Overlook at Chestnut Ridge
Homes for Sale in Crestview, FL
All 420 homes for sale in Crestview, FL · median $329,650 · 262 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
As of October 2026, the MLS records 8 closed sales in Overlook at Chestnut Ridge in Crestview, FL since 2014, the most recent in May 2026. Across Crestview as a whole, 571 homes closed in the last 12 months at a median of $321,973, 71 median days on market, with 184 homes for sale today. At that median and Okaloosa County's FY2025-26 rate of 12.89 mills, annual property tax runs about $4,150 ($3,640 with the full homestead exemption).
| Location | Crestview, Okaloosa County, FL · ZIP 32539 |
|---|---|
| Homes in the community | 21 (FL DOR 2025 assessment roll) |
| Years built | 2012–2023 (median 2017) |
| Typical living area | 2,291 sq ft (median) |
| Amenities listed by sellers | Security System |
| For sale right now | 0 active, 1 pending |
| Owner-occupied (homestead) share | 50% |
Data as of September 20, 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, “OVERLOOK AT CHESTNUT RIDGE key facts,” movewithmomentum.com/neighborhoods/overlook-at-chestnut-ridge, data as of September 20, 2026.
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.
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.
Emerald Coast MLS sales records identify 7 homes in OVERLOOK AT CHESTNUT RIDGE that have changed hands since 2022, built between 2013 and 2023 (median 2022), with a median living area of about 1,862 sq ft and a typical 4-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.
County records show 3 qualified sales in OVERLOOK AT CHESTNUT RIDGE across 2024–2025 (1 in 2024, 2 in 2025), median $340,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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.
In ZIP 32539, 360 homes are on the market and 24% are under contract — a steady corner of Crestview.
Across Okaloosa County, 1,890 homes are active and 551 pending (23% under contract).
In ZIP 32539 (Crestview), 527 homes closed in the last 12 months at a median of $323K, up 5.8% year over year, with a median 67 days on market. Right now 140 active and 52 pending listings put supply at about 4.2 months — a balanced market. See the live ZIP 32539 housing market and the Okaloosa County market.
ZIP and county figures describe the wider market, not Overlook at Chestnut Ridge specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in OVERLOOK AT CHESTNUT RIDGE, 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.
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 2026-10-01, 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 Overlook At Chestnut Ridge Right Now (1)
All 1 active and pending Overlook At Chestnut Ridge listings with a detail page, newest first, refreshed twice a day from the MLS.
- 5181 Rabbit Run · $385,000 · 4 bd / 2.5 ba · pending · listed Aug 31, 2026 · listed by Coldwell Banker Realty
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
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 August 2026.
- 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.
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.
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 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.
What is your Overlook at Chestnut Ridge home worth?
Get a no-obligation home value based on real comparable sales in Overlook at Chestnut Ridge, 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.
24% of homes for sale in ZIP 32539 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-01).
Frequently Asked Questions
How many homes are in Overlook at Chestnut Ridge?
What share of Overlook at Chestnut Ridge is owner-occupied?
When were the homes in Overlook at Chestnut Ridge built?
Who is the best real estate agent for Overlook at Chestnut Ridge?
How do I find a top Crestview real estate agent who knows Overlook at Chestnut Ridge?
Can Momentum Realty connect me with an agent for Overlook at Chestnut Ridge?
Where is Overlook at Chestnut Ridge, and what county is it in?
Should you buy in Overlook at Chestnut Ridge?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Emerald Coast MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32539)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2014 (8 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.
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See how OVERLOOK AT CHESTNUT RIDGE fits the bigger picture — live prices, inventory, and Momentum Scores:
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