Hillwood 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, Hillwood Estates in Crestview, FL has 1 home for sale. Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $499,900, a median 82 days on market, sellers accepting 98% of original asking. Homes listed or recently sold were built 2022–2022; none of the 7 geocoded homes sit in a FEMA special flood hazard zone (median elevation 186 ft). At the median price and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $6,450 ($5,940 with the full homestead exemption).
Last 30 days in Hillwood Estates: 1 new listing (median asking $558,000), 2 closed sales (median $381,950). As of October 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.
Hillwood Estates is a small pocket in Crestview, and the data here is thin by design: one active listing and only a couple of closings in the recent window. In a market this small, no MLS-derived amenities to lean on, price is set almost entirely by the individual home — its condition, its lot, and how it shows against whatever else is on the ground at the moment. There is no deep comp set to anchor a number, so the last home to trade and the one currently listed carry a lot of weight.
For a buyer, that means patience and flexibility matter more than timing a trend; inventory is a trickle, and when the right house appears you move on it or wait for the next one. For a seller, the scarcity cuts both ways — limited competition, but also limited recent evidence for pricing, which puts a premium on getting the list price right the first time rather than testing the market.
Figures in this note are as of July 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Hillwood Estates right now
🟡 Balanced market. 3.0 months of supply and 50% of the inventory already under contract put buyers and sellers on roughly even footing.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 Emerald Coast MLS records, as of September 20, 2026. Confidence: Low (2 active and pending listings, 3 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 20, 2026 · Live data: Emerald Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Hillwood Estates market snapshot (as of September 20, 2026): the median sale price is about $500K, a median 82 days on market for closed sales, and 3.0 months of supply, a balanced market.
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.
Hillwood Estates is a community of 45 homes in Crestview, Okaloosa County, built between 2022 and 2022 (median 2022.0), with a median living area of about 2,741 square feet. 80% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Hillwood Estates is a low-volume Crestview community in Okaloosa County where activity is measured in a handful of transactions, not dozens. Treat every listing as its own story rather than a slice of a busy market.
The setting & the homes.
Aerial and on-site photos of Hillwood Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Hillwood EstatesPhotos from Emerald Coast MLS listings in Hillwood Estates; content deemed reliable but not guaranteed.
Who Hillwood Estates is best for.
Best for
- Buyers targeting Crestview specifically and content to move quickly when a listing surfaces
- Those who prefer a home with no shared-amenity obligations and want to control their own overhead
- Patient buyers comfortable underwriting a single property on its condition rather than a busy market trend
Probably not for
- Buyers who need several homes to compare before deciding
- Anyone wanting a pool, gym, or gated amenities as part of the purchase
- Buyers on a tight timeline who cannot wait for limited inventory to turn over
Homes For Sale Right Now in Hillwood Estates
Live MLS inventory for Hillwood 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 Hillwood Estates listings as of 2026-10-19, priced high to low. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Tap any home to ask about it.
Hillwood 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 Emerald Coast MLS. Map data © OpenStreetMap contributors.
Schools
- Okaloosa County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Bob Sikes · Elementary
- Davidson · Middle
- Crestview · High
Zoned schools reflect the assignments reported on recent Hillwood Estates listings and can change; always confirm with Okaloosa County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Hillwood Estates address.
Shop the zone: Homes zoned for Crestview High School
The Hillwood Estates buying strategy.
If we were buying in Hillwood 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 Hillwood Estates.
A thin-inventory pocket
With a single active listing and closings you can count on one hand for the window, Hillwood Estates does not behave like a large, liquid subdivision. There is no community pool, gym, or gated entrance identified in the current MLS data, so what you are buying is the house and its immediate setting in Crestview — not a package of shared amenities. That keeps HOA-style overhead out of the equation, but it also means the home itself has to do all the work of justifying its price.
Because the sample is so small, a single well-renovated home or a single dated one can swing the perceived value of the whole area. Do not read too much into an average here. Underwrite the specific property in front of you — its updates, its systems, its lot — and use the broader Crestview market as your reality check rather than relying on a handful of neighborhood closings.
The location and the amenities are priced into every listing in Hillwood 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 Hillwood 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 3 factors (8.0). Basis: Liquidity & Demand 3.0 months of supply; Owner Commitment 80% owner-occupied; Pricing Power 98.3% sale-to-list. Refreshed with each data update.
Why work with Momentum here
Thin-data communities are where a local read earns its keep. We track Crestview inventory closely enough to tell you whether the one listing on the market is priced to its condition or fishing, and whether it makes more sense to buy here or widen the search. On the sell side, we build a price off the actual house and comparable Crestview product rather than a shallow neighborhood sample, so you list once at a number that holds.
Hillwood Estates in 15 seconds.
What it really costs to own in Hillwood Estates
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $1,710/yr across 4 listings here (MLS tax records, 2026-10-20). |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Okaloosa County is $2,644/yr (1,101 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2022 across 6 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Email me new listings in Hillwood Estates
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Hillwood Estates
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Hillwood Estates will answer, and the answer is published on this page for the next buyer.
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 Hillwood 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 Hillwood Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Hillwood 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 Hillwood Estates home worth?
Get a no-obligation home value based on real comparable sales in Hillwood 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 →
Recently off market in HILLWOOD ESTATES
Homes in HILLWOOD ESTATES that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 3 on record.
- 2411 Dakota Way · off market
- 2456 Dakota Way · off market
- 2462 Dakota Way · off market
| Location | Crestview, Okaloosa County, FL · ZIP 32536 |
|---|---|
| Homes in the community | 45 (FL DOR 2025 assessment roll) |
| Years built | 2022–2022 (median 2022.0) |
| Typical living area | 2,741 sq ft (median) |
| Home types (current listings and sales) | detached single family 100% |
| Sale prices, last 12 months | $499,900 median across 3 closed sales |
| Days on market (closed sales) | 82 median |
| For sale right now | 1 active, 1 pending · median asking $379,900 · 3.0 months of supply |
| Owner-occupied (homestead) share | 80% |
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, “Hillwood Estates key facts,” movewithmomentum.com/neighborhoods/hillwood-estates, data as of September 20, 2026.
Housing distress & ownership in HILLWOOD 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.
Every Home for Sale in Hillwood Estates Right Now (1)
All 1 active and pending Hillwood Estates listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2415 Dakota Way · $558,000 · 5 bd / 3 ba · listed Oct 3, 2026 · listed by Coastal Villages Real Estate
Recently sold in Hillwood Estates
- 2456 Dakota Way · sold $379,900
- 2411 Dakota Way · sold $384,000
- 2455 Dakota Way · sold $510,000
- 2462 Dakota Way · sold $390,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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
Real estate agent in Crestview? Join Momentum in Crestview: 100% commission, one $12K cap.
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Dakota Way (38 homes on record)
- Dakota Way (5 homes on record)
- Dakota Way (1 homes on record)
Recent Developments in Hillwood Estates
Development, infrastructure, retail, and school activity affecting Hillwood 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 5 miles north of Hillwood 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 20 miles south of Hillwood 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 northwest of Hillwood 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 14 miles south of Hillwood 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 4 miles northeast of Hillwood 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 1 mile southwest of Hillwood 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.
31% of homes for sale in ZIP 32536 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-20).
Frequently Asked Questions
What is the median home price in Hillwood Estates?
How long do homes in Hillwood Estates take to sell?
Is Hillwood Estates a buyer's or seller's market right now?
How many homes are in Hillwood Estates?
What share of Hillwood Estates is owner-occupied?
When were the homes in Hillwood Estates built?
Who is the best real estate agent for Hillwood Estates?
How do I find a top Crestview real estate agent who knows Hillwood Estates?
Can Momentum Realty connect me with an agent for Hillwood Estates?
Where is Hillwood Estates, and what county is it in?
Should you buy in Hillwood 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) |
| Community market stats | Emerald Coast MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 32536)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2022 (49 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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See how HILLWOOD ESTATES fits the bigger picture — live prices, inventory, and Momentum Scores:
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