308 Highland Ave · Waterbury, CT 06708

$335,000

3 bd · 2.0 ba · 2,254 sqft · MultiFamily public records · 10 Days on market

Built 1920 5,662 sqft lot Est $370k · 9% under

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Why this score? — see what drove the D+ 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 +15.2/30.0
• ARV discount +11.7/15.0
• 1% rule +4.9/10.0
• Rent growth +4.9/5.0
• DSCR +4.7/10.0
• Livability +4.0/5.0
• 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: 2 units. confirmed

Listing remarks

Opportunity presents itself in this attractive & well-situated 2 family home conveniently located near downtown, Rt 8, I84, bus lines & more! The 1st floor is the larger unit (long-term tenant occupied) consists of 2 Bedrooms, Living Room, Kitchen, Full Bath & possible Dining room (although the layout offers opportunity for other options, if needed & a stunning covered front porch. 2nd Floor (Owner occupied) is on "record" as 1 Bedroom BUT is being used as & definitely offers 2 Bedroom options (see Floorplan), Living Room, Kitchen & Full Bath, although again the layout offers various layout opportunities to reconfigure. The property also include

Key facts

• Covered front porch
• Natural gas option
• 5,662 sq ft lot

Tags

• COVERED FRONT PORCH
• OFF-STREET PARKING AREA
• NATURAL GAS OPTION
• SUMP PUMPS IN BASEMENT
• PLENTY OF ROOM FOR STORAGE
• PLENTY OF LAUNDRY SPACE

What this means for you Summary

Snapshot

• This is a 2 × 2-bed/1.0-bath units multifamily listed at $335k.

Deal economics

• At list price, monthly cash flow is $117 ($1k/yr) — positive. Per door: $59/mo.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $332k (0.8% below list).
• Recommended offer: $332k (0.8% below list) — sets the bar for 1% rule.
• Cap rate 6.7% vs local median 3.5% in Waterbury — 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 (#32 in CT, #2,205 nationally) — a middle-class / working-renter tenant base. Strengths: commute A+, cost of living A+, housing A+; Watch: crime D, employment D.
• Waterbury School District (suburban): math 12% / reading 23% proficiency, ranked #148 of 153 in CT (top 97%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 73% free/reduced lunch — lower-income household profile, screen leases tightly.
• Zoned schools: Driggs School (math 8% / reading 12%, grade F, #512 of 553 statewide, top 94%, 462 students, 78% FRL); West Side Middle School (math 8% / reading 23%, grade F, #165 of 175 statewide, top 94%, 817 students, 81% FRL); John F. Kennedy High School (math 17% / reading 37%, grade F, #147 of 194 statewide, top 78%, 1,297 students, 79% FRL).
• Market conditions: Rents rising fast (+9.8%/yr); 121 active listings in the ZIP; 22 comparable units currently listed for rent nearby; rentals at typical pace (median 26d on market — plan ~3-4 weeks tenant-placement turnaround); 41% of comp listings sitting > 30 days — soft ceiling on asking rent; 502 units permitted in Naugatuck Valley Planning Region in 2024 (171 in 5+ unit buildings).
• At $3,322/mo this rent would consume 59% of the median local household income ($67k/yr) (locally 1276% 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 $2k of loan paydown is wiped out by about $10k of value loss. Plan a longer hold.

Negotiation context

• Only 10 days on market — expect competitive offers; lowballing is unlikely to land.
• Current owner paid $142k; list at $335k implies a 135% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1920 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $332,200 (0.8% below list)

Questions for the listing agent

1. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
2. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
3. Built in 1920 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. Crime grade is D 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?
7. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
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: 0.99% ✗
• Cap rate: 6.71%
• Cash-on-cash: 1.50%
• DSCR: 1.07
• GRM: 8.4

CMA / ARV

• ARV (on-the-fly): $369,656
• Comps found: 1

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
332 Robbins St	0.44mi	4/2.0 (+1)	2,320 (+3%)	5mo	$380,000	$164	65

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 · 8.0% rent growth · sell at horizon

5-year hold

• IRR: -8.0%
• Equity multiple: 0.69×
• Total profit: $-29,091
• Equity at exit: $49,950

10-year hold

• IRR: 7.4%
• Equity multiple: 1.69×
• Total profit: $64,873
• Equity at exit: $28,965

Cash invested: $93,800 (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 06708

• Rents YoY: 9.8%
• Active inventory: 121
• Price-to-rent: 16.8×

Monthly cashflow live

• Estimated rent: $3,322 high
• Mortgage (P&I): −$1,757
• Tax from tax record: −$611 /mo · $7,329/yr
• Insurance: −$140
• HOA: −$0
• Vacancy / Maint / Mgmt: −$698
• Net cashflow: $117

Break-even live

Break-even rent $3,174

Max offer price $335,000

Occupancy floor 91%

Sensitivity live

Price	-10% $307	-5% $212	+0% $117	+5% $22	+10% $-72
Rent	-10% $-145	-5% $-14	+0% $117	+5% $248	+10% $380
Rate	-1.0pp $286	-0.5pp $202	base $117	+0.5pp $30	+1.0pp $-58

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

Units	Beds	Baths	Est. rent
▸ 2× units	2	1	$3,322
Total (2 units)			$3,322

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: $83,750
• Closing costs: $10,050
• Reserves months: —
• Total cash needed: —

Rent comps 22 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
95 Sunnyside Ave Waterbury, CT	2.0	1.0	3044	$1,500	$0.49	25d	1	0.26mi
41 Lawlor St Waterbury, CT	3.0	1.0	1750	$2,000	$1.14	16d	1	0.35mi
155 Congress Ave Unit 2 Waterbury, CT	3.0	1.0	3228	$1,750	$0.54	25d	1	0.64mi
324 Congress Ave Unit 2 Waterbury, CT	3.0	1.0	2760	$2,000	$0.72	45d	1	0.73mi
27 Waterville St Unit 3 Waterbury, CT	3.0	1.0	3195	$1,500	$0.47	5d	1	0.93mi
69 W Liberty St Waterbury, CT	3.0	1.0	2822	$1,800	$0.64	45d	1	0.93mi
69 W Liberty St Unit 2 Waterbury, CT	3.0	1.0	2822	$1,750	$0.62	45d	1	0.93mi
69 W Liberty St Unit 3 Waterbury, CT	2.0	1.0	2822	$1,500	$0.53	25d	1	0.93mi
218 Charles St Waterbury, CT	4.0	1.5	2600	$2,800	$1.08	45d	1	1.03mi
146 Chestnut Ave Unit 1st Floor Waterbury, CT	2.0	1.0	1659	$1,400	$0.84	5d	1	1.12mi
15 Ridgewood St Unit 2 Waterbury, CT	3.0	1.0	3229	$1,600	$0.50	46d	1	1.15mi
15 Ridgewood St Unit 2 Waterbury, CT	3.0	1.0	3229	$1,600	$0.50	25d	1	1.15mi
49 Hillside Ave Unit 2 Waterbury, CT	3.0	2.0	1600	$1,500	$0.94	13d	1	1.18mi
184 Buckingham St #2 Waterbury, CT	3.0	1.0	1600	$1,950	$1.22	25d	1	1.18mi
16 Arch St Unit 3 Waterbury, CT	3.0	1.0	3282	$2,200	$0.67	23d	1	1.22mi
73 Lounsbury St Unit 3 Waterbury, CT	3.0	1.0	3096	$1,600	$0.52	45d	1	1.28mi
73 Lounsbury St Unit 3 Waterbury, CT	3.0	1.0	3096	$1,600	$0.52	21d	1	1.28mi
124 Southview St Unit 1 Waterbury, CT	3.0	1.0	2980	$1,600	$0.54	45d	1	1.32mi
113 Southview St Waterbury, CT	2.0	1.0	1860	$1,250	$0.67	25d	1	1.33mi
260 Pine St Unit 3 Waterbury, CT	3.0	1.0	3361	$1,550	$0.46	45d	1	1.39mi
13 Woodcrest Dr Waterbury, CT	3.0	2.0	1628	$2,500	$1.54	5d	1	1.43mi
97 Clowes Ter Unit RT side Waterbury, CT	4.0	2.0	1649	$2,350	$1.43	45d	1	1.47mi

Listing history 4 events

1. 2026-04-03
   status Under Contract
2. 2026-03-24
   listed $335,000 Active
3. 2003-05-23
   soldstatus $142,500
4. 1993-07-14
   soldstatus $120,000

ⓘ 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: $7,329 · $611/mo
• Projected year-2 tax: $7,329 · $611/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 5/10 Major 7 d/yr ≥96°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $39,864
• − Mortgage interest: −$18,765
• − Property taxes: −$7,329
• − Insurance: −$1,675
• − Repairs & maintenance: −$3,189
• − Management: −$3,189
• − Depreciation: −$9,745
• Taxable loss: −$4,029
• Est. tax savings @ 24.0%: +$967
• After-tax cash flow: $2,374/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: Waterbury School District
• NCES district ID: 0904830
• Math proficiency: 12% ▼ -7.00%
• Reading proficiency: 23% ▼ -8.00%
• Median HH income: $40,040
• Composite: 14.85/100
• National rank: #9380
• State rank: #148 of 153 in CT

Livability — Waterbury

• Score: 79/100
• State rank: #32
• US rank: #2205

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Waterbury, CT
• County: New Haven County · 688,236 people
• City population: 115,012
• Metro: New Haven-Milford, CT
• Population (ZIP): 29,594
• Household income: $67,364
• Rent vs Own: 40.7% rent · 59.3% own
• Severe rent burden: 1276.0

Population outlook (Naugatuck Valley County) Hauer SSP2

• By 2040: 496,846

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.68)
• Race & ethnicity: White 43% Hispanic / Latino 33% Black 17% Two or more races 13% Asian 2%
• Hispanic origin (detail): Puerto Rican 17% Dominican 8%
• Common ancestry: Romanian 2% Russian 2% Estonian 2%
• Foreign-born: 20% · Canada, Jamaica, China
• Languages at home: 64% English-only · Spanish 23% Other Indo-European 8% French/Haitian/Cajun 1%

Political lean MEDSL · Naugatuck Valley

• 2024 margin: Lean R (+7.4) · D 45.6% · R 53.0% · Other 1.4%
• All cycles: 2024: R+7.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -297.81%
• Current HPI: 281.1446
• Rent YoY: ▲ 9.75%
• 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

+179.2% since first listed

4 events — show timeline

• 2026-04-03 Pending — Smart MLS
• 2026-03-24 Listed $335,000 Smart MLS
• 2003-05-23 Sold (Public Records) $142,500 Public Records
• 1993-07-14 Sold (Public Records) $120,000 Public Records

Property tax history

+5.2%/yr

Latest (2023): $7,329 · +67.9% YoY. Source: county tax records.