14 Freds Ln · Shelter Island Heights, NY 11964

$2,485,000

4 bd · 3.0 ba · 2,418 sqft · SingleFamily public records · 72 Days on market

Built 2014 0.99 ac lot $1028/sqft · 17% below area Est $4201k · 41% 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
• Appreciation +6.0/10.0
• Cash flow +4.3/30.0
• Schools +4.1/10.0
• Livability +2.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

Key facts

• 0.99 acre lot
• 2 garage spots
• Pool

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $2.48M.

Deal economics

• At list price, monthly cash flow is $-7k ($-79k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.32M (47.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.03M (58.5% below list).
• Recommended offer: $1.03M (58.5% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 56/100 on livability (#1,120 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Shelter Island Union Free School District (rural): math 40% / reading 45% proficiency, ranked #546 of 755 in NY (top 72%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 16% free/reduced lunch — higher-income household profile.
• Market conditions: 39 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% 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

• In year one you build about $66k of equity ($17k loan paydown + $49k appreciation (2.0% local appreciation)).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• By year 3, paydown + projected appreciation supports a ~$168k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 72 days — a 6% lower offer ($2.34M) is reasonable based on typical stale-listing flexibility.
• Current owner paid $325k; list at $2.48M implies a 665% 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 $1,031,927 (58.5% 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 72 days. Have you received any prior offers? Is the seller open to a 58% concession, seller financing, or rate buy-down credit?
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. 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?
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: 0.42% ✗
• Cap rate: 3.10%
• Cash-on-cash: -11.40%
• DSCR: 0.49
• GRM: 20.1

CMA / ARV

• ARV (median comp): $4,201,154
• List price: $2,485,000
• Delta: -40.85%
• Verdict: UNDERPRICED
• Comps: 5 within 2.0 mi

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1 Gazon Rd	0.34mi	4/3.0	2,618 (+8%)	3mo	$1,180,000	$451	68
1 Valley Rd	0.73mi	4/3.5	2,200 (-9%)	5mo	$1,900,000	$864	45
18 Dickerson Dr	0.54mi	4/3.5	2,774 (+15%)	16mo	$2,500,000	$901	34

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

Projected returns pro-forma

1.97% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -6.8%
• Equity multiple: 0.63×
• Total profit: $-255,826
• Equity at exit: $975,974

10-year hold

• IRR: -1.6%
• Equity multiple: 0.78×
• Total profit: $-149,661
• Equity at exit: $1,402,218

Cash invested: $695,800 (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 11964

• Home prices YoY: 0.4%
• Active inventory: 39
• Price-to-rent: 20.1×

Monthly cashflow live

• Estimated rent: $10,319 medium
• Mortgage (P&I): −$13,032
• Tax from tax record: −$694 /mo · $8,334/yr
• Insurance: −$1,035
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,167
• Net cashflow: $-6,609

Break-even live

Break-even rent $18,685

Max offer price $1,317,443

Occupancy floor —

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: $621,250
• Closing costs: $74,550
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
42 N Menantic Rd Shelter Island, NY	4.0	2.5	2825	$7,500	$2.65	43d	1	0.71mi
4 Glynn Dr Shelter Island Heights, NY	4.0	3.0	2604	$12,000	$4.61	24d	1	0.79mi
59 Peconic Ave Shelter Island Heights, NY	4.0	3.0	2018	$8,700	$4.31	24d	1	0.95mi
12 Dogwood Ln Shelter Island, NY	4.0	2.0	2669	$14,400	$5.40	43d	1	1.31mi

Listing history 17 events

1. 2026-06-18
   days on market $2,485,000 Active 72 DOM
2. 2026-06-17
   days on market $2,485,000 Active 71 DOM
3. 2026-06-16
   days on market $2,485,000 Active 70 DOM
4. 2026-06-15
   days on market $2,485,000 Active 69 DOM
5. 2026-06-13
   days on market $2,485,000 Active 67 DOM
6. 2026-06-13
   days on market $2,485,000 Active 66 DOM
7. 2026-06-09
   days on market $2,485,000 Active 63 DOM
8. 2026-06-08
   days on market $2,485,000 Active 62 DOM
9. 2026-06-07
   days on market $2,485,000 Active 61 DOM
10. 2026-06-04
    days on market $2,485,000 Active 58 DOM
11. 2026-06-03
    days on market $2,485,000 Active 57 DOM
12. 2026-06-02
    days on market $2,485,000 Active 56 DOM
13. 2026-06-01
    days on market $2,485,000 Active 55 DOM
14. 2026-05-31
    days on market $2,485,000 Active 54 DOM
15. 2026-04-08
    listed $2,485,000 Active 1521-char remark

    Show marketing remark (1521 chars)

    Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

16. 2026-04-03
    historical $2,485,000 1521-char remark

    Show marketing remark (1521 chars)

    Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

17. 2005-07-22
    soldstatus $325,000

ⓘ 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: $8,334 · $694/mo
• Projected year-2 tax: $25,165 · $2,097/mo
• Expected delta: +$16,831/yr (+$1,403/mo · 202.0%)

ⓘ 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 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $123,831
• − Mortgage interest: −$139,199
• − Property taxes: −$8,334
• − Insurance: −$12,425
• − Repairs & maintenance: −$9,906
• − Management: −$9,906
• − Depreciation: −$72,291
• Taxable loss: −$128,230
• Est. tax savings @ 24.0%: +$30,775
• After-tax cash flow: $-48,536/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: Shelter Island Union Free School District
• NCES district ID: 3626640
• Math proficiency: 40% ▼ -15.00%
• Reading proficiency: 45% ▼ -15.00%
• Median HH income: $75,456
• Composite: 41.31/100
• National rank: #7365
• State rank: #546 of 755 in NY

Livability — Shelter Island Heights

• Score: 56/100
• State rank: #1120
• US rank: #23056

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Shelter Island Heights, NY
• Population (ZIP): 2,858

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: Diverse neighborhood (Simpson 0.57)
• Race & ethnicity: White 62% Hispanic / Latino 21% Native American 15% Two or more races 7% Asian 6%
• Hispanic origin (detail): Mexican 16%
• Common ancestry: Italian 13% Romanian 5% Portuguese 1%
• Foreign-born: 15% · Canada
• Languages at home: 78% English-only · Spanish 18% Other Indo-European 3%

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: ▲ 1.97%
• Current HPI: 476.2348
• 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

+664.6% since first listed

3 events — show timeline

• 2026-04-08 Listed $2,485,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-03 Coming Soon $2,485,000 OneKey® MLS as Distributed by MLS Grid
• 2005-07-22 Sold (Public Records) $325,000 Public Records

Property tax history

+9.0%/yr

Latest (2025): $8,334 · +0.0% YoY. Source: county tax records.