14 Gilbert Ave · New Haven, CT 06511

$375,000

4 bd · 2.0 ba · 2,370 sqft · MultiFamily public records · 13 Days on market

Built 1880 5,227 sqft lot $158/sqft · 8% below area Est $409k · 8% 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 +11.3/15.0
• DSCR +10.0/10.0
• 1% rule +9.9/10.0
• Livability +4.0/5.0
• Rent growth +3.2/5.0
• Condition / age +2.5/5.0
• Schools +1.5/10.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 1 unit. estimate disagrees with records

Listing remarks MLS

Tucked into a well-connected pocket of New Haven, 14 Gilbert Ave offers a rare blend of flexibility, stability, and opportunity. Just moments from Yale New Haven Hospital, local bus lines, downtown, and commuter access, this property places daily convenience right outside your door. Configured as a true multi-level living setup, the home functions as three distinct spaces. The first floor features a spacious 3-bedroom apartment, while the second floor offers a comfortable 2-bedroom unit, both occupied by long-term tenants who take pride in where they live. Above, the third floor lives like a private owner's suite with its own entrance, 2 bedrooms, bath, and a cozy kitchenette and living area, ideal for an owner occupant or added income potential. Natural gas heat, separate electric meters, multiple hot water heaters, and city utilities support the home's efficiency. A freshly painted exterior, front porch, and partially fenced backyard round out the setting. Lead has been professionally remediated with documentation available. Whether you're looking to offset your mortgage or expand your portfolio, this is a property that adapts to your goals.

Key facts

• 5,227 sq ft lot
• Built 1880
• Listed 13 days

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath multifamily listed at $375k.

Deal economics

• At list price, monthly cash flow is $2k ($22k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $375k).
• Cap rate 12.1% 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; 40 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); 40% 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 $5,591/mo this rent would consume 112% 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 $11k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 2.6% rent growth), your $105k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• Only 13 days on market — expect competitive offers; lowballing is unlikely to land.
• 2 sale attempts since 4y 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 $20k; list at $375k implies a 1823% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1880 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 55% 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 $375,000

Questions for the listing agent

1. Built in 1880 — 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 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?
4. 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?
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 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: 1.49% ✓
• Cap rate: 12.10%
• Cash-on-cash: 20.76%
• DSCR: 1.92
• GRM: 5.6

CMA / ARV

• ARV (median comp): $409,394
• List price: $375,000
• Delta: -8.40%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 11 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
87 Orchard St	0.27mi	4/2.0	2,088 (-12%)	3mo	$362,500	$174	65
97 Scranton St	0.11mi	5/3.0 (+1)	2,169 (-8%)	9mo	$215,000	$99	64
800 George St	0.45mi	5/3.0 (+1)	2,282 (-4%)	4mo	$320,000	$140	60
706 George St	0.26mi	5/3.0 (+1)	2,318 (-2%)	23mo	$520,000	$224	56
38 Auburn St	0.28mi	5/3.0 (+1)	2,547 (+8%)	12mo	$470,000	$185	56
203 West St	0.56mi	4/3.0	2,288 (-4%)	11mo	$435,000	$190	55
56 Vernon St	0.30mi	4/2.0	2,160 (-9%)	21mo	$410,000	$190	54
55 Irving St	0.58mi	4/3.0	2,148 (-9%)	3mo	$407,000	$189	51
55 Carmel St	0.73mi	5/2.0 (+1)	2,116 (-11%)	1mo	$280,000	$132	42
56 Ann St	0.56mi	5/3.0 (+1)	2,067 (-13%)	6mo	$407,000	$197	38
866 Congress Ave	0.68mi	5/3.0 (+1)	2,341 (-1%)	23mo	$255,000	$109	38

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: 12.7%
• Equity multiple: 1.50×
• Total profit: $52,761
• Equity at exit: $55,914

10-year hold

• IRR: 21.3%
• Equity multiple: 2.77×
• Total profit: $186,141
• Equity at exit: $32,423

Cash invested: $105,000 (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 06511

• Home prices YoY: -20.8%
• Rents YoY: 2.6%
• Active inventory: 137
• Price-to-rent: 15.5×

Monthly cashflow live

• Estimated rent: $5,591 high
• Mortgage (P&I): −$1,967
• Tax from tax record: −$478 /mo · $5,734/yr
• Insurance: −$156
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,174
• Net cashflow: $1,816

Break-even live

Break-even rent $3,292

Max offer price $375,000

Occupancy floor 63%

Sensitivity live

Price	-10% $2,029	-5% $1,922	+0% $1,816	+5% $1,710	+10% $1,604
Rent	-10% $1,375	-5% $1,595	+0% $1,816	+5% $2,037	+10% $2,258
Rate	-1.0pp $2,005	-0.5pp $1,912	base $1,816	+0.5pp $1,719	+1.0pp $1,620

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

Units	Beds	Baths	Est. rent
1× unit	3	1.5	$2,010
▸ 2× units	2	1	$3,580
Total (3 units)			$5,591

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: $93,750
• Closing costs: $11,250
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
408 Legion Ave Unit 2 New Haven, CT	3.0	1.0	1610	$2,000	$1.24	44d	1	0.23mi
120 Dwight St New Haven, CT	3.0	2.0	1750	$3,175	$1.81	22d	2	0.24mi
1494 Chapel St Unit 1R New Haven, CT	3.0	1.0	1800	$2,000	$1.11	4d	1	0.30mi
41 Howe St New Haven, CT	4.0	2.0	1795	$3,750	$2.09	44d	1	0.31mi
41 Howe St Apt 2 New Haven, CT	3.0	1.0	1795	$3,200	$1.78	44d	1	0.31mi
41 Howe St Apt 2 New Haven, CT	3.0	1.0	1795	$3,200	$1.78	24d	1	0.31mi
66 Kensington St Unit 2 New Haven, CT	3.0	2.0	1800	$2,100	$1.17	24d	1	0.32mi
43 Howe St New Haven, CT	4.0	2.0	1995	$4,995	$2.50	15d	1	0.32mi
83 Norton St Unit 2 New Haven, CT	3.0	1.0	2869	$1,695	$0.59	15d	1	0.47mi
365 Winthrop Ave Unit 1 New Haven, CT	3.0	1.0	1600	$2,295	$1.43	4d	1	0.49mi
52 Goffe St New Haven, CT	3.0	2.0	1935	$2,600	$1.34	24d	1	0.59mi
117 Maple St New Haven, CT	3.0	1.5	2421	$3,995	$1.65	4d	1	0.62mi
591 Orchard St Unit 1 New Haven, CT	4.0	2.0	1696	$2,900	$1.71	4d	1	0.66mi
347 Sherman Ave New Haven, CT	5.0	3.0	3153	$2,300	$0.73	44d	1	0.70mi
119 Carmel St Unit 3 New Haven, CT	3.0	1.0	3282	$1,900	$0.58	44d	1	0.85mi
69 Adeline St Unit D New Haven, CT	3.0	1.5	2600	$2,250	$0.87	24d	1	0.87mi
355 Norton St Unit 1 New Haven, CT	5.0	2.5	2500	$3,300	$1.32	22d	1	0.88mi
28 Townsend St New Haven, CT	4.0	2.5	1580	$3,400	$2.15	44d	1	0.89mi
1519 Ella T Grasso Blvd Unit N/A New Haven, CT	5.0	2.0	2750	$4,450	$1.62	24d	1	0.94mi
50 Admiral St New Haven, CT	5.0	2.0	2157	$2,700	$1.25	19d	1	0.96mi
5 Oak Pl West Haven, CT	3.0	1.0	2300	$1,900	$0.83	3d	1	0.98mi
55 Admiral St Unit 2 New Haven, CT	5.0	3.0	2000	$3,295	$1.65	24d	1	0.98mi
49 Hubinger St New Haven, CT	4.0	1.5	2000	$2,950	$1.48	3d	1	0.99mi
1551 Ella T Grasso Blvd Unit 1 New Haven, CT	4.0	1.0	1700	$2,295	$1.35	15d	1	0.99mi
82 Gilbert St West Haven, CT	3.0	1.0	2641	$2,400	$0.91	44d	1	1.00mi
1563 Ella T Grasso Blvd Unit 2 New Haven, CT	4.0	1.0	1638	$2,500	$1.53	24d	1	1.02mi
1565 Ella T Grasso Blvd Unit 1563 2 New Haven, CT	4.0	1.0	1638	$2,500	$1.53	44d	1	1.02mi
56 Mansfield St Unit 1 New Haven, CT	3.0	1.0	2759	$2,800	$1.01	44d	1	1.02mi
432 Norton Pkwy New Haven, CT	5.0	3.0	2493	$4,195	$1.68	44d	1	1.04mi
134 Mansfield St New Haven, CT	5.0	2.0	1960	$5,500	$2.81	24d	1	1.11mi
1634 Ella T Grasso Blvd New Haven, CT	4.0	1.5	2018	$3,600	$1.78	44d	1	1.15mi
54 Trumbull St Unit 54-1 New Haven, CT	5.0	2.5	2250	$6,695	$2.98	15d	1	1.15mi
367 Orange St New Haven, CT	3.0	1.0–2.0	1075	$4,973	$4.63	3d	43	1.17mi
395 Orange St Unit 2 New Haven, CT	4.0	1.5	1650	$3,000	$1.82	44d	1	1.19mi
399 Orange St New Haven, CT	4.0	1.5	1650	$3,200	$1.94	12d	1	1.20mi
36 Cassius St New Haven, CT	4.0	1.5	1872	$2,300	$1.23	44d	1	1.22mi
34 Cassius St Unit 36 New Haven, CT	5.0	2.0	1872	$2,300	$1.23	44d	1	1.22mi
239 Bradley St Unit 1 New Haven, CT	3.0	1.0	1982	$3,650	$1.84	44d	1	1.23mi
30 Trumbull St New Haven, CT	5.0	4.0	2668	$5,000	$1.87	4d	1	1.23mi
804 Edgewood Ave Unit 2 New Haven, CT	3.0	1.0	1613	$2,800	$1.74	44d	1	1.31mi

Listing history 7 events

1. 2026-05-07
   status Under Contract 1164-char remark

   Show marketing remark (1164 chars)

   Tucked into a well-connected pocket of New Haven, 14 Gilbert Ave offers a rare blend of flexibility, stability, and opportunity. Just moments from Yale New Haven Hospital, local bus lines, downtown, and commuter access, this property places daily convenience right outside your door. Configured as a true multi-level living setup, the home functions as three distinct spaces. The first floor features a spacious 3-bedroom apartment, while the second floor offers a comfortable 2-bedroom unit, both occupied by long-term tenants who take pride in where they live. Above, the third floor lives like a private owner's suite with its own entrance, 2 bedrooms, bath, and a cozy kitchenette and living area, ideal for an owner occupant or added income potential. Natural gas heat, separate electric meters, multiple hot water heaters, and city utilities support the home's efficiency. A freshly painted exterior, front porch, and partially fenced backyard round out the setting. Lead has been professionally remediated with documentation available. Whether you're looking to offset your mortgage or expand your portfolio, this is a property that adapts to your goals.

2. 2026-04-25
   listed $375,000 Active 1164-char remark

   Show marketing remark (1164 chars)

   Tucked into a well-connected pocket of New Haven, 14 Gilbert Ave offers a rare blend of flexibility, stability, and opportunity. Just moments from Yale New Haven Hospital, local bus lines, downtown, and commuter access, this property places daily convenience right outside your door. Configured as a true multi-level living setup, the home functions as three distinct spaces. The first floor features a spacious 3-bedroom apartment, while the second floor offers a comfortable 2-bedroom unit, both occupied by long-term tenants who take pride in where they live. Above, the third floor lives like a private owner's suite with its own entrance, 2 bedrooms, bath, and a cozy kitchenette and living area, ideal for an owner occupant or added income potential. Natural gas heat, separate electric meters, multiple hot water heaters, and city utilities support the home's efficiency. A freshly painted exterior, front porch, and partially fenced backyard round out the setting. Lead has been professionally remediated with documentation available. Whether you're looking to offset your mortgage or expand your portfolio, this is a property that adapts to your goals.

3. 2026-04-16
   historical $375,000 1164-char remark

   Show marketing remark (1164 chars)

   Tucked into a well-connected pocket of New Haven, 14 Gilbert Ave offers a rare blend of flexibility, stability, and opportunity. Just moments from Yale New Haven Hospital, local bus lines, downtown, and commuter access, this property places daily convenience right outside your door. Configured as a true multi-level living setup, the home functions as three distinct spaces. The first floor features a spacious 3-bedroom apartment, while the second floor offers a comfortable 2-bedroom unit, both occupied by long-term tenants who take pride in where they live. Above, the third floor lives like a private owner's suite with its own entrance, 2 bedrooms, bath, and a cozy kitchenette and living area, ideal for an owner occupant or added income potential. Natural gas heat, separate electric meters, multiple hot water heaters, and city utilities support the home's efficiency. A freshly painted exterior, front porch, and partially fenced backyard round out the setting. Lead has been professionally remediated with documentation available. Whether you're looking to offset your mortgage or expand your portfolio, this is a property that adapts to your goals.

4. 2022-09-15
   historical
5. 2022-07-07
   price $310,000
6. 2022-06-05
   listed $314,900 Active
7. 1998-12-04
   soldstatus $19,500

ⓘ 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: $5,734 · $478/mo
• Projected year-2 tax: $6,880 · $573/mo
• Expected delta: +$1,146/yr (+$95/mo · 20.0%)

ⓘ 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 · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 55% 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: $67,092
• − Mortgage interest: −$21,006
• − Property taxes: −$5,734
• − Insurance: −$1,875
• − Repairs & maintenance: −$5,367
• − Management: −$5,367
• − Depreciation: −$10,909
• Taxable income: $16,833
• Est. tax owed @ 24.0%: −$4,040
• After-tax cash flow: $17,755/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

+1823.1% since first listed

7 events — show timeline

• 2026-05-07 Pending — Smart MLS
• 2026-04-25 Listed $375,000 Smart MLS
• 2026-04-16 Coming Soon $375,000 Smart MLS
• 2022-09-15 Listing Removed — Smart MLS
• 2022-07-07 Price Changed $310,000 Smart MLS
• 2022-06-05 Listed $314,900 Smart MLS
• 1998-12-04 Sold (Public Records) $19,500 Public Records

Property tax history

+6.9%/yr

Latest (2023): $5,734 · -6.4% YoY. Source: county tax records.