744 Canaan Road Rd #23 · Bridgeport, CT 06610

$59,000

2 bd · 1.0 ba · 650 sqft · Condo · 62 Days on market

Built 1956 $91/sqft · at area comps Est $57k · at est. $584/mo HOA · 34% of rent

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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 +5.8/15.0
• Livability +4.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Schools +1.2/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Welcome to 744 Canaan Road, Unit #23, Bridgeport, CT 06610-a cozy and inviting 2-bedroom, 1-bath unit perfect for someone looking for a fresh start. This well-maintained home offers plenty of closet space, an in-unit washer for added convenience, and comfortable living throughout. The association includes grounds maintenance, heat, hot water, and taxes, making for easy, worry-free ownership. Owner occupancy is required, creating a more stable and welcoming community atmosphere.

Key facts

• $584 HOA
• Built 1956
• Listed 62 days

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath condo listed at $59k.

Deal economics

• At list price, monthly cash flow is $376 ($5k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $59k).
• Recommended offer: $55k (6.0% below list) — sets the bar for market timing.
• Cap rate 13.9% vs local median 5.0% in Bridgeport — 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 (#15 in CT, #1,374 nationally) — a professional / high-income tenant draw. Strengths: amenities A+, commute A+, health & safety A+; Watch: crime C-, employment D+, schools D-.
• Bridgeport School District (urban): math 9% / reading 19% proficiency, ranked #151 of 153 in CT (top 99%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 97% free/reduced lunch — lower-income household profile, screen leases tightly.
• Market conditions: 68 active listings in the ZIP; 22 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); 852 units permitted in Greater Bridgeport Planning Region in 2024 (698 in 5+ unit buildings).
• This rent runs 40% of the median local income ($52k/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 $408 of loan paydown is wiped out by about $2k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $17k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• It's been on market 62 days — a 6% lower offer ($55k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 15y 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.
• Current owner paid $24k; list at $59k implies a 146% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: HOA is 34% of rent; built in 1956 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 51% 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 $55,460 (6.0% below list)

Questions for the listing agent

1. It's been on market 62 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Built in 1956 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. 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?
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: 2.93% ✓
• Cap rate: 13.94%
• Cash-on-cash: 27.30%
• DSCR: 2.21
• GRM: 2.8

CMA / ARV

• ARV (median comp): $56,881
• List price: $59,000
• Delta: 3.73%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 21.7%
• Equity multiple: 1.89×
• Total profit: $14,761
• Equity at exit: $8,797

10-year hold

• IRR: 30.1%
• Equity multiple: 3.74×
• Total profit: $45,239
• Equity at exit: $5,101

Cash invested: $16,520 (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 06610

• Home prices YoY: -7.5%
• Active inventory: 68
• Price-to-rent: 2.8×

Monthly cashflow live

• Estimated rent: $1,731 high
• Mortgage (P&I): −$309
• Tax est. 1.5%: −$74 /mo · $885/yr
• Insurance: −$25
• HOA: −$584
• Vacancy / Maint / Mgmt: −$364
• Net cashflow: $376

Break-even live

Break-even rent $1,255

Max offer price $59,000

Occupancy floor 73%

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: $14,750
• Closing costs: $1,770
• Reserves months: —
• Total cash needed: —

Rent comps 22 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
250 N Bishop Ave #19 Bridgeport, CT	1.0	1.0	638	$1,650	$2.59	43d	1	0.13mi
250 N Bishop Ave Bridgeport, CT	1.0	1.0	611	$1,425	$2.33	23d	2	0.13mi
250 N Bishop Ave #1 Bridgeport, CT	1.0	1.0	583	$1,650	$2.83	11d	1	0.13mi
235 Henry Ave Unit 12E Stratford, CT	1.0	1.0	692	$1,695	$2.45	10d	1	0.23mi
86 Birdsey St Unit 3R Bridgeport, CT	1.0	1.0	650	$1,350	$2.08	43d	1	0.46mi
192 Peace St Unit 1st floor Stratford, CT	2.0	1.0	712	$2,000	$2.81	43d	1	0.61mi
600 Bond St Unit 112 Bridgeport, CT	1.0	1.0	545	$2,250	$4.13	43d	1	0.68mi
556 Hollister St Stratford, CT	1.0–2.0	1.0	725	$2,295	$3.17	11d	4	0.77mi
1150 Ogden Street Ext Unit 102 Bridgeport, CT	1.0	1.0	700	$1,425	$2.04	14d	1	0.80mi
1525 Central Ave Bridgeport, CT	1.0	1.0	625	$1,550	$2.48	43d	3	0.94mi
231 Goddard Ave Unit 3RD Bridgeport, CT	2.0	1.0	618	$1,700	$2.75	3d	1	1.10mi
145 Cowles St Unit B7 Bridgeport, CT	1.0	1.0	600	$1,325	$2.21	3d	1	1.19mi
1254 Pembroke St Unit 1st Floor Bridgeport, CT	2.0	1.0	738	$1,850	$2.51	14d	1	1.19mi
186 Louisiana Ave Unit D Bridgeport, CT	1.0	1.0	650	$1,700	$2.62	21d	1	1.27mi
647 Union Ave Unit 2 Bridgeport, CT	2.0	1.0	750	$1,675	$2.23	3d	1	1.28mi
1333 E Main St Apt 1 Bridgeport, CT	2.0	1.0	700	$1,700	$2.43	3d	1	1.34mi
1333 E Main St #5 Bridgeport, CT	2.0	1.0	700	$1,650	$2.36	3d	1	1.34mi
154 Virginia Ave Unit B Bridgeport, CT	1.0	1.0	650	$1,800	$2.77	43d	1	1.34mi
498 Sherwood Pl Stratford, CT	3.0	1.0–2.0	984	$2,622	$2.66	21d	5	1.41mi
1111 Stratford Ave Stratford, CT	2.0	1.0–2.0	809	$2,750	$3.40	43d	7	1.47mi
3699 Broadbridge Ave #101 Stratford, CT	1.0	1.0	680	$1,700	$2.50	23d	1	1.49mi
3699 Broadbridge Ave #101 Stratford, CT	1.0	1.0	680	$1,700	$2.50	43d	1	1.49mi

HOA detail condo

• Monthly dues: $584 · $7,008/yr
• Likely covers: waterlandscaping
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 26 events

1. 2026-06-18
   days on market $59,000 Active 62 DOM
2. 2026-06-17
   days on market $59,000 Active 61 DOM
3. 2026-06-16
   days on market $59,000 Active 60 DOM
4. 2026-06-15
   days on market $59,000 Active 59 DOM
5. 2026-06-13
   days on market $59,000 Active 57 DOM
6. 2026-06-13
   days on market $59,000 Active 56 DOM
7. 2026-06-10
   days on market $59,000 Active 54 DOM
8. 2026-06-09
   days on market $59,000 Active 53 DOM
9. 2026-06-08
   days on market $59,000 Active 52 DOM
10. 2026-06-07
    days on market $59,000 Active 51 DOM
11. 2026-06-05
    days on market $59,000 Active 48 DOM
12. 2026-06-03
    days on market $59,000 Active 47 DOM
13. 2026-06-03
    days on market $59,000 Active 46 DOM
14. 2026-06-01
    days on market $59,000 Active 45 DOM
15. 2026-05-31
    days on market $59,000 Active 44 DOM
16. 2026-04-17
    listed $59,000 Active 482-char remark

    Show marketing remark (482 chars)

    Welcome to 744 Canaan Road, Unit #23, Bridgeport, CT 06610-a cozy and inviting 2-bedroom, 1-bath unit perfect for someone looking for a fresh start. This well-maintained home offers plenty of closet space, an in-unit washer for added convenience, and comfortable living throughout. The association includes grounds maintenance, heat, hot water, and taxes, making for easy, worry-free ownership. Owner occupancy is required, creating a more stable and welcoming community atmosphere.

17. 2026-01-31
    historical
18. 2025-11-11
    price $65,000
19. 2025-06-27
    listed $75,000 Active
20. 2019-02-26
    soldstatus $24,000 Closed
21. 2019-01-11
    historical Under Contract - Continue to Show
22. 2018-10-07
    listed $30,000 Active
23. 2017-01-18
    historical
24. 2016-07-18
    listed $45,000
25. 2012-09-07
    soldstatus $17,000
26. 2011-07-06
    listed $20,000

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

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 ≥97°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 51% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 5 unhealthy d/yr today · 7 by 30 yrs out

Taxation est. · year 1

• Rental income: $20,773
• − Mortgage interest: −$3,305
• − Property taxes: −$885
• − Insurance: −$295
• − Repairs & maintenance: −$1,662
• − Management: −$1,662
• − HOA: −$7,008
• − Depreciation: −$1,716
• Taxable income: $4,240
• Est. tax owed @ 24.0%: −$1,018
• After-tax cash flow: $3,492/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: Bridgeport School District
• NCES district ID: 0900450
• Math proficiency: 9% ▼ -7.00%
• Reading proficiency: 19% ▼ -10.00%
• Median HH income: $41,507
• Composite: 12.09/100
• National rank: #9656
• State rank: #151 of 153 in CT

Livability — Bridgeport

• Score: 81/100
• State rank: #15
• US rank: #1374

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Bridgeport, CT
• County: Fairfield County · 765,532 people
• City population: 149,153
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 22,020
• Household income: $51,634
• Rent vs Own: 50.6% rent · 49.4% own
• Severe rent burden: 1368.0

Population outlook (Greater Bridgeport County) Hauer SSP2

• By 2040: 365,581

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.65)
• Race & ethnicity: Hispanic / Latino 51% Black 23% White 20% Two or more races 14% Asian 3% Native American 1%
• Hispanic origin (detail): Mexican 3% Puerto Rican 30% Dominican 6%
• Common ancestry: Romanian 4% Estonian 3% Hispanic 2%
• Foreign-born: 31% · Canada, Jamaica, Vietnam
• Languages at home: 47% English-only · Spanish 40% Other Indo-European 5% Russian/Polish/Slavic 3%

Political lean MEDSL · Greater Bridgeport

• 2024 margin: Strong D (+23.3) · D 60.9% · R 37.6% · Other 1.5%
• All cycles: 2024: D+23.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -29.78%
• Current HPI: 370.1432
• Rent YoY: —
• Metro: Bridgeport-Stamford-Norwalk, 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

+195.0% since first listed

11 events — show timeline

• 2026-04-17 Listed $59,000 Smart MLS
• 2026-01-31 Listing Removed — Smart MLS
• 2025-11-11 Price Changed $65,000 Smart MLS
• 2025-06-27 Listed $75,000 Smart MLS
• 2019-02-26 Sold (MLS) $24,000 Smart MLS
• 2019-01-11 Contingent — Smart MLS
• 2018-10-07 Listed $30,000 Smart MLS
• 2017-01-18 Listing Removed — Smart MLS
• 2016-07-18 Listed $45,000 Smart MLS
• 2012-09-07 Sold (MLS) $17,000 Smart MLS
• 2011-07-06 Listed $20,000 Smart MLS