112 days on market (MLS)Detached Single Family▼ Price cut: $20,100 (9/12)
$359,900
4-Bedroom Detached Single Family in OAK TREE PARK
271 Gregory Drive, Mary Esther, FL 32569
Detached Single Family in OAK TREE PARK, Mary Esther · No CDD on record
OAK TREE PARK · Mary Esther, FL 32569 · Okaloosa County
Listing data updated October 1, 2026 · refreshed hourly
4Bedrooms
2Bathrooms
1967Year Built
No CDD on recordFEMA Zone X4 bedrooms
How to read this page: MLS listing facts carry their source; everything else is labelled as a public record, a calculation, an estimate, or something to verify. Where local data is too thin to support a number, the page says so instead of guessing.
Buyer leverage
Balanced market
112 days on market
3.4 months
Supply around this home
Seller <3 · balanced 3-6 · buyer >6
Zone X
Flood risk
Minimal hazard per FEMA; ~24 ft elevation
$2k–$4k/yr
Est. insurance · illustrative
Not a carrier quote; premiums vary widely by property. Get a real quote.
As of October 1, 2026, 271 Gregory Drive in Oak Tree Park, Mary Esther is listed at $359,900. That is 24% above Oak Tree Park's median closed sale of $289,900 over the last 12 months (7 recorded sales). It has been 112 days on market. Listing facts: built in 1967. The parcel maps to FEMA flood zone X, outside the special flood hazard area. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
No CDD assessment on record
Built 1967 · 59 yrs
112 days on market
Listing description
About this home
COMPLETELY REMODELED AND GORGEOUS HOME FROM TOP TO BOTTOM! This home has been completely rebuilt and is essentially a brand new home! No detail was overlooked and the craftsmanship is impeccable.
It offers a true split bedroom design with two full baths. All brand new appliances are included except washer/dryer. Inside laundry room, family room, living room and dining room provide ample room for all.
A breakfast bar big enough for the entire family. Fenced back yard and with a one car carport. Great location close to schools, Eglin AFB and Hurlburt.
Absolutely perfect home for anyone stationed at Hurlburt and just minutes to anywhere. Come see this beautiful home and make it yours today!
All 22 photos
Description provided by MAX3 Realty LLC and reproduced from the MLS; not independently verified.
Listing data, public records, our calculations, and what to verify — each fact shown once. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.
Listing facts MLS
List price$359,900
Bed / bath4 / 2
Year built1967
Property typeDetached Single Family
MLS #1005278
Listing status112 days on market (MLS)
Public records & third-party data
FEMA flood zoneZone X
Ground elevation~24 ft
CountyOkaloosa
Area listings2 active · 1 under contract
Estimated first-year tax~$4,000/yr
CDD assessmentNone on record
HOANot reported
Calculated estimates
Estimated monthly payment$2,450
Insurance (illustrative)$2k–$4k/yr
Comparable-sales median$289,900
Buyer should verify Buyer verify
Exact HOA dues, fees, and restrictionsRoof age and conditionHVAC age and conditionA property-specific insurance quoteSurvey and lot boundariesPermit historyFlood-insurance requirementsSchool zoning (confirm with the district)Property taxes after sale (homestead reset)CDD / community assessmentsSquare footage and room dimensions
Financing
Estimated monthly payment
$2,450/mo
Principal & interest $1,921/mo78%
Taxes $333/mo14%
Insurance $195/mo8%
$2,450/mo at 20% down, 30-yr @ 7.03% · edit any field to update.
Estimate: asking price less the $50,000 homestead exemption × Okaloosa County rate (12.89 mills, county-average millage, 2025; verify with the property appraiser). Not a bill.
⚠️
Property taxes in Florida are reassessed after a sale, so a buyer’s first full-year bill can be higher than the seller’s. Budget from this estimate, not the current bill, before you make an offer.
Current owner’s estimated bill $1,200/yr ($100/mo) — taxable value $93,255 × 12.89 mills
$2,800 more each year
(+233%)
The current owner’s taxable value is below today’s asking price; after a sale the assessment is set from market value, so the estimated bill is higher. Exemptions and portability can reduce it.
$93,255
Market value
$93,255
Assessed
$93,255
Taxable
Certified 2025 tax roll values for this parcel (Florida DOR). The roll gives values, not the bill; the current owner’s bill above is estimated from the taxable value.
Sources: Florida DOR certified tax roll (2025), Emerald Coast AR; millage: Florida TaxWatch 2025 How Florida Counties Compare (county-average millage); school portion estimated at ~42% of total, capped at 6.50 mills. County public record, not MLS data — matched to this home by parcel ID. Estimates are not a tax bill; the county property appraiser and tax collector set the actual amount.
Estimated ownership costs
Estimated costs & disclosures
Estimated ownership costs for general information. Confirm each with the county, your lender, and an insurer. See data & estimate notes.
CDD assessment
None on record
No CDD assessment appears in our records for this community. CDD assessments show on the county tax bill — confirm with the tax collector.
Insurance (illustrative range)
$2k–$4k/yr
An illustrative modeled range, not based on carrier underwriting and not a quote. Florida premiums vary significantly by roof age, wind-mitigation features, claims history, and carrier — a real quote can land well outside this range. Flood insurance not federally mandated (Zone X). Get a quote from a licensed insurer before relying on any figure.
HOA
Not reported
Not stated in the listing. Confirm with the listing agent or the county record; $0 is used in the payment estimate.
Environmental data
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
FEMA flood zone
Zone X
From the FEMA National Flood Hazard Layer. In this zone lender-required flood insurance is generally not mandated; confirm for the parcel.
Ground elevation
~24 ft
Approximate parcel elevation from USGS; confirm exact elevation with a survey.
Windstorm / insurance
Obtain a quote
Okaloosa County is on the Florida coast; wind coverage is a major part of the premium. Premiums and coverage vary by home (roof age, wind mitigation, claims history); obtain a quote from a licensed insurer.
Hazard risk
Natural hazard risk
FEMA National Risk Index for Okaloosa County, FL: overall Relatively Moderate. Ratings compare this county with every county in the United States for expected annual loss from each hazard.
HurricaneVery High
Coastal floodingRelatively Moderate
Inland floodingRelatively Moderate
Heat waveRelatively Moderate
WildfireRelatively Low
TornadoRelatively High
LightningVery High
Strong windRelatively Moderate
DroughtVery Low
HailVery Low
Cold waveRelatively Moderate
Winter weatherRelatively Low
Source: FEMA National Risk Index (county level, hazard risk ratings only). Ratings describe the county, not this parcel; the flood zone shown above is parcel-specific. Verify insurance requirements with your lender and agent.
Connectivity
Internet & broadband
Fiber
Check availability
Address-level fiber service is not confirmed for this home. Check the FCC National Broadband Map (broadbandmap.fcc.gov) or the provider for this address.
Cable
Check availability
Cable broadband is common in Florida and Georgia towns but not confirmed for this address; verify with the provider.
Fixed wireless / satellite
Check availability
5G home internet and satellite service depend on the exact location; check coverage for this address.
Momentum Research · OAK TREE PARK
Pricing & the OAK TREE PARK market
How this home is priced against recent nearby sales, and where OAK TREE PARK has been over 25 years. Momentum Research analysis of Emerald Coast MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
Median sale price by year
12-month median closed price, 2014–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2017–2026. Now 16 (cold).
Property timeline
This home’s history
1967BuiltPer public record
About Jun 2026Listed (per MLS)MLS reports 112 cumulative days on market as of October 1, 2026
Aug 4, 2026First seen on movewithmomentum.comObserved at $380,000
Sep 12, 2026Price cut$359,900 (-$20,100, -5.3%)
NowActiveCurrently for sale
Build year is from public record. The MLS list date is approximate (today minus the cumulative days on market the MLS reports, which can span relistings). Other milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.
Transparency
Price & listing history
Listed for $359,900Momentum Realty · on market 112 days
Public records
Building permits
Permit history not yet linkedConfirm permit history with the county building department.
How it stacks up
Comparable recent sales
No closed sales of a similar home within about 10 miles in Okaloosa County in the last 18 months are in our MLS data set, so this page shows no comparable-sales median or automated estimate for OAK TREE PARK. A licensed Momentum Realty agent can prepare a property-specific comparative market analysis on request.
Momentum Scores
Momentum Property Score
60/100
Strongest on: Flood safety (95), Market timing (84)
0 limited50100 exceptional
60/100 is solid, mid-pack across the objective indicators below. It reflects only those measures — not the home’s quality, condition, or desirability.
A 0-100 score built from objective property and market data: flood risk, insurance, pricing, supply, affordability, and recent sales. Higher means more measures line up in a buyer’s favor. It reflects only the factors below.
Affordability10
List price $359,900 vs the community median $289,900. Not a measure of personal affordability.
Flood safety95
FEMA Zone X, ~24 ft elevation. Verify the parcel with FEMA.
Insurance cost50
From FEMA Zone X and a 1967 build. Obtain a property-specific quote.
Market liquidity43
Community median 91 days on market, ~3.4 months of supply (12-month record).
Pricing power79
Recent sales closed at about 92.3% of original asking (~7.7% below). More room below asking generally favors buyers.
Market timing84
Momentum Market Heat is 16/100 (cold). Cooler readings generally favor buyers; hotter readings favor sellers.
Coverage: 6 of 8 indicators had valid data for this home; indicators without data are left out, not scored as zero. Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent comparable sales. They do not measure property condition, quality, or investment suitability, and they are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.
Momentum Research
The Momentum read
🟡 Balanced conditions around this listing. 3.4 months of supply in the surrounding market and 112 days on market for this home, against a 91-day area median.Days on market:this home 112Area median: 91 daysWhy it matters: above-median time on market, together with the level of supply, is a clear sign of how much leverage sits with buyers.Momentum Research interpretation of the MLS facts in the snapshot above. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate. As of September 20, 2026.
54% of homes in OAK TREE PARK are owner-occupied. An estimated 46% are non-owner-occupied, including 14% held in a company or trust and 11% out-of-state owners.Why it matters: a high owner-occupied share typically means fewer rentals nearby and steadier resale demand.Source: Florida Department of Revenue 2025 assessment roll (public records), 63 homes matched. Community-level context.
Recent OAK TREE PARK sales closed near 92.3% of original asking.Why it matters: the community’s own record shows how far opening prices typically move, and how often buyers compete without financing.Momentum Research analysis of Emerald Coast MLS records, community-level, 12 months ending September 20, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 2 active listings in OAK TREE PARK, no CDD assessment.
Updated October 1, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Seen enough photos?
Want to see 271 Gregory Drive?
Tell us when works for you and a local agent will reach out to arrange a showing and answer your questions about this home.
Listed by MAX3 Realty LLC · MLS # 1005278
Request a showing
Keep looking
Similar homes for sale near OAK TREE PARK
Active listings nearby at a comparable size and price. Listings held by brokerages other than Momentum Realty are marked with the listing broker. Deemed reliable but not guaranteed.
494 Aleta Avenue, Mary Esther · $229,900 · 2 bd / 2.0 ba · listed September 29, 2026 (courtesy of Joseph Walter Realty LLC)
434 Pristine Water Lane, Mary Esther · $365,000 · 3 bd / 2.0 ba · listed September 26, 2026 (courtesy of All American Realty and Investment Group PLLC)
651 Wildwood Street, Mary Esther · $308,000 · 3 bd / 2.0 ba · listed September 25, 2026 (courtesy of Realty ONE Group Emerald Coast)
14 Islandview Drive, Mary Esther · $1,775,000 · 3 bd / 3.5 ba · listed September 24, 2026 (courtesy of Scenic Sotheby's International Realty)
83 Stowe Road, Mary Esther · $315,000 · 3 bd / 2.0 ba · listed September 17, 2026 (courtesy of Gulfside Haven LLC)
433 Emerald Pointe Drive, Mary Esther · $749,900 · 5 bd / 3.0 ba · listed September 11, 2026 (courtesy of Lokation)
Recent local developments near this home, compiled from news and public sources. Provided for general information; verify details with the original source.
Jun 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.
Why it matters: Directs 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 8 miles north of Oak Tree Park.
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.
Why it matters: Adds 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 25 miles north of Oak Tree Park, elsewhere in Okaloosa County.
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.
Why it matters: Adds 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 21 miles north of Oak Tree Park, elsewhere in Okaloosa County.
See schools, amenities, builders, HOA/CDD detail, and every active & sold home in the community — the single biggest advantage of buying here over a portal.
Schools currently assigned to this address in Okaloosa County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.
GRADEA
FlorosaAssigned elementary school · Okaloosa County School District · Grade A (Florida DOE 2025-26)
BrunerAssigned middle school · Okaloosa County School District
GRADEB
Fort Walton BeachAssigned high school · Okaloosa County School District · Grade B (Florida DOE 2025-26)
Assigned schools per the MLS listing — assignments can change; confirm current zoning with the district. Browse school-zone pages →
Nearby & guides
City, county & community guides
Where this home sits, with links to the matching guides. General reference only.
Items worth confirming for 271 Gregory Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
Built in 1967 (59 years): ask for the roof and HVAC replacement dates — insurers commonly ask for roof age on homes this old, and it changes the premium.
Confirm whether a mandatory HOA applies to this parcel and what it charges.
FEMA flood zone X: flood insurance is not usually required, but get a quote anyway — FEMA reports roughly one in four flood claims come from outside high-risk zones.
Get a homeowners insurance quote for this specific address in Okaloosa County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
Confirm square footage and room dimensions independently.
Order a survey to confirm lot boundaries and easements.
Review permit history with the county.
Property taxes: the estimate on this page (about $4,000/yr) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $2,800 more per year than the current owner’s estimated bill (+233%). Exemptions and portability change the actual bill — confirm with the county property appraiser.
School zoning shown here comes from district data and changes; confirm the assigned schools directly with the district before relying on them.
Provenance
Data sources & freshness
Listing record
Emerald Coast MLS, refreshed hourly (last: October 1, 2026)
Comparable sales
Fewer than 3 defensible closed sales within about 10 miles in Okaloosa County — no medians or automated estimate shown
Flood zone & elevation
FEMA flood maps + USGS elevation (Zone X shown above)
Taxes & monthly cost
Certified county tax roll (parcel-matched) × county millage; an estimate, not a bill
Insurance figure
Modeled estimate; obtain a real quote before offering
Schools
2025-26 district assignments; verify with the district
Momentum Research lines are our own analysis of Emerald Coast MLS records; MLS data is deemed reliable but not guaranteed. Estimates are informational, not appraisals or advice. Methodology: how Momentum scores are computed.
Answered before you ask
Frequently asked questions
How big is 271 Gregory Drive and when was it built?
Per the listing record, 271 Gregory Drive was built in 1967 and has 4 bedrooms and 2.0 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 271 Gregory Drive in?
271 Gregory Drive is in Oak Tree Park in Mary Esther, Okaloosa County. Too few comparable closed sales exist nearby for this page to show local sales statistics; a licensed agent can prepare a comparative market analysis.
Why might property taxes on 271 Gregory Drive differ from the current owner's?
The estimate on this page (about $4,000 per year) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $2,800 more per year than the current owner’s estimated bill (+233%). Florida reassesses a home after it sells; for a homesteaded seller the Save Our Homes cap on their assessment does not transfer, and a buyer's own exemptions and portability are applied separately, so the two bills usually differ. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.
Is 271 Gregory Drive in a flood zone?
The FEMA flood map places this parcel in Zone X, outside the special flood hazard area, so flood insurance is not usually required by a lender. It is still available and worth quoting; confirm the parcel's status with FEMA and your insurer.
Can I rely on the figures on this page?
No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.
Ready when you are
See 271 Gregory Drive in person
Private tours available 7 days a week, in person or by live video walkthrough. Request a tour or send a question and a licensed Momentum Realty agent will follow up.
Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.
Estimate methodology. Tax estimates apply county millage to the list price (less the homestead exemption where the parcel is matched to the certified roll) and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.
Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.
Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.
No warranty; measurements & photos. No guarantee, warranty, or representation of any kind is made regarding the completeness or accuracy of any information, descriptions, or measurements on this page — including square-footage measurements and property condition — all of which should be independently verified through appropriate means, including in-person inspection and public records. Photographs may be virtually staged or digitally enhanced and may not reflect actual property conditions. Momentum Realty and its agents expressly disclaim any liability in connection with the information provided.
Sold price and details are from public records and the MLS, deemed reliable but not guaranteed. Shown for comparison only — not an appraisal or a statement of this home's value.
