5A/5B Jessup Ln · Quogue, NY 11959

$4,500,000

5 bd · 7.0 ba · 4,000 sqft · SingleFamily · 56 Days on market

Built 1953 Good condition 1.35 ac lot $1125/sqft · at area comps Est $4442k · at est. ↓ 27% since listing

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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 +13.7/30.0
• Appreciation +7.0/10.0
• ARV discount +6.9/15.0
• Schools +6.6/10.0
• DSCR +4.2/10.0
• 1% rule +3.8/10.0
• Condition / age +3.8/5.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0

Listing remarks

Historic Estate in the Village Quogue. Welcome to a rare opportunity to own two homes on an extraordinary compound offering privacy, elegance, and unparalleled charm. Each house has its very own private pool with pool house creating an idyllic retreat for extended family and guests. The Main House exudes warmth and comfort with three spacious bedrooms and three full bathrooms. A Sun-filled Living room with a fireplace provides the perfect gathering space. A thoughtfully designed and updated Chef’s kitchen with high end appliances. Ideal for everyday living and entertaining. Discover timeless elegance in the meticulously restored two bedroom and two full bathroom Barn situated behind

Key facts

• Private pool
• Pool house
• Organic gardens

Tags

• PRIVATE POOL
• POOL HOUSE
• CHEF KITCHEN
• ORGANIC GARDENS
• QUOGUE VILLAGE

Property features AI

Exterior

• Parking: Driveway
• Utilities: Electricity connected (PSEG); Cesspool sewer
• Home design: Single family residence
• Construction: Cedar and wood siding construction; Has a full basement and crawl space; Dormer attic
• Exterior features: Covered deck; Patio; Porch; Screened porch; Private in-ground pool; Not waterfront

Interior

• Kitchen: Cooktop; Dishwasher; Gas oven; Gas range; Microwave; Oven; Refrigerator; Stainless steel appliances; Kitchen island; Granite counters; Pantry
• Bedrooms: First-floor bedroom
• Bathrooms: 7 full bathrooms
• Heating & cooling: Propane heating; Central air conditioning
• Interior features: First-floor bedroom; First-floor full bath; Beamed ceilings; Cathedral ceilings; Ceiling fans; Chef's kitchen; Granite counters; High ceilings; Kitchen island; Primary bathroom; Master suite on main floor; Pantry
• Laundry & utility: Washer; Dryer; Laundry located in hall; Tankless water heater

What this means for you Summary

Snapshot

• This is a 5-bed/7.0-bath single-family listed at $4.50M. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $357 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $3.98M (11.5% below list).
• Recommended offer: $3.98M (11.5% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 67/100 on livability (#600 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.
• 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.
• Zoned schools: Quogue Elementary School (math 87% / reading 92%, grade A+, #45 of 2,108 statewide, top 3%, 84 students, 0% FRL) — zoned schools at 0% FRL track the district average.
• Zoned-school proficiency averages 90% at this address vs 75% district-wide (+14 pts) — the actual schools serving this property are materially stronger than the Quogue Union Free School District average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 37 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals at typical pace (median 25d 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

• In year one you build about $212k of equity ($31k loan paydown + $181k appreciation (4.0% local appreciation)).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• At projected returns (4.0% appreciation + 3.0% rent growth), your $1.26M cash investment doubles in ~5 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$341k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 56 days — a 3% lower offer ($4.37M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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.

Risks & watch-outs

• Watch-outs: built in 1953 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $3,981,701 (11.5% below list)

Questions for the listing agent

1. It's been on market 56 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1953 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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: 0.88% ✗
• Cap rate: 6.39%
• Cash-on-cash: 0.34%
• DSCR: 1.02
• GRM: 9.4

CMA / ARV

• ARV (median comp): $4,441,708
• List price: $4,500,000
• Delta: 1.31%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
3 Waters Edge Dr	0.64mi	4/4.0 (-1)	3,928 (-2%)	1mo	$3,800,000	$967	50
6 Assups Neck Ln	0.55mi	6/8.0 (+1)	4,515 (+13%)	12mo	$6,637,500	$1,470	33
17 Dune Rd	0.61mi	5/5.5	3,600 (-10%)	19mo	$6,800,000	$1,889	33
3 Assups Neck Ln	0.61mi	4/4.5 (-1)	3,793 (-5%)	19mo	$5,375,000	$1,417	32
21 Wildwood Ln	0.58mi	4/5.0 (-1)	3,786 (-5%)	24mo	$4,225,000	$1,116	31

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

4.01% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 10.6%
• Equity multiple: 1.64×
• Total profit: $811,232
• Equity at exit: $2,284,891

10-year hold

• IRR: 12.4%
• Equity multiple: 3.04×
• Total profit: $2,566,725
• Equity at exit: $3,739,779

Cash invested: $1,260,000 (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 11959

• Home prices YoY: 1.1%
• Active inventory: 37
• Price-to-rent: 9.4×

Monthly cashflow live

• Estimated rent: $39,817 medium
• Mortgage (P&I): −$23,598
• Tax est. 1.5%: −$5,625 /mo · $67,500/yr
• Insurance: −$1,875
• HOA: −$0
• Vacancy / Maint / Mgmt: −$8,362
• Net cashflow: $357

Break-even live

Break-even rent $39,365

Max offer price $4,500,000

Occupancy floor 94%

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: $1,125,000
• Closing costs: $135,000
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
19 Dune Rd Westhampton Beach, NY	4.0	5.5	3991	$50,000	$12.53	24d	1	0.56mi
50 Old Main Rd Quogue, NY	4.0	4.5	3702	$30,000	$8.10	24d	1	0.92mi
28 Old Meeting House Rd Quogue, NY	5.0	5.5	4500	$30,000	$6.67	24d	1	1.06mi
102 Dune Rd Westhampton Beach, NY	6.0	6.5	5297	$40,000	$7.55	24d	1	1.40mi

Listing history 21 events

1. 2026-06-18
   days on market $4,500,000 Active 56 DOM
2. 2026-06-17
   days on market $4,500,000 Active 55 DOM
3. 2026-06-16
   days on market $4,500,000 Active 54 DOM
4. 2026-06-15
   days on market $4,500,000 Active 53 DOM
5. 2026-06-13
   days on market $4,500,000 Active 51 DOM
6. 2026-06-13
   days on market $4,500,000 Active 50 DOM
7. 2026-06-09
   days on market $4,500,000 Active 47 DOM
8. 2026-06-08
   days on market $4,500,000 Active 46 DOM
9. 2026-06-07
   days on market $4,500,000 Active 45 DOM
10. 2026-06-04
    days on market $4,500,000 Active 42 DOM
11. 2026-06-03
    days on market $4,500,000 Active 41 DOM
12. 2026-06-02
    days on market $4,500,000 Active 40 DOM
13. 2026-06-01
    days on market $4,500,000 Active 39 DOM
14. 2026-05-31
    days on market $4,500,000 Active 38 DOM
15. 2026-04-23
    listed $4,500,000 Active 1125-char remark
16. 2025-12-08
    historical
17. 2025-10-02
    price $4,950,000
18. 2025-10-02
    price $49,500,000
19. 2025-07-24
    price $5,500,000
20. 2025-06-06
    price $5,800,000
21. 2025-05-09
    listed $6,200,000 Active

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $477,804
• − Mortgage interest: −$252,070
• − Property taxes: −$67,500
• − Insurance: −$22,500
• − Repairs & maintenance: −$38,224
• − Management: −$38,224
• − Depreciation: −$130,909
• Taxable loss: −$71,624
• Est. tax savings @ 24.0%: +$17,190
• After-tax cash flow: $21,473/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.

Condition & rehab AI · 12 photos

Good 75/100 Cosmetic rehab

This historic estate in Quogue offers two homes with private pools and a serene setting. The main house is in good condition with updated kitchen and bathrooms, while the barn is well-maintained. Both properties are move-in ready with minimal repairs needed.

Value-add opportunities

• Both Landscaping and curb appeal improvements — Enhances curb appeal and property value
• Resale Kitchen appliances and minor updates — Modernizes the kitchen and enhances functionality
• Resale Bathroom updates and minor updates — Enhances the overall aesthetic and functionality of the bathrooms

Renovation cost estimate screening

Value-add ROI direction

• Both Landscaping and curb appeal improvements — Enhances curb appeal and property value ↑
• Resale Kitchen appliances and minor updates — Modernizes the kitchen and enhances functionality ↑
• Resale Bathroom updates and minor updates — Enhances the overall aesthetic and functionality of the bathrooms ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

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 — Quogue

• Score: 67/100
• State rank: #600
• US rank: #10895

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Quogue, NY
• City population: 576
• Population (ZIP): 576

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 (71%)
• Race & ethnicity: White 71% Two or more races 23% Hispanic / Latino 23% Black 3%
• Common ancestry: Italian 21% Portuguese 7% Scotch-Irish 4%
• Foreign-born: 18% · Canada
• Languages at home: 83% English-only · Spanish 17%

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: ▲ 4.01%
• Current HPI: 364.8746
• 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

-27.4% since first listed

7 events — show timeline

• 2026-04-23 Listed $4,500,000 OneKey® MLS as Distributed by MLS Grid
• 2025-12-08 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-10-02 Price Changed $4,950,000 OneKey® MLS as Distributed by MLS Grid
• 2025-10-02 Price Changed $49,500,000 OneKey® MLS as Distributed by MLS Grid
• 2025-07-24 Price Changed $5,500,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-06 Price Changed $5,800,000 OneKey® MLS as Distributed by MLS Grid
• 2025-05-09 Listed $6,200,000 OneKey® MLS as Distributed by MLS Grid