145 Osprey Nest Rd · Greenport West, NY 11944

$1,500,000

4 bd · 3.0 ba · 2,528 sqft · SingleFamily · 58 Days on market

Built 1987 0.29 ac lot $593/sqft · 19% below area Est $1849k · 19% under $38/mo HOA

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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

Newly Reduced Price! Welcome to 145 Osprey Nest Road, a gem nestled in the heart of the charming Cleaves Point Beach Community. This home, with its resort-like atmosphere, offers an enticing blend of comfort and convenience. As a member of the Community, this property affords use of a private Bay Beach, in addition to having a community marina with some private docks and mooring lots, in a protected inlet off the Peconic Bay. This spacious home boasts four bedrooms and three bathrooms, designed with a modern aesthetic and an open, airy layout. The primary suite offers a private retreat, while three additional guest bedrooms share a full bath. The home's generous windows and soaring ceiling

Key facts

• Private deeded dock
• Village of greenport
• Outdoor shower

Tags

• PRIVATE DEEDED DOCK
• ENDLESS POOL SWIM SPA
• OUTDOOR SHOWER
• CORNER LOT
• MATURE HEDGES
• VILLAGE OF GREENPORT

Property features AI

Finance

• HOA & community: Part of Cleaves Point Beach Community association; Annual association fee of $450; Association amenities include powered boats allowed and other community features; Association fee covers common area maintenance and snow removal; Additional annual fee $450 (Annual Association Fee)

Exterior

• Parking: Attached garage and driveway; 2-car garage; No carport
• Security: Fire alarm; Smoke detectors
• Utilities: PSEG electric; Septic tank; Cable connected; Electricity connected; Water connected
• Home design: Single-family residence; Three or more levels; Measured living area
• Construction: Built with wood siding; Concrete perimeter foundation
• Exterior features: Wood siding; Corner lot; Landscaped grounds; Level lot; Near golf course; Near shops; Outdoor deck; Private outdoor pool (outdoor pool, other pool features); Garage(s) as other structures; No waterfront

Interior

• Kitchen: Granite counters; Open, eat-in kitchen; Electric oven and electric range; Microwave; Dishwasher; Refrigerator
• Bedrooms: Total of 8 rooms (includes bedrooms and living spaces)
• Flooring: Hardwood floors; Tile floors
• Bathrooms: 3 full bathrooms; Basement includes unfinished full bath access (basement present)
• Heating & cooling: Baseboard heating (oil); Central air conditioning; Wood-burning fireplace in living room
• Interior features: First-floor full bath; Ceiling fans; Eat-in kitchen; Granite counters; High ceilings; Open floorplan with open kitchen; Primary bathroom; Recessed lighting; Storage; Walk-through kitchen; Skylights; Wall of windows; Oversized windows; Deck
• Laundry & utility: Laundry room; Washer and dryer; Laundry located in bathroom (laundry on-bath option)

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $1.50M.

Deal economics

• At list price, monthly cash flow is $8k ($99k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($22k rent vs $1.50M).
• Recommended offer: $1.46M (3.0% below list) — sets the bar for market timing.
• Cap rate 12.9% vs local median 8.1% 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: amenities F, commute F, cost of living 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.
• Zoned schools: Greenport Elementary School (math 47% / reading 62%, grade C, #908 of 2,108 statewide, top 46%, 339 students, 61% FRL); Greenport High School (math 52% / reading 54%, grade C-, #934 of 1,100 statewide, top 86%, 356 students, 63% FRL).
• Market conditions: 69 active listings in the ZIP; 11 comparable units currently listed for rent nearby; rentals lingering (median 46d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 82% 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 $10k of loan paydown is wiped out by about $45k 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 $420k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 58 days — a 3% lower offer ($1.46M) is reasonable based on typical stale-listing flexibility.
• Current owner paid $278k; list at $1.50M implies a 440% 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; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,455,000 (3.0% below list)

Questions for the listing agent

1. It's been on market 58 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
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: 1.50% ✓
• Cap rate: 12.92%
• Cash-on-cash: 23.66%
• DSCR: 2.05
• GRM: 5.6

CMA / ARV

• ARV (median comp): $1,849,122
• List price: $1,500,000
• Delta: -18.88%
• Verdict: UNDERPRICED
• Comps: 14 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
430 Snug Harbor Rd	0.16mi	3/4.0 (-1)	2,455 (-3%)	12mo	$1,900,000	$774	69
165 Anglers Rd	0.34mi	4/4.0	2,650 (+5%)	19mo	$1,450,000	$547	56
2255 Old Orchard Rd	0.73mi	4/3.0	2,310 (-9%)	12mo	$1,131,000	$490	41
1117 Cedar Ln	0.61mi	4/2.0	2,200 (-13%)	9mo	$2,000,000	$909	39
3900 Route 25	0.41mi	3/2.5 (-1)	2,162 (-14%)	19mo	$1,090,000	$504	34

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: 16.8%
• Equity multiple: 1.68×
• Total profit: $284,238
• Equity at exit: $223,655

10-year hold

• IRR: 25.3%
• Equity multiple: 3.20×
• Total profit: $925,873
• Equity at exit: $129,693

Cash invested: $420,000 (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: 69
• Price-to-rent: 5.6×

Monthly cashflow live

• Estimated rent: $22,446 high
• Mortgage (P&I): −$7,866
• Tax from tax record: −$921 /mo · $11,051/yr
• Insurance: −$625
• HOA: −$38
• Vacancy / Maint / Mgmt: −$4,714
• Net cashflow: $8,283

Break-even live

Break-even rent $11,962

Max offer price $1,500,000

Occupancy floor 58%

Sensitivity live

Price	-10% $9,132	-5% $8,707	+0% $8,283	+5% $7,858	+10% $7,434
Rent	-10% $6,509	-5% $7,396	+0% $8,283	+5% $9,169	+10% $10,056
Rate	-1.0pp $9,038	-0.5pp $8,664	base $8,283	+0.5pp $7,894	+1.0pp $7,499

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: $375,000
• Closing costs: $45,000
• Reserves months: —
• Total cash needed: —

Rent comps 11 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
580 South Ln East Marion, NY	3.0	2.5	2000	$20,000	$10.00	21d	1	0.88mi
300 Marion Pl East Marion, NY	3.0	2.0	1750	$19,000	$10.86	26d	1	0.95mi
485 Sutton Pl Greenport, NY	4.0	2.5	2026	$20,000	$9.87	45d	1	1.13mi
312 5th Ave Greenport, NY	4.0	2.0	1900	$12,000	$6.32	45d	1	1.15mi
580 Stars Rd East Marion, NY	4.0	3.5	2700	$35,000	$12.96	45d	1	1.21mi
3045 Rocky Point Rd East Marion, NY	3.0	2.0	2025	$12,000	$5.93	45d	1	1.25mi
950 Tasker Ln Greenport, NY	4.0	3.5	3500	$36,000	$10.29	45d	1	1.26mi
11003 Main Rd East Marion, NY	3.0	2.0	3000	$15,000	$5.00	45d	1	1.37mi
3600 Rocky Point Rd East Marion, NY	3.0	2.5	3000	$16,000	$5.33	45d	1	1.38mi
1000 Sound Dr Greenport, NY	5.0	4.5	3700	$45,000	$12.16	45d	1	1.39mi
11930 Main Rd East Marion, NY	4.0	2.0	2200	$3,500	$1.59	45d	1	1.43mi

HOA detail

• Monthly dues: $38 · $456/yr

Listing history 20 events

1. 2026-06-22
   days on market $1,500,000 Active 58 DOM
2. 2026-06-21
   days on market $1,500,000 Active 57 DOM
3. 2026-06-21
   days on market $1,500,000 Active 56 DOM
4. 2026-06-18
   days on market $1,500,000 Active 54 DOM
5. 2026-06-17
   days on market $1,500,000 Active 53 DOM
6. 2026-06-16
   days on market $1,500,000 Active 52 DOM
7. 2026-06-15
   days on market $1,500,000 Active 51 DOM
8. 2026-06-13
   days on market $1,500,000 Active 49 DOM
9. 2026-06-12
   days on market $1,500,000 Active 48 DOM
10. 2026-06-09
    days on market $1,500,000 Active 45 DOM
11. 2026-06-08
    days on market $1,500,000 Active 44 DOM
12. 2026-06-07
    days on market $1,500,000 Active 43 DOM
13. 2026-06-05
    days on market $1,500,000 Active 41 DOM
14. 2026-06-04
    days on market $1,500,000 Active 39 DOM
15. 2026-06-02
    days on market $1,500,000 Active 38 DOM
16. 2026-06-01
    days on market $1,500,000 Active 37 DOM
17. 2026-05-31
    days on market $1,500,000 Active 36 DOM
18. 2026-04-25
    listed $1,650,000 Active 1988-char remark
19. 1998-06-30
    soldstatus $278,000
20. 1987-12-08
    soldstatus $115,000

ⓘ 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: $11,051 · $921/mo
• Projected year-2 tax: $18,200 · $1,517/mo
• Expected delta: +$7,150/yr (+$596/mo · 64.7%)

ⓘ 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 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 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $269,358
• − Mortgage interest: −$84,023
• − Property taxes: −$11,051
• − Insurance: −$7,500
• − Repairs & maintenance: −$21,549
• − Management: −$21,549
• − HOA: −$456
• − Depreciation: −$43,636
• Taxable income: $79,594
• Est. tax owed @ 24.0%: −$19,103
• After-tax cash flow: $80,289/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

+1204.3% since first listed

4 events — show timeline

• 2026-05-20 Price Changed $1,500,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-25 Listed $1,650,000 OneKey® MLS as Distributed by MLS Grid
• 1998-06-30 Sold (Public Records) $278,000 Public Records
• 1987-12-08 Sold (Public Records) $115,000 Public Records

Property tax history

+2.0%/yr

Latest (2025): $11,051 · +0.0% YoY. Source: county tax records.