305 Westport Tpke · Fairfield, CT 06824

$795,000

2 bd · 2.0 ba · 1,484 sqft · SingleFamily public records · 84 Days on market

Built 1966 2.25 ac lot $536/sqft · 11% above area Est $984k · 19% under

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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).

• ARV discount +15.0/15.0
• Schools +6.3/10.0
• Rent growth +5.0/5.0
• Cash flow +4.5/30.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.2/10.0
• DSCR +0.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Rare 2.25-acre riverfront opportunity on the Fairfield/Westport line. This exceptional 538-foot deep lot offers 158 feet of frontage along the Aspetuck River, creating a private, scenic setting with significant upside. A unique feature is the ability to site a new home further back from Westport Turnpike, maximizing privacy and long-term value. The existing 3-bedroom, 2-bath ranch offers comfortable single-level living with immediate usability or rental potential. The sun-filled living room and functional kitchen provide a warm, inviting layout, while the main level includes two bedrooms and a full bath. The walk-out lower level adds versatility with a third bedroom, second full bath, and additional living space, opening directly to the expansive backyard and riverfront. Whether you choose to enjoy as-is, renovate, or build new, this property offers a rare combination of depth, frontage, and location. Convenient to Westport, Fairfield, major highways, and local amenities. A unique opportunity to create a private estate in a premier riverfront setting.

Key facts

• Walk-out lower level
• 538 foot deep lot
• 158 feet of frontage

Tags

• 538 FOOT DEEP LOT
• 158 FEET OF FRONTAGE
• PRIVATE SCENIC SETTING
• WALK-OUT LOWER LEVEL
• EXPANSIVE BACKYARD
• PREMIER RIVERFRONT SETTING

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath single-family listed at $795k.

Deal economics

• At list price, monthly cash flow is $-2k ($-24k/yr) — negative.
• To cash-flow at today's rent, offer at most $435k (45.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $414k (47.9% below list).
• Recommended offer: $414k (47.9% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• Fairfield School District (suburban): math 61% / reading 72% proficiency, ranked #21 of 153 in CT (top 14%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 7% free/reduced lunch — higher-income household profile.
• Zoned schools: Burr Elementary School (math 72% / reading 77%, grade A, #44 of 553 statewide, top 10%, 352 students, 14% FRL); Tomlinson Middle School (math 40% / reading 63%, grade C, #77 of 175 statewide, top 44%, 621 students, 30% FRL); Fairfield Warde High School (math 52% / reading 73%, grade B-, #39 of 194 statewide, top 20%, 1,418 students, 25% FRL) — zoned schools average 23% FRL vs 7% district-wide (16 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: Rents rising fast (+12.4%/yr); 152 active listings in the ZIP; high-income renter base; 852 units permitted in Greater Bridgeport Planning Region in 2024 (698 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $5k of loan paydown is wiped out by about $24k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 84 days — a 6% lower offer ($747k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 31y 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 $450k; list at $795k implies a 77% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• 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 $414,132 (47.9% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 84 days. Have you received any prior offers? Is the seller open to a 48% concession, seller financing, or rate buy-down credit?
3. Built in 1966 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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.
8. 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.
9. 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: 0.52% ✗
• Cap rate: 3.21%
• Cash-on-cash: -11.00%
• DSCR: 0.51
• GRM: 16.0

CMA / ARV

• ARV (median comp): $983,511
• List price: $795,000
• Delta: -19.17%
• Verdict: UNDERPRICED
• Comps: 11 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
208 Wildflower Ln	0.51mi	3/2.0 (+1)	1,512 (+2%)	1mo	$977,000	$646	67

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 · 8.0% rent growth · sell at horizon

5-year hold

• IRR: -31.3%
• Equity multiple: -0.06×
• Total profit: $-236,927
• Equity at exit: $118,537

10-year hold

• IRR: -19.5%
• Equity multiple: -0.23×
• Total profit: $-274,220
• Equity at exit: $68,737

Cash invested: $222,600 (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 06824

• Rents YoY: 12.4%
• Active inventory: 152
• Price-to-rent: 16.0×

Monthly cashflow live

• Estimated rent: $4,141 medium
• Mortgage (P&I): −$4,169
• Tax from tax record: −$812 /mo · $9,738/yr
• Insurance: −$331
• HOA: −$0
• Vacancy / Maint / Mgmt: −$870
• Net cashflow: $-2,040

Break-even live

Break-even rent $6,724

Max offer price $434,595

Occupancy floor —

Sensitivity live

Price	-10% $-1,590	-5% $-1,815	+0% $-2,040	+5% $-2,265	+10% $-2,490
Rent	-10% $-2,367	-5% $-2,204	+0% $-2,040	+5% $-1,877	+10% $-1,713
Rate	-1.0pp $-1,640	-0.5pp $-1,838	base $-2,040	+0.5pp $-2,246	+1.0pp $-2,456

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: $198,750
• Closing costs: $23,850
• Reserves months: —
• Total cash needed: —

Listing history 27 events

1. 2026-06-22
   days on market $795,000 Active 84 DOM
2. 2026-06-18
   days on market $795,000 Active 81 DOM
3. 2026-06-17
   days on market $795,000 Active 80 DOM
4. 2026-06-16
   days on market $795,000 Active 79 DOM
5. 2026-06-15
   days on market $795,000 Active 78 DOM
6. 2026-06-13
   days on market $795,000 Active 76 DOM
7. 2026-06-10
   days on market $795,000 Active 73 DOM
8. 2026-06-09
   days on market $795,000 Active 72 DOM
9. 2026-06-08
   days on market $795,000 Active 71 DOM
10. 2026-06-07
    days on market $795,000 Active 70 DOM
11. 2026-06-05
    days on market $795,000 Active 67 DOM
12. 2026-06-03
    days on market $795,000 Active 66 DOM
13. 2026-06-03
    days on market $795,000 Active 65 DOM
14. 2026-06-01
    days on market $795,000 Active 64 DOM
15. 2026-05-31
    days on market $795,000 Active 63 DOM
16. 2026-05-01
    price $795,000 1071-char remark

    Show marketing remark (1071 chars)

    Rare 2.25-acre riverfront opportunity on the Fairfield/Westport line. This exceptional 538-foot deep lot offers 158 feet of frontage along the Aspetuck River, creating a private, scenic setting with significant upside. A unique feature is the ability to site a new home further back from Westport Turnpike, maximizing privacy and long-term value. The existing 3-bedroom, 2-bath ranch offers comfortable single-level living with immediate usability or rental potential. The sun-filled living room and functional kitchen provide a warm, inviting layout, while the main level includes two bedrooms and a full bath. The walk-out lower level adds versatility with a third bedroom, second full bath, and additional living space, opening directly to the expansive backyard and riverfront. Whether you choose to enjoy as-is, renovate, or build new, this property offers a rare combination of depth, frontage, and location. Convenient to Westport, Fairfield, major highways, and local amenities. A unique opportunity to create a private estate in a premier riverfront setting.

17. 2026-03-28
    listed $819,000 Active 1071-char remark

    Show marketing remark (1071 chars)

    Rare 2.25-acre riverfront opportunity on the Fairfield/Westport line. This exceptional 538-foot deep lot offers 158 feet of frontage along the Aspetuck River, creating a private, scenic setting with significant upside. A unique feature is the ability to site a new home further back from Westport Turnpike, maximizing privacy and long-term value. The existing 3-bedroom, 2-bath ranch offers comfortable single-level living with immediate usability or rental potential. The sun-filled living room and functional kitchen provide a warm, inviting layout, while the main level includes two bedrooms and a full bath. The walk-out lower level adds versatility with a third bedroom, second full bath, and additional living space, opening directly to the expansive backyard and riverfront. Whether you choose to enjoy as-is, renovate, or build new, this property offers a rare combination of depth, frontage, and location. Convenient to Westport, Fairfield, major highways, and local amenities. A unique opportunity to create a private estate in a premier riverfront setting.

18. 2025-01-19
    historical $4,750
19. 2024-12-05
    listed $4,750
20. 2024-09-28
    historical $5,000
21. 2024-09-28
    historical
22. 2024-08-14
    listed $5,000
23. 2024-08-13
    listed $749,000 Active
24. 2021-05-24
    soldstatus $450,000
25. 1995-12-14
    soldstatus $280,000
26. 1995-09-30
    historical
27. 1995-03-03
    listed $289,000

ⓘ 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: $9,738 · $812/mo
• Projected year-2 tax: $13,376 · $1,115/mo
• Expected delta: +$3,638/yr (+$303/mo · 37.4%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 5/10 Major 7 d/yr ≥98°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: $49,696
• − Mortgage interest: −$44,532
• − Property taxes: −$9,738
• − Insurance: −$3,975
• − Repairs & maintenance: −$3,976
• − Management: −$3,976
• − Depreciation: −$23,127
• Taxable loss: −$39,628
• Est. tax savings @ 24.0%: +$9,511
• After-tax cash flow: $-14,971/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: Fairfield School District
• NCES district ID: 0901530
• Math proficiency: 61% ▼ -10.00%
• Reading proficiency: 72% ▼ -7.00%
• Median HH income: $119,139
• Composite: 63.03/100
• National rank: #650
• State rank: #21 of 153 in CT

Livability — Fairfield

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• County: Fairfield County · 765,532 people
• City population: 58,698
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 36,716
• Household income: $193,300
• Rent vs Own: 15.6% rent · 84.4% own
• Severe rent burden: 380.0

Population outlook (Greater Bridgeport County) Hauer SSP2

• By 2040: 365,581

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (88%)
• Race & ethnicity: White 88% Asian 5% Hispanic / Latino 5% Two or more races 5%
• Common ancestry: Romanian 7% Lithuanian 2% Scotch-Irish 2%
• Foreign-born: 11% · Canada, China
• Languages at home: 87% English-only · Other Indo-European 4% Spanish 3% Arabic 1%

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: ▼ -723.44%
• Current HPI: 178.7206
• Rent YoY: ▲ 12.37%
• 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

+175.1% since first listed

12 events — show timeline

• 2026-05-01 Price Changed $795,000 Smart MLS
• 2026-03-28 Listed $819,000 Smart MLS
• 2025-01-19 Rental Removed $4,750 SMARTMLS
• 2024-12-05 Listed for Rent $4,750 SMARTMLS
• 2024-09-28 Rental Removed $5,000 SMARTMLS
• 2024-09-28 Listing Removed — Smart MLS
• 2024-08-14 Listed for Rent $5,000 SMARTMLS
• 2024-08-13 Listed $749,000 Smart MLS
• 2021-05-24 Sold (Public Records) $450,000 Public Records
• 1995-12-14 Sold (Public Records) $280,000 Public Records
• 1995-09-30 Listing Removed — Smart MLS
• 1995-03-03 Listed $289,000 Smart MLS

Property tax history

+1.2%/yr

Latest (2023): $9,738 · +1.0% YoY. Source: county tax records.