220 Pleasure Dr · Flanders, NY 11901

$1,497,000

4 bd · 2.0 ba · 2,860 sqft · SingleFamily public records · 17 Days on market

Built 2000 2.20 ac lot $523/sqft · 54% 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
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Schools +3.6/10.0
• Livability +2.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

HIDDEN GEM IN FLANDERS Private 2.2 acre retreat on Pleasure Drive, conveniently located between the South Fork beaches and North Fork vineyards. Easy on, easy off Rt. 27, 10 minutes to Hampton Bays, 12 minutes to Quogue, 15 minutes to West Hampton Beach, 20 minutes to Ponquogue Beach (ocean!) Open-flow design with light-filled Great room and Family room, kitchen & dining area. Primary suite with patio overlooking the grounds, plus 2 guest bedrooms. Media room in lower level. Designed for easy-flow entertaining, inside & out. Generous decking around pool and hot tub. Stone patio with outdoor kitchen for dining alfresco. Lush grounds, gardens, backing onto 200 acres of parkland. Southampton Township beach passes for all Southampton Town ocean & bay beaches. Must be seen to be truly appreciated., Additional information: Appearance:Very Good

Key facts

• Walk-in closets
• Exposed beams
• Vaulted ceilings

Tags

• TWO-SIDED BRICK FIREPLACE
• BREAKFAST BAR
• EXPANSIVE OUTDOOR DECK
• VAULTED CEILINGS
• EXPOSED BEAMS
• WALK-IN CLOSETS

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $1.50M.

Deal economics

• At list price, monthly cash flow is $38k ($456k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($60k rent vs $1.50M).
• Recommended offer: $1.47M (1.5% below list) — sets the bar for market timing.

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: schools F, amenities F, commute 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.
• Market conditions: 188 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 $10k of loan paydown is wiped out by about $45k 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 $419k cash investment doubles in ~1 year — after that, you're playing with house money.

Negotiation context

• It's been on market 17 days — a 2% lower offer ($1.47M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 2y ago; this cycle's ask has dropped $103k (6%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $900k; list at $1.50M implies a 66% 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; moderate wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,474,545 (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 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?
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: 4.01% ✓
• Cap rate: 36.73%
• Cash-on-cash: 108.69%
• DSCR: 5.84
• GRM: 2.1

CMA / ARV

• ARV (median comp): $971,131
• List price: $1,497,000
• Delta: 59.61%
• Verdict: OVERPRICED
• Comps: 7 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
220 Pleasure Dr	0.00mi	3/3.0 (-1)	2,860 (0%)	15mo	$900,000	$315	79
15 Tree Haven Ln	0.35mi	5/3.0 (+1)	2,444 (-14%)	23mo	$849,000	$347	31

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: —
• Equity multiple: 6.19×
• Total profit: $2,175,910
• Equity at exit: $223,208

10-year hold

• IRR: —
• Equity multiple: 12.95×
• Total profit: $5,009,890
• Equity at exit: $129,433

Cash invested: $419,160 (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: 188
• Price-to-rent: 2.1×

Monthly cashflow live

• Estimated rent: $60,000 medium
• Mortgage (P&I): −$7,850
• Tax from tax record: −$959 /mo · $11,505/yr
• Insurance: −$624
• HOA: −$0
• Vacancy / Maint / Mgmt: −$12,600
• Net cashflow: $37,967

Break-even live

Break-even rent $11,940

Max offer price $1,497,000

Occupancy floor 32%

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: $374,250
• Closing costs: $44,910
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
588 Pleasure Dr Riverhead, NY	4.0	4.0	2225	$60,000	$26.97	25d	1	0.74mi

Listing history 23 events

1. 2026-06-18
   days on market $1,497,000 Active 17 DOM
2. 2026-06-17
   days on market $1,497,000 Active 16 DOM
3. 2026-06-16
   days on market $1,497,000 Active 15 DOM
4. 2026-06-15
   days on market $1,497,000 Active 14 DOM
5. 2026-06-13
   days on market $1,497,000 Active 12 DOM
6. 2026-06-09
   days on market $1,497,000 Active 8 DOM
7. 2026-06-08
   days on market $1,497,000 Active 7 DOM
8. 2026-06-07
   days on market $1,497,000 Active 6 DOM
9. 2026-06-04
   days on market $1,497,000 Active 3 DOM
10. 2026-06-03
    days on market $1,497,000 Active 2 DOM
11. 2026-06-02
    pricestatusdays on marketlisting id $1,497,000 Active 1 DOM
12. 2026-05-20
    historical
13. 2026-01-12
    price $1,550,000
14. 2025-11-03
    price $1,575,000
15. 2025-09-25
    listed $1,600,000 Active
16. 2025-04-04
    soldstatus $900,000
17. 2025-03-28
    soldstatus $900,000 Closed 862-char remark

    Show marketing remark (862 chars)

    HIDDEN GEM IN FLANDERS Private 2.2 acre retreat on Pleasure Drive, conveniently located between the South Fork beaches and North Fork vineyards. Easy on, easy off Rt. 27, 10 minutes to Hampton Bays, 12 minutes to Quogue, 15 minutes to West Hampton Beach, 20 minutes to Ponquogue Beach (ocean!) Open-flow design with light-filled Great room and Family room, kitchen & dining area. Primary suite with patio overlooking the grounds, plus 2 guest bedrooms. Media room in lower level. Designed for easy-flow entertaining, inside & out. Generous decking around pool and hot tub. Stone patio with outdoor kitchen for dining alfresco. Lush grounds, gardens, backing onto 200 acres of parkland. Southampton Township beach passes for all Southampton Town ocean & bay beaches. Must be seen to be truly appreciated., Additional information: Appearance:Very Good

18. 2025-02-17
    status Pending 862-char remark

    Show marketing remark (862 chars)

    HIDDEN GEM IN FLANDERS Private 2.2 acre retreat on Pleasure Drive, conveniently located between the South Fork beaches and North Fork vineyards. Easy on, easy off Rt. 27, 10 minutes to Hampton Bays, 12 minutes to Quogue, 15 minutes to West Hampton Beach, 20 minutes to Ponquogue Beach (ocean!) Open-flow design with light-filled Great room and Family room, kitchen & dining area. Primary suite with patio overlooking the grounds, plus 2 guest bedrooms. Media room in lower level. Designed for easy-flow entertaining, inside & out. Generous decking around pool and hot tub. Stone patio with outdoor kitchen for dining alfresco. Lush grounds, gardens, backing onto 200 acres of parkland. Southampton Township beach passes for all Southampton Town ocean & bay beaches. Must be seen to be truly appreciated., Additional information: Appearance:Very Good

19. 2025-01-31
    price $1,049,000 862-char remark

    Show marketing remark (862 chars)

    HIDDEN GEM IN FLANDERS Private 2.2 acre retreat on Pleasure Drive, conveniently located between the South Fork beaches and North Fork vineyards. Easy on, easy off Rt. 27, 10 minutes to Hampton Bays, 12 minutes to Quogue, 15 minutes to West Hampton Beach, 20 minutes to Ponquogue Beach (ocean!) Open-flow design with light-filled Great room and Family room, kitchen & dining area. Primary suite with patio overlooking the grounds, plus 2 guest bedrooms. Media room in lower level. Designed for easy-flow entertaining, inside & out. Generous decking around pool and hot tub. Stone patio with outdoor kitchen for dining alfresco. Lush grounds, gardens, backing onto 200 acres of parkland. Southampton Township beach passes for all Southampton Town ocean & bay beaches. Must be seen to be truly appreciated., Additional information: Appearance:Very Good

20. 2024-10-31
    price $1,150,000 862-char remark

    Show marketing remark (862 chars)

    HIDDEN GEM IN FLANDERS Private 2.2 acre retreat on Pleasure Drive, conveniently located between the South Fork beaches and North Fork vineyards. Easy on, easy off Rt. 27, 10 minutes to Hampton Bays, 12 minutes to Quogue, 15 minutes to West Hampton Beach, 20 minutes to Ponquogue Beach (ocean!) Open-flow design with light-filled Great room and Family room, kitchen & dining area. Primary suite with patio overlooking the grounds, plus 2 guest bedrooms. Media room in lower level. Designed for easy-flow entertaining, inside & out. Generous decking around pool and hot tub. Stone patio with outdoor kitchen for dining alfresco. Lush grounds, gardens, backing onto 200 acres of parkland. Southampton Township beach passes for all Southampton Town ocean & bay beaches. Must be seen to be truly appreciated., Additional information: Appearance:Very Good

21. 2024-10-09
    listed $1,195,000 Active 862-char remark

    Show marketing remark (862 chars)

    HIDDEN GEM IN FLANDERS Private 2.2 acre retreat on Pleasure Drive, conveniently located between the South Fork beaches and North Fork vineyards. Easy on, easy off Rt. 27, 10 minutes to Hampton Bays, 12 minutes to Quogue, 15 minutes to West Hampton Beach, 20 minutes to Ponquogue Beach (ocean!) Open-flow design with light-filled Great room and Family room, kitchen & dining area. Primary suite with patio overlooking the grounds, plus 2 guest bedrooms. Media room in lower level. Designed for easy-flow entertaining, inside & out. Generous decking around pool and hot tub. Stone patio with outdoor kitchen for dining alfresco. Lush grounds, gardens, backing onto 200 acres of parkland. Southampton Township beach passes for all Southampton Town ocean & bay beaches. Must be seen to be truly appreciated., Additional information: Appearance:Very Good

22. 2005-05-09
    soldstatus $555,000
23. 1993-08-10
    soldstatus $205,000

ⓘ 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: $11,505 · $959/mo
• Projected year-2 tax: $18,402 · $1,534/mo
• Expected delta: +$6,897/yr (+$575/mo · 60.0%)

ⓘ 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 5/10 Major
• 🌡 Heat 4/10 Moderate 7 d/yr ≥90°F today · 17 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: $720,000
• − Mortgage interest: −$83,855
• − Property taxes: −$11,505
• − Insurance: −$7,485
• − Repairs & maintenance: −$57,600
• − Management: −$57,600
• − Depreciation: −$43,549
• Taxable income: $458,406
• Est. tax owed @ 24.0%: −$110,017
• After-tax cash flow: $345,588/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

+656.1% since first listed

12 events — show timeline

• 2026-05-20 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2026-01-12 Price Changed $1,550,000 OneKey® MLS as Distributed by MLS Grid
• 2025-11-03 Price Changed $1,575,000 OneKey® MLS as Distributed by MLS Grid
• 2025-09-25 Listed $1,600,000 OneKey® MLS as Distributed by MLS Grid
• 2025-04-04 Sold (Public Records) $900,000 Public Records
• 2025-03-28 Sold (MLS) $900,000 OneKey® MLS as Distributed by MLS Grid
• 2025-02-17 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-01-31 Price Changed $1,049,000 OneKey® MLS as Distributed by MLS Grid
• 2024-10-31 Price Changed $1,150,000 OneKey® MLS as Distributed by MLS Grid
• 2024-10-09 Listed $1,195,000 OneKey® MLS as Distributed by MLS Grid
• 2005-05-09 Sold (Public Records) $555,000 Public Records
• 1993-08-10 Sold (Public Records) $205,000 Public Records

Property tax history

+3.1%/yr

Latest (2024): $11,505 · +0.0% YoY. Source: county tax records.