45 Whippoorwill Ln · East Quogue, NY 11942

$1,975,000

4 bd · 4.0 ba · 3,480 sqft · SingleFamily public records · 232 Days on market

Built 1994 0.95 ac lot $568/sqft · 13% below area Est $2500k · 21% under

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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
• ARV discount +15.0/15.0
• DSCR +10.0/10.0
• 1% rule +8.2/10.0
• Schools +6.6/10.0
• Livability +3.1/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Welcome to 45 Whippoorwill, a stunning coastal retreat that perfectly blends indoor luxury with effortless outdoor living. Nestled on a beautifully landscaped, park-like acre, this expansive and light-filled home offers the ultimate in elegance, comfort, and privacy. Once inside you'll discover a bright open-concept layout designed for both entertaining and relaxed everyday living. The expansive great room features soaring ceilings, a large wood-burning fireplace, and multiple sliders that open to an oversized deck with views to the pool and court, creating a seamless transition to the outdoors. With multiple seating areas throughout, this home is thoughtfully designed to host gatherings of any size or to simply unwind in comfort. Outdoors, enjoy resort-style amenities including a heated pool, hot tub, Har-Tru tennis court, and a fabulous built-in outdoor chef's kitchen - all perfect for year-round entertaining. At the heart of the home is a large, fully equipped chef's kitchen featuring extensive counter space, two working islands, and double counter seating - ideal for casual meals or entertaining with ease. The kitchen flows effortlessly into the open dining area, creating a welcoming and connected living space. There are four (convertible to five) spacious bedrooms and six full baths, including two luxurious en-suite primary suites - one conveniently located on the first floor with direct deck access, and another upstairs featuring its own private deck with evergreen sunset views. A full basement offers endless potential for recreation and entertaining. Enjoy west-facing sunset views over the Quogue Wildlife Refuge, along with the benefit of low Quogue taxes - making this property as smart an investment as it is beautiful.

Key facts

• Landscaped acre
• Oversized deck
• Great room

Tags

• LANDSCAPED ACRE
• OPEN-CONCEPT LAYOUT
• GREAT ROOM
• WOOD-BURNING FIREPLACE
• OVERSIZED DECK
• HEATED POOL

What this means for you Summary

Snapshot

• This is a 4-bed/4.0-bath single-family listed at $1.98M.

Deal economics

• At list price, monthly cash flow is $9k ($108k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($26k rent vs $1.98M).
• Recommended offer: $1.74M (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 61/100 on livability (#943 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Quogue Union Free School District (suburban): math 70% / reading 80% proficiency, ranked #125 of 755 in NY (top 17%) — strong family-tenant draw, lease renewals of 3-5y typical; only 4% free/reduced lunch — higher-income household profile.
• Market conditions: 75 active listings in the ZIP; 10 comparable units currently listed for rent nearby; rentals at typical pace (median 26d on market — plan ~3-4 weeks tenant-placement turnaround); 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 $14k of loan paydown is wiped out by about $59k 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 $553k cash investment doubles in ~7 years — after that, you're playing with house money.

Negotiation context

• It's been on market 232 days — a 12% lower offer ($1.74M) is reasonable based on typical stale-listing flexibility.
• 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 $1.11M; list at $1.98M implies a 78% 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 — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,738,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 232 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. Schools are B-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: 1.32% ✓
• Cap rate: 11.78%
• Cash-on-cash: 19.58%
• DSCR: 1.87
• GRM: 6.3

CMA / ARV

• ARV (median comp): $2,499,545
• List price: $1,975,000
• Delta: -20.99%
• Verdict: UNDERPRICED
• Comps: 11 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
2 Blueberry	0.25mi	4/4.5	3,800 (+9%)	18mo	$1,725,000	$454	56
3 Sachem Ln	0.63mi	4/4.5	4,000 (+15%)	0mo	$2,700,000	$675	44

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: 11.6%
• Equity multiple: 1.46×
• Total profit: $253,918
• Equity at exit: $294,479

10-year hold

• IRR: 20.5%
• Equity multiple: 2.73×
• Total profit: $957,812
• Equity at exit: $170,762

Cash invested: $553,000 (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 11942

• Home prices YoY: -25.0%
• Active inventory: 75
• Price-to-rent: 6.3×

Monthly cashflow live

• Estimated rent: $26,143 high
• Mortgage (P&I): −$10,357
• Tax from tax record: −$448 /mo · $5,381/yr
• Insurance: −$823
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,490
• Net cashflow: $9,025

Break-even live

Break-even rent $14,720

Max offer price $1,975,000

Occupancy floor 60%

Sensitivity live

Price	-10% $10,143	-5% $9,584	+0% $9,025	+5% $8,466	+10% $7,907
Rent	-10% $6,960	-5% $7,992	+0% $9,025	+5% $10,058	+10% $11,090
Rate	-1.0pp $10,019	-0.5pp $9,527	base $9,025	+0.5pp $8,513	+1.0pp $7,992

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: $493,750
• Closing costs: $59,250
• Reserves months: —
• Total cash needed: —

Rent comps 10 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
69 Whippoorwill Ln Patchogue, NY	4.0	4.0	2945	$20,000	$6.79	0d	1	0.16mi
1 Whippoorwill Ln East Quogue, NY	4.0	4.0	2483	$29,000	$11.68	6d	1	0.29mi
10 Fox Hollow Dr East Quogue, NY	4.0	3.5	2750	$30,000	$10.91	44d	1	0.52mi
3 Cherry Blossom Ln East Quogue, NY	5.0	4.5	3632	$40,000	$11.01	44d	1	0.72mi
10 Pennant Ln East Quogue, NY	4.0	3.5	2800	$80,000	$28.57	22d	1	1.15mi
9 The Registry East Quogue, NY	4.0	4.5	2734	$30,000	$10.97	44d	1	1.17mi
99 Spinney Rd East Quogue, NY	5.0	4.5	3512	$95,000	$27.05	25d	1	1.19mi
73 Spinney Rd East Quogue, NY	3.0	2.5	2400	$25,000	$10.42	19d	1	1.28mi
20 Jennifers Path Westhampton Beach, NY	4.0	3.5	3000	$20,000	$6.67	22d	1	1.47mi
28 Old Meeting House Rd Quogue, NY	5.0	5.5	4500	$30,000	$6.67	25d	1	1.49mi

Listing history 7 events

1. 2026-05-08
   status Pending 1756-char remark

   Show marketing remark (1756 chars)

   Welcome to 45 Whippoorwill, a stunning coastal retreat that perfectly blends indoor luxury with effortless outdoor living. Nestled on a beautifully landscaped, park-like acre, this expansive and light-filled home offers the ultimate in elegance, comfort, and privacy. Once inside you'll discover a bright open-concept layout designed for both entertaining and relaxed everyday living. The expansive great room features soaring ceilings, a large wood-burning fireplace, and multiple sliders that open to an oversized deck with views to the pool and court, creating a seamless transition to the outdoors. With multiple seating areas throughout, this home is thoughtfully designed to host gatherings of any size or to simply unwind in comfort. Outdoors, enjoy resort-style amenities including a heated pool, hot tub, Har-Tru tennis court, and a fabulous built-in outdoor chef's kitchen - all perfect for year-round entertaining. At the heart of the home is a large, fully equipped chef's kitchen featuring extensive counter space, two working islands, and double counter seating - ideal for casual meals or entertaining with ease. The kitchen flows effortlessly into the open dining area, creating a welcoming and connected living space. There are four (convertible to five) spacious bedrooms and six full baths, including two luxurious en-suite primary suites - one conveniently located on the first floor with direct deck access, and another upstairs featuring its own private deck with evergreen sunset views. A full basement offers endless potential for recreation and entertaining. Enjoy west-facing sunset views over the Quogue Wildlife Refuge, along with the benefit of low Quogue taxes - making this property as smart an investment as it is beautiful.

2. 2025-09-18
   listed $1,975,000 Active 1756-char remark

   Show marketing remark (1756 chars)

   Welcome to 45 Whippoorwill, a stunning coastal retreat that perfectly blends indoor luxury with effortless outdoor living. Nestled on a beautifully landscaped, park-like acre, this expansive and light-filled home offers the ultimate in elegance, comfort, and privacy. Once inside you'll discover a bright open-concept layout designed for both entertaining and relaxed everyday living. The expansive great room features soaring ceilings, a large wood-burning fireplace, and multiple sliders that open to an oversized deck with views to the pool and court, creating a seamless transition to the outdoors. With multiple seating areas throughout, this home is thoughtfully designed to host gatherings of any size or to simply unwind in comfort. Outdoors, enjoy resort-style amenities including a heated pool, hot tub, Har-Tru tennis court, and a fabulous built-in outdoor chef's kitchen - all perfect for year-round entertaining. At the heart of the home is a large, fully equipped chef's kitchen featuring extensive counter space, two working islands, and double counter seating - ideal for casual meals or entertaining with ease. The kitchen flows effortlessly into the open dining area, creating a welcoming and connected living space. There are four (convertible to five) spacious bedrooms and six full baths, including two luxurious en-suite primary suites - one conveniently located on the first floor with direct deck access, and another upstairs featuring its own private deck with evergreen sunset views. A full basement offers endless potential for recreation and entertaining. Enjoy west-facing sunset views over the Quogue Wildlife Refuge, along with the benefit of low Quogue taxes - making this property as smart an investment as it is beautiful.

3. 2012-11-05
   soldstatus $1,112,500
4. 2012-10-11
   soldstatus $1,112,500 317-char remark

   Show marketing remark (317 chars)

   Beautifully Landscaped Post Modern On An Acre Of Property With 5 Bedrooms, 5.5 Baths, Bright Sunny Great Room W/Fireplace, Heated Inground Pool & Har-Tru Tennis Court Backing The Preserve. A True Gem Not To Be Missed! , Additional information: Appearance:Mint,ExterioFeatures:Tennis,Separate Hotwater Heater:Yes

5. 2012-04-07
   listed $1,395,000 317-char remark

   Show marketing remark (317 chars)

   Beautifully Landscaped Post Modern On An Acre Of Property With 5 Bedrooms, 5.5 Baths, Bright Sunny Great Room W/Fireplace, Heated Inground Pool & Har-Tru Tennis Court Backing The Preserve. A True Gem Not To Be Missed! , Additional information: Appearance:Mint,ExterioFeatures:Tennis,Separate Hotwater Heater:Yes

6. 1999-12-20
   soldstatus $590,000
7. 1989-01-03
   soldstatus $950,000

ⓘ 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: $5,381 · $448/mo
• Projected year-2 tax: $19,379 · $1,615/mo
• Expected delta: +$13,998/yr (+$1,167/mo · 260.2%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 4/10 Moderate 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 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $313,721
• − Mortgage interest: −$110,631
• − Property taxes: −$5,381
• − Insurance: −$9,875
• − Repairs & maintenance: −$25,098
• − Management: −$25,098
• − Depreciation: −$57,455
• Taxable income: $80,185
• Est. tax owed @ 24.0%: −$19,244
• After-tax cash flow: $89,054/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: Quogue Union Free School District
• NCES district ID: 3624060
• Math proficiency: 70% ▼ -10.00%
• Reading proficiency: 80% ▬ 0.00%
• Median HH income: $66,746
• Composite: 66.09/100
• National rank: #960
• State rank: #125 of 755 in NY

Livability — East Quogue

• Score: 61/100
• State rank: #943
• US rank: #18348

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: East Quogue, NY
• City population: 5,871
• Population (ZIP): 5,871

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 (80%)
• Race & ethnicity: White 80% Hispanic / Latino 16% Asian 2% Two or more races 2%
• Hispanic origin (detail): Mexican 3%
• Common ancestry: Romanian 6% Scotch-Irish 3% Lithuanian 3%
• Foreign-born: 13% · Canada, Jamaica, Guatemala
• Languages at home: 80% English-only · Spanish 12% Other Indo-European 2% 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: ▼ -145.33%
• Current HPI: 435.8017
• 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

+107.9% since first listed

7 events — show timeline

• 2026-05-08 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-09-18 Listed $1,975,000 OneKey® MLS as Distributed by MLS Grid
• 2012-11-05 Sold (Public Records) $1,112,500 Public Records
• 2012-10-11 Sold (MLS) $1,112,500 OneKey® MLS as Distributed by MLS Grid
• 2012-04-07 Listed $1,395,000 OneKey® MLS as Distributed by MLS Grid
• 1999-12-20 Sold (Public Records) $590,000 Public Records
• 1989-01-03 Sold (Public Records) $950,000 Public Records

Property tax history

+2.0%/yr

Latest (2022): $5,381 · +0.0% YoY. Source: county tax records.