165 Grand St · Middletown, CT 06457

$229,900

4 bd · 2.0 ba · 1,336 sqft · SingleFamily public records · 5 Days on market

Built 1900 6,098 sqft lot $172/sqft · 19% below area Est $284k · 19% 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 +16.8/30.0
• ARV discount +15.0/15.0
• DSCR +5.2/10.0
• 1% rule +4.5/10.0
• 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

Listing remarks

Classic Colonial brimming with character and opportunity! This home features low-maintenance vinyl siding and a welcoming front porch, perfect for relaxing or entertaining. Step inside to a freshly painted interior where the first floor offers a bright living room with a bow window and hardwood floors, a formal dining room with hardwood flooring, a kitchen, and a full bath (shower in need of repair). Upstairs, you'll find three comfortable bedrooms plus a dedicated office-ideal for today's work-from-home lifestyle. A spacious walk-up attic provides excellent storage or future expansion potential. Major updates include a furnace and oil tank replaced in 2016. With solid bones and timeless ap

Key facts

• Furnace replaced
• Front porch
• Vinyl siding

Tags

• VINYL SIDING
• FRONT PORCH
• FRESHLY PAINTED INTERIOR
• DEDICATED OFFICE
• WALK-UP ATTIC
• FURNACE REPLACED

Property features AI

Exterior

• Utilities: Public water connected; Public sewer connected; Domestic hot water; Oil tank located in basement
• Home design: Single-family home
• Construction: Frame construction; Concrete foundation; Asphalt shingle gable roof; Vinyl siding
• Exterior features: Partial fencing; Level lot; Porch; Shed

Interior

• Kitchen: Oven/Range; Refrigerator
• Bedrooms: 4 bedrooms
• Bathrooms: 2 full bathrooms
• Heating & cooling: Hot water heating (oil-fired); Whole-house fan; Window unit cooling
• Interior features: Foyer entry; Full basement with hatchway; Attic with walk-up access and storage space; Whole-house fan; Window cooling units
• Laundry & utility: Washer and dryer located on the lower level

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $230k.

Deal economics

• At list price, monthly cash flow is $146 ($2k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $219k (4.6% below list).
• Recommended offer: $219k (4.6% below list) — sets the bar for 1% rule.
• Cap rate 7.1% 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: Middletown High School (math 25% / reading 52%, grade F, #111 of 194 statewide, top 57%, 1,214 students, 49% FRL).
• Market conditions: Rents flat; 143 active listings in the ZIP; 17 comparable units currently listed for rent nearby; rentals leasing fast (median 3d 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).
• This rent runs 33% of the median local income ($79k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.

Negotiation context

• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• Current owner paid $110k; list at $230k implies a 109% gain — meaningful room to come down on a strong offer.

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 $219,255 (4.6% below list)

Questions for the listing agent

1. Built in 1900 — 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 for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.95% ✗
• Cap rate: 7.05%
• Cash-on-cash: 2.72%
• DSCR: 1.12
• GRM: 8.7

CMA / ARV

• ARV (median comp): $283,702
• List price: $229,900
• Delta: -18.96%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 11 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
21 Rome Ave	0.37mi	3/1.0 (-1)	1,344 (+1%)	6mo	$246,000	$183	68
20 Prospect St	0.13mi	3/1.0 (-1)	1,210 (-9%)	5mo	$301,000	$249	65
20 Berlin Ct	0.27mi	4/1.0	1,274 (-5%)	15mo	$275,000	$216	63
177 Pearl St	0.20mi	3/1.0 (-1)	1,186 (-11%)	2mo	$272,500	$230	61
46 Johnson St	0.36mi	3/2.0 (-1)	1,480 (+11%)	9mo	$319,900	$216	53
85 Grand St	0.18mi	3/1.0 (-1)	1,177 (-12%)	13mo	$274,000	$233	51
155 Newfield St	0.52mi	3/2.0 (-1)	1,331 (-0%)	24mo	$289,000	$217	50
85 Meech Rd	0.58mi	3/1.0 (-1)	1,267 (-5%)	7mo	$315,000	$249	50
126 Newfield St	0.45mi	3/2.0 (-1)	1,487 (+11%)	11mo	$431,250	$290	46
310 Newfield St	0.67mi	3/2.0 (-1)	1,404 (+5%)	12mo	$360,000	$256	46
67 Catherine St	0.48mi	3/1.5 (-1)	1,176 (-12%)	23mo	$275,000	$234	32

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: -15.2%
• Equity multiple: 0.47×
• Total profit: $-33,894
• Equity at exit: $34,279

10-year hold

• IRR: -12.1%
• Equity multiple: 0.37×
• Total profit: $-40,578
• Equity at exit: $19,878

Cash invested: $64,372 (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: 8.7×

Monthly cashflow live

• Estimated rent: $2,193 high
• Mortgage (P&I): −$1,206
• Tax from tax record: −$285 /mo · $3,417/yr
• Insurance: −$96
• HOA: −$0
• Vacancy / Maint / Mgmt: −$460
• Net cashflow: $146

Break-even live

Break-even rent $2,008

Max offer price $229,900

Occupancy floor 88%

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: $57,475
• Closing costs: $6,897
• Reserves months: —
• Total cash needed: —

Rent comps 17 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
94 Liberty St Middletown, CT	3.0	1.5	978	$1,850	$1.89	44d	1	0.16mi
3 Clinton Ave Unit 3 CLINTON Middletown, CT	3.0	1.0	1200	$1,450	$1.21	21d	1	0.23mi
103 Spring St Middletown, CT	4.0	1.0	1602	$2,500	$1.56	44d	1	0.23mi
39 Grand St Unit 3 Middletown, CT	3.0	1.0	1076	$2,000	$1.86	2d	1	0.27mi
580 High St Middletown, CT	3.0	1.0	1466	$1,900	$1.30	2d	1	0.32mi
505 Main St Middletown, CT	3.0	2.0	1263	$2,000	$1.58	2d	1	0.38mi
582 Main St Middletown, CT	3.0	1.0	1200	$2,000	$1.67	2d	1	0.39mi
57 Ferry St Unit 1 Middletown, CT	3.0	1.5	1500	$2,000	$1.33	10d	1	0.45mi
14 Portland St Middletown, CT	4.0	1.0	1000	$1,495	$1.50	2d	1	0.49mi
184 Rose Cir Middletown, CT	1.0–3.0	1.0–1.5	1220	$2,000	$1.64	2d	6	0.52mi
11 Huber Ave Middletown, CT	3.0	1.0	1102	$2,300	$2.09	24d	1	0.79mi
200 Main St Unit 1 Portland, CT	3.0	2.0	1300	$2,227	$1.71	10d	1	1.16mi
200 Main St Unit 1 Portland, CT	3.0	2.0	1300	$2,227	$1.71	2d	1	1.16mi
27 Woodside Cir Unit 37 Middletown, CT	3.0	2.0	1600	$2,300	$1.44	44d	1	1.17mi
207 E Main St Middletown, CT	4.0	1.0	1207	$2,200	$1.82	3d	1	1.26mi
252 Main St Apt 1 Portland, CT	3.0	1.0	1200	$1,850	$1.54	2d	1	1.33mi
260 Main St Unit 2 Portland, CT	3.0	1.0	1100	$2,350	$2.14	3d	1	1.35mi

Listing history 3 events

1. 2026-05-05
   status Under Contract 805-char remark
2. 2026-04-30
   listed $229,900 Active 805-char remark
3. 1999-04-05
   soldstatus $110,000

ⓘ 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: $3,417 · $285/mo
• Projected year-2 tax: $4,168 · $347/mo
• Expected delta: +$751/yr (+$63/mo · 22.0%)

ⓘ 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 ≥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: $26,311
• − Mortgage interest: −$12,878
• − Property taxes: −$3,417
• − Insurance: −$1,150
• − Repairs & maintenance: −$2,105
• − Management: −$2,105
• − Depreciation: −$6,688
• Taxable loss: −$2,032
• Est. tax savings @ 24.0%: +$488
• After-tax cash flow: $2,239/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

+109.0% since first listed

3 events — show timeline

• 2026-05-05 Pending — Smart MLS
• 2026-04-30 Listed $229,900 Smart MLS
• 1999-04-05 Sold (Public Records) $110,000 Public Records

Property tax history

-0.5%/yr

Latest (2022): $3,417 · +0.0% YoY. Source: county tax records.