25 Lighthouse Rd · Southold, NY 11971

$1,899,000

4 bd · 2.5 ba · 3,800 sqft · SingleFamily · 57 Days on market

Built 2007 0.85 ac lot $500/sqft · 36% above area Est $1397k · 36% over

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +4.8/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• ARV discount +0.0/15.0
• Appreciation +0.0/10.0

Listing remarks MLS

Tucked at the end of a long, private drive on one of Southold’s historic streets, this custom-built, designer's own Nantucket-style home delivers 3,800 square feet of luxury on just under an acre of manicured gardens. Minutes from both the Sound and Peconic Bay, plus the restaurants, wineries, and village charm that make North Fork living feel like a permanent vacation. Step onto the mahogany porch, and the vibe hits immediately. Inside, a dramatic two-story foyer flows into an inviting light-filled living room. The oversized, well-appointed kitchen is an entertainer's delight with Carrera marble countertops and huge island with seating for 5. Dinner parties? Handled. The adjacent formal dining room is ready when the guest list grows. Main-level primary suite with soaking tub, Carrera-tiled shower, and walk-in closet is a romantic escape. There is also a main level laundry room, guest bath, and library/office. Upstairs, a loft adds natural light and a space to sit and read or relax, and 3 additional oversized bedrooms that offer everyone a private space. The yard is outdoor living at its finest. Stone patio, sprawling exotic wood deck with pergola, and a fire pit lounge make for late-night conversations in the lush, thoughtfully designed yard (which has plenty of space for a pool!). The detached two-car garage gives you room to grow. Polished yet comfortable. Private yet not remote. A true North Fork experience for all seasons.

Key facts

• 0.85 acre lot
• 2 garage spots
• Built 2007

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $1.90M.

Deal economics

• At list price, monthly cash flow is $11k ($131k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($29k rent vs $1.90M).
• Recommended offer: $1.84M (3.0% below list) — sets the bar for market timing.
• Cap rate 13.2% vs local median 6.9% in Southold — 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 67/100 on livability (#583 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, schools A-; Watch: amenities F, commute F, cost of living F.
• Southold Union Free School District (town): math 46% / reading 59% proficiency, ranked #298 of 590 in NY (top 50%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 17% free/reduced lunch — higher-income household profile.
• Market conditions: 79 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 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 $13k of loan paydown is wiped out by about $57k 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 $532k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• It's been on market 57 days — a 3% lower offer ($1.84M) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 2y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $450k; list at $1.90M implies a 322% 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 $1,842,030 (3.0% below list)

Questions for the listing agent

1. It's been on market 57 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
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: 1.51% ✓
• Cap rate: 13.20%
• Cash-on-cash: 24.68%
• DSCR: 2.10
• GRM: 5.5

CMA / ARV

• ARV (median comp): $1,397,069
• List price: $1,899,000
• Delta: 35.93%
• Verdict: OVERPRICED
• Comps: 5 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 18.1%
• Equity multiple: 1.73×
• Total profit: $388,396
• Equity at exit: $283,147

10-year hold

• IRR: 26.5%
• Equity multiple: 3.32×
• Total profit: $1,233,329
• Equity at exit: $164,191

Cash invested: $531,720 (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 11971

• Home prices YoY: -15.8%
• Active inventory: 79
• Price-to-rent: 5.5×

Monthly cashflow live

• Estimated rent: $28,645 medium
• Mortgage (P&I): −$9,959
• Tax from tax record: −$943 /mo · $11,316/yr
• Insurance: −$791
• HOA: −$0
• Vacancy / Maint / Mgmt: −$6,015
• Net cashflow: $10,937

Break-even live

Break-even rent $14,801

Max offer price $1,899,000

Occupancy floor 57%

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: $474,750
• Closing costs: $56,970
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
590 Soundview Avenue Ext Southold, NY	4.0	4.5	3100	$27,000	$8.71	43d	1	0.56mi
365 Chablis Path Southold, NY	4.0	3.5	3800	$30,000	$7.89	43d	1	0.57mi

Listing history 21 events

1. 2026-06-18
   days on market $1,899,000 Active 57 DOM
2. 2026-06-17
   days on market $1,899,000 Active 56 DOM
3. 2026-06-16
   days on market $1,899,000 Active 55 DOM
4. 2026-06-15
   days on market $1,899,000 Active 54 DOM
5. 2026-06-13
   days on market $1,899,000 Active 52 DOM
6. 2026-06-12
   days on market $1,899,000 Active 51 DOM
7. 2026-06-09
   days on market $1,899,000 Active 48 DOM
8. 2026-06-08
   days on market $1,899,000 Active 47 DOM
9. 2026-06-07
   days on market $1,899,000 Active 46 DOM
10. 2026-06-07
    days on market $1,899,000 Active 45 DOM
11. 2026-06-04
    days on market $1,899,000 Active 42 DOM
12. 2026-06-02
    days on market $1,899,000 Active 41 DOM
13. 2026-06-01
    days on market $1,899,000 Active 40 DOM
14. 2026-05-31
    days on market $1,899,000 Active 39 DOM
15. 2026-04-22
    listed $1,899,000 Active 1457-char remark

    Show marketing remark (1457 chars)

    Tucked at the end of a long, private drive on one of Southold’s historic streets, this custom-built, designer's own Nantucket-style home delivers 3,800 square feet of luxury on just under an acre of manicured gardens. Minutes from both the Sound and Peconic Bay, plus the restaurants, wineries, and village charm that make North Fork living feel like a permanent vacation. Step onto the mahogany porch, and the vibe hits immediately. Inside, a dramatic two-story foyer flows into an inviting light-filled living room. The oversized, well-appointed kitchen is an entertainer's delight with Carrera marble countertops and huge island with seating for 5. Dinner parties? Handled. The adjacent formal dining room is ready when the guest list grows. Main-level primary suite with soaking tub, Carrera-tiled shower, and walk-in closet is a romantic escape. There is also a main level laundry room, guest bath, and library/office. Upstairs, a loft adds natural light and a space to sit and read or relax, and 3 additional oversized bedrooms that offer everyone a private space. The yard is outdoor living at its finest. Stone patio, sprawling exotic wood deck with pergola, and a fire pit lounge make for late-night conversations in the lush, thoughtfully designed yard (which has plenty of space for a pool!). The detached two-car garage gives you room to grow. Polished yet comfortable. Private yet not remote. A true North Fork experience for all seasons.

16. 2026-04-11
    historical $1,899,000 1457-char remark

    Show marketing remark (1457 chars)

    Tucked at the end of a long, private drive on one of Southold’s historic streets, this custom-built, designer's own Nantucket-style home delivers 3,800 square feet of luxury on just under an acre of manicured gardens. Minutes from both the Sound and Peconic Bay, plus the restaurants, wineries, and village charm that make North Fork living feel like a permanent vacation. Step onto the mahogany porch, and the vibe hits immediately. Inside, a dramatic two-story foyer flows into an inviting light-filled living room. The oversized, well-appointed kitchen is an entertainer's delight with Carrera marble countertops and huge island with seating for 5. Dinner parties? Handled. The adjacent formal dining room is ready when the guest list grows. Main-level primary suite with soaking tub, Carrera-tiled shower, and walk-in closet is a romantic escape. There is also a main level laundry room, guest bath, and library/office. Upstairs, a loft adds natural light and a space to sit and read or relax, and 3 additional oversized bedrooms that offer everyone a private space. The yard is outdoor living at its finest. Stone patio, sprawling exotic wood deck with pergola, and a fire pit lounge make for late-night conversations in the lush, thoughtfully designed yard (which has plenty of space for a pool!). The detached two-car garage gives you room to grow. Polished yet comfortable. Private yet not remote. A true North Fork experience for all seasons.

17. 2025-08-02
    historical
18. 2025-03-19
    listed $1,999,000 Active
19. 2024-08-09
    historical
20. 2024-02-12
    listed $2,050,000 Active
21. 2006-10-18
    soldstatus $450,000

ⓘ 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: $11,316 · $943/mo
• Projected year-2 tax: $21,705 · $1,809/mo
• Expected delta: +$10,389/yr (+$866/mo · 91.8%)

ⓘ 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 2/10 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: $343,739
• − Mortgage interest: −$106,374
• − Property taxes: −$11,316
• − Insurance: −$9,495
• − Repairs & maintenance: −$27,499
• − Management: −$27,499
• − Depreciation: −$55,244
• Taxable income: $106,313
• Est. tax owed @ 24.0%: −$25,515
• After-tax cash flow: $105,725/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: Southold Union Free School District
• NCES district ID: 3627620
• Math proficiency: 46% ▼ -10.00%
• Reading proficiency: 59% ▲ 6.00%
• Median HH income: $78,622
• Composite: 47.54/100
• National rank: #2269
• State rank: #298 of 590 in NY

Livability — Southold

• Score: 67/100
• State rank: #583
• US rank: #10545

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Southold, NY
• City population: 6,507
• Population (ZIP): 6,507

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 (78%)
• Race & ethnicity: White 78% Hispanic / Latino 14% Two or more races 5% Asian 4%
• Hispanic origin (detail): Mexican 3% Puerto Rican 1% Dominican 3%
• Common ancestry: Romanian 6% Italian 2% Slovak 2%
• Foreign-born: 14% · Canada, China, Dominican Republic
• Languages at home: 83% English-only · Spanish 11% Russian/Polish/Slavic 2% Other Indo-European 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: ▼ -74.14%
• Current HPI: 396.5481
• 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

+322.0% since first listed

7 events — show timeline

• 2026-04-22 Listed $1,899,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-11 Coming Soon $1,899,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-02 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-03-19 Listed $1,999,000 OneKey® MLS as Distributed by MLS Grid
• 2024-08-09 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-02-12 Listed $2,050,000 OneKey® MLS as Distributed by MLS Grid
• 2006-10-18 Sold (Public Records) $450,000 Public Records

Property tax history

-0.8%/yr

Latest (2025): $11,316 · +0.0% YoY. Source: county tax records.