55 Woodland Dr · Fenwick, CT 06475

$499,900

4 bd · 1.0 ba · 1,080 sqft · SingleFamily public records · 8 Days on market

Built 1950 0.33 ac lot Est $636k · 21% under

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Why this score? — see what drove the B+ 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 +30.0/30.0
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +4.9/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Tremendous opportunity in the sought-after Knollwood Beach Association! This coastal property is ideal for builders, flippers, investors, or buyers looking to create a custom beach retreat. Included in the sale is a rare undeveloped . 40-acre lot at 53 Woodland Drive with its own separate field card, offering exceptional flexibility and future potential. The existing home needs significant cosmetic renovation and is being sold strictly "as is, " but the layout, bones, and mechanical systems appear solid. Dry basement adds additional value and utility. The home was occupied until several months ago, though sellers have never lived in the property and no disclosures are available. P

Key facts

• Shoreline location
• Rare undeveloped lot
• Private sandy beach

Tags

• RARE UNDEVELOPED LOT
• DRY BASEMENT
• PRIVATE SANDY BEACH
• SHORELINE LOCATION

Property features AI

Finance

• HOA & community: Association required for waterfront access

Exterior

• Parking: Unpaved parking; 4 parking spaces
• Utilities: Public water connected; Septic system; Oil hot water (domestic)
• Home design: Single-family home for sale
• Construction: Frame construction; Stucco exterior; Asphalt shingle roof; Concrete foundation; Blue exterior color
• Exterior features: Level lot; Walk-to-water access (association required); Nearby amenities include basketball court, golf course, health club, park, and tennis courts; Located in a flood zone

Interior

• Bedrooms: 4 bedrooms
• Bathrooms: 1 full bathroom
• Heating & cooling: Hot air heating (oil)
• Interior features: 6 total rooms; 2 fireplaces; Full basement with concrete floor, sump pump, and hatchway access; Attic with crawl space accessed via hatch
• Laundry & utility: Oil-fired domestic hot water; Oil fuel tank located in basement

What this means for you Summary

Snapshot

• This is a 4-bed/1.0-bath single-family listed at $500k.

Deal economics

• At list price, monthly cash flow is $5k ($63k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($11k rent vs $500k).

Location & tenants

• Location reads 60/100 on livability (#139 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, housing B; Watch: amenities F, commute F, cost of living F.
• Old Saybrook School District (suburban): math 45% / reading 64% proficiency, ranked #66 of 153 in CT (top 43%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 13% free/reduced lunch — higher-income household profile.
• Zoned schools: Kathleen E. Goodwin School (math 52% / reading 67%, grade B-, #159 of 553 statewide, top 31%, 401 students, 24% FRL); Old Saybrook Senior High School (math 42% / reading 62%, grade D+, #80 of 194 statewide, top 44%, 347 students, 22% FRL).
• Market conditions: 69 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $15k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $140k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• Only 8 days on market — expect competitive offers; lowballing is unlikely to land.

Risks & watch-outs

• Watch-outs: flood insurance adds $460/mo; built in 1950 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: in FEMA flood zone AE (mandatory federal flood insurance); severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $499,900

Questions for the listing agent

1. Built in 1950 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
5. 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.
6. 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.
7. 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: 2.27% ✓
• Cap rate: 20.02%
• Cash-on-cash: 49.04%
• DSCR: 3.18
• GRM: 3.7

CMA / ARV

• ARV (on-the-fly): $636,120
• Comps found: 6

Show comp detail 6 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
12 Bellaire Dr	0.57mi	3/1.0 (-1)	1,104 (+2%)	7mo	$650,000	$589	59
99 Maple Ave	0.61mi	3/1.5 (-1)	1,170 (+8%)	4mo	$675,000	$577	48
6 Briarwood Dr	0.58mi	3/1.5 (-1)	1,008 (-7%)	17mo	$553,000	$549	41
12 Hartlands Dr	0.51mi	3/1.0 (-1)	956 (-12%)	18mo	$740,000	$774	37
11 George Dr	0.52mi	3/1.5 (-1)	925 (-14%)	13mo	$610,000	$659	34
20 George Dr	0.57mi	3/1.0 (-1)	925 (-14%)	18mo	$525,000	$568	29

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 · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 42.2%
• Equity multiple: 2.82×
• Total profit: $254,314
• Equity at exit: $74,537

10-year hold

• IRR: 48.4%
• Equity multiple: 5.67×
• Total profit: $654,111
• Equity at exit: $43,222

Cash invested: $139,972 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 27 Tenant-Leaning
• State Connecticut: 27 Tenant-Leaning · D+7
• County: — inherits STATE
• City: — inherits STATE

Strong tenant statutes; rent commissions in some towns; courts slow especially in cities.

Methodology + full state rankings →

ZIP-level market 06475

• Active inventory: 69
• Price-to-rent: 3.7×

Monthly cashflow live

• Estimated rent: $11,333 medium
• Mortgage (P&I): −$2,622
• Tax from tax record: −$403 /mo · $4,838/yr
• Insurance: −$208
• Flood insurance flood zone: −$460 /mo · $5,525/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,380
• Net cashflow: $5,260

Break-even live

Break-even rent $4,675

Max offer price $499,900

Occupancy floor 49%

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: $124,975
• Closing costs: $14,997
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
8 Bellaire Dr Old Saybrook, CT	4.0	3.0	1120	$18,000	$16.07	43d	1	0.58mi
38 Seabreeze Rd Old Saybrook, CT	3.0	1.0	912	$2,400	$2.63	43d	1	0.68mi

Listing history 5 events

1. 2026-06-02
   status $499,900 Under Contract 8 DOM
2. 2026-06-01
   days on market $499,900 Active 8 DOM
3. 2026-05-31
   days on market $499,900 Active 7 DOM
4. 2026-05-31
   days on market $499,900 Active 6 DOM
5. 2026-05-24
   listed $499,900 Active

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $4,838 · $403/mo
• Projected year-2 tax: $7,768 · $647/mo
• Expected delta: +$2,930/yr (+$244/mo · 60.6%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone AE · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥92°F today · 17 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 4 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $135,999
• − Mortgage interest: −$28,002
• − Property taxes: −$4,838
• − Insurance: −$8,024
• − Repairs & maintenance: −$10,880
• − Management: −$10,880
• − Depreciation: −$14,543
• Taxable income: $58,832
• Est. tax owed @ 24.0%: −$14,120
• After-tax cash flow: $48,998/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: Old Saybrook School District
• NCES district ID: 0903180
• Math proficiency: 45% ▼ -19.00%
• Reading proficiency: 64% ▼ -10.00%
• Median HH income: $74,710
• Composite: 48.81/100
• National rank: #2090
• State rank: #66 of 153 in CT

Livability — Fenwick

• Score: 60/100
• State rank: #139
• US rank: #19067

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 10,515

Population outlook (Lower Connecticut River Valley County) Hauer SSP2

• By 2040: 188,651

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (90%)
• Race & ethnicity: White 90% Hispanic / Latino 7% Two or more races 4% Asian 1% Native American 1%
• Hispanic origin (detail): Puerto Rican 2%
• Common ancestry: Romanian 8% Lithuanian 4% Iranian 2%
• Foreign-born: 8% · Canada, China
• Languages at home: 89% English-only · Spanish 7% Russian/Polish/Slavic 1% Other Indo-European 1%

Political lean MEDSL · Lower Connecticut River Valley

• 2024 margin: D (+13.4) · D 55.9% · R 42.4% · Other 1.7%
• All cycles: 2024: D+13.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -222.11%
• Current HPI: 301.8614
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 1.06%
• F500 in state: 38

Industry mix (Fortune 500 HQ in CT)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$38B
▸Insurance	3	$71B
▸Financial Services	2	$25B
▸Transportation / Logistics	2	$18B
▸Healthcare	1	$247B
▸Telecommunications	1	$55B

Price history

1 event — show timeline

• 2026-05-24 Listed $499,900 Smart MLS

Property tax history

+1.2%/yr

Latest (2023): $4,838 · +1.8% YoY. Source: county tax records.