530 Main St · Middletown, CT 06457

$1,500,000

1 bd · 1.0 ba · 11,033 sqft · MultiFamily · 17 Days on market

Built 1860 Good condition 3,920 sqft lot

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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
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Livability +4.0/5.0
• Condition / age +3.8/5.0
• Schools +3.0/10.0
• Rent growth +2.6/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 1 unit. estimate disagrees with records

5+ unit building — per-unit beds/baths from public records are typically unavailable; the breakdown below (if shown) is an estimate from the listing text.

Listing remarks

Prime Mixed-Use Investment Opportunity - Downtown Middletown, CT. This asset currently produces 9.7 cap annually, features a total of 16 units, including 4 retail storefronts and 12 on1-bedroom residential apartments. The retail spaces are currently occupied by established neighborhood businesses, including a grocery store, Boost Mobile, a barber shop, and a convenience store-providing steady foot traffic and consistent rental income. The residential component consists of twelve 1-bedroom units, offering strong demand in this vibrant downtown location. The asset include: mostly of windows recently replaced, hardwired smoke detectors throughout, fire sprinkler system installed, tenants cover

Key facts

• Street parking
• High visibility
• Retail storefronts

Tags

• RETAIL STOREFRONTS
• RECENTLY REPLACED WINDOWS
• HARDWIRED SMOKE DETECTORS
• FIRE SPRINKLER SYSTEM
• STREET PARKING
• HIGH VISIBILITY

Property features AI

Finance

• Other: Total living area approximately 11,033 (public record); Total rooms: 4; Total number of units: 16
• Financial info: Assessed value available

Exterior

• Utilities: Public water connected; Public sewer connected; Other type of hot water system
• Home design: Multi-family property (5+ units)
• Construction: Frame construction; Concrete foundation
• Exterior features: Vinyl siding; Level lot

Interior

• Bedrooms: 1 bedroom
• Bathrooms: 1 full bathroom
• Heating & cooling: Hot water heating; Heated by electric and natural gas
• Interior features: Full basement

What this means for you Summary

Snapshot

• This is a 1-bed/1.0-bath multifamily listed at $1.50M. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $9k ($112k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($25k rent vs $1.50M).
• Recommended offer: $1.48M (1.5% below list) — sets the bar for market timing.
• Cap rate 13.8% 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: Macdonough School (math 32% / reading 42%, grade F, #318 of 553 statewide, top 60%, 227 students, 66% FRL); Middletown High School (math 25% / reading 52%, grade F, #111 of 194 statewide, top 57%, 1,214 students, 49% FRL) — zoned schools average 58% FRL vs 38% district-wide (19 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: Rents flat; 143 active listings in the ZIP; 1 comparable units currently listed for rent nearby; solid renter incomes; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 in 5+ unit buildings).
• At $24,961/mo this rent would consume 377% 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 $10k of loan paydown is wiped out by about $45k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 0.2% rent growth), your $420k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 17 days — a 2% lower offer ($1.48M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 16y 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.

Risks & watch-outs

• Watch-outs: built in 1860 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $1,477,500 (1.5% below list)

Questions for the listing agent

1. Built in 1860 — 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. 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.
4. 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.
5. 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: 1.66% ✓
• Cap rate: 13.78%
• Cash-on-cash: 26.72%
• DSCR: 2.19
• GRM: 5.0

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 0.22% rent growth · sell at horizon

5-year hold

• IRR: 17.4%
• Equity multiple: 1.68×
• Total profit: $285,078
• Equity at exit: $223,655

10-year hold

• IRR: 23.8%
• Equity multiple: 2.79×
• Total profit: $753,151
• Equity at exit: $129,693

Cash invested: $420,000 (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 06457

• Rents YoY: 0.2%
• Active inventory: 143
• Price-to-rent: 79.6×

Monthly cashflow live

• Estimated rent: $24,961 high
• Mortgage (P&I): −$7,866
• Tax est. 1.5%: −$1,875 /mo · $22,500/yr
• Insurance: −$625
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,242
• Net cashflow: $9,353

Break-even live

Break-even rent $13,122

Max offer price $1,500,000

Occupancy floor 58%

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

Units	Beds	Baths	Est. rent
▸ 12× units	1	1	$18,852
▸ 4× units	0	0	$6,108
Total (16 units)			$24,961

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: $375,000
• Closing costs: $45,000
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
230 Main St Unit 2B Portland, CT	1.0	1.0	7748	$1,295	$0.17	23d	1	0.97mi

Listing history 10 events

1. 2026-04-29
   status Under Contract
2. 2026-04-11
   listed $1,500,000 Active
3. 2015-05-31
   historical
4. 2014-12-03
   listed $950,000
5. 2013-06-07
   historical
6. 2011-08-14
   listed $599,000
7. 2011-07-31
   historical
8. 2011-04-15
   listed $1,000,000
9. 2011-03-31
   historical
10. 2010-12-08
    listed $999,990

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $299,532
• − Mortgage interest: −$84,023
• − Property taxes: −$22,500
• − Insurance: −$7,500
• − Repairs & maintenance: −$23,963
• − Management: −$23,963
• − Depreciation: −$43,636
• Taxable income: $93,947
• Est. tax owed @ 24.0%: −$22,547
• After-tax cash flow: $89,689/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.

Condition & rehab AI · 12 photos

Good 75/100 Cosmetic rehab

This multi-family property in downtown Middletown, CT is in good condition with minimal repairs needed. It offers a good investment opportunity with steady rental income from retail and residential units.

Value-add opportunities

• Both Painting exterior and interior — Fresh paint enhances curb appeal and interior aesthetics
• Both Landscaping improvements — Enhances curb appeal and attracts potential tenants
• Both HVAC maintenance — Ensures comfort and energy efficiency
• Both Smoke detector replacement — Ensures safety and complies with regulations

Renovation cost estimate screening

Value-add ROI direction

• Both Painting exterior and interior — Fresh paint enhances curb appeal and interior aesthetics ↑
• Both Landscaping improvements — Enhances curb appeal and attracts potential tenants ↑
• Both HVAC maintenance — Ensures comfort and energy efficiency ↑
• Both Smoke detector replacement — Ensures safety and complies with regulations ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

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

+50.0% since first listed

10 events — show timeline

• 2026-04-29 Pending — Smart MLS
• 2026-04-11 Listed $1,500,000 Smart MLS
• 2015-05-31 Listing Removed — Smart MLS
• 2014-12-03 Listed $950,000 Smart MLS
• 2013-06-07 Listing Removed — Smart MLS
• 2011-08-14 Listed $599,000 Smart MLS
• 2011-07-31 Listing Removed — Smart MLS
• 2011-04-15 Listed $1,000,000 Smart MLS
• 2011-03-31 Listing Removed — Smart MLS
• 2010-12-08 Listed $999,990 Smart MLS