259 Pearl St · Middletown, CT 06457

$395,000

9 bd · 3.0 ba · 3,906 sqft · MultiFamily public records · 8 Days on market

Built 1917 4,356 sqft lot Est $449k · 12% 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 +12.9/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• 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: 3 units. confirmed

Listing remarks MLS

Great investment opportunity! Clean and well maintained 3 unit multi-family. All three units have very similar floor plans and all have been updated. Each unit includes 3 bedrooms, spacious eat-in kitchen with panty and large living room. Two units are currently rented. The second floor is vacant . Perfect for an owner occupant. New (as of 2017), Navien on-demand gas furnace, updated electrical/breakers, updated plumbing and much more. Basement is clean and dry. Five off street parking spots. Near to state parks, restaurants, museums, shopping, medical facilities, plus much more.

Key facts

• 4,356 sq ft lot
• 5 parking spots
• Built 1917

Property features AI

Exterior

• Parking: Parking lot; Off-street parking; 5 total parking spaces
• Utilities: Public water connected; Public sewer connected; Natural gas
• Home design: Multi-family property (3-family)
• Construction: Frame construction; Stone foundation; Flat roof; Vinyl siding
• Exterior features: Level lot; Deck

Interior

• Bedrooms: 9 total bedrooms
• Bathrooms: 3 full bathrooms
• Heating & cooling: Hot water heating; Natural gas fuel; Tankless hot water
• Interior features: Total of 15 rooms; Full basement; Has attic with hatch access; Three total units (multi-family)

What this means for you Summary

Snapshot

• This is a 3 × 3-bed/1.0-bath units multifamily listed at $395k.

Deal economics

• At list price, monthly cash flow is $2k ($24k/yr) — positive. Per door: $664/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($6k rent vs $395k).
• Cap rate 12.3% vs local median 3.6% 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; 147 active listings in the ZIP; solid renter incomes; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 in 5+ unit buildings).
• At $6,078/mo this rent would consume 92% 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 $3k of loan paydown is wiped out by about $12k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 0.2% rent growth), your $111k cash investment doubles in ~7 years — after that, you're playing with house money.

Negotiation context

• Only 8 days on market — expect competitive offers; lowballing is unlikely to land.
• 6 sale attempts since 20y 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 1917 — 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 $395,000

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 1917 — 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. 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: 1.54% ✓
• Cap rate: 12.35%
• Cash-on-cash: 21.62%
• DSCR: 1.96
• GRM: 5.4

CMA / ARV

• ARV (on-the-fly): $449,190
• Comps found: 3

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
259 Pearl St	0.00mi	9/3.0	3,906 (0%)	1mo	$450,000	$115	99
32 Spring St	0.11mi	9/3.0	3,606 (-8%)	3mo	$550,000	$153	80
57 Ferry St	0.35mi	9/4.5	3,334 (-15%)	3mo	$375,000	$112	51

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: 11.0%
• Equity multiple: 1.42×
• Total profit: $46,497
• Equity at exit: $58,896

10-year hold

• IRR: 17.6%
• Equity multiple: 2.27×
• Total profit: $140,265
• Equity at exit: $34,152

Cash invested: $110,600 (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: 147
• Price-to-rent: 16.2×

Monthly cashflow live

• Estimated rent: $6,078 high
• Mortgage (P&I): −$2,071
• Tax from tax record: −$573 /mo · $6,877/yr
• Insurance: −$165
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,276
• Net cashflow: $1,993

Break-even live

Break-even rent $3,556

Max offer price $395,000

Occupancy floor 62%

Sensitivity live

Price	-10% $2,216	-5% $2,104	+0% $1,993	+5% $1,881	+10% $1,769
Rent	-10% $1,512	-5% $1,752	+0% $1,993	+5% $2,233	+10% $2,473
Rate	-1.0pp $2,191	-0.5pp $2,093	base $1,993	+0.5pp $1,890	+1.0pp $1,786

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

Units	Beds	Baths	Est. rent
▸ 3× units	3	1	$6,078
Total (3 units)			$6,078

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: $98,750
• Closing costs: $11,850
• Reserves months: —
• Total cash needed: —

Listing history 22 events

1. 2026-04-17
   status Under Contract
2. 2026-04-10
   listed $395,000 Active
3. 2026-04-07
   historical $395,000
4. 2023-06-02
   soldstatus $380,000
5. 2023-05-17
   soldstatus $380,000 Closed 587-char remark

   Show marketing remark (587 chars)

   Great investment opportunity! Clean and well maintained 3 unit multi-family. All three units have very similar floor plans and all have been updated. Each unit includes 3 bedrooms, spacious eat-in kitchen with panty and large living room. Two units are currently rented. The second floor is vacant . Perfect for an owner occupant. New (as of 2017), Navien on-demand gas furnace, updated electrical/breakers, updated plumbing and much more. Basement is clean and dry. Five off street parking spots. Near to state parks, restaurants, museums, shopping, medical facilities, plus much more.

6. 2023-05-08
   status Under Contract 587-char remark

   Show marketing remark (587 chars)

   Great investment opportunity! Clean and well maintained 3 unit multi-family. All three units have very similar floor plans and all have been updated. Each unit includes 3 bedrooms, spacious eat-in kitchen with panty and large living room. Two units are currently rented. The second floor is vacant . Perfect for an owner occupant. New (as of 2017), Navien on-demand gas furnace, updated electrical/breakers, updated plumbing and much more. Basement is clean and dry. Five off street parking spots. Near to state parks, restaurants, museums, shopping, medical facilities, plus much more.

7. 2023-04-16
   historical Under Contract - Continue to Show 587-char remark

   Show marketing remark (587 chars)

   Great investment opportunity! Clean and well maintained 3 unit multi-family. All three units have very similar floor plans and all have been updated. Each unit includes 3 bedrooms, spacious eat-in kitchen with panty and large living room. Two units are currently rented. The second floor is vacant . Perfect for an owner occupant. New (as of 2017), Navien on-demand gas furnace, updated electrical/breakers, updated plumbing and much more. Basement is clean and dry. Five off street parking spots. Near to state parks, restaurants, museums, shopping, medical facilities, plus much more.

8. 2023-04-07
   listed $319,900 Active 587-char remark

   Show marketing remark (587 chars)

   Great investment opportunity! Clean and well maintained 3 unit multi-family. All three units have very similar floor plans and all have been updated. Each unit includes 3 bedrooms, spacious eat-in kitchen with panty and large living room. Two units are currently rented. The second floor is vacant . Perfect for an owner occupant. New (as of 2017), Navien on-demand gas furnace, updated electrical/breakers, updated plumbing and much more. Basement is clean and dry. Five off street parking spots. Near to state parks, restaurants, museums, shopping, medical facilities, plus much more.

9. 2023-04-03
   historical $319,900 587-char remark

   Show marketing remark (587 chars)

   Great investment opportunity! Clean and well maintained 3 unit multi-family. All three units have very similar floor plans and all have been updated. Each unit includes 3 bedrooms, spacious eat-in kitchen with panty and large living room. Two units are currently rented. The second floor is vacant . Perfect for an owner occupant. New (as of 2017), Navien on-demand gas furnace, updated electrical/breakers, updated plumbing and much more. Basement is clean and dry. Five off street parking spots. Near to state parks, restaurants, museums, shopping, medical facilities, plus much more.

10. 2020-06-04
    soldstatus $210,000
11. 2020-06-01
    soldstatus $210,000 Closed 301-char remark

    Show marketing remark (301 chars)

    Great investment opportunity! All 3 units have updated, spacious eat-in kitchens with new cabinets and new appliances. Floors have been refinished and bathrooms updated as well. New roof (2017), Navien on-demand gas furnace, updated electrical/breakers. You don't want to miss this! Motivated Sellers.

12. 2020-04-10
    status Under Contract 301-char remark

    Show marketing remark (301 chars)

    Great investment opportunity! All 3 units have updated, spacious eat-in kitchens with new cabinets and new appliances. Floors have been refinished and bathrooms updated as well. New roof (2017), Navien on-demand gas furnace, updated electrical/breakers. You don't want to miss this! Motivated Sellers.

13. 2020-03-26
    listed $219,900 Active 301-char remark

    Show marketing remark (301 chars)

    Great investment opportunity! All 3 units have updated, spacious eat-in kitchens with new cabinets and new appliances. Floors have been refinished and bathrooms updated as well. New roof (2017), Navien on-demand gas furnace, updated electrical/breakers. You don't want to miss this! Motivated Sellers.

14. 2016-11-17
    soldstatus $165,000
15. 2015-02-20
    soldstatus $60,000
16. 2015-02-03
    historical
17. 2015-01-29
    listed $56,000
18. 2007-10-01
    historical
19. 2007-04-03
    listed $330,000
20. 2006-07-05
    soldstatus $279,900
21. 2006-06-30
    soldstatus $279,900
22. 2006-03-18
    listed $279,900

ⓘ 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: $6,877 · $573/mo
• Projected year-2 tax: $7,665 · $639/mo
• Expected delta: +$788/yr (+$66/mo · 11.5%)

ⓘ 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 ≥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: $72,936
• − Mortgage interest: −$22,126
• − Property taxes: −$6,877
• − Insurance: −$1,975
• − Repairs & maintenance: −$5,835
• − Management: −$5,835
• − Depreciation: −$11,491
• Taxable income: $18,797
• Est. tax owed @ 24.0%: −$4,511
• After-tax cash flow: $19,399/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

+41.1% since first listed

22 events — show timeline

• 2026-04-17 Pending — Smart MLS
• 2026-04-10 Listed $395,000 Smart MLS
• 2026-04-07 Coming Soon $395,000 Smart MLS
• 2023-06-02 Sold (Public Records) $380,000 Public Records
• 2023-05-17 Sold (MLS) $380,000 Smart MLS
• 2023-05-08 Pending — Smart MLS
• 2023-04-16 Contingent — Smart MLS
• 2023-04-07 Listed $319,900 Smart MLS
• 2023-04-03 Coming Soon $319,900 Smart MLS
• 2020-06-04 Sold (Public Records) $210,000 Public Records
• 2020-06-01 Sold (MLS) $210,000 Smart MLS
• 2020-04-10 Pending — Smart MLS
• 2020-03-26 Listed $219,900 Smart MLS
• 2016-11-17 Sold (Public Records) $165,000 Public Records
• 2015-02-20 Sold (MLS) $60,000 Smart MLS
• 2015-02-03 Listing Removed — Smart MLS
• 2015-01-29 Listed $56,000 Smart MLS
• 2007-10-01 Listing Removed — Smart MLS
• 2007-04-03 Listed $330,000 Smart MLS
• 2006-07-05 Sold (Public Records) $279,900 Public Records
• 2006-06-30 Sold (MLS) $279,900 Smart MLS
• 2006-03-18 Listed $279,900 Smart MLS

Property tax history

+1.8%/yr

Latest (2022): $6,877 · +0.0% YoY. Source: county tax records.