44 Chester St · Milford city (balance), CT 06460

$250,000

3 bd · 1.0 ba · 936 sqft · SingleFamily public records · 7 Days on market

Built 1960 6,969 sqft lot Est $419k · 40% 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 +22.9/30.0
• ARV discount +15.0/15.0
• DSCR +7.4/10.0
• 1% rule +6.6/10.0
• Schools +4.6/10.0
• Rent growth +3.0/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

INVESTORS TAKE NOTICE! SHORT SALE APPROVAL NEEDED!! A single family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!

Key facts

• Close to town
• Close to schools
• Plenty of storage

Tags

• SINGLE FAMILY HOME
• PLENTY OF STORAGE
• CLOSE TO TOWN
• CLOSE TO TRANSPORTATION
• CLOSE TO SCHOOLS
• CLOSE TO SHOPPING

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $250k.

Deal economics

• At list price, monthly cash flow is $440 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $250k).
• Cap rate 8.4% vs local median 3.6% in Milford city (balance) — 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: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• Milford School District (urban): math 44% / reading 58% proficiency, ranked #73 of 153 in CT (top 48%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 15% free/reduced lunch — higher-income household profile.
• Zoned schools: Calf Pen Meadow School (math 47% / reading 52%, grade D, #237 of 553 statewide, top 45%, 265 students, 23% FRL); Joseph A. Foran High School (math 47% / reading 67%, grade C, #52 of 194 statewide, top 31%, 765 students, 26% FRL).
• Market conditions: Rents rising (+2.2%/yr); 175 active listings in the ZIP; 7 comparable units currently listed for rent nearby; rentals leasing fast (median 4d on market — plan ~1-2 weeks tenant-placement turnaround); solid renter incomes; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• This rent runs 33% of the median local income ($104k/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 $8k of value loss. Plan a longer hold.

Negotiation context

• Only 7 days on market — expect competitive offers; lowballing is unlikely to land.

Risks & watch-outs

• Climate carrying-cost: major flood risk; major wind risk, 61% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $250,000

Questions for the listing agent

1. Built in 1960 — 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. 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.
4. 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.
5. 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: 1.16% ✓
• Cap rate: 8.40%
• Cash-on-cash: 7.54%
• DSCR: 1.34
• GRM: 7.2

CMA / ARV

• ARV (on-the-fly): $419,328
• Comps found: 12

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
19 Summer Pl	0.24mi	4/1.0 (+1)	972 (+4%)	12mo	$435,000	$448	68
6 Milesfield Ave	0.55mi	3/1.0	920 (-2%)	23mo	$450,000	$489	52
13 Catherine Ct	0.52mi	2/1.0 (-1)	961 (+3%)	17mo	$402,000	$418	52
26 Deerfield Ave	0.63mi	3/1.5	1,008 (+8%)	7mo	$640,000	$635	50
154 Yale Ave	0.55mi	2/1.0 (-1)	874 (-7%)	11mo	$341,500	$391	49
39 Westland Ave	0.61mi	2/1.0 (-1)	951 (+2%)	22mo	$620,000	$652	45
16 Morehouse Ave	0.49mi	2/1.0 (-1)	1,000 (+7%)	21mo	$397,500	$398	43
33 Elaine Rd	0.57mi	2/2.0 (-1)	1,008 (+8%)	11mo	$500,000	$496	42
112 Bird Ln	0.72mi	3/1.0	1,000 (+7%)	16mo	$410,000	$410	42
28 Entrance Rd	0.67mi	2/1.0 (-1)	864 (-8%)	12mo	$375,000	$434	41
335 Edgefield Ave	0.61mi	3/1.0	1,008 (+8%)	23mo	$400,000	$397	40
42 Warren St	0.34mi	2/1.0 (-1)	796 (-15%)	18mo	$390,000	$490	39

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 · 2.19% rent growth · sell at horizon

5-year hold

• IRR: -5.7%
• Equity multiple: 0.79×
• Total profit: $-14,728
• Equity at exit: $37,276

10-year hold

• IRR: 2.9%
• Equity multiple: 1.20×
• Total profit: $14,262
• Equity at exit: $21,615

Cash invested: $70,000 (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 06460

• Rents YoY: 2.2%
• Active inventory: 175
• Price-to-rent: 7.2×

Monthly cashflow live

• Estimated rent: $2,898 high
• Mortgage (P&I): −$1,311
• Tax from tax record: −$435 /mo · $5,218/yr
• Insurance: −$104
• HOA: −$0
• Vacancy / Maint / Mgmt: −$609
• Net cashflow: $440

Break-even live

Break-even rent $2,342

Max offer price $250,000

Occupancy floor 80%

Sensitivity live

Price	-10% $581	-5% $511	+0% $440	+5% $369	+10% $298
Rent	-10% $211	-5% $325	+0% $440	+5% $554	+10% $669
Rate	-1.0pp $566	-0.5pp $503	base $440	+0.5pp $375	+1.0pp $309

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: $62,500
• Closing costs: $7,500
• Reserves months: —
• Total cash needed: —

Rent comps 7 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
18 Melba St Milford, CT	2.0	1.0	702	$2,200	$3.13	3d	1	0.23mi
27 Melba St Unit B Milford, CT	3.0	1.0	1008	$2,799	$2.78	44d	1	0.24mi
17 W Orland St Milford, CT	3.0	1.0	1004	$3,999	$3.98	44d	1	0.27mi
54 Milesfield Ave Milford, CT	3.0	1.0	1056	$2,000	$1.89	3d	1	0.52mi
32 Lawrence Ave Milford, CT	3.0	1.5	1120	$3,200	$2.86	3d	1	0.67mi
42 Whalley Ave Milford, CT	3.0	1.0	958	$2,500	$2.61	3d	1	0.98mi
42 Whalley Ave Milford, CT	3.0	1.0	958	$2,500	$2.61	22d	1	0.98mi

Listing history 2 events

1. 2025-02-24
   status Under Contract
2. 2025-02-17
   listed $250,000 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: $5,218 · $435/mo
• Projected year-2 tax: $5,284 · $440/mo
• Expected delta: +$66/yr (+$6/mo · 1.3%)

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

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone X (unshaded) · 92% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥98°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 61% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 5 unhealthy d/yr today · 7 by 30 yrs out

Taxation est. · year 1

• Rental income: $34,781
• − Mortgage interest: −$14,004
• − Property taxes: −$5,218
• − Insurance: −$1,250
• − Repairs & maintenance: −$2,783
• − Management: −$2,783
• − Depreciation: −$7,273
• Taxable income: $1,472
• Est. tax owed @ 24.0%: −$353
• After-tax cash flow: $4,924/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: Milford School District
• NCES district ID: 0902520
• Math proficiency: 44% ▼ -14.00%
• Reading proficiency: 58% ▼ -11.00%
• Median HH income: $80,198
• Composite: 46.45/100
• National rank: #2444
• State rank: #73 of 153 in CT

Livability — Milford city (balance)

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• Census place: Milford city (balance), CT
• County: New Haven County · 688,236 people
• City population: 52,340
• Metro: New Haven-Milford, CT
• Population (ZIP): 37,649
• Household income: $104,360
• Rent vs Own: 28.8% rent · 71.2% own
• Severe rent burden: 1254.0

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (82%)
• Race & ethnicity: White 82% Hispanic / Latino 8% Two or more races 7% Asian 3% Black 3%
• Hispanic origin (detail): Puerto Rican 4%
• Common ancestry: Romanian 6% Lithuanian 4% Scotch-Irish 2%
• Foreign-born: 10% · Canada, China, Jamaica
• Languages at home: 88% English-only · Spanish 4% Other Indo-European 3% Other Asian/Pacific 1%

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: ▼ -396.40%
• Current HPI: 287.7738
• Rent YoY: ▲ 2.19%
• Metro: New Haven-Milford, CT
• 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

2 events — show timeline

• 2025-02-24 Pending — Smart MLS
• 2025-02-17 Listed $250,000 Smart MLS

Property tax history

+2.2%/yr

Latest (2023): $5,218 · +2.0% YoY. Source: county tax records.