39 Shepard St · New Haven, CT 06511

$499,900

3 bd · 3.0 ba · 2,646 sqft · MultiFamily public records · 41 Days on market

Built 1910 3,920 sqft lot $189/sqft · 59% above area Est $422k · 18% 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 +26.3/30.0
• DSCR +8.9/10.0
• 1% rule +6.7/10.0
• Livability +4.0/5.0
• Rent growth +3.2/5.0
• Condition / age +2.5/5.0
• Schools +1.5/10.0
• ARV discount +0.0/15.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 3 units. confirmed

Listing remarks MLS

Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

Key facts

• 3,920 sq ft lot
• Built 1910
• Listed 41 days

Property features AI

Exterior

• Utilities: Public water connected; Public sewer connected; Hot water: Other
• Home design: Multi-family property (3-family)
• Construction: Frame construction; Concrete foundation; Asphalt shingle roof
• Exterior features: Level lot; Vinyl siding

Interior

• Bedrooms: 6 bedrooms
• Bathrooms: 3 full bathrooms
• Heating & cooling: Gas heating
• Interior features: 12 total rooms; Full basement

What this means for you Summary

Snapshot

• This is a 3 × 2-bed/1.0-bath units multifamily listed at $500k.

Deal economics

• At list price, monthly cash flow is $1k ($15k/yr) — positive. Per door: $429/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $500k).
• Recommended offer: $485k (3.0% below list) — sets the bar for market timing.
• Cap rate 9.4% 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 (+2.6%/yr); 137 active listings in the ZIP; 39 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 54% of comp listings sitting > 30 days — soft ceiling on asking rent; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).
• At $5,842/mo this rent would consume 117% of the median local household income ($60k/yr) (locally 4999% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

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.

Negotiation context

• It's been on market 41 days — a 3% lower offer ($485k) is reasonable based on typical stale-listing flexibility.
• 8 sale attempts since 15y 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 $174k; list at $500k implies a 188% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1910 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 53% 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 $484,903 (3.0% below list)

Questions for the listing agent

1. It's been on market 41 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 1910 — 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: 1.17% ✓
• Cap rate: 9.38%
• Cash-on-cash: 11.04%
• DSCR: 1.49
• GRM: 7.1

CMA / ARV

• ARV (median comp): $422,450
• List price: $499,900
• Delta: 18.33%
• Verdict: OVERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
245 Goodrich St	0.20mi	4/4.0 (+1)	2,880 (+9%)	6mo	$420,000	$146	62
272 Bassett St	0.42mi	4/2.0 (+1)	2,854 (+8%)	10mo	$265,000	$93	50
25 Lander St	0.18mi	4/2.0 (+1)	2,365 (-11%)	21mo	$350,000	$148	47
374 Shelton Ave	0.15mi	4/2.0 (+1)	3,021 (+14%)	19mo	$370,000	$122	45

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 · 2.6% rent growth · sell at horizon

5-year hold

• IRR: -0.3%
• Equity multiple: 0.99×
• Total profit: $-1,345
• Equity at exit: $74,537

10-year hold

• IRR: 9.0%
• Equity multiple: 1.68×
• Total profit: $94,916
• 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 06511

• Home prices YoY: -20.8%
• Rents YoY: 2.6%
• Active inventory: 137
• Price-to-rent: 21.4×

Monthly cashflow live

• Estimated rent: $5,842 high
• Mortgage (P&I): −$2,622
• Tax from tax record: −$498 /mo · $5,976/yr
• Insurance: −$208
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,227
• Net cashflow: $1,287

Break-even live

Break-even rent $4,212

Max offer price $499,900

Occupancy floor 73%

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

Units	Beds	Baths	Est. rent
▸ 3× units	2	1	$5,841
Total (3 units)			$5,842

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 39 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
106 Butler St New Haven, CT	4.0	2.0	3045	$2,600	$0.85	14d	1	0.07mi
327 Newhall St New Haven, CT	3.0	1.0	2742	$1,950	$0.71	43d	1	0.10mi
35 Goodyear St Unit 2 New Haven, CT	2.0	1.0	3046	$1,800	$0.59	14d	1	0.17mi
918 Winchester Ave Unit 2 New Haven, CT	3.0	1.0	3603	$1,900	$0.53	43d	1	0.22mi
761 Winchester Ave Unit 3 New Haven, CT	2.0	1.0	3052	$1,800	$0.59	43d	1	0.22mi
165 Starr St Unit 2nd Floor New Haven, CT	4.0	1.0	2099	$2,200	$1.05	18d	1	0.37mi
165 Starr St Unit 2nd Floor New Haven, CT	4.0	2.0	2099	$2,150	$1.02	14d	1	0.37mi
233 Highland St New Haven, CT	4.0	3.5	2200	$3,950	$1.80	43d	1	0.39mi
247 W Ivy St Unit 2 New Haven, CT	3.0	1.0	3531	$2,200	$0.62	43d	1	0.40mi
322 Bassett St Unit 2 New Haven, CT	3.0	1.0	2936	$1,900	$0.65	43d	1	0.50mi
327 Augur St Unit 3 Hamden, CT	3.0	1.0	3036	$1,800	$0.59	2d	1	0.62mi
1097 Dixwell Ave Hamden, CT	4.0	1.0	2005	$1,750	$0.87	11d	1	0.76mi
105 1st St Hamden, CT	2.0	1.0	2870	$2,100	$0.73	2d	1	0.84mi
266 Everit St New Haven, CT	4.0	3.5	3259	$4,500	$1.38	43d	1	0.90mi
30 Tilton St Unit 1 New Haven, CT	2.0	1.0	2128	$1,995	$0.94	43d	1	0.90mi
420 Whitney Ave New Haven, CT	3.0–4.0	2.0–3.0	1800	$2,395	$1.33	11d	2	0.93mi
420 Whitney Ave Unit 424-3B New Haven, CT	4.0	3.0	1800	$4,700	$2.61	3d	1	0.93mi
125 Stimson Rd New Haven, CT	3.0	2.5	3434	$3,500	$1.02	43d	1	0.97mi
339 Willow St Unit 1 New Haven, CT	4.0	2.0	2163	$4,050	$1.87	11d	1	0.97mi
156 Putnam Ave Hamden, CT	3.0	1.0	2304	$1,800	$0.78	2d	1	0.98mi
75 Stimson Rd New Haven, CT	4.0	1.0	1890	$3,500	$1.85	14d	1	1.00mi
1768 Ella T Grasso Blvd New Haven, CT	4.0	2.0	2193	$3,950	$1.80	43d	1	1.01mi
190 Pine Rock Ave Hamden, CT	1.0–4.0	1.0–3.0	1850	$2,905	$1.57	43d	1	1.01mi
119 Carmel St Unit 3 New Haven, CT	3.0	1.0	3282	$1,900	$0.58	43d	1	1.09mi
56 Mansfield St Unit 1 New Haven, CT	3.0	1.0	2759	$2,800	$1.01	43d	1	1.14mi
1634 Ella T Grasso Blvd New Haven, CT	4.0	1.5	2018	$3,600	$1.78	43d	1	1.21mi
47 Dickerman St Unit 1 New Haven, CT	3.0	1.0	3729	$2,100	$0.56	43d	1	1.25mi
151 Fitch St #161 New Haven, CT	3.0	2.0	2200	$2,481	$1.13	43d	1	1.28mi
604 Orange St #3 New Haven, CT	2.0	1.0	3453	$2,595	$0.75	2d	1	1.30mi
1428 Dixwell Ave Fl 2 Hamden, CT	3.0	1.0	3096	$2,100	$0.68	43d	1	1.31mi
146 Hartford Tpke Hamden, CT	3.0	2.5	3644	$6,900	$1.89	2d	1	1.34mi
52 Goffe St New Haven, CT	3.0	2.0	1935	$2,600	$1.34	23d	1	1.34mi
239 Bradley St Unit 1 New Haven, CT	3.0	1.0	1982	$3,650	$1.84	43d	1	1.40mi
315 Humphrey St Unit A New Haven, CT	4.0	3.5	2465	$4,500	$1.83	3d	1	1.44mi
84 Church St Unit 2 Hamden, CT	2.0	1.0	2913	$1,900	$0.65	43d	1	1.44mi
52 Edwards St Unit 1 New Haven, CT	2.0	1.0	2348	$2,850	$1.21	2d	1	1.47mi
799 Elm St New Haven, CT	2.0	1.0	3613	$1,590	$0.44	43d	1	1.47mi
300 Humphrey St Unit 2 New Haven, CT	3.0	2.0	2868	$3,295	$1.15	43d	1	1.48mi
30 Platt St Unit 3rd New Haven, CT	2.0	1.0	2957	$2,000	$0.68	11d	1	1.50mi

Listing history 34 events

1. 2026-06-16
   statusdays on market $499,900 Under Contract 41 DOM
2. 2026-06-15
   days on market $499,900 Active 40 DOM
3. 2026-06-14
   days on market $499,900 Active 38 DOM
4. 2026-06-13
   days on market $499,900 Active 37 DOM
5. 2026-06-10
   days on market $499,900 Active 35 DOM
6. 2026-06-09
   days on market $499,900 Active 34 DOM
7. 2026-06-09
   status $499,900 Active 33 DOM
8. 2026-06-08
   days on market $499,900 Under Contract - Continue to Show 33 DOM
9. 2026-06-07
   days on market $499,900 Under Contract - Continue to Show 32 DOM
10. 2026-06-05
    days on market $499,900 Under Contract - Continue to Show 29 DOM
11. 2026-06-03
    days on market $499,900 Under Contract - Continue to Show 28 DOM
12. 2026-06-03
    statusdays on market $499,900 Under Contract - Continue to Show 27 DOM
13. 2026-06-01
    days on market $499,900 Active 26 DOM
14. 2026-05-31
    days on market $499,900 Active 25 DOM
15. 2026-05-06
    listed $499,900 Active 259-char remark
16. 2021-03-22
    historical
17. 2021-02-23
    historical Under Contract - Continue to Show
18. 2021-02-08
    listed $265,000 Active
19. 2018-09-06
    soldstatus $173,775
20. 2018-09-05
    soldstatus $173,775 Closed

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

21. 2018-07-29
    historical

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

22. 2018-07-29
    status Active

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

23. 2018-07-04
    historical

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

24. 2018-06-12
    status Active

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

25. 2018-05-31
    historical

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

26. 2018-03-10
    status Under Contract

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

27. 2018-03-08
    price $189,999

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

28. 2018-03-02
    price $220,039

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

29. 2018-03-01
    listed $179,917 Active

    Show marketing remark (127 chars)

    Occupied 3 family in good condition with hard wood floors. Close to Yale, Albertus & Southern, homeowner real estate agent

30. 2014-09-25
    soldstatus $122,000
31. 2014-09-23
    soldstatus $122,000
32. 2014-08-14
    listed $129,900
33. 2011-11-08
    historical
34. 2011-03-08
    listed $114,900

ⓘ 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: $5,976 · $498/mo
• Projected year-2 tax: $8,337 · $695/mo
• Expected delta: +$2,361/yr (+$197/mo · 39.5%)

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

Climate risk First Street

• 🌊 Flood 3/10 Moderate FEMA zone X (unshaded) · 20% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥99°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 53% 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: $70,104
• − Mortgage interest: −$28,002
• − Property taxes: −$5,976
• − Insurance: −$2,500
• − Repairs & maintenance: −$5,608
• − Management: −$5,608
• − Depreciation: −$14,543
• Taxable income: $7,867
• Est. tax owed @ 24.0%: −$1,888
• After-tax cash flow: $13,560/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): 54,730
• Household income: $59,969
• Rent vs Own: 80.3% rent · 19.7% own
• Severe rent burden: 4999.0

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Highly diverse neighborhood (Simpson 0.73)
• Race & ethnicity: Black 34% White 32% Hispanic / Latino 21% Two or more races 8% Asian 7%
• Hispanic origin (detail): Mexican 4% Puerto Rican 10% Dominican 2%
• Common ancestry: Romanian 2% Lithuanian 1% Russian 1%
• Foreign-born: 17% · Canada, China, South Korea
• Languages at home: 74% English-only · Spanish 15% Chinese 3% Other Indo-European 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: ▼ -86.05%
• Current HPI: 328.1353
• Rent YoY: ▲ 2.60%
• 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

+335.1% since first listed

23 events — show timeline

• 2026-06-16 Pending — Smart MLS
• 2026-06-08 Relisted — Smart MLS
• 2026-06-02 Contingent — Smart MLS
• 2026-05-06 Listed $499,900 Smart MLS
• 2021-03-22 Listing Removed — Smart MLS
• 2021-02-23 Contingent — Smart MLS
• 2021-02-08 Listed $265,000 Smart MLS
• 2018-09-06 Sold (Public Records) $173,775 Public Records
• 2018-09-05 Sold (MLS) $173,775 Smart MLS
• 2018-07-29 Listing Removed — Smart MLS
• 2018-07-29 Relisted — Smart MLS
• 2018-07-04 Listing Removed — Smart MLS
• 2018-06-12 Relisted — Smart MLS
• 2018-05-31 Listing Removed — Smart MLS
• 2018-03-10 Pending — Smart MLS
• 2018-03-08 Price Changed $189,999 Smart MLS
• 2018-03-02 Price Changed $220,039 Smart MLS
• 2018-03-01 Listed $179,917 Smart MLS
• 2014-09-25 Sold (Public Records) $122,000 Public Records
• 2014-09-23 Sold (MLS) $122,000 Smart MLS
• 2014-08-14 Listed $129,900 Smart MLS
• 2011-11-08 Listing Removed — Smart MLS
• 2011-03-08 Listed $114,900 Smart MLS

Property tax history

+6.7%/yr

Latest (2023): $5,976 · -6.4% YoY. Source: county tax records.