239 Cherry Hill Dr Unit 1A · Bridgeport, CT 06606

$184,000

2 bd · 1.0 ba · 850 sqft · Condo public records · 98 Days on market

Built 1969 $216/sqft · 10% below area Est $205k · 10% under $500/mo HOA · 22% of rent

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Why this score? — see what drove the D+ 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 +14.5/30.0
• ARV discount +12.1/15.0
• 1% rule +7.4/10.0
• DSCR +4.4/10.0
• Livability +4.0/5.0
• Rent growth +3.3/5.0
• Condition / age +2.5/5.0
• Schools +1.2/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

First-floor 2-bedroom, 1-bath condo located in Bridgeport's sought-after North End neighborhood. This unit features an eat-in kitchen, spacious living room, hardwood floors throughout the living room, hallway, and bedrooms, and a private outdoor deck off the kitchen perfect for relaxing or entertaining. For just $500 per month, the HOA covers heat, hot water, water, sewer, grounds maintenance, snow removal, and trash pickup-making ownership both convenient and cost-effective. The unit is currently tenant occupied, however the seller will deliver the property vacant at closing as the HOA requires owner-occupant buyers only. The tenant has agreed to vacate and has requested up to 60 days to relocate (no later than 5/31/2026). With a simple sand and refinish, the hardwood floors can be brought back to life and the unit can easily shine again. Property is being sold as-is, but inspections are welcome for buyer due diligence. Great opportunity to get into Bridgeport's North End for under $200K. Bring your vision and make it your own. Schedule your showing today! Note: Pictures Include Photos of Unit Before Tenant Move In & Current Photos As Well (Before & Current)

Key facts

• Eat-in kitchen
• Private outdoor deck
• Hardwood floors

Tags

• EAT-IN KITCHEN
• PRIVATE OUTDOOR DECK
• HARDWOOD FLOORS

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath condo listed at $184k.

Deal economics

• At list price, monthly cash flow is $39 ($474/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $184k).
• Recommended offer: $167k (9.0% below list) — sets the bar for market timing.
• Cap rate 6.6% 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: Rents rising (+3.1%/yr); 152 active listings in the ZIP; 36 comparable units currently listed for rent nearby; rentals at typical pace (median 24d 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 37% of the median local income ($73k/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 $1k of loan paydown is wiped out by about $6k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 98 days — a 9% lower offer ($167k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 25y 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 $76k; list at $184k implies a 142% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: HOA is 22% of rent.
• Climate carrying-cost: major wind risk, 27% 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 $167,440 (9.0% below list)

Questions for the listing agent

1. It's been on market 98 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Built in 1969 — 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. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
9. 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.
10. 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.
11. 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: 1.24% ✓
• Cap rate: 6.55%
• Cash-on-cash: 0.92%
• DSCR: 1.04
• GRM: 6.7

CMA / ARV

• ARV (median comp): $204,699
• List price: $184,000
• Delta: -10.11%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Projected returns pro-forma

-3.0% appreciation · 3.12% rent growth · sell at horizon

5-year hold

• IRR: -14.4%
• Equity multiple: 0.48×
• Total profit: $-26,695
• Equity at exit: $27,435

10-year hold

• IRR: -5.1%
• Equity multiple: 0.66×
• Total profit: $-17,528
• Equity at exit: $15,909

Cash invested: $51,520 (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 06606

• Rents YoY: 3.1%
• Active inventory: 152
• Price-to-rent: 6.7×

Monthly cashflow live

• Estimated rent: $2,273 high
• Mortgage (P&I): −$965
• Tax from tax record: −$215 /mo · $2,580/yr
• Insurance: −$77
• HOA: −$500
• Vacancy / Maint / Mgmt: −$477
• Net cashflow: $39

Break-even live

Break-even rent $2,224

Max offer price $184,000

Occupancy floor 93%

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: $46,000
• Closing costs: $5,520
• Reserves months: —
• Total cash needed: —

Rent comps 36 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
239 Cherry Hill Dr Unit 2A Bridgeport, CT	2.0	1.0	850	$2,100	$2.47	43d	1	0.03mi
3004 Madison Ave Unit A Bridgeport, CT	1.0	1.0	755	$2,000	$2.65	21d	1	0.11mi
104 Kennedy Dr Bridgeport, CT	2.0	1.0	1023	$2,600	$2.54	43d	1	0.14mi
127 Kennedy Dr #127 Bridgeport, CT	2.0	1.0	1023	$2,250	$2.20	11d	1	0.15mi
333 Vincellette St #59 Bridgeport, CT	1.0	1.0	975	$2,000	$2.05	11d	1	0.35mi
365 Glendale Ave Unit B2 Bridgeport, CT	1.0	1.0	661	$1,600	$2.42	43d	1	0.37mi
3900 Park Ave Unit 4L Bridgeport, CT	1.0	1.0	870	$1,895	$2.18	43d	1	0.40mi
3900 Park Ave Unit 7K Bridgeport, CT	1.0	1.0	850	$1,895	$2.23	23d	1	0.40mi
150 Anton St Bridgeport, CT	1.0	1.0–1.5	532	$2,090	$3.92	3d	4	0.44mi
765 Birmingham St Bridgeport, CT	3.0	1.0	1094	$3,600	$3.29	2d	1	0.67mi
275 Burnsford Ave Bridgeport, CT	3.0	1.0	1116	$3,200	$2.87	23d	1	0.72mi
25 Rena Pl Fairfield, CT	2.0	1.0	930	$3,200	$3.44	43d	1	0.76mi
524 Beechmont Ave Bridgeport, CT	3.0	1.0	1104	$3,500	$3.17	23d	1	0.87mi
39 Lance Cir #39 Bridgeport, CT	2.0	1.0	915	$2,500	$2.73	43d	1	0.96mi
170 Sequoia Rd Bridgeport, CT	1.0	1.0	850	$1,850	$2.18	23d	1	0.99mi
97 Wentworth St Unit 3 Bridgeport, CT	2.0	1.0	950	$2,000	$2.11	2d	1	1.05mi
30 Quarry St Bridgeport, CT	1.0–2.0	1.0	805	$1,825	$2.27	23d	3	1.07mi
3250 Main St Unit B209 Bridgeport, CT	2.0	2.0	813	$2,000	$2.46	43d	1	1.12mi
2496 Easton Tpke Unit B Fairfield, CT	2.0	1.0	900	$2,395	$2.66	43d	1	1.13mi
151-153 Alexander Ave Unit 1 Bridgeport, CT	3.0	1.0	1100	$2,400	$2.18	11d	1	1.15mi
343 Wayne St Unit 1st Bridgeport, CT	1.0	1.0	650	$1,300	$2.00	43d	1	1.16mi
343 Wayne St Unit 1st Bridgeport, CT	1.0	1.0	650	$1,300	$2.00	3d	1	1.16mi
5085 Main St Trumbull, CT	1.0–2.0	1.0–2.0	985	$3,175	$3.22	2d	9	1.16mi
68-70 Westfield Ave Bridgeport, CT	2.0	1.0	888	$2,200	$2.48	3d	1	1.19mi
1455 Madison Ave Unit A6 Bridgeport, CT	1.0	1.0	776	$1,700	$2.19	43d	1	1.24mi
454 Summit St Bridgeport, CT	2.0	1.0	1010	$2,000	$1.98	43d	1	1.27mi
160 Fairfield Woods Rd #57 Fairfield, CT	2.0	2.0	1100	$3,500	$3.18	2d	1	1.32mi
173 Fairview Ave Unit 3 Bridgeport, CT	3.0	1.0	1000	$2,300	$2.30	43d	1	1.37mi
610 Hawley Ave #2 Bridgeport, CT	2.0	1.0	1000	$2,000	$2.00	14d	1	1.40mi
5545 Park Ave Fairfield, CT	1.0–2.0	1.0–2.0	1040	$3,900	$3.75	2d	1	1.42mi
380 Gurdon St Unit 1 Bridgeport, CT	1.0	1.0	744	$2,000	$2.69	21d	1	1.42mi
614 Earl Ave Bridgeport, CT	2.0	1.0	748	$2,300	$3.07	43d	1	1.44mi
62 High Ridge Dr Bridgeport, CT	2.0	1.0	950	$2,350	$2.47	43d	1	1.45mi
2600 Park Ave Bridgeport, CT	1.0–2.0	1.0–2.0	940	$2,345	$2.49	14d	4	1.46mi
2600 Park Ave Bridgeport, CT	1.0–2.0	1.0	830	$1,970	$2.37	23d	3	1.47mi
980 Lindley St Unit 304F Bridgeport, CT	2.0	2.0	936	$2,200	$2.35	23d	1	1.50mi

HOA detail condo

• Monthly dues: $500 · $6,000/yr
• Likely covers: watersewertrashlandscapingsnow removal
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 19 events

1. 2026-06-18
   days on market $184,000 Active 98 DOM
2. 2026-06-17
   days on market $184,000 Active 97 DOM
3. 2026-06-16
   pricedays on market $184,000 Active 96 DOM
4. 2026-06-15
   days on market $189,900 Active 95 DOM
5. 2026-06-13
   days on market $189,900 Active 93 DOM
6. 2026-06-13
   days on market $189,900 Active 92 DOM
7. 2026-06-10
   days on market $189,900 Active 90 DOM
8. 2026-06-09
   days on market $189,900 Active 89 DOM
9. 2026-06-08
   days on market $189,900 Active 88 DOM
10. 2026-06-07
    days on market $189,900 Active 87 DOM
11. 2026-06-05
    days on market $189,900 Active 84 DOM
12. 2026-06-03
    days on market $189,900 Active 83 DOM
13. 2026-06-03
    days on market $189,900 Active 82 DOM
14. 2026-06-01
    days on market $189,900 Active 81 DOM
15. 2026-05-31
    days on market $189,900 Active 80 DOM
16. 2026-03-12
    listed $189,900 Active 1190-char remark

    Show marketing remark (1190 chars)

    First-floor 2-bedroom, 1-bath condo located in Bridgeport's sought-after North End neighborhood. This unit features an eat-in kitchen, spacious living room, hardwood floors throughout the living room, hallway, and bedrooms, and a private outdoor deck off the kitchen perfect for relaxing or entertaining. For just $500 per month, the HOA covers heat, hot water, water, sewer, grounds maintenance, snow removal, and trash pickup-making ownership both convenient and cost-effective. The unit is currently tenant occupied, however the seller will deliver the property vacant at closing as the HOA requires owner-occupant buyers only. The tenant has agreed to vacate and has requested up to 60 days to relocate (no later than 5/31/2026). With a simple sand and refinish, the hardwood floors can be brought back to life and the unit can easily shine again. Property is being sold as-is, but inspections are welcome for buyer due diligence. Great opportunity to get into Bridgeport's North End for under $200K. Bring your vision and make it your own. Schedule your showing today! Note: Pictures Include Photos of Unit Before Tenant Move In & Current Photos As Well (Before & Current)

17. 2002-01-31
    soldstatus $76,000
18. 2001-08-30
    soldstatus $76,000 180-char remark

    Show marketing remark (180 chars)

    1St Floor Unit In Excellent Condition. This Unit Is Slightly Larger Than Most. Heat, Hot Water Wpca And Water Included In Cc. Close To Shopping. New Rear Porch To Be Built.

19. 2001-04-21
    listed $77,900 180-char remark

    Show marketing remark (180 chars)

    1St Floor Unit In Excellent Condition. This Unit Is Slightly Larger Than Most. Heat, Hot Water Wpca And Water Included In Cc. Close To Shopping. New Rear Porch To Be Built.

ⓘ 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: $2,580 · $215/mo
• Projected year-2 tax: $3,259 · $272/mo
• Expected delta: +$679/yr (+$57/mo · 26.3%)

ⓘ 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 ≥97°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% 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: $27,282
• − Mortgage interest: −$10,307
• − Property taxes: −$2,580
• − Insurance: −$920
• − Repairs & maintenance: −$2,183
• − Management: −$2,183
• − HOA: −$6,000
• − Depreciation: −$5,353
• Taxable loss: −$2,243
• Est. tax savings @ 24.0%: +$538
• After-tax cash flow: $1,012/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): 49,308
• Household income: $73,372
• Rent vs Own: 42.9% rent · 57.1% own
• Severe rent burden: 2163.0

Population outlook (Greater Bridgeport County) Hauer SSP2

• By 2040: 365,581

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Highly diverse neighborhood (Simpson 0.73)
• Race & ethnicity: Hispanic / Latino 37% White 31% Black 19% Two or more races 11% Asian 7%
• Hispanic origin (detail): Mexican 5% Puerto Rican 12% Dominican 4%
• Common ancestry: Estonian 5% Russian 4% Romanian 3%
• Foreign-born: 37% · Canada, Jamaica, Vietnam
• Languages at home: 50% English-only · Spanish 27% Other Indo-European 15% French/Haitian/Cajun 2%

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: ▼ -270.11%
• Current HPI: 345.647
• Rent YoY: ▲ 3.12%
• 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

+143.8% since first listed

4 events — show timeline

• 2026-03-12 Listed $189,900 Smart MLS
• 2002-01-31 Sold (Public Records) $76,000 Public Records
• 2001-08-30 Sold (MLS) $76,000 Smart MLS
• 2001-04-21 Listed $77,900 Smart MLS

Property tax history

-3.7%/yr

Latest (2023): $2,580 · +0.0% YoY. Source: county tax records.