Trailwood Estates
Homes for Sale in Crestview, FL
All 427 homes for sale in Crestview, FL · median $327,852 · 120 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
Over the 12 months ending 2026-09-20, 6 recorded sales closed at a median of $310,500, a median 77 days on market, sellers accepting 95% of original asking. Homes listed or recently sold were built 2007–2021. At the median price and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $4,000 ($3,490 with the full homestead exemption).
| Location | Crestview, Okaloosa County, FL · ZIP 32536, 32539 |
|---|---|
| Homes in the community | 124 (FL DOR 2025 assessment roll) |
| Years built | 1945–2024 (median 2006.0) |
| Typical living area | 1,699 sq ft (median) |
| Home types (current listings and sales) | detached single family 100% |
| Amenities listed by sellers | Security System |
| Sale prices, last 12 months | $310,500 median across 6 closed sales |
| Days on market (closed sales) | 77 median |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 69% |
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, “TRAILWOOD ESTATES key facts,” movewithmomentum.com/neighborhoods/trailwood-estates, data as of September 20, 2026.
In Trailwood Estates, condition and vintage drive price more than location does. With a housing stock spanning 1945 to 2024 and a median build year around 2006, you're shopping across genuinely different eras of construction under one community name. The median sits at $310,500, but that single figure hides a wide spread — a mid-century original and a nearly new build simply aren't the same product, and the price gap between them reflects that.
The market posture here is patient. A median of 77 days on market tells you homes are not moving on urgency, which gives buyers room to inspect, negotiate, and walk away. Sellers should price to condition and plan for a longer runway rather than assuming a quick close. With homestead occupancy near 69 percent, most homes here are lived in rather than turned over, which tends to keep inventory measured.
Nearby homes for sale
No active listings inside TRAILWOOD 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
Trailwood Estates market snapshot (as of September 20, 2026): the median sale price is about $310K, and a median 77 days on market for closed sales.
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.
County records show 9 qualified sales in TRAILWOOD ESTATES across 2024–2025 (7 in 2024, 2 in 2025), median $259,900 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Trailwood Estates is a community of 124 homes in Crestview, Okaloosa County, built between 1945 and 2024 (median 2006.0), with a median living area of about 1,699 square feet. 69% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Trailwood Estates is a 124-home community in Crestview where the appeal is the mix — everything from postwar houses to 2024 builds — rather than a uniform look or a shared amenity set. The median home runs about 1,699 square feet.
The setting & the homes.
Aerial and on-site photos of Trailwood Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Trailwood EstatesPhotos from Emerald Coast MLS listings in Trailwood Estates; content deemed reliable but not guaranteed.
Who Trailwood Estates is best for.
Best for
- Buyers around the mid-$300s who want a mid-sized home and will shop on condition
- Renovation-minded buyers open to an older build with upside
- Patient buyers who value a longer market timeline for diligence and negotiation
Probably not for
- Buyers who need a pool, clubhouse, or other shared amenities
- Buyers wanting a uniform, single-era subdivision with predictable homes
- Sellers expecting a fast close without pricing to condition
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Emerald Coast MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($310K) IS the median in the snapshot above.
Windows contain 0 to 15 sales each (6 in the current window); every figure carries its sample size, and thin markets swing on single closings. 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.
32% 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 (2026-09-20).
Trailwood Estates Market Scorecard
Trailwood Estates is currently a balanced market..
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Emerald Coast MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in TRAILWOOD 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.
Trailwood 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, tiles © CARTO.
The Trailwood Estates buying strategy.
If we were buying in Trailwood 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 Trailwood Estates.
A vintage-spread community, priced on condition
The defining feature here is the year-built range: 1945 to 2024. That is roughly eight decades of building standards, footprints, and mechanical systems sitting side by side. The median year built near 2006 means the community leans toward newer than its oldest stock suggests, but you should expect to encounter both. Inspection matters more than usual — roof, HVAC, and electrical age will vary dramatically from one address to the next, and that variance is exactly what the median price papers over.
No community amenities were identified from current MLS listings, so buy for the house and the location, not for shared facilities. At a median around 1,699 square feet, the typical home is mid-sized rather than sprawling. With a 77-day median on market, there is generally time to do the diligence a mixed-vintage community demands.
The location and the amenities are priced into every listing in Trailwood Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community with an eight-decade build range rewards local eyes. We help you read which era a home belongs to, what that implies for systems and renovation cost, and how to price against a median that blends very different products. On the sell side, we position your home against comparable vintage and condition rather than a blunt community average, and we set expectations around a market that has been trading closer to 77 days than to a bidding war.
Trailwood 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 Trailwood 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 Trailwood Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Trailwood 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 Trailwood Estates home worth?
Get a no-obligation home value based on real comparable sales in Trailwood 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 →
Frequently Asked Questions
What is the median home price in Trailwood Estates?
How long do homes in Trailwood Estates take to sell?
How many homes are in Trailwood Estates?
What share of Trailwood Estates is owner-occupied?
When were the homes in Trailwood Estates built?
Who is the best real estate agent for Trailwood Estates?
How do I find a top Crestview real estate agent who knows Trailwood Estates?
Can Momentum Realty connect me with an agent for Trailwood Estates?
Where is Trailwood Estates, and what county is it in?
Is Trailwood Estates a good place to live?
Should you buy in Trailwood 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: September 26, 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 (5 streets, ZIP 32536/32539)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2012 (62 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.
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 Emerald Coast MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how TRAILWOOD ESTATES fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Trailwood Estates with Momentum Realty’s local guides.