108 Dewitt St · New Haven, CT 06519

$485,000

5 bd · 3.0 ba · 2,330 sqft · MultiFamily public records · 37 Days on market

Built 1900 2,613 sqft lot $208/sqft · 24% above area Est $390k · 24% over

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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 +23.3/30.0
• Appreciation +9.9/10.0
• DSCR +7.5/10.0
• 1% rule +5.6/10.0
• Livability +4.0/5.0
• Rent growth +3.3/5.0
• Condition / age +2.5/5.0
• Schools +1.5/10.0
• ARV discount +0.0/15.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 2 units. confirmed

Listing remarks MLS

Attention all home owners and investors!!! This one of a kind 2 family property is completely renovated. The first floor apartment consists of 3 bedrooms and 1 bathroom. The second apartment is very spacious containing 5 bedrooms and 2 bathrooms. Both units are extremely turn key and have brand new hardwood floors throughout the entire apartments, new kitchens with quartz countertops, updated electrical, fresh paint, three new bathrooms with tiled showers, two new furnaces, two new hot water heaters, etc. This property is a must see!

Key facts

• New kitchens
• Quartz countertops
• Updated electrical

Tags

• COMPLETELY RENOVATED
• BRAND NEW HARDWOOD FLOORS
• NEW KITCHENS
• QUARTZ COUNTERTOPS
• UPDATED ELECTRICAL
• FRESH PAINT

What this means for you Summary

Snapshot

• This is a 1×4bd/1.5ba + 1×5bd/1.5ba units multifamily listed at $485k.

Deal economics

• At list price, monthly cash flow is $886 ($11k/yr) — positive. Per door: $443/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $485k).
• Recommended offer: $470k (3.0% below list) — sets the bar for market timing.
• Cap rate 8.5% vs local median 4.8% in New 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 79/100 on livability (#31 in CT, #2,190 nationally) — a middle-class / working-renter tenant base. Strengths: amenities A+, commute A+, health & safety A+; Watch: schools D+, employment D, crime F.
• New Haven School District (urban): math 12% / reading 25% proficiency, ranked #147 of 153 in CT (top 96%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 66% free/reduced lunch — lower-income household profile, screen leases tightly.
• Market conditions: Rents rising (+3.3%/yr); 46 active listings in the ZIP; 15 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).
• At $5,145/mo this rent would consume 124% of the median local household income ($50k/yr) (locally 1321% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $51k of equity ($3k loan paydown + $48k appreciation (9.8% local appreciation)).
• At projected returns (9.8% appreciation + 3.3% rent growth), your $136k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$82k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 37 days — a 3% lower offer ($470k) is reasonable based on typical stale-listing flexibility.
• 6 sale attempts since 22y ago 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.
• Current owner paid $121k; list at $485k implies a 301% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 56% 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 $470,450 (3.0% below list)

Questions for the listing agent

1. It's been on market 37 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
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 apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 1.06% ✓
• Cap rate: 8.48%
• Cash-on-cash: 7.83%
• DSCR: 1.35
• GRM: 7.9

CMA / ARV

• ARV (median comp): $390,356
• List price: $485,000
• Delta: 24.25%
• Verdict: OVERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
20-22 Hurlburt St	0.24mi	6/3.0 (+1)	2,429 (+4%)	0mo	$362,500	$149	76
95 Frank St	0.28mi	6/3.0 (+1)	2,243 (-4%)	2mo	$385,000	$172	74
45 Frank St	0.26mi	6/3.0 (+1)	2,120 (-9%)	4mo	$430,000	$203	65
46 Liberty St	0.28mi	4/2.0 (-1)	2,110 (-9%)	2mo	$320,000	$152	60
133 Plymouth St	0.34mi	6/3.0 (+1)	2,100 (-10%)	4mo	$275,000	$131	60
11 White St	0.32mi	6/3.0 (+1)	2,502 (+7%)	10mo	$445,000	$178	60
312 Davenport Ave	0.59mi	6/2.0 (+1)	2,348 (+1%)	6mo	$312,000	$133	57
109 Hurlburt St	0.12mi	6/3.0 (+1)	2,677 (+15%)	9mo	$290,000	$108	57
152 Lamberton St	0.30mi	6/3.0 (+1)	2,080 (-11%)	8mo	$340,000	$163	57
121 Plymouth St	0.36mi	5/2.0	2,539 (+9%)	10mo	$355,000	$140	56
56 Ann St	0.53mi	5/3.0	2,067 (-11%)	6mo	$407,000	$197	51
87 Orchard St	0.75mi	4/2.0 (-1)	2,088 (-10%)	3mo	$362,500	$174	37

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

Projected returns pro-forma

9.81% appreciation · 3.3% rent growth · sell at horizon

5-year hold

• IRR: 29.7%
• Equity multiple: 3.33×
• Total profit: $315,767
• Equity at exit: $430,204

10-year hold

• IRR: 25.9%
• Equity multiple: 7.53×
• Total profit: $887,004
• Equity at exit: $920,688

Cash invested: $135,800 (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 06519

• Home prices YoY: 2.7%
• Rents YoY: 3.3%
• Active inventory: 46
• Price-to-rent: 16.5×

Monthly cashflow live

• Estimated rent: $5,145 high
• Mortgage (P&I): −$2,543
• Tax from tax record: −$433 /mo · $5,200/yr
• Insurance: −$202
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,080
• Net cashflow: $886

Break-even live

Break-even rent $4,024

Max offer price $485,000

Occupancy floor 78%

2-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
1× unit	4	1.5	$2,447
1× unit	5	1.5	$2,698
Total (2 units)			$5,145

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: $121,250
• Closing costs: $14,550
• Reserves months: —
• Total cash needed: —

Rent comps 15 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
36 Cassius St New Haven, CT	4.0	1.5	1872	$2,300	$1.23	43d	1	0.21mi
34 Cassius St Unit 36 New Haven, CT	5.0	2.0	1872	$2,300	$1.23	43d	1	0.21mi
41 Howe St New Haven, CT	4.0	2.0	1795	$3,750	$2.09	43d	1	0.98mi
43 Howe St New Haven, CT	4.0	2.0	1995	$4,995	$2.50	14d	1	0.99mi
395 Crown St New Haven, CT	6.0	3.5	2889	$7,195	$2.49	43d	1	1.00mi
131 Dwight St Unit 1 New Haven, CT	6.0	3.0	3000	$6,250	$2.08	14d	1	1.05mi
131 Dwight St Unit 1 New Haven, CT	6.0	3.0	3097	$6,250	$2.02	23d	1	1.05mi
37 Center St Unit 2 West Haven, CT	5.0	2.0	2500	$3,300	$1.32	2d	1	1.17mi
229 Dwight St New Haven, CT	6.0	2.0	2400	$4,995	$2.08	2d	1	1.22mi
441 Chapel St Unit 2A1 (shared) New Haven, CT	4.0	4.0	2151	$3,600	$1.67	2d	1	1.35mi
395 Orange St Unit 2 New Haven, CT	4.0	1.5	1650	$3,000	$1.82	43d	1	1.44mi
203 Main St Unit 2nd fl West Haven, CT	4.0	1.0	1967	$2,400	$1.22	23d	1	1.44mi
399 Orange St New Haven, CT	4.0	1.5	1650	$3,200	$1.94	11d	1	1.45mi
54 Trumbull St Unit 54-1 New Haven, CT	5.0	2.5	2250	$6,695	$2.98	14d	1	1.47mi
30 Trumbull St New Haven, CT	5.0	4.0	2668	$5,000	$1.87	3d	1	1.48mi

Listing history 19 events

1. 2026-04-14
   listed $485,000 Active 539-char remark

   Show marketing remark (539 chars)

   Attention all home owners and investors!!! This one of a kind 2 family property is completely renovated. The first floor apartment consists of 3 bedrooms and 1 bathroom. The second apartment is very spacious containing 5 bedrooms and 2 bathrooms. Both units are extremely turn key and have brand new hardwood floors throughout the entire apartments, new kitchens with quartz countertops, updated electrical, fresh paint, three new bathrooms with tiled showers, two new furnaces, two new hot water heaters, etc. This property is a must see!

2. 2026-04-13
   historical
3. 2026-02-25
   listed $485,000 Active
4. 2024-05-01
   historical
5. 2024-03-16
   price $260,000
6. 2023-12-01
   price $265,000
7. 2023-07-13
   price $270,000
8. 2023-06-05
   price $275,000
9. 2023-05-09
   listed $285,000 Active
10. 2009-05-29
    soldstatus $121,000
11. 2009-05-21
    soldstatus $55,000
12. 2009-04-07
    listed $55,900
13. 2005-07-27
    soldstatus $235,000
14. 2004-11-04
    soldstatus $150,000
15. 2004-10-27
    soldstatus $150,000
16. 2004-06-09
    soldstatus $96,000
17. 2004-05-19
    listed $159,000
18. 2004-01-25
    listed $96,000
19. 2000-04-20
    soldstatus $115,000

ⓘ 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: $5,200 · $433/mo
• Projected year-2 tax: $7,790 · $649/mo
• Expected delta: +$2,590/yr (+$216/mo · 49.8%)

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 7/10 Severe 7 d/yr ≥99°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 56% chance of damaging wind over 30 yrs
• 🫁 Air quality 5/10 Major 6 unhealthy d/yr today · 8 by 30 yrs out

Taxation est. · year 1

• Rental income: $61,740
• − Mortgage interest: −$27,168
• − Property taxes: −$5,200
• − Insurance: −$2,425
• − Repairs & maintenance: −$4,939
• − Management: −$4,939
• − Depreciation: −$14,109
• Taxable income: $2,960
• Est. tax owed @ 24.0%: −$710
• After-tax cash flow: $9,918/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: New Haven School District
• NCES district ID: 0902790
• Math proficiency: 12% ▼ -10.00%
• Reading proficiency: 25% ▼ -10.00%
• Median HH income: $38,058
• Composite: 15.48/100
• National rank: #9308
• State rank: #147 of 153 in CT

Livability — New Haven

• Score: 79/100
• State rank: #31
• US rank: #2190

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: New Haven, CT
• County: New Haven County · 688,236 people
• City population: 132,813
• Metro: New Haven-Milford, CT
• Population (ZIP): 15,605
• Household income: $49,619
• Rent vs Own: 73.7% rent · 26.3% own
• Severe rent burden: 1321.0

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.67)
• Race & ethnicity: Hispanic / Latino 49% Black 26% White 15% Two or more races 13% Asian 4% Native American 1%
• Hispanic origin (detail): Mexican 15% Puerto Rican 25% Dominican 3%
• Common ancestry: Romanian 1% Lithuanian 1%
• Foreign-born: 25% · Canada, Jamaica, China
• Languages at home: 50% English-only · Spanish 42% Other Indo-European 4% Arabic 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: ▲ 9.81%
• Current HPI: 377.4885
• Rent YoY: ▲ 3.30%
• 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

+321.7% since first listed

19 events — show timeline

• 2026-04-14 Listed $485,000 Smart MLS
• 2026-04-13 Listing Removed — Smart MLS
• 2026-02-25 Listed $485,000 Smart MLS
• 2024-05-01 Listing Removed — Smart MLS
• 2024-03-16 Price Changed $260,000 Smart MLS
• 2023-12-01 Price Changed $265,000 Smart MLS
• 2023-07-13 Price Changed $270,000 Smart MLS
• 2023-06-05 Price Changed $275,000 Smart MLS
• 2023-05-09 Listed $285,000 Smart MLS
• 2009-05-29 Sold (Public Records) $121,000 Public Records
• 2009-05-21 Sold (MLS) $55,000 Smart MLS
• 2009-04-07 Listed $55,900 Smart MLS
• 2005-07-27 Sold (Public Records) $235,000 Public Records
• 2004-11-04 Sold (Public Records) $150,000 Public Records
• 2004-10-27 Sold (MLS) $150,000 Smart MLS
• 2004-06-09 Sold (MLS) $96,000 Smart MLS
• 2004-05-19 Listed $159,000 Smart MLS
• 2004-01-25 Listed $96,000 Smart MLS
• 2000-04-20 Sold (Public Records) $115,000 Public Records

Property tax history

+6.2%/yr

Latest (2023): $5,200 · -6.4% YoY. Source: county tax records.