Rolling Pines
Homes for Sale in Crestview, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Emerald Coast MLS
As of November 2026, Rolling Pines in Crestview, FL has 5 homes for sale and 1 pending, asking from $173,500 to $190,000 (median $179,000). Over the 12 months ending 2026-11-09, 3 recorded sales closed at a median of $174,480, a median 60 days on market, sellers accepting 97% of original asking. Homes listed or recently sold were built 2005–2007; 12 of 13 report an HOA (median $35/mo); none of the 13 geocoded homes sit in a FEMA special flood hazard zone (median elevation 170 ft). At the median price and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $2,250 ($1,740 with the full homestead exemption).
| Location | Crestview, Okaloosa County, FL · ZIP 32539 |
|---|---|
| Homes in the community | 251 (FL DOR 2025 assessment roll) |
| Years built | 2005–2007 (median 2006.0) |
| Typical living area | 1,587 sq ft (median) |
| Home types (current listings and sales) | townhouses 100% |
| Amenities listed by sellers | Fire Alarm, Short Term Rental - Not Allowed |
| Sale prices, last 12 months | $174,480 median across 3 closed sales |
| Days on market (closed sales) | 60 median |
| For sale right now | 5 active, 1 pending · median asking $179,000 · 8.6 months of supply |
| Owner-occupied (homestead) share | 16% |
Data as of November 9, 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 Pines key facts,” movewithmomentum.com/neighborhoods/rolling-pines, data as of November 9, 2026.
Homes For Sale Right Now in Rolling Pines
Live MLS inventory for Rolling Pines. 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 · 147 daysTop listing
Active · 154 daysActive · 60 days
Active · 136 days
Active · 38 days
Pending · 42 daysActive and pending Rolling Pines listings as of 2026-11-09, 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.
Every Home for Sale in Rolling Pines Right Now (6)
All 6 active and pending Rolling Pines listings with a detail page, newest first, refreshed twice a day from the MLS.
- 109 Swaying Pine Court · $173,500 · 3 bd / 2.5 ba · listed Oct 2, 2026 · listed by Anchor Realty Florida
- 171 Swaying Pine Court · $179,000 · 3 bd / 2.5 ba · listed Sep 10, 2026 · listed by Salt & Light Realty
- 290 Swaying Pine Court · $169,000 · 3 bd / 2.5 ba · pending · listed Sep 10, 2026 · listed by homecoin.com
- 232 Swaying Pine Court · $174,900 · 3 bd / 2.5 ba · listed Aug 11, 2026 · listed by REV Realty
- 105 Swaying Pine Court · $190,000 · 3 bd / 2 ba · listed Aug 11, 2026 · listed by Coldwell Banker Realty
- 178 Swaying Pine Court · $190,000 · 3 bd / 2.5 ba · listed Aug 11, 2026 · listed by Bastion Realty LLC
Rolling Pines is a tight-built pocket of Crestview homes from a two-year construction stretch in the mid-2000s, and that uniformity is the story. With a median around 1,587 square feet and a median build near 2006, price here is driven less by floor plan variety and more by condition, updates, and how a given home has been kept. The median sits at $180,000, and with a build cohort this consistent, what separates one sale from another is usually the work done inside the walls.
The posture right now is slow and patient. A median of roughly 114 days on market and a heat score of 17 tell you buyers have time to think and sellers should not expect a bidding war. Year-over-year price movement is essentially flat at 0.6%, so this is a hold-and-live market, not a flip market. With only 4 active listings against 251 homes, inventory is thin — which means the right buyer may wait, and the right seller needs to be sharp on pricing and presentation to move.
Figures in this note are as of July 25, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Rolling Pines right now
🟢 Buyer-leaning market. 8.6 months of supply and 17% of the inventory already under contract give buyers above-average negotiating leverage.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 November 9, 2026. Confidence: Medium (6 active and pending listings, 3 closed sales in 12 months).
What's unique here: the median sale price is about 53% below the typical Okaloosa County sale ($174K vs $372K, trailing 12 months, Emerald Coast MLS records).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 9, 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
Rolling Pines market snapshot (as of November 9, 2026): the median sale price is about $174K, a median 60 days on market for closed sales, and 8.6 months of supply, a buyer-leaning market.
Rolling Pines is a community of 251 homes in Crestview, Okaloosa County, built between 2005 and 2007 (median 2006.0), with a median living area of about 1,587 square feet. 16% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Rolling Pines is a compact, consistent Crestview subdivision built in a short mid-2000s window, where homes trade on condition rather than on floor-plan variety. Turnover is modest and the pace is unhurried.
The setting & the homes.
Aerial and on-site photos of Rolling Pines. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Rolling Pines
Rolling PinesPhotos from Emerald Coast MLS listings in Rolling Pines; content deemed reliable but not guaranteed.
Who Rolling Pines is best for.
Best for
- Buyers with a budget around the $180,000 median looking for a straightforward, comparably-sized single-family home
- Patient buyers who can wait out a slow market and negotiate from a position of time
- Long-hold owners focused on living in the home rather than short-term resale
Probably not for
- Buyers who want community amenities like a pool, clubhouse, or trails
- Sellers who need to close quickly and expect a fast, competitive sale
- Buyers counting on near-term price appreciation to build equity
Housing distress & ownership in ROLLING PINES, 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.
Rolling Pines 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
- Riverside · Elementary
- Shoal River · Middle
- Crestview · High
Zoned schools reflect the assignments reported on recent Rolling Pines 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 Rolling Pines address.
The Rolling Pines buying strategy.
If we were buying in Rolling Pines 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Pines.
A uniform vintage in a slow lane
When nearly every home shares a build era and a similar size, the market gets legible: you can compare like against like, and the premium goes to homes that have been updated and maintained. That is good news for a buyer who wants to underwrite a purchase cleanly. It also means a tired home stands out for the wrong reasons, so a seller who invests in condition tends to be rewarded relative to one who does not.
The value trajectory over the long run has been strong — up 200% since 2012 — but the near term is flat, and the roughly 114-day median on market signals a deal will take time. No community amenities show up in current MLS listings, so the pitch here is the homes themselves and the Crestview location in Okaloosa County, not shared facilities. The low homestead share of about 16% is worth noting: it points to a meaningful non-owner-occupied presence, which a buyer intending to live here should factor into their read of the street.
The location and the amenities are priced into every listing in Rolling Pines. 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 Rolling Pines 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 (3.6). Basis: Liquidity & Demand 8.6 months of supply; Owner Commitment 16% owner-occupied; Pricing Power 96.6% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a market this quiet and this uniform, the edge is in reading condition against comparable sales and pricing to the actual pace — not to hope. We know how to position a well-kept home so it does not get lumped in with tired ones, and we know how to negotiate for a buyer who has the patience these 114-day timelines reward. With only a handful of active listings, timing and preparation matter more than volume.
Rolling Pines in 15 seconds.
Tools for a Rolling Pines 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 Pines sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Rolling Pines, 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 Pines home worth?
Get a no-obligation home value based on real comparable sales in Rolling Pines, 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 ROLLING PINES
Homes in ROLLING PINES 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. 2 on record.
- 164 Swaying Pine Court · off market
- 197 Swaying Pine Court · off market
Recently sold in Rolling Pines
- 197 Swaying Pine Court · sold $144,000
- 164 Swaying Pine Court · sold $174,480
Closed sales from the MLS; each page shows the sold price, taxes and value history.
Frequently Asked Questions
What is the median home price in Rolling Pines?
How long do homes in Rolling Pines take to sell?
Is Rolling Pines a buyer's or seller's market right now?
How many homes are in Rolling Pines?
What share of Rolling Pines is owner-occupied?
When were the homes in Rolling Pines built?
Who is the best real estate agent for Rolling Pines?
How do I find a top Crestview real estate agent who knows Rolling Pines?
Can Momentum Realty connect me with an agent for Rolling Pines?
Should you buy in Rolling Pines?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Rolling Pines with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Emerald Coast MLS, refreshed twice daily (last: November 9, 2026) |
| Community market stats | Emerald Coast MLS closed sales, 12-month windows ending November 9, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32539)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-11-09 |
| Historical depth | Closed-sale records back to 2026 (3 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 ROLLING PINES fits the bigger picture — live prices, inventory, and Momentum Scores: