38 Pleasure Dr · Flanders, NY 11901

$775,000

4 bd · 2.0 ba · 1,600 sqft · SingleFamily public records · 4 Days on market

Built 1860 2.10 ac lot Est $629k · 23% 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 +3.6/10.0
• Livability +2.8/5.0
• 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

This Is More Than A Home, It Is A Piece of Long Island History, Offering Space, Character, Low Taxes and An Unbeatable East End Lifestyle. Perfectly Situated On A Picturesque 2 Acre Property. A Hidden Gem Within The Town of Southampton. Offering Exceptionally Low Taxes of Just $5,599. This Rare East End Treasure Combines Timeless Character With Thoughtful Updates. Rich in History and Overflowing With Charm, This 3 Bedroom, 3 Bath Residence Features An Updated Kitchen (2023), New Roof (2022) Rustic Hardwood Floors, Spacious Primary Suite Complete With 2nd Floor Laundry. Welcoming You Into The Home is The All Seasons Room, Complete With New Eze-Breeze Windows. The Full Basement Was Recreated

Key facts

• All seasons room
• Walk up attic
• Full basement

Tags

• 2 ACRE PROPERTY
• UPDATED KITCHEN
• NEW ROOF
• ALL SEASONS ROOM
• FULL BASEMENT
• WALK UP ATTIC

Property features AI

Exterior

• Parking: Driveway parking; Oversized, private parking
• Utilities: PSEG electric service; Water connected; Cesspool sewer; Cable connected; Trash collection (private)
• Home design: Single-family residence; Updated / remodeled; Three or more levels; Partially finished basement with walk-out access; Attic with stairs, walk-up and storage
• Construction: Cedar exterior; Concrete perimeter foundation
• Exterior features: Back and front yard with landscaping and garden; Level lot, partly wooded and private; Near golf course; Sprinklers in front and rear; No waterfront; No fencing

Interior

• Kitchen: Dishwasher; Electric cooktop; Microwave; Oven; Refrigerator; Stainless steel appliances
• Bedrooms: Home includes a primary suite (see primary bathroom); Additional bedroom(s) — total rooms: 7
• Flooring: Wood flooring; Laminate flooring
• Bathrooms: Three full bathrooms
• Heating & cooling: Oil heating; Central air conditioning; Wood-burning fireplace (1)
• Interior features: First-floor full bathroom; Eat-in kitchen; Entrance foyer; Formal dining room; Natural woodwork; Open floor plan; Open kitchen; Primary bathroom; Recessed lighting; Storage space; Covered patio and porch
• Laundry & utility: Washer and dryer; Laundry located in bathroom; Oil water heater

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $775k.

Deal economics

• At list price, monthly cash flow is $15k ($176k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($25k rent vs $775k).

Location & tenants

• Location reads 56/100 on livability (#1,107 in NY) — a working-class tenant base; expect higher turnover. Strengths: employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Riverhead Central School District (suburban): math 34% / reading 48% proficiency, ranked #489 of 590 in NY (top 83%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Phillips Avenue School (math 17% / reading 32%, grade F, #1,846 of 2,108 statewide, top 91%, 578 students, 50% FRL); Riverhead Middle School (math 18% / reading 35%, grade F, #594 of 729 statewide, top 81%, 827 students, 57% FRL); Riverhead Senior High School (math 80% / reading 86%, grade A, #440 of 1,100 statewide, top 40%, 2,001 students, 52% FRL).
• Market conditions: 191 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 $5k of loan paydown is wiped out by about $23k 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 $217k cash investment doubles in ~2 years — after that, you're playing with house money.

Negotiation context

• Only 4 days on market — expect competitive offers; lowballing is unlikely to land.
• 2 sale attempts since 14y 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 $438k; list at $775k implies a 77% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1860 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $775,000

Questions for the listing agent

1. Built in 1860 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are F-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
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: 3.18% ✓
• Cap rate: 29.02%
• Cash-on-cash: 81.16%
• DSCR: 4.61
• GRM: 2.6

CMA / ARV

• ARV (on-the-fly): $628,800
• Comps found: 2

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
133 Royal Ave	0.74mi	3/2.0 (-1)	1,400 (-12%)	1mo	$550,000	$393	38
207 Brookhaven Ave	0.61mi	4/2.0	1,800 (+12%)	17mo	$635,000	$353	36

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: 81.4%
• Equity multiple: 4.73×
• Total profit: $809,161
• Equity at exit: $115,555

10-year hold

• IRR: 84.7%
• Equity multiple: 9.79×
• Total profit: $1,908,361
• Equity at exit: $67,008

Cash invested: $217,000 (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 11901

• Home prices YoY: -29.5%
• Active inventory: 191
• Price-to-rent: 2.6×

Monthly cashflow live

• Estimated rent: $24,682 medium
• Mortgage (P&I): −$4,064
• Tax from tax record: −$436 /mo · $5,236/yr
• Insurance: −$323
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,183
• Net cashflow: $14,676

Break-even live

Break-even rent $6,106

Max offer price $775,000

Occupancy floor 36%

Sensitivity live

Price	-10% $15,114	-5% $14,895	+0% $14,676	+5% $14,456	+10% $14,237
Rent	-10% $12,726	-5% $13,701	+0% $14,676	+5% $15,651	+10% $16,626
Rate	-1.0pp $15,066	-0.5pp $14,873	base $14,676	+0.5pp $14,475	+1.0pp $14,271

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: $193,750
• Closing costs: $23,250
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
420 Maple Ave S Riverhead, NY	3.0	3.0	1710	$11,000	$6.43	26d	1	0.58mi
588 Pleasure Dr Riverhead, NY	4.0	4.0	2225	$60,000	$26.97	26d	1	1.15mi

Listing history 3 events

1. 2026-06-21
   days on market $775,000 Active 4 DOM
2. 2026-06-18
   remarks 699-char remark
3. 2026-06-18
   listed $775,000 Active 1 DOM

ⓘ 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: $5,236 · $436/mo
• Projected year-2 tax: $9,167 · $764/mo
• Expected delta: +$3,931/yr (+$328/mo · 75.1%)

ⓘ 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 4/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥91°F today · 18 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: $296,189
• − Mortgage interest: −$43,412
• − Property taxes: −$5,236
• − Insurance: −$3,875
• − Repairs & maintenance: −$23,695
• − Management: −$23,695
• − Depreciation: −$22,545
• Taxable income: $173,730
• Est. tax owed @ 24.0%: −$41,695
• After-tax cash flow: $134,412/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: Riverhead Central School District
• NCES district ID: 3624690
• Math proficiency: 34% ▼ -4.00%
• Reading proficiency: 48% ▲ 13.00%
• Median HH income: $61,607
• Composite: 36.38/100
• National rank: #4683
• State rank: #489 of 590 in NY

Livability — Flanders

• Score: 56/100
• State rank: #1107
• US rank: #22674

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Flanders, NY
• Population (ZIP): 32,921

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 0.63)
• Race & ethnicity: White 52% Hispanic / Latino 29% Two or more races 14% Black 11% Asian 3%
• Hispanic origin (detail): Mexican 4%
• Common ancestry: Romanian 8% Iranian 1% Portuguese 1%
• Foreign-born: 25% · Canada, Jamaica
• Languages at home: 68% English-only · Spanish 26% Other Indo-European 3% Russian/Polish/Slavic 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: ▼ -182.60%
• Current HPI: 436.7781
• 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

+1007.1% since first listed

8 events — show timeline

• 2026-06-17 Listed $775,000 OneKey® MLS as Distributed by MLS Grid
• 2023-04-11 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2020-08-20 Sold (Public Records) $437,750 Public Records
• 2012-09-22 Listed $399,000 OneKey® MLS as Distributed by MLS Grid
• 2008-05-20 Sold (Public Records) $400,000 Public Records
• 2001-04-04 Sold (Public Records) $90,000 Public Records
• 2001-01-24 Sold (Public Records) $59,000 Public Records
• 1996-05-23 Sold (Public Records) $70,000 Public Records

Property tax history

+2.3%/yr

Latest (2024): $5,236 · +0.0% YoY. Source: county tax records.