790 N Sea Dr · Southold, NY 11971

$3,450,000

5 bd · 3.5 ba · 4,500 sqft · SingleFamily · 45 Days on market

Built 2009 0.90 ac lot $767/sqft · 71% above area

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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
• DSCR +10.0/10.0
• 1% rule +8.0/10.0
• ARV discount +7.5/15.0
• Schools +4.8/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set on nearly a full acre, the property is an entertainer’s dream with a heated saltwater pool, outdoor shower, and a screened-in porch ideal for summer evenings. The home also boasts a 3-car garage, whole-house sound system, security system, elevator, and a full irrigation system that kee

Key facts

• 0.9 acre lot
• 3 garage spots
• Pool

Property features AI

Exterior

• Parking: Private garage with three spaces; Garage door opener
• Utilities: Electricity connected (PSEG); Septic tank sewer
• Home design: Single family residence
• Construction: Built with cedar and advanced framing techniques
• Exterior features: Covered, screened and wrap-around porch; Deck; Patio; Speakers outdoors; Partial fenced backyard

Interior

• Kitchen: Chef's kitchen with kitchen island; Eat-in kitchen; Open layout; Pantry; Cooktop; Dishwasher; Freezer
• Bedrooms: Includes a bedroom on the first floor
• Flooring: Hardwood floors
• Bathrooms: Three full bathrooms; One half bathroom
• Heating & cooling: Oil heating; Central air conditioning; Wood-burning fireplace in the living room
• Interior features: First-floor bedroom; First-floor full bathroom; Cathedral ceilings; Ceiling fans; Central vacuum; Chandelier; Chef's kitchen; Crown molding; Eat-in kitchen; Elevator; Entrance foyer; Formal dining room; High ceilings; Kitchen island; Open kitchen; Pantry; Primary bathroom; Whole-house sound/entertainment system; Speakers
• Laundry & utility: Laundry in multiple locations; Dryer

What this means for you Summary

Snapshot

• This is a 5-bed/3.5-bath single-family listed at $3.45M.

Deal economics

• At list price, monthly cash flow is $14k ($168k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($45k rent vs $3.45M).
• Recommended offer: $3.35M (3.0% below list) — sets the bar for market timing.
• Cap rate 11.3% 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+, health & safety B+; 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.
• Zoned schools: Southold Elementary School (math 37% / reading 62%, grade D, #1,085 of 2,108 statewide, top 56%, 317 students, 35% FRL); Southold Junior-Senior High School (math 52% / reading 52%, grade D+, #946 of 1,100 statewide, top 88%, 380 students, 40% FRL) — zoned schools average 38% FRL vs 17% district-wide (21 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 79 active listings in the ZIP; 1 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 $24k of loan paydown is wiped out by about $104k 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 $966k cash investment doubles in ~7 years — after that, you're playing with house money.

Negotiation context

• It's been on market 45 days — a 3% lower offer ($3.35M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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 $125k; list at $3.45M implies a 2660% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $460/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 $3,346,500 (3.0% below list)

Questions for the listing agent

1. It's been on market 45 days. Have you received any prior offers? Is the seller open to a 3% 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. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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: 1.30% ✓
• Cap rate: 11.31%
• Cash-on-cash: 17.93%
• DSCR: 1.80
• GRM: 6.4

CMA / ARV

• ARV (median comp): $2,020,921
• List price: $3,450,000
• Delta: 70.71%
• Verdict: OVERPRICED
• Comps: 5 within 1.0 mi

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1490 Kenneys Rd	0.44mi	4/4.0 (-1)	4,700 (+4%)	23mo	$2,565,000	$546	46
1820 Kenneys Rd	0.42mi	6/4.0 (+1)	4,000 (-11%)	16mo	$1,870,000	$468	42
40817 County Road 48	0.73mi	5/5.5	4,200 (-7%)	24mo	$3,950,000	$940	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: 8.7%
• Equity multiple: 1.34×
• Total profit: $330,159
• Equity at exit: $514,406

10-year hold

• IRR: 17.9%
• Equity multiple: 2.48×
• Total profit: $1,430,516
• Equity at exit: $298,293

Cash invested: $966,000 (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 11971

• Home prices YoY: -15.8%
• Active inventory: 79
• Price-to-rent: 6.4×

Monthly cashflow live

• Estimated rent: $45,000 medium
• Mortgage (P&I): −$18,092
• Tax from tax record: −$1,587 /mo · $19,048/yr
• Insurance: −$1,438
• Flood insurance flood zone: −$460 /mo · $5,525/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$9,450
• Net cashflow: $13,973

Break-even live

Break-even rent $27,313

Max offer price $3,450,000

Occupancy floor 64%

Sensitivity live

Price	-10% $15,926	-5% $14,949	+0% $13,973	+5% $12,996	+10% $12,020
Rent	-10% $10,418	-5% $12,195	+0% $13,973	+5% $15,750	+10% $17,528
Rate	-1.0pp $15,710	-0.5pp $14,850	base $13,973	+0.5pp $13,079	+1.0pp $12,169

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: $862,500
• Closing costs: $103,500
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
57305 Rte 48 Southold, NY	6.0	5.5	6600	$45,000	$6.82	45d	1	1.36mi

Listing history 20 events

1. 2026-06-21
   days on market $3,450,000 Active 45 DOM
2. 2026-06-21
   days on market $3,450,000 Active 44 DOM
3. 2026-06-18
   days on market $3,450,000 Active 42 DOM
4. 2026-06-17
   days on market $3,450,000 Active 41 DOM
5. 2026-06-16
   days on market $3,450,000 Active 40 DOM
6. 2026-06-15
   days on market $3,450,000 Active 39 DOM
7. 2026-06-13
   days on market $3,450,000 Active 37 DOM
8. 2026-06-12
   days on market $3,450,000 Active 36 DOM
9. 2026-06-09
   days on market $3,450,000 Active 33 DOM
10. 2026-06-08
    days on market $3,450,000 Active 32 DOM
11. 2026-06-07
    days on market $3,450,000 Active 31 DOM
12. 2026-06-07
    days on market $3,450,000 Active 30 DOM
13. 2026-06-04
    days on market $3,450,000 Active 27 DOM
14. 2026-06-02
    days on market $3,450,000 Active 26 DOM
15. 2026-06-01
    days on market $3,450,000 Active 25 DOM
16. 2026-05-31
    days on market $3,450,000 Active 24 DOM
17. 2026-05-07
    listed $3,450,000 Active 1167-char remark
18. 2026-02-17
    historical
19. 2025-09-04
    listed $3,950,000 Active
20. 1996-05-23
    soldstatus $125,000

ⓘ 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: $19,048 · $1,587/mo
• Projected year-2 tax: $38,677 · $3,223/mo
• Expected delta: +$19,628/yr (+$1,636/mo · 103.0%)

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

Climate risk First Street

• 🌊 Flood 10/10 Extreme FEMA zone AE · 99% 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 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $540,000
• − Mortgage interest: −$193,254
• − Property taxes: −$19,048
• − Insurance: −$22,775
• − Repairs & maintenance: −$43,200
• − Management: −$43,200
• − Depreciation: −$100,364
• Taxable income: $118,160
• Est. tax owed @ 24.0%: −$28,358
• After-tax cash flow: $139,312/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

+2660.0% since first listed

4 events — show timeline

• 2026-05-07 Listed $3,450,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-17 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-09-04 Listed $3,950,000 OneKey® MLS as Distributed by MLS Grid
• 1996-05-23 Sold (Public Records) $125,000 Public Records

Property tax history

+7.8%/yr

Latest (2025): $19,048 · +0.0% YoY. Source: county tax records.