53 E Gray Owl Dr · Freeport, FL 32439

$393,176

5 bd · 3.0 ba · 2,107 sqft · Land · 118 Days on market

Built 2026 6,534 sqft lot $92/mo HOA · 3% of rent ↓ 7% since listing

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Why this score? — see what drove the D- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +9.8/30.0
• ARV discount +7.5/15.0
• Schools +5.2/10.0
• Livability +3.4/5.0
• 1% rule +3.2/10.0
• Rent growth +2.9/5.0
• DSCR +2.8/10.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

The Riverside floor plan is a gorgeous 5 bed, 3 bath home with a 2 car garage all on one level. The kitchen has a large quartz island bar and a corner pantry. The kitchen flows right into the family room, making it perfect for entertaining and family gatherings. A separate dining area is just off the kitchen. Lots of natural light and a very relaxing feel is throughout the home, with a wide porch leading to the back yard. The Primary bedroom is spacious with an adjoining bath that offers a double vanity, large shower, and a walk-in closet. Two other pairs of bedrooms share a bathroom making this ideal for children or guests to have their own spaces. This home comes standard with Smart Home

Key facts

• Quartz island bar
• Wide porch
• Corner pantry

Tags

• QUARTZ ISLAND BAR
• CORNER PANTRY
• SEPARATE DINING AREA
• WIDE PORCH
• SMART HOME TECHNOLOGY
• KWIKSET KEYLESS ENTRY

Property features AI

Finance

• Other: Subdivision: Owl's Head Farms
• HOA & community: Community association in place; Association fees include management and master association services; Community amenities include playground and pickleball; short-term rentals not allowed

Exterior

• Parking: Attached 2-car garage; Driveway with space for 2 vehicles; Garage door opener
• Security: Smoke detectors
• Utilities: Electric service; Public water; Public sewer (not specified separately); Electric water heater
• Home design: Single-story Craftsman-style home; Built in 2026; Interior lot on a paved road
• Construction: Siding: brick and cement fiberboard; Composite shingle roof; Building area per plan
• Exterior features: Sprinkler system; Rain gutters; Covered patio; Porch; Community pool

Interior

• Kitchen: Dishwasher; Disposal; Microwave; Refrigerator; Electric water heater
• Bedrooms: 5 bedrooms; Primary bedroom on the first floor with double vanity, separate shower, and walk-in closet
• Flooring: Vinyl flooring; Carpet
• Bathrooms: 3 full bathrooms
• Heating & cooling: Central heating; Central air; Ceiling fans; Electric heat control
• Interior features: Breakfast bar; Kitchen island; Recessed lighting; Pantry; Washer/dryer hookup
• Laundry & utility: Laundry room on the first floor; Washer/dryer hookup

What this means for you Summary

Snapshot

• This is a 5-bed/3.0-bath land listed at $393k.

Deal economics

• At list price, monthly cash flow is $-252 ($-3k/yr) — negative.
• To cash-flow at today's rent, offer at most $357k (9.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $324k (17.7% below list).
• Recommended offer: $324k (17.7% below list) — sets the bar for 1% rule.
• Cap rate 5.5% vs local median 3.0% in Freeport — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 68/100 on livability (#520 in FL) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment B+; Watch: health & safety C-, amenities F, commute F.
• Walton (rural): math 62% / reading 61% proficiency, ranked #10 of 73 in FL (top 14%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Freeport Elementary School (math 50% / reading 57%, grade C, #949 of 2,144 statewide, top 45%, 1,123 students, 55% FRL); Emerald Coast Middle School (math 70% / reading 65%, grade A-, #77 of 571 statewide, top 14%, 868 students, 24% FRL); Freeport Senior High School (math 47% / reading 62%, grade C-, #138 of 667 statewide, top 21%, 557 students, 43% FRL).
• Market conditions: Rents rising (+1.4%/yr); 1020 active listings in the ZIP; 2 comparable units currently listed for rent nearby; solid renter incomes; 2,883 units permitted in Walton County in 2024 (1,322 in 5+ unit buildings).
• At $3,237/mo this rent would consume 47% of the median local household income ($83k/yr) (locally 172% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $12k of value loss. Plan a longer hold.
• Walton County population projected at +46% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 118 days — a 9% lower offer ($358k) is reasonable based on typical stale-listing flexibility.

Recommended offer $323,745 (17.7% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 118 days. Have you received any prior offers? Is the seller open to a 18% concession, seller financing, or rate buy-down credit?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
7. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
8. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
9. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.82% ✗
• Cap rate: 5.53%
• Cash-on-cash: -2.74%
• DSCR: 0.88
• GRM: 10.1

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 1.4% rent growth · sell at horizon

5-year hold

• IRR: -22.7%
• Equity multiple: 0.23×
• Total profit: $-84,759
• Equity at exit: $58,624

10-year hold

• IRR: -21.8%
• Equity multiple: -0.04×
• Total profit: $-114,395
• Equity at exit: $33,995

Cash invested: $110,089 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Florida: 87 Strongly Landlord-Friendly · R+3
• County: — inherits STATE
• City: — inherits STATE

3-day pay-or-quit; preempts local rent control; landlord-friendly statutes. Court speed varies by county.

Methodology + full state rankings →

ZIP-level market 32439

• Home prices YoY: -4.2%
• Rents YoY: 1.4%
• Active inventory: 1020
• Price-to-rent: 10.1×

Monthly cashflow live

• Estimated rent: $3,237 medium
• Mortgage (P&I): −$2,062
• Tax est. 1.5%: −$491 /mo · $5,898/yr
• Insurance: −$164
• HOA: −$92
• Vacancy / Maint / Mgmt: −$680
• Net cashflow: $-252

Break-even live

Break-even rent $3,556

Max offer price $356,774

Occupancy floor —

Sensitivity live

Price	-10% $20	-5% $-116	+0% $-252	+5% $-387	+10% $-523
Rent	-10% $-507	-5% $-379	+0% $-252	+5% $-124	+10% $4
Rate	-1.0pp $-54	-0.5pp $-152	base $-252	+0.5pp $-353	+1.0pp $-457

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $98,294
• Closing costs: $11,795
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
36 Gray Owl Dr E Freeport, FL	4.0	2.0	2108	$2,800	$1.33	22d	1	0.04mi
133 Staggerbush St Freeport, FL	4.0	2.5	2048	$2,645	$1.29	15d	1	0.90mi

HOA detail

• Monthly dues: $92 · $1,104/yr

Listing history 12 events

1. 2026-04-15
   price $393,176
2. 2026-04-13
   price $390,176
3. 2026-04-03
   price $394,960
4. 2026-04-03
   price $390,960
5. 2026-03-26
   price $400,048
6. 2026-03-25
   price $395,048
7. 2026-03-13
   price $399,342
8. 2026-03-05
   price $403,636
9. 2026-02-23
   price $425,900
10. 2026-02-10
    price $422,900
11. 2026-02-02
    price $426,400
12. 2026-01-31
    listed $422,900 Active

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $38,849
• − Mortgage interest: −$22,024
• − Property taxes: −$5,898
• − Insurance: −$1,966
• − Repairs & maintenance: −$3,108
• − Management: −$3,108
• − HOA: −$1,104
• − Depreciation: −$11,438
• Taxable loss: −$9,796
• Est. tax savings @ 24.0%: +$2,351
• After-tax cash flow: $-668/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Walton
• NCES district ID: 1201980
• Math proficiency: 62% ▼ -4.00%
• Reading proficiency: 61% ▼ -2.00%
• Median HH income: $46,794
• Composite: 52.03/100
• National rank: #1634
• State rank: #10 of 73 in FL

Livability — Freeport

• Score: 68/100
• State rank: #520
• US rank: #9579

Category grades

Amenities F Commute F Cost of living B Crime A+ Employment B+ Housing A+ Health & safety C- User ratings A

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Freeport, FL
• County: Walton County · 70,839 people
• City population: 15,328
• Metro: Crestview-Fort Walton Beach-Destin, FL
• Population (ZIP): 15,328
• Household income: $83,227
• Rent vs Own: 19.9% rent · 80.1% own
• Severe rent burden: 172.0

Population outlook (Walton County) Hauer SSP2

• Today (2025): 80,014 people
• By 2030: 88,120 · +10.1%
• By 2040: 103,537 · +29.4%
• By 2050: 117,034 · +46.3%
• By 2075: 143,901 · +79.8%
• By 2100: 155,138 · +93.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (76%)
• Race & ethnicity: White 76% Hispanic / Latino 16% Two or more races 8% Native American 5% Black 1%
• Hispanic origin (detail): Mexican 8% Puerto Rican 2% Cuban 1%
• Common ancestry: Slovak 3% Italian 3% Serbian 2%
• Foreign-born: 8% · Canada, Jamaica
• Languages at home: 86% English-only · Spanish 13% Other Indo-European 1%

Political lean MEDSL · Walton

• 2024 margin: Solid R (+57.8) · D 20.7% · R 78.6%
• 2008→2024 swing: -12.0pp toward R · 2008: -45.8pp · 2024: -57.8pp
• All cycles: 2024: R+57.8 2020: R+51.7 2016: R+56.1 2012: R+52.0 2008: R+45.8

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -15.18%
• Current HPI: 350.4692
• Rent YoY: ▲ 1.40%
• Metro: Crestview-Fort Walton Beach-Destin, FL
• State GDP YoY: ▲ 3.28%
• F500 in state: 36

Industry mix (Fortune 500 HQ in FL)

Industry	F500 HQs	Revenue
▸Industrial Technology	2	$29B
▸Insurance	2	$17B
▸Retail	1	$60B
▸Technology Distribution	1	$58B
▸Homebuilding	1	$35B
▸Technology Manufacturing	1	$35B

Price history

-7.0% since first listed

12 events — show timeline

• 2026-04-15 Price Changed $393,176 ECAR
• 2026-04-13 Price Changed $390,176 ECAR
• 2026-04-03 Price Changed $394,960 ECAR
• 2026-04-03 Price Changed $390,960 ECAR
• 2026-03-26 Price Changed $400,048 ECAR
• 2026-03-25 Price Changed $395,048 ECAR
• 2026-03-13 Price Changed $399,342 ECAR
• 2026-03-05 Price Changed $403,636 ECAR
• 2026-02-23 Price Changed $425,900 ECAR
• 2026-02-10 Price Changed $422,900 ECAR
• 2026-02-02 Price Changed $426,400 ECAR
• 2026-01-31 Listed $422,900 ECAR

Property tax history

+774.0%/yr

Latest (2025): $208 · +774.0% YoY. Source: county tax records.