285 Sandy Beach Rd · Greenport West, NY 11944

$1,095,000

4 bd · 3.5 ba · 2,500 sqft · SingleFamily · 92 Days on market

Built 2025 0.33 ac lot $438/sqft · 25% below area Est $1454k · 25% under

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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
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +4.5/10.0
• Livability +2.9/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

Key facts

• Chef style kitchen
• Soaking tub
• Raised deck

Tags

• GAS BURNING FIREPLACE
• CHEF STYLE KITCHEN
• RAISED DECK
• PEEK A BOO WATER VIEWS
• SPA INSPIRED EN SUITE BATH
• SOAKING TUB

What this means for you Summary

Snapshot

• This is a 4-bed/3.5-bath single-family listed at $1.09M.

Deal economics

• At list price, monthly cash flow is $12k ($138k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($24k rent vs $1.09M).
• Recommended offer: $996k (9.0% below list) — sets the bar for market timing.
• Cap rate 19.4% vs local median 8.0% in Greenport West — 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 58/100 on livability (#1,073 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: schools D+, amenities F, commute F.
• Greenport Union Free School District (town): math 55% / reading 45% proficiency, ranked #450 of 755 in NY (top 60%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 67 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 62% of comp listings sitting > 30 days — soft ceiling on asking rent; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $8k of loan paydown is wiped out by about $33k 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.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $307k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• It's been on market 92 days — a 9% lower offer ($996k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $200k (15%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $275k; list at $1.09M implies a 298% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $427/mo.
• Climate carrying-cost: in FEMA flood zone AE (mandatory federal flood insurance); severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $996,450 (9.0% below list)

Questions for the listing agent

1. It's been on market 92 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
6. 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.
7. 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.
8. 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: 2.18% ✓
• Cap rate: 19.38%
• Cash-on-cash: 46.73%
• DSCR: 3.08
• GRM: 3.8

CMA / ARV

• ARV (median comp): $1,453,647
• List price: $1,095,000
• Delta: -24.67%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 8 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
165 Anglers Rd	0.06mi	4/4.0	2,650 (+6%)	19mo	$1,450,000	$547	69
430 Snug Harbor Rd	0.42mi	3/4.0 (-1)	2,455 (-2%)	12mo	$1,900,000	$774	60
155 Bridge St	0.57mi	5/3.5 (+1)	2,400 (-4%)	2mo	$1,470,000	$613	60
168 Bay Ave	0.50mi	3/1.5 (-1)	2,600 (+4%)	3mo	$999,000	$384	54
675 Champlin Pl	0.54mi	4/2.5	2,650 (+6%)	10mo	$2,200,000	$830	52
1111 Main St	0.69mi	3/2.0 (-1)	2,363 (-6%)	6mo	$1,200,000	$508	42
529 2nd St	0.58mi	3/1.5 (-1)	2,200 (-12%)	10mo	$1,100,000	$500	32
3900 Route 25	0.55mi	3/2.5 (-1)	2,162 (-14%)	19mo	$1,090,000	$504	27

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 · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 42.2%
• Equity multiple: 2.81×
• Total profit: $556,056
• Equity at exit: $163,268

10-year hold

• IRR: 48.3%
• Equity multiple: 5.66×
• Total profit: $1,429,273
• Equity at exit: $94,676

Cash invested: $306,600 (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 11944

• Home prices YoY: -23.7%
• Active inventory: 67
• Price-to-rent: 3.8×

Monthly cashflow live

• Estimated rent: $23,841 high
• Mortgage (P&I): −$5,742
• Tax from tax record: −$696 /mo · $8,353/yr
• Insurance: −$456
• Flood insurance flood zone: −$427 /mo · $5,118/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,007
• Net cashflow: $11,513

Break-even live

Break-even rent $9,267

Max offer price $1,095,000

Occupancy floor 47%

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: $273,750
• Closing costs: $32,850
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
312 5th Ave Greenport, NY	4.0	2.0	1900	$12,000	$6.32	44d	1	0.77mi
485 Sutton Pl Greenport, NY	4.0	2.5	2026	$20,000	$9.87	44d	1	0.93mi
950 Tasker Ln Greenport, NY	4.0	3.5	3500	$36,000	$10.29	44d	1	1.10mi
1000 Sound Dr Greenport, NY	5.0	4.5	3700	$45,000	$12.16	44d	1	1.24mi
580 South Ln East Marion, NY	3.0	2.5	2000	$20,000	$10.00	19d	1	1.25mi
131 6th St Unit G Greenport, NY	3.0	2.5	2238	$5,000	$2.23	24d	1	1.31mi
300 Marion Pl East Marion, NY	3.0	2.0	1750	$19,000	$10.86	24d	1	1.33mi
2700 Sound Dr Greenport, NY	5.0	3.0	3700	$25,000	$6.76	44d	1	1.40mi

Listing history 6 events

1. 2026-05-18
   status Pending 1133-char remark

   Show marketing remark (1133 chars)

   Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

2. 2026-05-05
   price $1,095,000 1133-char remark

   Show marketing remark (1133 chars)

   Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

3. 2026-03-24
   price $1,195,000 1133-char remark

   Show marketing remark (1133 chars)

   Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

4. 2026-02-18
   status Active 1133-char remark

   Show marketing remark (1133 chars)

   Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

5. 2026-02-11
   listed $1,295,000 Active 1133-char remark

   Show marketing remark (1133 chars)

   Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

6. 2023-03-23
   soldstatus $275,000

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

Tax reassessment forecast NY · Partial reset (capped growth)

• Current annual tax: $8,353 · $696/mo
• Projected year-2 tax: $13,429 · $1,119/mo
• Expected delta: +$5,076/yr (+$423/mo · 60.8%)

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

Climate risk First Street

• 🌊 Flood 5/10 Major FEMA zone AE · 41% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥90°F today · 19 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $286,093
• − Mortgage interest: −$61,337
• − Property taxes: −$8,353
• − Insurance: −$10,594
• − Repairs & maintenance: −$22,887
• − Management: −$22,887
• − Depreciation: −$31,855
• Taxable income: $128,180
• Est. tax owed @ 24.0%: −$30,763
• After-tax cash flow: $107,396/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: Greenport Union Free School District
• NCES district ID: 3612840
• Math proficiency: 55% ▲ 5.00%
• Reading proficiency: 45% ▼ -5.00%
• Median HH income: $54,490
• Composite: 45.25/100
• National rank: #5759
• State rank: #450 of 755 in NY

Livability — Greenport West

• Score: 58/100
• State rank: #1073
• US rank: #21520

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Greenport West, NY
• Population (ZIP): 4,744

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 (69%)
• Race & ethnicity: White 69% Hispanic / Latino 23% Two or more races 6% Black 4% Asian 2%
• Hispanic origin (detail): Mexican 5% Puerto Rican 2%
• Common ancestry: Romanian 6% Lithuanian 2% Subsaharan African 2%
• Foreign-born: 19% · Canada, China
• Languages at home: 69% English-only · Spanish 22% German/W. Germanic 3% Russian/Polish/Slavic 2%

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: ▼ -143.97%
• Current HPI: 462.3431
• Rent YoY: —
• Metro: —
• 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

+298.2% since first listed

6 events — show timeline

• 2026-05-18 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-05-05 Price Changed $1,095,000 OneKey® MLS as Distributed by MLS Grid
• 2026-03-24 Price Changed $1,195,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-18 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-02-11 Listed $1,295,000 OneKey® MLS as Distributed by MLS Grid
• 2023-03-23 Sold (Public Records) $275,000 Public Records

Property tax history

+16.1%/yr

Latest (2025): $8,353 · +0.0% YoY. Source: county tax records.