Oak Hollow
Homes for Sale in Crestview, FL
All 419 homes for sale in Crestview, FL · median $325,900 · 208 homes for sale in 32539 · Okaloosa County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 14 recorded sales closed at a median of $281,000, a median 53 days on market, sellers accepting 100% of original asking (+1% versus the prior year). At the median price and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $3,620 ($3,110 with the full homestead exemption).
Oak Hollow is a small pocket in Crestview, and price here is driven less by the community and more by the individual home. With no amenities identified in current listings, you are paying for the house itself — its condition, its updates, its lot — not for shared features. The median sits at $281,000, and the spread around that number tends to track condition more than anything else.
The market posture is patient. At a median of 50 days on market and year-over-year values off by 1.7%, this is not a place where sellers can name a price and walk away. Buyers have room to inspect, negotiate, and be selective. Sellers who price to the home's actual condition, rather than to hope, are the ones who close.
Oak Hollow right now
🟡 Still climbing. The trailing-12-month median ($281K) is up 0.8% from the prior 12 months ($279K). With about a dozen sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Emerald Coast MLS closed sales, 12-month windows ending September 12. Confidence: Medium (14 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 16, 2026 · Live data: Emerald Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside OAK HOLLOW 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
Oak Hollow market snapshot (as of September 12, 2026): the median sale price is about $281K, and a median 54 days on market for closed sales. The trailing-12-month median is up 1% from the prior 12 months, computed from record-level Emerald Coast MLS closed sales (14 closings in the current window).
In ZIP 32539 (Crestview), 538 homes closed in the last 12 months at a median of $322K, up 7.5% year over year, with a median 67 days on market. Right now 141 active and 45 pending listings put supply at about 4.3 months — a balanced market. See the live ZIP 32539 housing market and the Okaloosa County market.
Emerald Coast MLS sales records identify 21 homes in OAK HOLLOW that have changed hands since 2025, built between 2025 and 2026 (median 2025), with a median living area of about 1,398 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.
Oak Hollow is a compact Crestview community of 22 homes with no shared amenities identified in current MLS listings, so value rests entirely on the individual property rather than any community draw.
Who Oak Hollow is best for.
Best for
- Buyers targeting a home near the mid-$280s who want to weigh condition over community features
- Patient shoppers comfortable waiting through a roughly 50-day market to find the right house
- Value-minded buyers willing to negotiate in a slightly softening market
Probably not for
- Buyers who want pools, trails, or other shared amenities built into the community
- Anyone needing to buy and sell fast in a competitive, fast-moving market
- Buyers counting on quick value gains rather than a home to live in
Housing distress & ownership in OAK HOLLOW, 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.
The Oak Hollow buying strategy.
If we were buying in Oak Hollow 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 Oak Hollow.
A condition-driven market with no shortcuts
With 17 closings in the tracked window against 22 homes, this is a small, thinly traded pocket. That means each sale carries weight, and one updated or one tired home can move the picture. Buyers should read each listing on its own merits rather than assume a neighborhood baseline.
The homestead share reads at 0.0%, which suggests owner-occupancy is not the story that current data tells here. Combined with the slight year-over-year softening and the 50-day median, this is a market that rewards diligence — comparing homes closely on condition and being willing to wait for the right one.
The location and the amenities are priced into every listing in Oak Hollow. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, thinly traded pocket like Oak Hollow, comps are scarce and each home stands on its own condition. We read the individual property rather than lean on a neighborhood average, and we price and negotiate to what the house actually is — which matters most when the market is patient and slightly soft.
Oak Hollow 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 Oak Hollow 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 Oak Hollow sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oak Hollow, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oak Hollow home worth?
Get a no-obligation home value based on real comparable sales in Oak Hollow, 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 →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Okaloosa County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Okaloosa County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Frequently Asked Questions
What is the median home price in Oak Hollow?
How long do homes in Oak Hollow take to sell?
Who is the best real estate agent for Oak Hollow?
How do I find a top Crestview real estate agent who knows Oak Hollow?
Can Momentum Realty connect me with an agent for Oak Hollow?
Should you buy in Oak Hollow?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Emerald Coast MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Emerald Coast MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2025 (21 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.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how OAK HOLLOW fits the bigger picture — live prices, inventory, and Momentum Scores:
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