3277 Chappelwood Dr · Crestview, FL 32539

$289,900

4 bd · 2.0 ba · 1,729 sqft · SingleFamily public records · 175 Days on market

Built 2021 0.29 ac lot $168/sqft · 14% below area Est $336k · 14% under $62/mo HOA · 3% of rent

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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).

• ARV discount +13.7/15.0
• Cash flow +8.0/30.0
• Schools +5.2/10.0
• Livability +3.8/5.0
• 1% rule +2.7/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +2.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

VA assumable loan available at 2.25% interest rate small gap. Located in North Crestview, this 2021-built Cali Plan offers 4 bedrooms, 2 bathrooms, and 1,729 sq ft of living space on a 0.29-acre lot. EVP wood-look flooring runs throughout with frieze carpet in the bedrooms. Smart Home Connect system included with doorbell camera and keyless entry. The kitchen features a backsplash, island, and pantry with added shelving. Finished garage includes added shelving and a custom screen door allowing ventilation and full vehicle access. Whole-house generator with a 250-gallon propane tank (approx. 80% full) provides full-home power. Fully fenced backyard. Buyer to verify all information. Shed does not convey.

Key facts

• Finished garage
• 0.29 acre lot
• 2 garage spots

Tags

• SMART HOME CONNECT SYSTEM
• EVP WOOD-LOOK FLOORING
• FINISHED GARAGE
• WHOLE-HOUSE GENERATOR
• FULLY FENCED BACKYARD
• NEWLY BUILT STORAGE SHED

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $290k.

Deal economics

• At list price, monthly cash flow is $-299 ($-4k/yr) — negative.
• To cash-flow at today's rent, offer at most $247k (14.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $224k (22.9% below list).
• Recommended offer: $224k (22.9% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 75/100 on livability (#252 in FL, #3,858 nationally) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+, health & safety A+; Watch: employment D, amenities F, commute F.
• Okaloosa (other): math 60% / reading 60% proficiency, ranked #12 of 73 in FL (top 16%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: Rents flat; 526 active listings in the ZIP; 1,268 units permitted in Okaloosa County in 2024 (175 in 5+ unit buildings).
• This rent runs 36% of the median local income ($74k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $9k of value loss. Plan a longer hold.
• Okaloosa County population projected at +37% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 175 days — a 12% lower offer ($255k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 5y ago; this cycle's ask is 14767% above the opening price — seller raised mid-cycle; expect resistance to lowballs.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 99% chance of damaging wind over 30y; major wildfire risk; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $223,554 (22.9% 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 175 days. Have you received any prior offers? Is the seller open to a 23% 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. Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
7. 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?
8. 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.
9. 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.
10. 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: 0.77% ✗
• Cap rate: 5.05%
• Cash-on-cash: -4.43%
• DSCR: 0.80
• GRM: 10.8

CMA / ARV

• ARV (median comp): $336,206
• List price: $289,900
• Delta: -13.77%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
6136 Clover St	0.44mi	4/2.0	1,640 (-5%)	0mo	$303,400	$185	71
6116 Clover St	0.44mi	4/2.0	1,640 (-5%)	1mo	$289,450	$176	70
6160 Sundew St	0.60mi	4/2.0	1,575 (-9%)	3mo	$299,900	$190	54
6158 Sundew St	0.60mi	4/2.0	1,575 (-9%)	4mo	$299,900	$190	54
6168 Hayes Dr	0.73mi	3/2.0 (-1)	1,769 (+2%)	8mo	$230,000	$130	50
3156 Auburn Rd	0.37mi	3/2.0 (-1)	1,478 (-14%)	7mo	$275,000	$186	48
6159 Old Hickory Rd	0.62mi	3/2.0 (-1)	1,884 (+9%)	4mo	$273,000	$145	47
3152 Auburn Rd	0.40mi	3/2.0 (-1)	1,478 (-14%)	6mo	$275,000	$186	47
3154 Auburn Rd	0.38mi	3/2.0 (-1)	1,478 (-14%)	10mo	$285,000	$193	45
3358 Peeble Dr	0.75mi	4/2.0	1,566 (-9%)	18mo	$307,900	$197	34
6174 Hayes Dr	0.73mi	4/2.0	1,571 (-9%)	21mo	$279,900	$178	33
6196 Winstead Cv	0.70mi	3/2.0 (-1)	1,505 (-13%)	19mo	$272,000	$181	25

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 0.12% rent growth · sell at horizon

5-year hold

• IRR: -27.1%
• Equity multiple: 0.11×
• Total profit: $-72,268
• Equity at exit: $43,225

10-year hold

• IRR: -40.2%
• Equity multiple: -0.37×
• Total profit: $-111,581
• Equity at exit: $25,065

Cash invested: $81,172 (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 32539

• Home prices YoY: -17.8%
• Rents YoY: 0.1%
• Active inventory: 526
• Price-to-rent: 10.8×

Monthly cashflow live

• Estimated rent: $2,236 medium
• Mortgage (P&I): −$1,520
• Tax est. 1.5%: −$362 /mo · $4,348/yr
• Insurance: −$121
• HOA: −$62
• Vacancy / Maint / Mgmt: −$469
• Net cashflow: $-299

Break-even live

Break-even rent $2,614

Max offer price $246,583

Occupancy floor —

Sensitivity live

Price	-10% $-99	-5% $-199	+0% $-299	+5% $-400	+10% $-500
Rent	-10% $-476	-5% $-388	+0% $-299	+5% $-211	+10% $-123
Rate	-1.0pp $-153	-0.5pp $-226	base $-299	+0.5pp $-374	+1.0pp $-451

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: $72,475
• Closing costs: $8,697
• Reserves months: —
• Total cash needed: —

HOA detail

• Monthly dues: $62 · $744/yr

Listing history 27 events

1. 2026-06-21
   days on market $289,900 Active 175 DOM
2. 2026-06-18
   days on market $289,900 Active 172 DOM
3. 2026-06-17
   days on market $289,900 Active 171 DOM
4. 2026-06-16
   days on market $289,900 Active 170 DOM
5. 2026-06-15
   days on market $289,900 Active 169 DOM
6. 2026-06-14
   days on market $289,900 Active 167 DOM
7. 2026-06-13
   days on market $289,900 Active 166 DOM
8. 2026-06-10
   days on market $289,900 Active 164 DOM
9. 2026-06-09
   days on market $289,900 Active 163 DOM
10. 2026-06-08
    days on market $289,900 Active 162 DOM
11. 2026-06-07
    days on market $289,900 Active 161 DOM
12. 2026-06-05
    days on market $289,900 Active 158 DOM
13. 2026-06-02
    days on market $289,900 Active 156 DOM
14. 2026-06-01
    days on market $289,900 Active 155 DOM
15. 2026-05-31
    days on market $289,900 Active 154 DOM
16. 2026-05-30
    days on market $289,900 Active 153 DOM
17. 2026-04-27
    price $292,900 711-char remark

    Show marketing remark (711 chars)

    VA assumable loan available at 2.25% interest rate small gap. Located in North Crestview, this 2021-built Cali Plan offers 4 bedrooms, 2 bathrooms, and 1,729 sq ft of living space on a 0.29-acre lot. EVP wood-look flooring runs throughout with frieze carpet in the bedrooms. Smart Home Connect system included with doorbell camera and keyless entry. The kitchen features a backsplash, island, and pantry with added shelving. Finished garage includes added shelving and a custom screen door allowing ventilation and full vehicle access. Whole-house generator with a 250-gallon propane tank (approx. 80% full) provides full-home power. Fully fenced backyard. Buyer to verify all information. Shed does not convey.

18. 2026-04-27
    price $292,000 711-char remark

    Show marketing remark (711 chars)

    VA assumable loan available at 2.25% interest rate small gap. Located in North Crestview, this 2021-built Cali Plan offers 4 bedrooms, 2 bathrooms, and 1,729 sq ft of living space on a 0.29-acre lot. EVP wood-look flooring runs throughout with frieze carpet in the bedrooms. Smart Home Connect system included with doorbell camera and keyless entry. The kitchen features a backsplash, island, and pantry with added shelving. Finished garage includes added shelving and a custom screen door allowing ventilation and full vehicle access. Whole-house generator with a 250-gallon propane tank (approx. 80% full) provides full-home power. Fully fenced backyard. Buyer to verify all information. Shed does not convey.

19. 2026-04-02
    listed $1,950
20. 2026-04-02
    historical $1,950
21. 2026-03-31
    listed $1,950
22. 2026-02-13
    price $319,000 711-char remark

    Show marketing remark (711 chars)

    VA assumable loan available at 2.25% interest rate small gap. Located in North Crestview, this 2021-built Cali Plan offers 4 bedrooms, 2 bathrooms, and 1,729 sq ft of living space on a 0.29-acre lot. EVP wood-look flooring runs throughout with frieze carpet in the bedrooms. Smart Home Connect system included with doorbell camera and keyless entry. The kitchen features a backsplash, island, and pantry with added shelving. Finished garage includes added shelving and a custom screen door allowing ventilation and full vehicle access. Whole-house generator with a 250-gallon propane tank (approx. 80% full) provides full-home power. Fully fenced backyard. Buyer to verify all information. Shed does not convey.

23. 2025-12-28
    listed $340,000 Active 711-char remark

    Show marketing remark (711 chars)

    VA assumable loan available at 2.25% interest rate small gap. Located in North Crestview, this 2021-built Cali Plan offers 4 bedrooms, 2 bathrooms, and 1,729 sq ft of living space on a 0.29-acre lot. EVP wood-look flooring runs throughout with frieze carpet in the bedrooms. Smart Home Connect system included with doorbell camera and keyless entry. The kitchen features a backsplash, island, and pantry with added shelving. Finished garage includes added shelving and a custom screen door allowing ventilation and full vehicle access. Whole-house generator with a 250-gallon propane tank (approx. 80% full) provides full-home power. Fully fenced backyard. Buyer to verify all information. Shed does not convey.

24. 2021-09-10
    soldstatus $292,900 761-char remark

    Show marketing remark (761 chars)

    NOW UNDER CONSTRUCTION! The Cali is a one story floor plan 4 bedrooms, 2 baths, covered back patio & 2 car garage. Sought-after open design offers a nice kitchen featuring an island bar for extra seating, stainless appliances, corner panty, quiet dishwasher, eating area that opens to the great room with access to the covered Patio. Bedroom 1 is just off the back side of the house & the adjoining bath features a walk-in closet, dual sinks and large 5' shower. Beautiful EVP the newest in wood look flooring throughout and nice Frieze carpet in the bedrooms. The Smart Home Connect System includes your video/camera doorbell & keyless entry at an affordable price. Gorgeous 3-sided brick Craftsman style home located in fast growing N. Crestview.

25. 2021-09-10
    soldstatus $292,900 Sold 761-char remark

    Show marketing remark (761 chars)

    NOW UNDER CONSTRUCTION! The Cali is a one story floor plan 4 bedrooms, 2 baths, covered back patio & 2 car garage. Sought-after open design offers a nice kitchen featuring an island bar for extra seating, stainless appliances, corner panty, quiet dishwasher, eating area that opens to the great room with access to the covered Patio. Bedroom 1 is just off the back side of the house & the adjoining bath features a walk-in closet, dual sinks and large 5' shower. Beautiful EVP the newest in wood look flooring throughout and nice Frieze carpet in the bedrooms. The Smart Home Connect System includes your video/camera doorbell & keyless entry at an affordable price. Gorgeous 3-sided brick Craftsman style home located in fast growing N. Crestview.

26. 2021-06-28
    listed $292,900 761-char remark

    Show marketing remark (761 chars)

    NOW UNDER CONSTRUCTION! The Cali is a one story floor plan 4 bedrooms, 2 baths, covered back patio & 2 car garage. Sought-after open design offers a nice kitchen featuring an island bar for extra seating, stainless appliances, corner panty, quiet dishwasher, eating area that opens to the great room with access to the covered Patio. Bedroom 1 is just off the back side of the house & the adjoining bath features a walk-in closet, dual sinks and large 5' shower. Beautiful EVP the newest in wood look flooring throughout and nice Frieze carpet in the bedrooms. The Smart Home Connect System includes your video/camera doorbell & keyless entry at an affordable price. Gorgeous 3-sided brick Craftsman style home located in fast growing N. Crestview.

27. 2021-01-15
    soldstatus $924,000

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 6/10 Major
• 🌡 Heat 8/10 Severe 7 d/yr ≥107°F today · 19 d/yr by 30 yrs out
• 💨 Wind 9/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $26,826
• − Mortgage interest: −$16,239
• − Property taxes: −$4,348
• − Insurance: −$1,450
• − Repairs & maintenance: −$2,146
• − Management: −$2,146
• − HOA: −$744
• − Depreciation: −$8,433
• Taxable loss: −$8,680
• Est. tax savings @ 24.0%: +$2,083
• After-tax cash flow: $-1,509/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: Okaloosa
• NCES district ID: 1201380
• Math proficiency: 60% ▼ -12.00%
• Reading proficiency: 60% ▼ -4.00%
• Median HH income: $55,601
• Composite: 51.62/100
• National rank: #1705
• State rank: #12 of 73 in FL

Livability — Crestview

• Score: 75/100
• State rank: #252
• US rank: #3858

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• County: Okaloosa County · 194,352 people
• City population: 58,889
• Metro: Crestview-Fort Walton Beach-Destin, FL
• Population (ZIP): 33,290
• Household income: $74,369
• Rent vs Own: 21.7% rent · 78.3% own
• Severe rent burden: 371.0

Population outlook (Okaloosa County) Hauer SSP2

• Today (2025): 235,133 people
• By 2030: 253,483 · +7.8%
• By 2040: 289,537 · +23.1%
• By 2050: 322,954 · +37.3%
• By 2075: 399,624 · +70.0%
• By 2100: 425,311 · +80.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (73%)
• Race & ethnicity: White 73% Black 12% Two or more races 8% Hispanic / Latino 7% Asian 1%
• Hispanic origin (detail): Mexican 3% Puerto Rican 2%
• Common ancestry: Lithuanian 4% Iranian 2% Romanian 2%
• Foreign-born: 3% · Canada
• Languages at home: 94% English-only · Spanish 3% Russian/Polish/Slavic 1% Other Asian/Pacific 1%

Political lean MEDSL · Okaloosa

• 2024 margin: Solid R (+42.4) · D 28.2% · R 70.7% · Other 1.1%
• 2008→2024 swing: +2.5pp toward D · 2008: -44.9pp · 2024: -42.4pp
• All cycles: 2024: R+42.4 2020: R+39.1 2016: R+47.8 2012: R+49.4 2008: R+44.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -56.52%
• Current HPI: 261.1557
• Rent YoY: ▲ 0.12%
• 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

-68.3% since first listed

11 events — show timeline

• 2026-04-27 Price Changed $292,900 ECAR
• 2026-04-27 Price Changed $292,000 ECAR
• 2026-04-02 Listed for Rent $1,950 ECAR
• 2026-04-02 Rental Removed $1,950 ECAR
• 2026-03-31 Listed for Rent $1,950 ECAR
• 2026-02-13 Price Changed $319,000 ECAR
• 2025-12-28 Listed $340,000 ECAR
• 2021-09-10 Sold (MLS) $292,900 ECAR
• 2021-09-10 Sold (MLS) $292,900 NAMLS
• 2021-06-28 Listed $292,900 NAMLS
• 2021-01-15 Sold (Public Records) $924,000 Public Records

Property tax history

-3.7%/yr

Latest (2025): $124 · +6.5% YoY. Source: county tax records.