WOODLANDS OF WHISPERING PINES
Homes for Sale in Crestview, FL

Community in Crestview · Okaloosa County · ZIP 32539
24 homesBuilt 1990–2016
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Built fromLive emeraldcoast data6 years of closingsFL DOR public recordsUpdated twice daily
Live · WOODLANDS OF WHISPERING PINES Housing Pulse emeraldcoast + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
76%
Owner-occupied · WOODLANDS OF WHISPERING PINES
19 of 25 parcels homesteaded (FL DOR 2025)
24%
Non-owner-occupied · WOODLANDS OF WHISPERING PINES
incl. 8% trust or LLC-held · 12% out-of-state
24
Homes in the community
plus 1 vacant residential lots · 25 residential parcels (FL DOR 2025)
Track record · 6 years of records
Est. 1990
Community established
homes built 1990-2016, median 2015 (FL DOR 2025)
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Woodlands of Whispering Pines is a small pocket of 24 homes in Crestview, and at that size the market here is thin by definition — a single sale or two can move the read. Most of the inventory skews newer, with a median build year of 2015 and living space centered around 2,347 square feet, so what sets price here is less about vintage and more about condition, updates, and lot specifics on any given home that trades.

With about three-quarters of homes carrying a homestead exemption, turnover tends to be limited and listings are owner-occupied rather than churned by investors. For a seller, that scarcity can work in your favor when a well-kept home hits the market with little competition. For a buyer, it means patience: you may wait for the right home rather than choose among several, and you should price your offer to the specific house, not to a neighborhood average that barely exists at this scale.

Best for

  • Buyers seeking a newer-built home around 2,347 square feet who value construction over vintage
  • Owner-occupants planning to stay put, comfortable in a low-turnover setting
  • Buyers who are patient enough to wait for the right home rather than shop several at once

Probably not for

  • Amenity-driven buyers who want a pool, clubhouse, or gated entry on site
  • Buyers who need many active listings to compare before committing
  • Investors chasing quick turnover, given the high owner-occupied share

If we were buying in WOODLANDS OF WHISPERING PINES today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 WOODLANDS OF WHISPERING PINES.

Best Buy
Buyers who want a newer, full-sized single-family home in an established, low-turnover Crestview pocket.
Biggest Risk
With only 24 homes, thin comps make valuation home-specific and swing on any single sale.
Sweet Spot
An updated, move-in-ready home near the ~2,347 sq ft median that trades when little else is listed.
Avoid If
You need shared amenities or a wide slate of homes to choose from at once.

A small, newer-built pocket in Crestview

The build range runs from 1990 to 2016, but the median year built of 2015 tells you the weight of this community is on the newer end. That matters for a buyer: floor plans, systems, and construction here lean modern, and a median footprint around 2,347 square feet suggests full-sized single-family homes rather than starter product or tight infill.

No community amenities were identified from current MLS listings — no pool, clubhouse, or gated entry to point to. That is not a knock; it means you are buying the house and the location, not an amenity package, and it keeps carrying costs simpler. If shared recreation is central to your search, this is a straightforward place to rule in or out.

The location and the amenities are priced into every listing in WOODLANDS OF WHISPERING PINES. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a 24-home community, comps are scarce and every trade counts. We price and negotiate off the specific home in front of us — condition, updates, lot — rather than leaning on a neighborhood average that barely holds up at this scale. For sellers, we time a listing to the thin competition; for buyers, we help you value a house on its merits and structure an offer that reflects them.

WOODLANDS OF WHISPERING PINES in 15 seconds.

Best forBuyers who want a newer, full-sized single-family home in an established, low-turnover Crestview pocket.
Biggest advantageScarce inventory and predominantly newer construction give well-kept homes room to stand out.
Biggest riskWith only 24 homes, thin comps make valuation home-specific and swing on any single sale.
Sweet spotAn updated, move-in-ready home near the ~2,347 sq ft median that trades when little else is listed.
Avoid ifYou need shared amenities or a wide slate of homes to choose from at once.

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed WOODLANDS OF WHISPERING PINES sales matched to your home.

What is your WOODLANDS OF WHISPERING PINES home worth?

Get a no-obligation home value based on real comparable sales in WOODLANDS OF WHISPERING 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 homes for sale in WOODLANDS OF WHISPERING PINES on the map →

Real comps, not an automated estimate.

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.

$2,193/mo
Okaloosa County typical true cost to own
$220/mo
Okaloosa County typical home insurance
Check CDD
Confirm before you offer

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.

Recent Developments in Woodlands Of Whispering Pines

Development, infrastructure, retail, and school activity affecting Woodlands Of Whispering Pines, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.

  1. June 2026
    Civic

    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 18 miles south of Woodlands Of Whispering Pines.

    Source: Get The Coast
  2. May 2026
    Development

    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 site is about 1 mile east of Woodlands Of Whispering Pines.

    Source: Get The Coast
  3. May 2026
    Infrastructure

    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 project is about 4 miles southwest of Woodlands Of Whispering Pines, elsewhere in Okaloosa County.

    Source: Get The Coast

Development alerts for Woodlands Of Whispering PinesGet a short monthly email when something new is approved, funded, or opens near Woodlands Of Whispering Pines.

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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 WOODLANDS OF WHISPERING PINES?
The Florida DOR 2025 assessment roll shows 24 homes plus 1 vacant residential lots in WOODLANDS OF WHISPERING PINES (public records).
What share of WOODLANDS OF WHISPERING PINES is owner-occupied?
76% of WOODLANDS OF WHISPERING PINES parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in WOODLANDS OF WHISPERING PINES built?
Homes in WOODLANDS OF WHISPERING PINES were built between 1990 and 2016, with a median year built of 2015 (FL DOR 2025 roll).
Who is the best real estate agent for WOODLANDS OF WHISPERING PINES?
The best agent for WOODLANDS OF WHISPERING PINES is one who actively works Crestview and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for WOODLANDS OF WHISPERING PINES.
How do I find a top Crestview real estate agent who knows WOODLANDS OF WHISPERING PINES?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows WOODLANDS OF WHISPERING PINES and the wider Crestview area.
Can Momentum Realty connect me with an agent for WOODLANDS OF WHISPERING PINES?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your WOODLANDS OF WHISPERING PINES purchase or sale - no call center and no pressure.
Buyers seeking a newer-built home around 2,347 square feet who value construction over vintageExcellent fit
Owner-occupants planning to stay put, comfortable in a low-turnover settingExcellent fit
Buyers who are patient enough to wait for the right home rather than shop several at onceExcellent fit
Amenity-driven buyers who want a pool, clubhouse, or gated entry on siteProbably not
Buyers who need many active listings to compare before committingProbably not
Investors chasing quick turnover, given the high owner-occupied shareProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 32539))
Historical depthClosed-sale records back to 2020 (7 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 emeraldcoast 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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