500 Woodlawn Ave Ext · Bridgeport, CT 06606

$320,000

4 bd · 1.0 ba · 1,152 sqft · SingleFamily public records · 54 Days on market

Built 1971 5,227 sqft lot $278/sqft · 14% below area Est $371k · 14% under ↓ 17% since listing

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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 +18.0/30.0
• ARV discount +13.7/15.0
• DSCR +5.6/10.0
• 1% rule +5.4/10.0
• 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

Step into timeless charm and endless opportunity in this inviting 4-bedroom, 1-bath single-family home nestled on a quiet dead-end street in Bridgeport's highly sought-after North End. Brimming with character and solid craftsmanship, this home offers the perfect canvas to create your dream space. Original hardwood floors grace the second level and portions of the main floor, while wood beam ceilings in the living room and kitchen add warmth, texture, and architectural appeal. Classic details throughout create a welcoming atmosphere you'll love coming home to. Outside, enjoy a generously sized yard ideal for entertaining, gardening, or relaxing in your own private retreat. The large deck is perfect for gatherings, and a convenient storage shed adds practical functionality. A partially finished basement offers exciting potential for a playroom, home office, gym, or hobby space or whatever fits your lifestyle. Additional highlights include off-street parking, a private driveway, and a newer roof, providing peace of mind for years to come. With great bones, character-filled details, and room to personalize, this North End gem is ready for its next chapter. With your vision and some TLC you can unlock its full potential. Schedule your private showing today and experience all this special home has to offer!

Key facts

• Large deck
• Wood beam ceilings
• 5,227 sq ft lot

Tags

• ORIGINAL HARDWOOD FLOORS
• WOOD BEAM CEILINGS
• GENEROUSLY SIZED YARD
• LARGE DECK
• CONVENIENT STORAGE SHED
• PARTIALLY FINISHED BASEMENT

What this means for you Summary

Snapshot

• This is a 4-bed/1.0-bath single-family listed at $320k.

Deal economics

• At list price, monthly cash flow is $275 ($3k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $320k).
• Recommended offer: $310k (3.0% below list) — sets the bar for market timing.
• Cap rate 7.3% 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; 30 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 852 units permitted in Greater Bridgeport Planning Region in 2024 (698 in 5+ unit buildings).
• At $3,320/mo this rent would consume 54% of the median local household income ($73k/yr) (locally 2163% 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 $2k of loan paydown is wiped out by about $10k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 54 days — a 3% lower offer ($310k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts 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

• Climate carrying-cost: major flood risk; major wind risk, 41% 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 $310,400 (3.0% below list)

Questions for the listing agent

1. It's been on market 54 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1971 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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 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: 1.04% ✓
• Cap rate: 7.33%
• Cash-on-cash: 3.69%
• DSCR: 1.16
• GRM: 8.0

CMA / ARV

• ARV (median comp): $370,957
• List price: $320,000
• Delta: -13.74%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
500 Woodlawn Ave Ext	0.00mi	4/1.0	1,152 (0%)	1mo	$280,000	$243	99
675 Platt St	0.14mi	3/1.0 (-1)	1,152 (0%)	2mo	$310,000	$269	87
365 Platt St	0.16mi	3/3.0 (-1)	1,152 (0%)	4mo	$470,000	$408	76
85 Platt St	0.40mi	4/2.0	1,152 (0%)	3mo	$459,900	$399	75
235 Douglas St	0.15mi	3/1.0 (-1)	1,056 (-8%)	3mo	$350,000	$331	72
33 Victory Ave	0.57mi	3/1.0 (-1)	1,152 (0%)	0mo	$344,000	$299	68
150 Trumbull Ave	0.73mi	4/1.0	1,152 (0%)	0mo	$370,000	$321	66
81 Dodd Ave	0.61mi	3/1.0 (-1)	1,076 (-7%)	0mo	$440,000	$409	55
385 Chamberlain Ave	0.42mi	3/2.0 (-1)	1,055 (-8%)	4mo	$345,000	$327	54
105 Pond St	0.63mi	3/1.5 (-1)	1,224 (+6%)	1mo	$315,000	$257	52
209 Trumbull Ave	0.68mi	3/1.0 (-1)	995 (-14%)	1mo	$350,000	$352	39
153 Marigold Ave	0.63mi	3/2.0 (-1)	994 (-14%)	1mo	$360,000	$362	38

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 · 3.12% rent growth · sell at horizon

5-year hold

• IRR: -10.3%
• Equity multiple: 0.62×
• Total profit: $-33,775
• Equity at exit: $47,713

10-year hold

• IRR: -0.7%
• Equity multiple: 0.95×
• Total profit: $-4,626
• Equity at exit: $27,668

Cash invested: $89,600 (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 06606

• Rents YoY: 3.1%
• Active inventory: 152
• Price-to-rent: 8.0×

Monthly cashflow live

• Estimated rent: $3,320 high
• Mortgage (P&I): −$1,678
• Tax from tax record: −$536 /mo · $6,435/yr
• Insurance: −$133
• HOA: −$0
• Vacancy / Maint / Mgmt: −$697
• Net cashflow: $275

Break-even live

Break-even rent $2,972

Max offer price $320,000

Occupancy floor 87%

Sensitivity live

Price	-10% $457	-5% $366	+0% $275	+5% $185	+10% $94
Rent	-10% $13	-5% $144	+0% $275	+5% $407	+10% $538
Rate	-1.0pp $437	-0.5pp $357	base $275	+0.5pp $193	+1.0pp $108

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: $80,000
• Closing costs: $9,600
• Reserves months: —
• Total cash needed: —

Rent comps 30 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
70 Pitt St Bridgeport, CT	4.0	1.0	1208	$3,200	$2.65	22d	1	0.28mi
845 Hart St Unit 2 Bridgeport, CT	3.0	1.0	1200	$2,500	$2.08	44d	1	0.31mi
180 Pleasantview Ave Bridgeport, CT	3.0	2.0	1373	$3,700	$2.69	44d	1	0.32mi
524 Beechmont Ave Bridgeport, CT	3.0	1.0	1104	$3,500	$3.17	24d	1	0.41mi
131 Infield St Bridgeport, CT	3.0	1.5	1199	$3,450	$2.88	44d	1	0.47mi
14 Infield St Bridgeport, CT	3.0	2.5	1344	$3,200	$2.38	44d	1	0.49mi
110 Grenelle St Bridgeport, CT	3.0	1.0	1351	$4,000	$2.96	4d	1	0.66mi
208 Fairview Ave Bridgeport, CT	3.0	1.0	1200	$2,300	$1.92	24d	1	0.74mi
173 Fairview Ave Unit 3 Bridgeport, CT	3.0	1.0	1000	$2,300	$2.30	44d	1	0.74mi
68-70 Westfield Ave Bridgeport, CT	4.0	2.0	1470	$3,200	$2.18	15d	1	0.74mi
275 Burnsford Ave Bridgeport, CT	3.0	1.0	1116	$3,200	$2.87	24d	1	0.76mi
95 Marcel St Bridgeport, CT	5.0	2.0	1404	$4,000	$2.85	44d	1	0.76mi
51 Indian Ave Unit 1546115P Bridgeport, CT	3.0	1.0	1388	$3,871	$2.79	12d	1	0.76mi
5 Cloverhill Ave Bridgeport, CT	4.0	2.0	1344	$4,000	$2.98	3d	1	0.81mi
74 Village Ln Bridgeport, CT	3.0	2.0	1428	$3,500	$2.45	3d	1	0.84mi
207 Hillcrest Rd Bridgeport, CT	3.0	2.0	1264	$3,600	$2.85	11d	1	0.91mi
100 Avalon Gates Trumbull, CT	1.0–3.0	1.0–2.0	1082	$3,390	$3.13	3d	28	1.07mi
765 Birmingham St Bridgeport, CT	3.0	1.0	1094	$3,600	$3.29	3d	1	1.14mi
139 Little Deer Rd Bridgeport, CT	4.0	2.0	1420	$3,600	$2.54	44d	1	1.18mi
151-153 Alexander Ave Unit 1 Bridgeport, CT	3.0	1.0	1100	$2,400	$2.18	12d	1	1.24mi
666 Capitol Ave Unit 2 Bridgeport, CT	3.0	1.0	1247	$2,400	$1.92	44d	1	1.27mi
2395 Main St Unit Second Floor Bridgeport, CT	3.0	1.0	1262	$2,400	$1.90	44d	1	1.29mi
2395 Main St Unit First Floor Bridgeport, CT	3.0	1.0	1262	$2,300	$1.82	12d	1	1.29mi
927 Birmingham St Bridgeport, CT	4.0	2.0	1362	$3,800	$2.79	3d	1	1.29mi
145 Rooster River Blvd Bridgeport, CT	5.0	2.0	1452	$3,800	$2.62	3d	1	1.30mi
23 Ochsner Pl Unit 1 Bridgeport, CT	3.0	1.0	1250	$3,800	$3.04	44d	1	1.30mi
200 Robin St Unit 2 Bridgeport, CT	3.0	1.0	1152	$2,400	$2.08	22d	1	1.31mi
130 Deramo Pl Bridgeport, CT	3.0	1.5	1252	$3,700	$2.96	3d	1	1.39mi
923 Madison Ave Unit 3rd floor Bridgeport, CT	3.0	1.0	1100	$2,000	$1.82	44d	1	1.43mi
204 Wheeler Ave Bridgeport, CT	3.0	1.0–2.0	485	$2,600	$5.36	12d	3	1.46mi

Listing history 9 events

1. 2026-05-05
   status Under Contract 1322-char remark

   Show marketing remark (1322 chars)

   Step into timeless charm and endless opportunity in this inviting 4-bedroom, 1-bath single-family home nestled on a quiet dead-end street in Bridgeport's highly sought-after North End. Brimming with character and solid craftsmanship, this home offers the perfect canvas to create your dream space. Original hardwood floors grace the second level and portions of the main floor, while wood beam ceilings in the living room and kitchen add warmth, texture, and architectural appeal. Classic details throughout create a welcoming atmosphere you'll love coming home to. Outside, enjoy a generously sized yard ideal for entertaining, gardening, or relaxing in your own private retreat. The large deck is perfect for gatherings, and a convenient storage shed adds practical functionality. A partially finished basement offers exciting potential for a playroom, home office, gym, or hobby space or whatever fits your lifestyle. Additional highlights include off-street parking, a private driveway, and a newer roof, providing peace of mind for years to come. With great bones, character-filled details, and room to personalize, this North End gem is ready for its next chapter. With your vision and some TLC you can unlock its full potential. Schedule your private showing today and experience all this special home has to offer!

2. 2026-04-06
   price $320,000 1322-char remark

   Show marketing remark (1322 chars)

   Step into timeless charm and endless opportunity in this inviting 4-bedroom, 1-bath single-family home nestled on a quiet dead-end street in Bridgeport's highly sought-after North End. Brimming with character and solid craftsmanship, this home offers the perfect canvas to create your dream space. Original hardwood floors grace the second level and portions of the main floor, while wood beam ceilings in the living room and kitchen add warmth, texture, and architectural appeal. Classic details throughout create a welcoming atmosphere you'll love coming home to. Outside, enjoy a generously sized yard ideal for entertaining, gardening, or relaxing in your own private retreat. The large deck is perfect for gatherings, and a convenient storage shed adds practical functionality. A partially finished basement offers exciting potential for a playroom, home office, gym, or hobby space or whatever fits your lifestyle. Additional highlights include off-street parking, a private driveway, and a newer roof, providing peace of mind for years to come. With great bones, character-filled details, and room to personalize, this North End gem is ready for its next chapter. With your vision and some TLC you can unlock its full potential. Schedule your private showing today and experience all this special home has to offer!

3. 2026-03-28
   status Active 1322-char remark

   Show marketing remark (1322 chars)

   Step into timeless charm and endless opportunity in this inviting 4-bedroom, 1-bath single-family home nestled on a quiet dead-end street in Bridgeport's highly sought-after North End. Brimming with character and solid craftsmanship, this home offers the perfect canvas to create your dream space. Original hardwood floors grace the second level and portions of the main floor, while wood beam ceilings in the living room and kitchen add warmth, texture, and architectural appeal. Classic details throughout create a welcoming atmosphere you'll love coming home to. Outside, enjoy a generously sized yard ideal for entertaining, gardening, or relaxing in your own private retreat. The large deck is perfect for gatherings, and a convenient storage shed adds practical functionality. A partially finished basement offers exciting potential for a playroom, home office, gym, or hobby space or whatever fits your lifestyle. Additional highlights include off-street parking, a private driveway, and a newer roof, providing peace of mind for years to come. With great bones, character-filled details, and room to personalize, this North End gem is ready for its next chapter. With your vision and some TLC you can unlock its full potential. Schedule your private showing today and experience all this special home has to offer!

4. 2026-03-17
   status Under Contract 1322-char remark

   Show marketing remark (1322 chars)

   Step into timeless charm and endless opportunity in this inviting 4-bedroom, 1-bath single-family home nestled on a quiet dead-end street in Bridgeport's highly sought-after North End. Brimming with character and solid craftsmanship, this home offers the perfect canvas to create your dream space. Original hardwood floors grace the second level and portions of the main floor, while wood beam ceilings in the living room and kitchen add warmth, texture, and architectural appeal. Classic details throughout create a welcoming atmosphere you'll love coming home to. Outside, enjoy a generously sized yard ideal for entertaining, gardening, or relaxing in your own private retreat. The large deck is perfect for gatherings, and a convenient storage shed adds practical functionality. A partially finished basement offers exciting potential for a playroom, home office, gym, or hobby space or whatever fits your lifestyle. Additional highlights include off-street parking, a private driveway, and a newer roof, providing peace of mind for years to come. With great bones, character-filled details, and room to personalize, this North End gem is ready for its next chapter. With your vision and some TLC you can unlock its full potential. Schedule your private showing today and experience all this special home has to offer!

5. 2026-03-01
   listed $335,000 Active 1322-char remark

   Show marketing remark (1322 chars)

   Step into timeless charm and endless opportunity in this inviting 4-bedroom, 1-bath single-family home nestled on a quiet dead-end street in Bridgeport's highly sought-after North End. Brimming with character and solid craftsmanship, this home offers the perfect canvas to create your dream space. Original hardwood floors grace the second level and portions of the main floor, while wood beam ceilings in the living room and kitchen add warmth, texture, and architectural appeal. Classic details throughout create a welcoming atmosphere you'll love coming home to. Outside, enjoy a generously sized yard ideal for entertaining, gardening, or relaxing in your own private retreat. The large deck is perfect for gatherings, and a convenient storage shed adds practical functionality. A partially finished basement offers exciting potential for a playroom, home office, gym, or hobby space or whatever fits your lifestyle. Additional highlights include off-street parking, a private driveway, and a newer roof, providing peace of mind for years to come. With great bones, character-filled details, and room to personalize, this North End gem is ready for its next chapter. With your vision and some TLC you can unlock its full potential. Schedule your private showing today and experience all this special home has to offer!

6. 2026-02-19
   historical
7. 2025-11-05
   price $350,000
8. 2025-09-18
   price $374,900
9. 2025-09-02
   listed $384,900 Active

ⓘ 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: $6,435 · $536/mo
• Projected year-2 tax: $6,642 · $553/mo
• Expected delta: +$206/yr (+$17/mo · 3.2%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone X (unshaded) · 57% 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 41% 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: $39,845
• − Mortgage interest: −$17,925
• − Property taxes: −$6,435
• − Insurance: −$1,600
• − Repairs & maintenance: −$3,188
• − Management: −$3,188
• − Depreciation: −$9,309
• Taxable loss: −$1,799
• Est. tax savings @ 24.0%: +$432
• After-tax cash flow: $3,737/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

-16.9% since first listed

9 events — show timeline

• 2026-05-05 Pending — Smart MLS
• 2026-04-06 Price Changed $320,000 Smart MLS
• 2026-03-28 Relisted — Smart MLS
• 2026-03-17 Pending — Smart MLS
• 2026-03-01 Listed $335,000 Smart MLS
• 2026-02-19 Listing Removed — Smart MLS
• 2025-11-05 Price Changed $350,000 Smart MLS
• 2025-09-18 Price Changed $374,900 Smart MLS
• 2025-09-02 Listed $384,900 Smart MLS

Property tax history

+2.3%/yr

Latest (2023): $6,435 · +0.0% YoY. Source: county tax records.