Overlook at Chestnut Ridge
Homes for Sale in Crestview, FL
All 361 homes for sale in Crestview, FL · median $325,000 · 241 homes for sale in 32539 · Okaloosa County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Emerald Coast MLS
Overlook at Chestnut Ridge 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 383 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).
Overlook at Chestnut Ridge is a small, newer enclave of 21 homes in Crestview, built between 2012 and 2023 with a median year of 2017. With a median living area around 2,291 square feet, price here is driven less by any published range and more by condition, finish level, and where in that build window a given home falls. There is no published price range for this community — the number that matters is the median, and everything else is a function of the specific house.
The market posture is thin: one active listing against one closing in the window, in a pocket of only 21 homes. That is a low-turnover community by nature, so both sides are working with limited comps. For a seller, scarcity can work in your favor if the home shows well. For a buyer, patience matters — you may wait for the right house rather than choose among many, and you should lean on recent closings rather than assume a broad menu of options.
Figures in this note are as of July 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
This is a compact, relatively young subdivision — construction runs from 2012 through 2023, so homes carry modern layouts and systems. With roughly half of the homes claiming a homestead exemption, it reads as a settled, owner-occupied pocket rather than a churn of investor turnover.
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 Overlook at Chestnut Ridge is best for.
Best for
- Buyers targeting a newer, roughly 2,300-square-foot home who can be patient for inventory
- Owner-occupants who value a settled, low-turnover pocket over constant listing activity
- Buyers who care more about the individual house and Crestview location than a shared amenity package
Probably not for
- Buyers who want a clubhouse, pool, or other community amenities
- Shoppers who need many active listings to compare side by side
- Investors relying on frequent turnover and deep comp data to underwrite a deal
The market around Overlook at Chestnut Ridge
Overlook at Chestnut Ridge 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 Overlook at Chestnut Ridge specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Overlook at Chestnut Ridge
Live MLS inventory for Overlook at Chestnut Ridge. 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 and pending Overlook at Chestnut Ridge listings as of 2026-11-12, 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.
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 Overlook at Chestnut Ridge 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 Overlook at Chestnut Ridge address.
Shop the zone: Homes zoned for Crestview High School
The Overlook at Chestnut Ridge buying strategy.
If we were buying in Overlook at Chestnut Ridge 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 Overlook at Chestnut Ridge.
A small, newer pocket that trades on the individual house
At 21 homes with a median build year of 2017, Overlook at Chestnut Ridge is small enough that a single listing meaningfully changes the picture. The living areas cluster near 2,291 square feet at the median, which points to a fairly consistent product type rather than a wide mix of tiny-to-sprawling floor plans. That consistency helps with valuation, but the newness of the stock — nothing older than 2012 — means condition and updates, not age, will separate one price from another.
No community amenities were identified from current MLS listings, so this is not a lifestyle-package neighborhood — you are buying the house and the Crestview location in Okaloosa County, not a clubhouse or pool. Judge it on the physical home, lot, and proximity to what you use, and set expectations that inventory will be sporadic given how few homes exist here.
The location and the amenities are priced into every listing in Overlook at Chestnut Ridge. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 21-home community with one active listing and one recent closing, the data is too thin to lean on averages alone. We read the individual house against what has actually transacted, tell you plainly when a price is condition-inflated or genuinely fair, and help you time an entry or exit around inventory that surfaces only occasionally.
Overlook at Chestnut Ridge in 15 seconds.
Tools for a Overlook at Chestnut Ridge 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 Overlook at Chestnut Ridge sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Overlook at Chestnut Ridge, 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 12, 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 Overlook At Chestnut Ridge
Development, infrastructure, retail, and school activity affecting Overlook At Chestnut Ridge, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Retail & Dining
7 Brew drive-thru coffee stand opens on Beal Parkway in Fort Walton Beach
The stand at 799 Beal Parkway opened Oct. 19 and is the chain's second in Fort Walton Beach. It is expected to add 75 local jobs, and an opening fundraiser raised $4,661 for an equine therapy nonprofit.
What it may mean for the marketA new drive-thru option along Beal Parkway adds early-morning and late-night food and beverage access and about 75 jobs nearby. The project is about 23 miles south of Overlook At Chestnut Ridge, elsewhere in Okaloosa County.
Source: Get The Coast - 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 northeast of Overlook At Chestnut Ridge.
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 south of Overlook At Chestnut Ridge.
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 18 miles south of Overlook At Chestnut Ridge.
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 project is about 3 miles east of Overlook At Chestnut Ridge, elsewhere in Okaloosa County.
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 south of Overlook At Chestnut Ridge.
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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