44 Upper State St · North Haven, CT 06473

$269,000

3 bd · 1.0 ba · 1,290 sqft · SingleFamily public records · 23 Days on market

Built 1954 0.49 ac lot Est $441k · 39% under

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Why this score? — see what drove the C+ 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 +20.2/30.0
• ARV discount +15.0/15.0
• DSCR +6.4/10.0
• 1% rule +5.8/10.0
• Schools +5.2/10.0
• Livability +3.9/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Opportunity at 44 Upper State Street in North Haven. This ranch-style home offers convenient one-level living with 3 bedrooms and 1 full bathroom. Very functional layout, this home features a 2-car attached garage with a mudroom entry. A full unfinished basement offers future finishing potential and includes a walkout to the backyard, opening up additional possibilities for expanded living space. Commuter-friendly location close to major highways. With strong comparable sales in the area, this is a great value-add property. Property is in need of repairs and strictly sold as-is. Contingent on probate approval.

Key facts

• Attached garage
• One-level living
• Unfinished basement

Tags

• ONE-LEVEL LIVING
• ATTACHED GARAGE
• UNFINISHED BASEMENT
• COMMUTER-FRIENDLY LOCATION

Property features AI

Exterior

• Utilities: Public water connected; Septic system
• Home design: Single-family home
• Construction: Frame construction; Concrete foundation
• Exterior features: Level lot; Vinyl siding; Asphalt shingle roof

Interior

• Kitchen: Refrigerator included
• Bedrooms: Three bedrooms
• Bathrooms: One full bathroom
• Heating & cooling: Hot air heating (oil fuel)
• Interior features: Full unfinished basement; Attic with access via hatch; One fireplace; Six total rooms
• Laundry & utility: Oil-fired hot air heating (fuel tank in basement)

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $269k.

Deal economics

• At list price, monthly cash flow is $338 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $269k).
• Recommended offer: $265k (1.5% below list) — sets the bar for market timing.
• Cap rate 7.8% vs local median 4.0% in North Haven — 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 78/100 on livability (#39 in CT, #2,723 nationally) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+, health & safety A+; Watch: amenities F, commute F, cost of living D-.
• North Haven School District (suburban): math 49% / reading 64% proficiency, ranked #55 of 153 in CT (top 36%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 8% free/reduced lunch — higher-income household profile.
• Market conditions: 77 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals at typical pace (median 14d on market — plan ~3-4 weeks tenant-placement turnaround); 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $8k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 23 days — a 2% lower offer ($265k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.

Risks & watch-outs

• Watch-outs: built in 1954 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $264,965 (1.5% below list)

Questions for the listing agent

1. Built in 1954 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are A-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?
4. 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.
5. 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.
6. 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: 1.08% ✓
• Cap rate: 7.80%
• Cash-on-cash: 5.38%
• DSCR: 1.24
• GRM: 7.7

CMA / ARV

• ARV (on-the-fly): $441,180
• Comps found: 3

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
15 Kings Hwy	0.38mi	2/1.0 (-1)	1,314 (+2%)	10mo	$418,000	$318	66
113 Kings Hwy	0.57mi	2/1.0 (-1)	1,248 (-3%)	10mo	$460,000	$369	54
25 Mansfield Rd	0.45mi	3/2.5	1,448 (+12%)	21mo	$495,500	$342	36

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: -7.9%
• Equity multiple: 0.71×
• Total profit: $-21,973
• Equity at exit: $40,109

10-year hold

• IRR: 1.7%
• Equity multiple: 1.12×
• Total profit: $8,980
• Equity at exit: $23,258

Cash invested: $75,320 (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 06473

• Active inventory: 77
• Price-to-rent: 7.7×

Monthly cashflow live

• Estimated rent: $2,897 medium
• Mortgage (P&I): −$1,411
• Tax from tax record: −$428 /mo · $5,141/yr
• Insurance: −$112
• HOA: −$0
• Vacancy / Maint / Mgmt: −$608
• Net cashflow: $338

Break-even live

Break-even rent $2,470

Max offer price $269,000

Occupancy floor 83%

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: $67,250
• Closing costs: $8,070
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
23 Maiden Ln North Haven, CT	2.0	1.5	879	$2,662	$3.03	2d	6	0.70mi
100 Avalon Haven Dr North Haven, CT	1.0–3.0	1.0–2.0	1009	$3,000	$2.97	14d	5	0.73mi
1400 Hartford Tpke #10 North Haven, CT	3.0	2.0	1295	$2,990	$2.31	43d	1	0.91mi
1298 Hartford Tpke North Haven, CT	2.0	2.0	1118	$2,925	$2.62	11d	2	1.26mi

Listing history 4 events

1. 2026-04-14
   status Under Contract
2. 2026-04-09
   status Active
3. 2026-04-03
   status Under Contract
4. 2026-03-16
   listed $269,000 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: $5,141 · $428/mo
• Projected year-2 tax: $5,449 · $454/mo
• Expected delta: +$308/yr (+$26/mo · 6.0%)

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

Taxation est. · year 1

• Rental income: $34,770
• − Mortgage interest: −$15,068
• − Property taxes: −$5,141
• − Insurance: −$1,345
• − Repairs & maintenance: −$2,782
• − Management: −$2,782
• − Depreciation: −$7,825
• Taxable loss: −$173
• Est. tax savings @ 24.0%: +$42
• After-tax cash flow: $4,096/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: North Haven School District
• NCES district ID: 0903030
• Math proficiency: 49% ▼ -12.00%
• Reading proficiency: 64% ▼ -8.00%
• Median HH income: $85,727
• Composite: 51.53/100
• National rank: #1714
• State rank: #55 of 153 in CT

Livability — North Haven

• Score: 78/100
• State rank: #39
• US rank: #2723

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: North Haven, CT
• City population: 24,527
• Population (ZIP): 24,527

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (79%)
• Race & ethnicity: White 79% Hispanic / Latino 7% Asian 7% Two or more races 6% Black 4%
• Hispanic origin (detail): Mexican 1% Puerto Rican 4%
• Common ancestry: Romanian 7% Lithuanian 2% Scotch-Irish 1%
• Foreign-born: 11% · China, South Korea, Canada
• Languages at home: 86% English-only · Other Indo-European 4% Spanish 3% Chinese 2%

Political lean MEDSL · South Central Connecticut

• 2024 margin: Strong D (+20.1) · D 59.0% · R 38.9% · Other 2.1%
• All cycles: 2024: D+20.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -294.57%
• Current HPI: 168.0717
• 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

4 events — show timeline

• 2026-04-14 Pending — Smart MLS
• 2026-04-09 Relisted — Smart MLS
• 2026-04-03 Pending — Smart MLS
• 2026-03-16 Listed $269,000 Smart MLS

Property tax history

+0.5%/yr

Latest (2023): $5,141 · +6.3% YoY. Source: county tax records.