250 Paradise Point Rd · Southold, NY 11971

$1,299,000

4 bd · 3.0 ba · 2,200 sqft · SingleFamily · 22 Days on market

Built 1982 0.93 ac lot Est $1188k · 9% over

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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
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +4.8/10.0
• Livability +3.4/5.0
• ARV discount +3.3/15.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Welcome to 250 Paradise Point Rd, Southold NY, a beautiful ranch-style home complete with an in-ground pool is nestled in a serene location, just a stone's throw away from Cedar Beach. This spacious home boasts four bedrooms, two of which are en suites with full bathrooms, ensuring ample space and privacy for everyone. The heart of the home is the cozy family room, complete with a fireplace and sliding glass doors that open to a charming back deck. The eat-in kitchen is perfect for casual meals, while the dining room, featuring sliding doors to the sunroom, is ideal for more formal gatherings. The sunroom, overlooking an acre of property and an in-ground pool, is the perfect spot to unwind

Key facts

• In-ground pool
• Acre of property
• Sunroom

Tags

• IN-GROUND POOL
• BACK DECK
• EAT-IN KITCHEN
• DINING ROOM
• SUNROOM
• ACRE OF PROPERTY

Property features AI

Exterior

• Parking: Driveway
• Utilities: Septic tank; Cable connected; Electricity connected; Phone connected; Water connected
• Home design: Single family residence; One story
• Construction: Frame construction; Full basement (unfinished attic)
• Exterior features: Back yard; Front yard; Landscaped grounds; Level and private lot; Views; Private in-ground vinyl pool with solar heating

Interior

• Kitchen: Cooktop; Electric cooktop; Electric oven; Oven; Microwave; Dishwasher; Refrigerator
• Bedrooms: One-level home (all bedrooms on the main level implied)
• Flooring: Hardwood floors; Tile floors
• Bathrooms: Three full bathrooms
• Heating & cooling: Oil heating; Ductless cooling; Oil water heater; Electric water heater
• Interior features: First-floor bedroom; First-floor full bathroom; Cathedral ceilings; Ceiling fans; Eat-in kitchen; Open floor plan with open kitchen; Primary bathroom; Master suite on the main level; Interior storage; Washer/dryer hookup
• Laundry & utility: Washer; Dryer; Washer hookup; Electric dryer hookup; Laundry located in basement

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $1.30M.

Deal economics

• At list price, monthly cash flow is $8k ($101k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($21k rent vs $1.30M).
• Recommended offer: $1.28M (1.5% below list) — sets the bar for market timing.
• Cap rate 14.1% 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; 3 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 67% 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 $9k of loan paydown is wiped out by about $39k 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 $364k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• It's been on market 22 days — a 2% lower offer ($1.28M) is reasonable based on typical stale-listing flexibility.

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 $1,279,515 (1.5% below list)

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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?
3. 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.
4. 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.
5. 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: 1.62% ✓
• Cap rate: 14.08%
• Cash-on-cash: 27.82%
• DSCR: 2.24
• GRM: 5.1

CMA / ARV

• ARV (on-the-fly): $1,188,000
• Comps found: 4

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1750 Water Ter	0.44mi	4/2.5	2,000 (-9%)	23mo	$1,080,000	$540	43
265 Cedar Point Dr E	0.56mi	3/2.5 (-1)	2,000 (-9%)	20mo	$1,450,000	$725	35
75 Reydon Dr	0.56mi	3/3.0 (-1)	2,492 (+13%)	22mo	$999,999	$401	28
295 Grove Dr	0.65mi	3/2.5 (-1)	2,492 (+13%)	19mo	$1,268,000	$509	25

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: 21.9%
• Equity multiple: 1.90×
• Total profit: $326,396
• Equity at exit: $193,685

10-year hold

• IRR: 30.0%
• Equity multiple: 3.68×
• Total profit: $975,090
• Equity at exit: $112,314

Cash invested: $363,720 (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: 5.1×

Monthly cashflow live

• Estimated rent: $21,041 medium
• Mortgage (P&I): −$6,812
• Tax from tax record: −$836 /mo · $10,038/yr
• Insurance: −$541
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,419
• Net cashflow: $8,432

Break-even live

Break-even rent $10,367

Max offer price $1,299,000

Occupancy floor 55%

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: $324,750
• Closing costs: $38,970
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
1265 Brigantine Dr Southold, NY	3.0	2.0	1750	$9,000	$5.14	44d	1	0.80mi
215 Northfield Ln Southold, NY	4.0	3.0	2300	$13,000	$5.65	18d	1	1.24mi
1160 Goose Creek Ln Southold, NY	5.0	3.0	2000	$50,000	$25.00	44d	1	1.45mi

Listing history 15 events

1. 2026-06-18
   days on market $1,299,000 Active 22 DOM
2. 2026-06-17
   days on market $1,299,000 Active 21 DOM
3. 2026-06-16
   days on market $1,299,000 Active 20 DOM
4. 2026-06-15
   days on market $1,299,000 Active 19 DOM
5. 2026-06-13
   days on market $1,299,000 Active 17 DOM
6. 2026-06-12
   days on market $1,299,000 Active 16 DOM
7. 2026-06-09
   days on market $1,299,000 Active 13 DOM
8. 2026-06-08
   days on market $1,299,000 Active 12 DOM
9. 2026-06-07
   days on market $1,299,000 Active 11 DOM
10. 2026-06-07
    days on market $1,299,000 Active 10 DOM
11. 2026-06-04
    days on market $1,299,000 Active 7 DOM
12. 2026-06-02
    days on market $1,299,000 Active 6 DOM
13. 2026-06-01
    days on market $1,299,000 Active 5 DOM
14. 2026-05-31
    days on market $1,299,000 Active 4 DOM
15. 2026-01-09
    listed $1,299,000 Active

ⓘ 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: $10,038 · $836/mo
• Projected year-2 tax: $15,995 · $1,333/mo
• Expected delta: +$5,958/yr (+$496/mo · 59.4%)

ⓘ 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 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $252,488
• − Mortgage interest: −$72,764
• − Property taxes: −$10,038
• − Insurance: −$6,495
• − Repairs & maintenance: −$20,199
• − Management: −$20,199
• − Depreciation: −$37,789
• Taxable income: $85,004
• Est. tax owed @ 24.0%: −$20,401
• After-tax cash flow: $80,786/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

1 event — show timeline

• 2026-01-09 Listed $1,299,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+2.3%/yr

Latest (2025): $10,038 · +0.0% YoY. Source: county tax records.