395 Linnet St · Greenport West, NY 11944

$749,999

5 bd · 4.0 ba · 2,800 sqft · SingleFamily · 238 Days on market

Built 2000 Fair condition 5,227 sqft lot $268/sqft · 47% below area Est $1.404M · 47% 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 +5.4/10.0
• Livability +2.9/5.0
• Rent growth +2.5/5.0
• Condition / age +2.2/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

An exceptional opportunity to own in the highly sought-after Greenport / North Fork region, where lifestyle, flexibility, and long-term value come together. Whether you are seeking a year-round residence, weekend retreat, or property with extended living possibilities, this well-maintained ranch offers outstanding versatility in one of Long Island’s most desirable coastal destinations. Welcome to 395 Linnet Street, also known as 806 Linnet Street, Southold. Designed for today’s casual lifestyle, the home features an open-concept layout, 3 bedrooms and 2 full baths on the main level, along with an updated eat-in kitchen showcasing quartz countertops. The expansive backyard creates the perfect setting for entertaining, outdoor dining, or simply enjoying the peaceful North Fork atmosphere. The fully finished lower level with outside entrance (OSE) offers additional bedrooms and baths (all on Certificate of Occupancy), creating exceptional flexibility for extended living, guests, private work-from-home space, recreation, or separate accommodations. Located just minutes from bay beaches, marinas, parks, vineyards, farm stands, acclaimed restaurants, boutique shopping, the historic Greenport waterfront village, LIRR, and Hampton Jitney, this property places you in the center of the North Fork lifestyle that continues to attract homeowners and weekend visitors alike.

Key facts

• Expansive backyard
• Open-concept layout
• 5,227 sq ft lot

Tags

• OPEN-CONCEPT LAYOUT
• EXPANSIVE BACKYARD
• UPDATED EAT-IN-KITCHEN
• FULLY FINISHED BASEMENT
• CLOSE PROXIMITY TO BAY BEACHES
• CLOSE PROXIMITY TO LOCAL PARKS

What this means for you Summary

Snapshot

• This is a 5-bed/4.0-bath single-family listed at $750k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $14k ($163k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($23k rent vs $750k).
• Recommended offer: $660k (12.0% below list) — sets the bar for market timing.
• Cap rate 28.0% 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: 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: 74 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals lingering (median 93d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 88% of comp listings sitting > 30 days — soft ceiling on asking rent; solid renter incomes; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $23,279/mo this rent would consume 350% of the median local household income ($80k/yr) (locally 21% 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 $5k of loan paydown is wiped out by about $22k 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 $210k cash investment doubles in ~2 years — after that, you're playing with house money.

Negotiation context

• It's been on market 238 days — a 12% lower offer ($660k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $40k (5%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $340k; list at $750k implies a 121% 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→20/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $659,999 (12.0% below list)

Questions for the listing agent

1. It's been on market 238 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
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: 3.10% ✓
• Cap rate: 27.96%
• Cash-on-cash: 77.39%
• DSCR: 4.44
• GRM: 2.7

CMA / ARV

• ARV (median comp): $1,404,309
• List price: $749,999
• Delta: -46.59%
• Verdict: UNDERPRICED
• Comps: 6 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
133 6th St	0.22mi	6/3.5 (+1)	3,000 (+7%)	14mo	$2,875,000	$958	60
3200 Bay Shore Rd	1.11mi	4/3.5 (-1)	2,600 (-7%)	9mo	$2,025,000	$779	38
155 Bridge St	1.01mi	5/3.5	2,400 (-14%)	3mo	$1,470,000	$613	36
675 Champlin Pl	1.11mi	4/2.5 (-1)	2,650 (-5%)	12mo	$2,200,000	$830	35
2055 Bay Shore Rd	1.04mi	5/2.5	2,500 (-11%)	10mo	$2,150,000	$860	32

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: 77.4%
• Equity multiple: 4.53×
• Total profit: $741,170
• Equity at exit: $111,827

10-year hold

• IRR: 81.0%
• Equity multiple: 9.37×
• Total profit: $1,756,668
• Equity at exit: $64,846

Cash invested: $210,000 (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 →

Active competition Active MLS

• For sale now: 2 active · 1 under contract
• Median asking: $1,974,500 ($720/sqft)
• Median days on market: 390 d
• This list price: lowest-priced of the active set
• ARV vs active asking: -30.4% vs current asking $/sqft

Closed sales set the value; these active listings set current market conditions and a practical price ceiling.

ZIP-level market 11944

• Home prices YoY: -23.7%
• Active inventory: 74
• Price-to-rent: 2.7×

Monthly cashflow live

• Estimated rent: $23,279 high
• Mortgage (P&I): −$3,933
• Tax from tax record: −$602 /mo · $7,222/yr
• Insurance: −$312
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,889
• Net cashflow: $13,543

Break-even live

Break-even rent $6,136

Max offer price $749,999

Occupancy floor 37%

Sensitivity live

Price	-10% $13,968	-5% $13,755	+0% $13,543	+5% $13,331	+10% $13,118
Rent	-10% $11,704	-5% $12,623	+0% $13,543	+5% $14,462	+10% $15,382
Rate	-1.0pp $13,921	-0.5pp $13,734	base $13,543	+0.5pp $13,349	+1.0pp $13,151

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: $187,500
• Closing costs: $22,500
• Club membership (one-time): —
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
64230 North Rd Greenport, NY	4.0	3.0	2800	$6,500	$2.32	93d	1	0.90mi
63615 North Rd Greenport, NY	4.0	4.5	3500	$7,000	$2.00	93d	1	1.01mi
485 Sutton Pl Greenport, NY	4.0	2.5	2026	$20,000	$9.87	93d	1	1.23mi
185 Inlet Ln Greenport, NY	6.0	4.5	2800	$12,000	$4.29	18d	1	1.23mi
750 Kerwin Blvd Greenport, NY	4.0	4.0	3200	$11,200	$3.50	73d	1	1.31mi
2700 Sound Dr Greenport, NY	5.0	3.0	3700	$25,000	$6.76	93d	1	1.38mi
950 Tasker Ln Greenport, NY	4.0	3.5	3500	$36,000	$10.29	93d	1	1.41mi
1000 Sound Dr Greenport, NY	5.0	4.5	3700	$45,000	$12.16	93d	1	1.50mi

Listing history 50 events

1. 2026-08-06
   days on market $749,999 Active 238 DOM
2. 2026-08-05
   days on market $749,999 Active 237 DOM
3. 2026-08-04
   days on market $749,999 Active 236 DOM
4. 2026-08-03
   days on market $749,999 Active 235 DOM
5. 2026-07-31
   days on market $749,999 Active 232 DOM
6. 2026-07-29
   days on market $749,999 Active 230 DOM
7. 2026-07-27
   days on market $749,999 Active 228 DOM
8. 2026-07-25
   days on market $749,999 Active 226 DOM
9. 2026-07-24
   days on market $749,999 Active 225 DOM
10. 2026-07-23
    days on market $749,999 Active 224 DOM
11. 2026-07-22
    days on market $749,999 Active 223 DOM
12. 2026-07-21
    days on market $749,999 Active 222 DOM
13. 2026-07-20
    days on market $749,999 Active 221 DOM
14. 2026-07-18
    days on market $749,999 Active 219 DOM
15. 2026-07-16
    days on market $749,999 Active 217 DOM
16. 2026-07-15
    days on market $749,999 Active 216 DOM
17. 2026-07-14
    days on market $749,999 Active 215 DOM
18. 2026-07-13
    days on market $749,999 Active 214 DOM
19. 2026-07-12
    days on market $749,999 Active 213 DOM
20. 2026-07-12
    days on market $749,999 Active 212 DOM
21. 2026-07-10
    days on market $749,999 Active 211 DOM
22. 2026-07-09
    days on market $749,999 Active 210 DOM
23. 2026-07-07
    days on market $749,999 Active 208 DOM
24. 2026-07-06
    days on market $749,999 Active 207 DOM
25. 2026-07-05
    days on market $749,999 Active 206 DOM
26. 2026-07-05
    days on market $749,999 Active 205 DOM
27. 2026-07-03
    days on market $749,999 Active 204 DOM
28. 2026-07-02
    days on market $749,999 Active 203 DOM
29. 2026-07-01
    days on market $749,999 Active 202 DOM
30. 2026-06-30
    days on market $749,999 Active 201 DOM
31. 2026-06-29
    days on market $749,999 Active 200 DOM
32. 2026-06-28
    days on market $749,999 Active 199 DOM
33. 2026-06-27
    days on market $749,999 Active 198 DOM
34. 2026-06-26
    days on market $749,999 Active 197 DOM
35. 2026-06-22
    days on market $749,999 Active 193 DOM
36. 2026-06-21
    days on market $749,999 Active 192 DOM
37. 2026-06-21
    days on market $749,999 Active 191 DOM
38. 2026-06-18
    days on market $749,999 Active 189 DOM
39. 2026-06-17
    days on market $749,999 Active 188 DOM
40. 2026-06-16
    days on market $749,999 Active 187 DOM
41. 2026-06-15
    days on market $749,999 Active 186 DOM
42. 2026-06-13
    days on market $749,999 Active 184 DOM
43. 2026-06-12
    days on market $749,999 Active 183 DOM
44. 2026-06-09
    days on market $749,999 Active 180 DOM
45. 2026-06-08
    days on market $749,999 Active 179 DOM
46. 2026-06-07
    days on market $749,999 Active 178 DOM
47. 2026-06-05
    days on market $749,999 Active 176 DOM
48. 2026-06-04
    days on market $749,999 Active 174 DOM
49. 2026-06-02
    days on market $749,999 Active 173 DOM
50. 2026-06-01
    days on market $749,999 Active 172 DOM

ⓘ 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: $7,222 · $602/mo
• Projected year-2 tax: $9,948 · $829/mo
• Expected delta: +$2,727/yr (+$227/mo · 37.8%)

ⓘ 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 · 20 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: $279,347
• − Mortgage interest: −$42,012
• − Property taxes: −$7,222
• − Insurance: −$3,750
• − Repairs & maintenance: −$22,348
• − Management: −$22,348
• − Depreciation: −$21,818
• Taxable income: $159,850
• Est. tax owed @ 24.0%: −$38,364
• After-tax cash flow: $124,151/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.

Condition & rehab AI · 9 photos

Fair 45/100 Moderate rehab Est. rehab $70,000–$126,000 screening

This property requires moderate repairs and maintenance, including painting and landscaping, to improve its curb appeal and overall value.

Repairs flagged

• Major Paint — Chipped and peeling in multiple areas
• Moderate Siding — Weathered and showing signs of wear

Value-add opportunities

• Both Painting and repainting the exterior — Enhances curb appeal and value ↑
• Both Landscaping and trimming — Improves curb appeal and enhances property value ↑
• Both Reconditioning the siding — Extends the life of the exterior and improves curb appeal ↑

ⓘ Rehab cost is a screening estimate — Moderate scope × the home's square footage at US $/sqft rules of thumb (the same model as the Flip Finder). Get contractor quotes + a written scope before underwriting.

D Composite school gradezoned avg 54/100

Zoned Schools

Elementary Greenport Elementary School C NY #908/2,108 Nat'l #9,801/41,679 High Greenport High School C- NY #934/1,100 Nat'l #4,871/17,239

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

D Composite livability gradescore 58/100

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
• County: Suffolk · 1,505,262 people
• Metro: New York-Newark-Jersey City, NY-NJ
• Population (ZIP): 4,744
• Household income: $79,917
• Rent vs Own: 36.5% rent · 63.5% own
• Severe rent burden: 21% of renters

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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%

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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%

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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

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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

+120.6% since first listed

4 events — show timeline

• 2026-04-14 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-04-13 Price Changed $749,999 OneKey® MLS as Distributed by MLS Grid
• 2025-08-06 Listed $790,000 OneKey® MLS as Distributed by MLS Grid
• 2005-04-12 Sold (Public Records) $340,000 Public Records

Property tax history

+5.6%/yr

Latest (2025): $7,222 · +0.0% YoY. Source: county tax records.