161 Monroe Dr · Montauk, NY 11954

$2,895,000

5 bd · 4.0 ba · 2,380 sqft · SingleFamily · 301 Days on market

Built 1982 10,019 sqft lot $1216/sqft · 31% below area Est $4194k · 31% 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 +15.8/30.0
• ARV discount +15.0/15.0
• Schools +5.1/10.0
• DSCR +4.9/10.0
• Appreciation +4.1/10.0
• Livability +3.5/5.0
• 1% rule +3.1/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Welcome to 161 Monroe Drive, Montauk, NY - a haven of tranquility and modern living. This property boasts five spacious bedrooms and four full bathrooms, making it an ideal space for comfort and relaxation. The main house, featuring Living with fireplace, kitchen, dining, three bedrooms and three baths, offers a full basement for extra storage or living space. Experience the luxury of a newly installed inground heated pool, complete with an automatic cover for ease and convenience. Adjacent to the pool, a hot tub awaits for those chillier evenings or when you just need to unwind. The property also includes an attached, legal cottage with two additional bedrooms, a bathroom, a living area, and a kitchenette. This space provides flexibility for guests or a potential home office. Located in the serene Hither Hills neighborhood, this home comes with private ocean beach rights, allowing you to enjoy the beautiful Montauk shoreline at your leisure. The property is also equipped with a new septic system for peace of mind. Come explore this gem in Montauk, where modern amenities meet the charm of coastal living., Additional information: Appearance:Very good,Interior Features:Guest Quarters,Lr/Dr

Key facts

• Hot tub
• Automatic cover
• New septic system

Tags

• AUTOMATIC COVER
• HOT TUB
• ATTACHED LEGAL COTTAGE
• PRIVATE OCEAN BEACH RIGHTS
• NEW SEPTIC SYSTEM

What this means for you Summary

Snapshot

• This is a 5-bed/4.0-bath single-family listed at $2.90M.

Deal economics

• At list price, monthly cash flow is $1k ($16k/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 $2.33M (19.4% below list).
• Recommended offer: $2.33M (19.4% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 69/100 on livability (#474 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, health & safety A; Watch: housing C-, amenities F, commute F.
• Montauk Union Free School District (town): math 50% / reading 60% proficiency, ranked #311 of 755 in NY (top 41%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 39 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals leasing fast (median 0d on market — plan ~1-2 weeks tenant-placement turnaround); high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $23,331/mo this rent would consume 196% of the median local household income ($143k/yr) (locally 20% 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 (-1.8%/yr); year-one equity from $20k of loan paydown is wiped out by about $52k of value loss. Plan a longer hold.
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.

Negotiation context

• It's been on market 301 days — a 12% lower offer ($2.55M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 2y ago; this cycle's ask has dropped $400k (12%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $846k; list at $2.90M implies a 242% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $2,333,118 (19.4% below list)

Questions for the listing agent

1. It's been on market 301 days. Have you received any prior offers? Is the seller open to a 19% concession, seller financing, or rate buy-down credit?
2. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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.
5. 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.
6. 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: 0.81% ✗
• Cap rate: 6.85%
• Cash-on-cash: 1.98%
• DSCR: 1.09
• GRM: 10.3

CMA / ARV

• ARV (median comp): $4,193,911
• List price: $2,895,000
• Delta: -30.97%
• Verdict: UNDERPRICED
• Comps: 3 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
74 Adams Dr	0.16mi	4/4.5 (-1)	2,500 (+5%)	19mo	$2,850,000	$1,140	62

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-1.78% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -7.1%
• Equity multiple: 0.71×
• Total profit: $-234,961
• Equity at exit: $591,759

10-year hold

• IRR: 0.5%
• Equity multiple: 1.04×
• Total profit: $34,879
• Equity at exit: $534,137

Cash invested: $810,600 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 15 Strongly Tenant-Friendly
• State New York: 15 Strongly Tenant-Friendly · D+10
• County: — inherits STATE
• City: — inherits STATE

NYC rent stabilization (~1M units); 2019 HSTPA strengthened tenant rights; courts deeply backlogged.

Methodology + full state rankings →

ZIP-level market 11954

• Home prices YoY: -0.3%
• Active inventory: 39
• Price-to-rent: 10.3×

Monthly cashflow live

• Estimated rent: $23,331 medium
• Mortgage (P&I): −$15,182
• Tax from tax record: −$708 /mo · $8,492/yr
• Insurance: −$1,206
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,900
• Net cashflow: $1,336

Break-even live

Break-even rent $21,640

Max offer price $2,895,000

Occupancy floor 89%

Sensitivity live

Price	-10% $2,975	-5% $2,155	+0% $1,336	+5% $517	+10% $-303
Rent	-10% $-507	-5% $414	+0% $1,336	+5% $2,258	+10% $3,179
Rate	-1.0pp $2,794	-0.5pp $2,072	base $1,336	+0.5pp $586	+1.0pp $-177

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: $723,750
• Closing costs: $86,850
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
104 Bryan Rd Montauk, NY	4.0	3.5	2000	$30,000	$15.00	0d	1	0.16mi
70 S Delrey Rd Montauk, NY	4.0	3.0	2000	$30,000	$15.00	0d	1	0.54mi
155 S Essex St Montauk, NY	5.0	2.0	2348	$55,000	$23.42	22d	1	1.45mi

Listing history 19 events

1. 2026-06-18
   days on market $2,895,000 Active 301 DOM
2. 2026-06-17
   days on market $2,895,000 Active 300 DOM
3. 2026-06-16
   days on market $2,895,000 Active 299 DOM
4. 2026-06-15
   days on market $2,895,000 Active 298 DOM
5. 2026-06-13
   days on market $2,895,000 Active 296 DOM
6. 2026-06-13
   days on market $2,895,000 Active 295 DOM
7. 2026-06-09
   days on market $2,895,000 Active 292 DOM
8. 2026-06-08
   days on market $2,895,000 Active 291 DOM
9. 2026-06-07
   days on market $2,895,000 Active 290 DOM
10. 2026-06-04
    days on market $2,895,000 Active 287 DOM
11. 2026-06-03
    days on market $2,895,000 Active 286 DOM
12. 2026-06-02
    days on market $2,895,000 Active 285 DOM
13. 2026-06-01
    days on market $2,895,000 Active 284 DOM
14. 2026-05-31
    days on market $2,895,000 Active 283 DOM
15. 2025-10-10
    price $2,895,000 1210-char remark

    Show marketing remark (1210 chars)

    Welcome to 161 Monroe Drive, Montauk, NY - a haven of tranquility and modern living. This property boasts five spacious bedrooms and four full bathrooms, making it an ideal space for comfort and relaxation. The main house, featuring Living with fireplace, kitchen, dining, three bedrooms and three baths, offers a full basement for extra storage or living space. Experience the luxury of a newly installed inground heated pool, complete with an automatic cover for ease and convenience. Adjacent to the pool, a hot tub awaits for those chillier evenings or when you just need to unwind. The property also includes an attached, legal cottage with two additional bedrooms, a bathroom, a living area, and a kitchenette. This space provides flexibility for guests or a potential home office. Located in the serene Hither Hills neighborhood, this home comes with private ocean beach rights, allowing you to enjoy the beautiful Montauk shoreline at your leisure. The property is also equipped with a new septic system for peace of mind. Come explore this gem in Montauk, where modern amenities meet the charm of coastal living., Additional information: Appearance:Very good,Interior Features:Guest Quarters,Lr/Dr

16. 2025-08-21
    listed $3,295,000 Active 1210-char remark

    Show marketing remark (1210 chars)

    Welcome to 161 Monroe Drive, Montauk, NY - a haven of tranquility and modern living. This property boasts five spacious bedrooms and four full bathrooms, making it an ideal space for comfort and relaxation. The main house, featuring Living with fireplace, kitchen, dining, three bedrooms and three baths, offers a full basement for extra storage or living space. Experience the luxury of a newly installed inground heated pool, complete with an automatic cover for ease and convenience. Adjacent to the pool, a hot tub awaits for those chillier evenings or when you just need to unwind. The property also includes an attached, legal cottage with two additional bedrooms, a bathroom, a living area, and a kitchenette. This space provides flexibility for guests or a potential home office. Located in the serene Hither Hills neighborhood, this home comes with private ocean beach rights, allowing you to enjoy the beautiful Montauk shoreline at your leisure. The property is also equipped with a new septic system for peace of mind. Come explore this gem in Montauk, where modern amenities meet the charm of coastal living., Additional information: Appearance:Very good,Interior Features:Guest Quarters,Lr/Dr

17. 2024-10-29
    price $2,995,000
18. 2024-09-20
    listed $3,195,000 Active
19. 2020-08-25
    soldstatus $846,250

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

Tax reassessment forecast NY · Partial reset (capped growth)

• Current annual tax: $8,492 · $708/mo
• Projected year-2 tax: $28,709 · $2,392/mo
• Expected delta: +$20,217/yr (+$1,685/mo · 238.1%)

ⓘ 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 4/10 Moderate 7 d/yr ≥88°F today · 20 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $279,974
• − Mortgage interest: −$162,165
• − Property taxes: −$8,492
• − Insurance: −$14,475
• − Repairs & maintenance: −$22,398
• − Management: −$22,398
• − Depreciation: −$84,218
• Taxable loss: −$34,172
• Est. tax savings @ 24.0%: +$8,201
• After-tax cash flow: $24,233/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: Montauk Union Free School District
• NCES district ID: 3619710
• Math proficiency: 50% ▼ -10.00%
• Reading proficiency: 60% ▬ 0.00%
• Median HH income: $73,702
• Composite: 50.99/100
• National rank: #3831
• State rank: #311 of 755 in NY

Livability — Montauk

• Score: 69/100
• State rank: #474
• US rank: #8373

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Montauk, NY
• County: Suffolk County · 679,920 people
• City population: 4,223
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 4,223
• Household income: $142,961
• Rent vs Own: 21.3% rent · 78.7% own
• Severe rent burden: 20.0

Population outlook (Suffolk County) Hauer SSP2

• Today (2025): 1,505,262 people
• By 2030: 1,498,318 · -0.5%
• By 2040: 1,471,101 · -2.3%
• By 2050: 1,424,848 · -5.3%
• By 2075: 1,337,157 · -11.2%
• By 2100: 1,217,720 · -19.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (89%)
• Race & ethnicity: White 89% Hispanic / Latino 6% Two or more races 4% Black 1%
• Hispanic origin (detail): Mexican 2% Dominican 1%
• Common ancestry: Romanian 4% Scotch-Irish 3% Italian 3%
• Foreign-born: 10% · Canada, Jamaica
• Languages at home: 90% English-only · Spanish 4% Russian/Polish/Slavic 4% Other Indo-European 1%

Political lean MEDSL · Suffolk

• 2024 margin: Lean R (+10.0) · D 45.0% · R 55.0%
• 2008→2024 swing: -16.0pp toward R · 2008: 6.0pp · 2024: -10.0pp
• All cycles: 2024: R+10.0 2020: R+0.0 2016: R+8.2 2012: D+2.9 2008: D+6.0

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -1.78%
• Current HPI: 577.7344
• Rent YoY: —
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

Industry mix (Fortune 500 HQ in NY)

Industry	F500 HQs	Revenue
▸Financial Services	10	$950B
▸Consumer Goods	9	$162B
▸Insurance	4	$225B
▸Telecommunications	2	$144B
▸Pharmaceuticals	2	$112B
▸Media / Entertainment	2	$69B

Price history

+242.1% since first listed

5 events — show timeline

• 2025-10-10 Price Changed $2,895,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-21 Listed $3,295,000 OneKey® MLS as Distributed by MLS Grid
• 2024-10-29 Price Changed $2,995,000 OneKey® MLS as Distributed by MLS Grid
• 2024-09-20 Listed $3,195,000 OneKey® MLS as Distributed by MLS Grid
• 2020-08-25 Sold (Public Records) $846,250 Public Records

Property tax history

+1.9%/yr

Latest (2025): $8,492 · +0.0% YoY. Source: county tax records.