handful of recent closings, inventory is thin and sporadic. Buyers should be ready to move when the right updated home appears; sellers should know comparable sales may be limited enough that pricing takes real analysis rather than a quick glance.
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 thin, condition-driven market like this, the wrong comp leads to the wrong price. We read each listing against its actual updates and square footage instead of leaning on a single median, and with an 82-day median on market, we help buyers negotiate from a position of time and help sellers price to condition before the clock works against them.
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 all homes for sale in Crestview →
| Location | Crestview, Okaloosa County, FL · ZIP 32536, 32539 |
|---|---|
| Homes in the community | 41 (FL DOR 2025 assessment roll) |
| Years built | 1988–2005 (median 1996) |
| Typical living area | 2,045 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 78% |
Data as of September 20, 2026. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Rolling Hills Estates key facts,” movewithmomentum.com/neighborhoods/rolling-hills-estates, data as of September 20, 2026.
Housing distress & ownership in ROLLING HILLS ESTATES, Crestview
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. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
More Crestview home searches
- All homes for sale in Crestview, FL
- Homes for sale in Okaloosa County, FL
- Crestview waterfront homes for sale
- Gated communities in Crestview
- Homes under $300K in Crestview
- Homes from $300K to $500K in Crestview
- 4-bedroom homes for sale in Crestview
- Crestview home values: what is my house worth?
- ZIP 32536 housing scorecard
- 2 coming-soon communities in Okaloosa County
Crestview guides & data
- Market data
- Best neighborhoods (ranked by data)
- Property taxes (Okaloosa County)
- Homestead exemption (Okaloosa County)
- Home insurance cost
- New construction
- New construction (Okaloosa County)
- ZIP codes
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
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Ask an agent about Rolling Hills Estates
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Recent Developments in Rolling Hills Estates
Development, infrastructure, retail, and school activity affecting Rolling Hills Estates, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- October 2026Infrastructure
Okaloosa County stabilizes 180 miles of dirt roads in north county
Okaloosa County has stabilized 180 miles of dirt roads using the voter-approved infrastructure surtax, more than triple the original goal of 50 miles in five years. The roads received a limerock base topped with chip-seal or hot-mix, and the county says only a handful of roads remain. The work is in north Okaloosa County.
What it may mean for the marketPaved rural roads in north Okaloosa could improve year-round access and reduce road maintenance costs for areas near Crestview. The site is about 3 miles north of Rolling Hills Estates.
Source: Get The Coast - October 2026Parks & Amenities
Okaloosa and Cinco Bayou open upgraded boat ramp with new trailer parking
Okaloosa County and the Town of Cinco Bayou held a ribbon cutting for upgraded boat ramp facilities, including 16 new boat trailer parking spaces, a new restroom and landscaping. The $4.1 million total, funded largely by tourism development funds, also covers the $2.95 million purchase of a former bank building at 198 Eglin Parkway NE. Future dock improvements are planned.
What it may mean for the marketAdded trailer parking and ramp access improve waterfront recreation access for Fort Walton Beach area boaters. The project is about 22 miles south of Rolling Hills Estates, elsewhere in Okaloosa County.
Source: Get The Coast - September 2026Civic
Okaloosa commissioners reject 12-month data center moratorium 3-2
Okaloosa County commissioners voted 3-2 on September 15 against a 12-month data center moratorium. On September 3 the board unanimously directed staff to develop a regulatory framework for data centers, with an outline due within 60 days. No specific project or site was proposed, and commissioners discussed protecting the Shoal River Industrial Park.
What it may mean for the marketThe pending rules will shape where large power-and-land-intensive facilities can locate in the county, including industrial land near Crestview. The site is about 2 miles west of Rolling Hills Estates.
Source: Get The Coast - June 2026Civic
DeSantis signs state budget with funding for Okaloosa County projects
Governor DeSantis signed the state budget that included roughly $15 million for 20 Okaloosa County projects, among them $5 million for the Northwest Florida State College Workforce Innovation Center in Niceville, $1.5 million for Shalimar Bridge Park, and $3 million for Destin road and drainage work. About $7.26 million in other local requests were vetoed.
What it may mean for the marketDirects state funding toward workforce, park, road, and drainage infrastructure across Okaloosa County, supporting public facilities and capacity in Niceville, Shalimar, and Destin. The site is about 16 miles south of Rolling Hills Estates.
Source: Get The Coast - May 2026Development
Okaloosa commissioners approve master plan for 392-lot River Park subdivision in Crestview
Okaloosa County commissioners unanimously approved the master plan for River Park, a 392 lot single family subdivision on 263 acres east of Main Drive and north of Airport Road in Crestview. The project by River Park Landing LLC will be built in three phases, with each phase requiring a separate development order approval.
What it may mean for the marketAdds substantial single family housing supply to the Crestview market and phases new residential construction onto a large tract in north Okaloosa County. The project is about 2 miles north of Rolling Hills Estates, elsewhere in Okaloosa County.
Source: Get The Coast - May 2026Infrastructure
Okaloosa County opens $212M Southwest Crestview Bypass
Okaloosa County opened the $212 million Southwest Crestview Bypass, a 3.5 mile four lane corridor connecting Antioch Road to State Road 85 with access from U.S. Highway 90. The project includes a 1,713 foot bridge, sidewalks, a multi use path, and direct access to the new Pineview K-8 school opening in August 2026.
What it may mean for the marketAdds a major four lane traffic corridor serving southwest Crestview and expands regional road capacity for surrounding growth in north Okaloosa County. The site is about 3 miles southwest of Rolling Hills Estates.
Source: Get The Coast
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
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 Crestview real estate agent who knows Rolling Hills Estates?
Can Momentum Realty connect me with an agent for Rolling Hills Estates?
Where is Rolling Hills Estates, and what county is it in?
Should you buy in Rolling Hills Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Emerald Coast MLS, refreshed twice daily (last: October 19, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32536/32539)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2002 (31 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 Emerald Coast 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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