Mccaskill
Homes for Sale in Crestview, FL
All 380 homes for sale in Crestview, FL · median $325,450 · Okaloosa County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Emerald Coast MLS
Mccaskill 2ND Addn is a community in Crestview, Okaloosa County, FL. Across Crestview as a whole, 136 homes closed in the last 12 months at a median of $319,000, 82 median days on market, with 384 homes for sale today. At that median and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $4,110 ($3,600 with the full homestead exemption).
Price here is driven by condition and the specific structure, not by any uniform build. With homes dating from 1941 to 2024 and a median build year of 1984, McCaskill 2nd Addn is a genuinely mixed pocket of Crestview — you have prewar and midcentury stock sitting alongside recent construction on the same map. The median home runs about 1,442 square feet, so this is a modest-footprint area where what you pay tracks how much work a given house needs.
For buyers, that spread is the opportunity and the homework: two listings at similar asking prices can be very different underneath. For sellers, generic comps won't do the job — a renovated or newer home should be priced on its own merits, not dragged toward the median by older neighbors. Expect to underwrite each property individually rather than lean on a neighborhood-wide number.
Figures in this note are as of July 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside MCCASKILL 2ND ADDN 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
This is a small, long-established Crestview community of 56 homes where the housing stock spans more than eight decades, so the character shifts block to block rather than presenting as a single planned look.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Mccaskill is best for.
Best for
- Buyers targeting a compact, sub-1,500-square-foot home who value being in an established part of Crestview
- Owner-occupant buyers who plan to stay and want a homestead-heavy street rather than a rental-dominated one
- Renovation-minded buyers willing to trade an older structure for a lower entry point and add value themselves
Probably not for
- Buyers who want amenities like a pool, clubhouse, or HOA-maintained common areas
- Buyers who need a large-footprint home well above the area's median size
- Buyers who want a uniform, single-era subdivision where every house looks and dates the same
The market around Mccaskill
Mccaskill is too small for its own price trend, so here is the market around it.
Across Okaloosa County, 1,691 homes are active and 403 pending (19% under contract).
ZIP and county figures describe the wider market, not Mccaskill specifically. Momentum Research analysis of MLS records.
The Mccaskill buying strategy.
If we were buying in Mccaskill 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 Mccaskill.
A mixed-vintage infill pocket
The defining fact of McCaskill 2nd Addn is age range. A build window from 1941 to 2024 means you can find original older homes, decades of infill, and brand-new construction within the same 56-home footprint. The median year built of 1984 tells you the center of gravity is older, but the newer end of the range is real and worth chasing if you want lower maintenance.
Roughly 54% of homes here are homesteaded, which points to a core of owner-occupants rather than a listing pool dominated by rentals or flips. No community amenities show up in current MLS listings — no HOA-run facilities, no shared recreation — so value rests entirely on the individual home, the lot, and the location within Crestview and Okaloosa County.
The location and the amenities are priced into every listing in Mccaskill. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a neighborhood this varied, the number that matters is the one attached to the specific house, and getting it right takes property-by-property analysis. We price and evaluate on condition, age, and square footage rather than a blanket neighborhood figure — which protects sellers from underpricing a renovated home and keeps buyers from overpaying for one that needs work.
Mccaskill in 15 seconds.
Tools for a Mccaskill 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 Mccaskill sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Mccaskill, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
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Data sources & freshness
| Live listings | Emerald Coast MLS, refreshed twice daily (last: November 10, 2026) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-11-09 |
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.
Recent Developments in Mccaskill 2nd Addn
Development, infrastructure, retail, and school activity affecting Mccaskill 2nd Addn, 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 2 miles north of Mccaskill 2nd Addn.
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 24 miles south of Mccaskill 2nd Addn, 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 southwest of Mccaskill 2nd Addn.
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 17 miles south of Mccaskill 2nd Addn.
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 site is about 2 miles northeast of Mccaskill 2nd Addn.
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 4 miles southwest of Mccaskill 2nd Addn.
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.
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