37-39 Hotchkiss St · Middletown, CT 06457

$339,900

4 bd · 2.0 ba · 1,616 sqft · MultiFamily public records · 49 Days on market

Built 1900 4,791 sqft lot $210/sqft · 8% below area Est $370k · 8% 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 +20.5/30.0
• ARV discount +11.1/15.0
• DSCR +6.5/10.0
• 1% rule +5.2/10.0
• Livability +4.0/5.0
• Schools +3.0/10.0
• Rent growth +2.6/5.0
• Condition / age +2.5/5.0
• 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

Updated two-family in a fantastic Middletown location just minutes from Wesleyan University, downtown shopping, and Route 9 - great for an owner-occupant or investor, with one unit delivered open at the end of the month and ready for immediate occupancy. Recent improvements have all the major boxes checked: brand new roof, brand new water heaters, plus updated kitchens, updated baths, and newer flooring throughout - all completed within the last five years. Everything is properly split for hassle-free two-family living: separate natural gas heat with two boilers, two electric panels, and two gas meters - no shared utilities, clean books, easy management. The first-floor unit features in-uni

Key facts

• Covered front porch
• Updated baths
• Level yard

Tags

• UPDATED KITCHENS
• UPDATED BATHS
• IN-UNIT LAUNDRY
• COVERED FRONT PORCH
• PRIVATE OFF-STREET DRIVEWAY
• LEVEL YARD

Property features AI

Exterior

• Parking: Off-street parking; 4 total parking spaces
• Utilities: Public water connected; Public sewer connected
• Home design: Multi-family property; 2-family; Living area ~1616 (public record)
• Construction: Frame construction; Stone foundation; Asphalt shingle roof
• Exterior features: Level lot; Vinyl siding

Interior

• Bedrooms: 4 bedrooms
• Bathrooms: 2 full bathrooms
• Heating & cooling: Hot water heating; Natural gas fuel; 40-gallon hot water tank
• Interior features: 8 total rooms; Full basement; Attic with pull-down stairs

What this means for you Summary

Snapshot

• This is a 2 × 2-bed/1.0-bath units multifamily listed at $340k.

Deal economics

• At list price, monthly cash flow is $448 ($5k/yr) — positive. Per door: $224/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $340k).
• Recommended offer: $330k (3.0% below list) — sets the bar for market timing.
• Cap rate 7.9% vs local median 3.7% in Middletown — 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 81/100 on livability (#17 in CT, #1,390 nationally) — a professional / high-income tenant draw. Strengths: crime A+, amenities A+, health & safety A+; Watch: commute F.
• Middletown School District (urban): math 24% / reading 44% proficiency, ranked #113 of 153 in CT (top 74%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Farm Hill School (math 27% / reading 37%, grade F, #361 of 553 statewide, top 68%, 277 students, 56% FRL); Beman Middle School (math 19% / reading 44%, grade F, #134 of 175 statewide, top 77%, 968 students, 49% FRL); Middletown High School (math 25% / reading 52%, grade F, #111 of 194 statewide, top 57%, 1,214 students, 49% FRL).
• Market conditions: Rents flat; 150 active listings in the ZIP; 17 comparable units currently listed for rent nearby; rentals leasing fast (median 13d on market — plan ~1-2 weeks tenant-placement turnaround); solid renter incomes; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 in 5+ unit buildings).
• At $3,458/mo this rent would consume 52% of the median local household income ($79k/yr) (locally 2196% 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

• It's been on market 49 days — a 3% lower offer ($330k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% 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 $329,703 (3.0% below list)

Questions for the listing agent

1. It's been on market 49 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. 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.
7. 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.
8. 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: 1.02% ✓
• Cap rate: 7.87%
• Cash-on-cash: 5.65%
• DSCR: 1.25
• GRM: 8.2

CMA / ARV

• ARV (median comp): $369,789
• List price: $339,900
• Delta: -8.08%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
102 Main St Ext	0.41mi	4/2.0	1,518 (-6%)	6mo	$405,000	$267	65
9 Maple Pl	0.58mi	4/2.0	1,516 (-6%)	18mo	$174,000	$115	48
108 Main ST EXT	0.42mi	5/2.0 (+1)	1,780 (+10%)	22mo	$285,000	$160	40
87 Woodward Ave	0.68mi	3/2.0 (-1)	1,712 (+6%)	18mo	$280,000	$164	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 · 0.22% rent growth · sell at horizon

5-year hold

• IRR: -10.7%
• Equity multiple: 0.62×
• Total profit: $-35,962
• Equity at exit: $50,680

10-year hold

• IRR: -5.7%
• Equity multiple: 0.67×
• Total profit: $-31,075
• Equity at exit: $29,388

Cash invested: $95,172 (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 06457

• Rents YoY: 0.2%
• Active inventory: 150
• Price-to-rent: 16.4×

Monthly cashflow live

• Estimated rent: $3,458 high
• Mortgage (P&I): −$1,782
• Tax from tax record: −$360 /mo · $4,320/yr
• Insurance: −$142
• HOA: −$0
• Vacancy / Maint / Mgmt: −$726
• Net cashflow: $448

Break-even live

Break-even rent $2,891

Max offer price $339,900

Occupancy floor 82%

Sensitivity live

Price	-10% $640	-5% $544	+0% $448	+5% $352	+10% $255
Rent	-10% $175	-5% $311	+0% $448	+5% $584	+10% $721
Rate	-1.0pp $619	-0.5pp $534	base $448	+0.5pp $360	+1.0pp $270

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

Units	Beds	Baths	Est. rent
▸ 2× units	2	1	$3,458
Total (2 units)			$3,458

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: $84,975
• Closing costs: $10,197
• Reserves months: —
• Total cash needed: —

Rent comps 17 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
11 Huber Ave Middletown, CT	3.0	1.0	1102	$2,300	$2.09	26d	1	0.19mi
27 Woodside Cir Unit 37 Middletown, CT	3.0	2.0	1600	$2,300	$1.44	46d	1	0.45mi
505 Main St Middletown, CT	3.0	2.0	1263	$2,000	$1.58	0d	1	0.61mi
207 E Main St Middletown, CT	4.0	1.0	1207	$2,200	$1.82	6d	1	0.61mi
57 Ferry St Unit 1 Middletown, CT	3.0	1.5	1500	$2,000	$1.33	13d	1	0.68mi
582 Main St Middletown, CT	3.0	1.0	1200	$2,000	$1.67	0d	1	0.70mi
39 Grand St Unit 3 Middletown, CT	3.0	1.0	1076	$2,000	$1.86	0d	1	0.72mi
3 Clinton Ave Unit 3 CLINTON Middletown, CT	3.0	1.0	1200	$1,450	$1.21	24d	1	0.73mi
32 Wall St Unit 2 Middletown, CT	3.0	1.0	2081	$2,400	$1.15	46d	1	0.76mi
103 Spring St Middletown, CT	4.0	1.0	1602	$2,500	$1.56	46d	1	0.90mi
177 Russell St Unit 2 Middletown, CT	3.0	3.0	2000	$2,200	$1.10	26d	1	0.90mi
580 High St Middletown, CT	3.0	1.0	1466	$1,900	$1.30	0d	1	1.00mi
73 Silver St Middletown, CT	4.0	2.0	1322	$2,500	$1.89	26d	1	1.02mi
184 Rose Cir Middletown, CT	1.0–3.0	1.0–1.5	1220	$2,000	$1.64	0d	6	1.16mi
200 Main St Unit 1 Portland, CT	3.0	2.0	1300	$2,227	$1.71	13d	1	1.44mi
200 Main St Unit 1 Portland, CT	3.0	2.0	1300	$2,227	$1.71	4d	1	1.44mi
200 Main St Unit 1 Portland, CT	3.0	2.0	1300	$2,227	$1.71	0d	1	1.44mi

Listing history 17 events

1. 2026-06-22
   days on market $339,900 Active 49 DOM
2. 2026-06-21
   days on market $339,900 Active 48 DOM
3. 2026-06-18
   days on market $339,900 Active 45 DOM
4. 2026-06-17
   days on market $339,900 Active 44 DOM
5. 2026-06-16
   days on market $339,900 Active 43 DOM
6. 2026-06-15
   days on market $339,900 Active 42 DOM
7. 2026-06-13
   days on market $339,900 Active 40 DOM
8. 2026-06-13
   days on market $339,900 Active 39 DOM
9. 2026-06-10
   days on market $339,900 Active 37 DOM
10. 2026-06-09
    days on market $339,900 Active 36 DOM
11. 2026-06-08
    days on market $339,900 Active 35 DOM
12. 2026-06-07
    days on market $339,900 Active 34 DOM
13. 2026-06-03
    days on market $339,900 Active 30 DOM
14. 2026-06-02
    days on market $339,900 Active 29 DOM
15. 2026-06-01
    days on market $339,900 Active 28 DOM
16. 2026-05-31
    days on market $339,900 Active 27 DOM
17. 2026-05-04
    listed $339,900 Active 1359-char remark

ⓘ 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: $4,320 · $360/mo
• Projected year-2 tax: $5,797 · $483/mo
• Expected delta: +$1,477/yr (+$123/mo · 34.2%)

ⓘ 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 6/10 Major 7 d/yr ≥99°F today · 16 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 · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $41,496
• − Mortgage interest: −$19,040
• − Property taxes: −$4,320
• − Insurance: −$1,700
• − Repairs & maintenance: −$3,320
• − Management: −$3,320
• − Depreciation: −$9,888
• Taxable loss: −$91
• Est. tax savings @ 24.0%: +$22
• After-tax cash flow: $5,394/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: Middletown School District
• NCES district ID: 0902490
• Math proficiency: 24% ▼ -15.00%
• Reading proficiency: 44% ▼ -8.00%
• Median HH income: $60,733
• Composite: 30.47/100
• National rank: #6224
• State rank: #113 of 153 in CT

Livability — Middletown

• Score: 81/100
• State rank: #17
• US rank: #1390

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Middletown, CT
• County: Middlesex County · 63,941 people
• City population: 46,720
• Metro: Hartford-East Hartford-Middletown, CT
• Population (ZIP): 46,720
• Household income: $79,463
• Rent vs Own: 47.1% rent · 52.9% own
• Severe rent burden: 2196.0

Population outlook (Lower Connecticut River Valley County) Hauer SSP2

• By 2040: 188,651

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Majority White (65%)
• Race & ethnicity: White 65% Black 13% Hispanic / Latino 12% Two or more races 9% Asian 5%
• Hispanic origin (detail): Mexican 1% Puerto Rican 7%
• Common ancestry: Romanian 9% Lithuanian 5% Slovak 2%
• Foreign-born: 12% · Canada, China
• Languages at home: 82% English-only · Spanish 6% Other Indo-European 4% Russian/Polish/Slavic 2%

Political lean MEDSL · Lower Connecticut River Valley

• 2024 margin: D (+13.4) · D 55.9% · R 42.4% · Other 1.7%
• All cycles: 2024: D+13.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -470.20%
• Current HPI: 255.1597
• Rent YoY: ▲ 0.22%
• Metro: Hartford-East Hartford-Middletown, 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

1 event — show timeline

• 2026-05-04 Listed $339,900 Smart MLS

Property tax history

+0.7%/yr

Latest (2022): $4,320 · +0.0% YoY. Source: county tax records.