1025 Long Creek Dr · Southold, NY 11971

$1,399,000

4 bd · 2.5 ba · 2,690 sqft · SingleFamily · 18 Days on market

Built 1997 0.75 ac lot Est $1321k · 6% over

---

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).

• Cash flow +12.7/30.0
• ARV discount +4.8/15.0
• Schools +4.8/10.0
• DSCR +3.8/10.0
• Livability +3.4/5.0
• 1% rule +2.9/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Welcome to your North Fork waterfront oasis in highly desirable Yennecott Park, offering the rare combination of privacy, natural beauty, and effortless access to all. Perfectly positioned along scenic Long Creek with views toward Hashamomuck Preserve, this 4-bedroom waterfront home delivers a relaxed coastal lifestyle. Set on . 75 acres with lush mature landscaping and generous water frontage, the property is ideal for kayaking, paddleboarding, sailing, jet skiing, power boating, and fishing — creating a true creekside retreat. Inside, the home features a light filled open layout with thoughtfully designed gathering spaces. The spacious kitchen with stainless steel appliances and amp

Key facts

• Water frontage
• Waterfront oasis
• Spacious kitchen

Tags

• WATERFRONT OASIS
• MATURE LANDSCAPING
• WATER FRONTAGE
• LIGHT FILLED OPEN LAYOUT
• SPACIOUS KITCHEN
• STAINLESS STEEL APPLIANCES

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $1.40M.

Deal economics

• At list price, monthly cash flow is $-147 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $1.37M (1.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.10M (21.3% below list).
• Recommended offer: $1.10M (21.3% below list) — sets the bar for 1% rule.

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; 5 comparable units currently listed for rent nearby; rentals lingering (median 45d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% 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 $10k of loan paydown is wiped out by about $42k 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.

Negotiation context

• It's been on market 18 days — a 2% lower offer ($1.38M) is reasonable based on typical stale-listing flexibility.
• 4 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 $106k; list at $1.40M implies a 1220% 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 $1,100,573 (21.3% 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. 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. 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?
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: 0.79% ✗
• Cap rate: 6.17%
• Cash-on-cash: -0.45%
• DSCR: 0.98
• GRM: 10.6

CMA / ARV

• ARV (on-the-fly): $1,320,790
• Comps found: 5

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1830 Laurel Ave	0.25mi	4/2.5	2,700 (+0%)	18mo	$1,325,000	$491	72
4710 Old North Rd	0.54mi	4/2.5	2,400 (-11%)	10mo	$1,350,000	$563	49
3520 Old North Rd	0.75mi	3/3.0 (-1)	3,000 (+12%)	7mo	$1,307,000	$436	33
320 Mount Beulah Ave	0.68mi	4/3.5	3,000 (+12%)	19mo	$1,130,000	$377	29
500 Arshamomaque Ave	0.70mi	4/4.0	2,334 (-13%)	17mo	$1,573,500	$674	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: -17.1%
• Equity multiple: 0.40×
• Total profit: $-236,376
• Equity at exit: $208,595

10-year hold

• IRR: -9.0%
• Equity multiple: 0.44×
• Total profit: $-219,244
• Equity at exit: $120,960

Cash invested: $391,720 (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: 10.6×

Monthly cashflow live

• Estimated rent: $11,006 high
• Mortgage (P&I): −$7,337
• Tax from tax record: −$922 /mo · $11,060/yr
• Insurance: −$583
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,311
• Net cashflow: $-147

Break-even live

Break-even rent $11,191

Max offer price $1,373,106

Occupancy floor 96%

Sensitivity live

Price	-10% $645	-5% $249	+0% $-147	+5% $-543	+10% $-939
Rent	-10% $-1,016	-5% $-581	+0% $-147	+5% $288	+10% $723
Rate	-1.0pp $558	-0.5pp $209	base $-147	+0.5pp $-509	+1.0pp $-878

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: $349,750
• Closing costs: $41,970
• Reserves months: —
• Total cash needed: —

Rent comps 5 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
215 Leon Rd Southold, NY	4.0	4.0	1800	$6,000	$3.33	44d	1	0.29mi
275 Maier Pl Southold, NY	3.0	2.0	2000	$10,000	$5.00	44d	1	0.65mi
3400 Youngs Ave Southold, NY	4.0	2.0	2000	$7,500	$3.75	44d	1	0.86mi
590 Soundview Avenue Ext Southold, NY	4.0	4.5	3100	$27,000	$8.71	44d	1	1.36mi
950 Blue Marlin Dr Southold, NY	4.0	4.0	3200	$20,000	$6.25	44d	1	1.38mi

Listing history 13 events

1. 2026-03-16
   status Pending
2. 2026-02-25
   listed $1,399,000 Active
3. 2025-11-27
   historical
4. 2025-05-21
   price $1,450,000
5. 2025-02-27
   listed $1,495,000 Active
6. 2025-02-14
   historical
7. 2024-11-28
   historical
8. 2024-11-09
   price $1,590,000
9. 2024-09-25
   price $1,625,000
10. 2024-09-23
    status Active
11. 2024-09-22
    historical
12. 2024-04-02
    listed $1,650,000 Active
13. 1997-10-09
    soldstatus $106,000

ⓘ 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: $11,060 · $922/mo
• Projected year-2 tax: $17,352 · $1,446/mo
• Expected delta: +$6,291/yr (+$524/mo · 56.9%)

ⓘ 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: $132,069
• − Mortgage interest: −$78,366
• − Property taxes: −$11,060
• − Insurance: −$6,995
• − Repairs & maintenance: −$10,566
• − Management: −$10,566
• − Depreciation: −$40,698
• Taxable loss: −$26,181
• Est. tax savings @ 24.0%: +$6,284
• After-tax cash flow: $4,525/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

+1219.8% since first listed

13 events — show timeline

• 2026-03-16 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-02-25 Listed $1,399,000 OneKey® MLS as Distributed by MLS Grid
• 2025-11-27 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-05-21 Price Changed $1,450,000 OneKey® MLS as Distributed by MLS Grid
• 2025-02-27 Listed $1,495,000 OneKey® MLS as Distributed by MLS Grid
• 2025-02-14 Coming Soon — OneKey® MLS as Distributed by MLS Grid
• 2024-11-28 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-11-09 Price Changed $1,590,000 OneKey® MLS as Distributed by MLS Grid
• 2024-09-25 Price Changed $1,625,000 OneKey® MLS as Distributed by MLS Grid
• 2024-09-23 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2024-09-22 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-04-02 Listed $1,650,000 OneKey® MLS as Distributed by MLS Grid
• 1997-10-09 Sold (Public Records) $106,000 Public Records

Property tax history

+0.3%/yr

Latest (2025): $11,060 · +0.0% YoY. Source: county tax records.