290 Windward Rd · Orient, NY 11957

$2,499,999

5 bd · 4.0 ba · 4,200 sqft · SingleFamily · 481 Days on market

Built 2023 1.02 ac lot $595/sqft · at area comps Est $2568k · at est.

---

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 +17.7/30.0
• Appreciation +10.0/10.0
• ARV discount +8.7/15.0
• DSCR +5.5/10.0
• Schools +4.3/10.0
• 1% rule +3.8/10.0
• Livability +2.9/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you're greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef's dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it's perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you're lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you'll find serenity and relaxation at every turn. Beyond the property's boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there's something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you're seeking a tranquil retreat or a sophisticated entertainer's paradise, this custom-built home is sure to exceed your expectations.

Key facts

• Custom cabinetry
• Spacious island
• Breathtaking views

Tags

• BREATHTAKING VIEWS
• STATE-OF-THE-ART APPLIANCES
• EXPANSIVE PATIO
• CUSTOM CABINETRY
• SPACIOUS ISLAND

What this means for you Summary

Snapshot

• This is a 5-bed/4.0-bath single-family listed at $2.50M.

Deal economics

• At list price, monthly cash flow is $2k ($24k/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 $2.20M (12.0% below list).
• Recommended offer: $2.20M (12.0% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 57/100 on livability (#1,080 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Oysterponds Union Free School District (rural): math 30% / reading 60% proficiency, ranked #506 of 755 in NY (top 67%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 4% free/reduced lunch — higher-income household profile.
• Zoned schools: Oysterponds Elementary School (math 54% / reading 64%, grade B-, #745 of 2,108 statewide, top 39%, 80 students, 0% FRL) — zoned schools at 0% FRL track the district average.
• Zoned-school proficiency averages 60% at this address vs 45% district-wide (+14 pts) — the actual schools serving this property are materially stronger than the Oysterponds Union Free School District average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 25 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals lingering (median 46d 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

• In year one you build about $267k of equity ($17k loan paydown + $250k appreciation (10.0% 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 (10.0% appreciation + 3.0% rent growth), your $700k cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$430k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 481 days — a 12% lower offer ($2.20M) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 2y ago; this cycle's ask has dropped $199k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $300k; list at $2.50M implies a 733% 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 $2,199,758 (12.0% below list)

Questions for the listing agent

1. It's been on market 481 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. 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: 0.88% ✗
• Cap rate: 7.26%
• Cash-on-cash: 3.44%
• DSCR: 1.15
• GRM: 9.5

CMA / ARV

• ARV (median comp): $2,567,838
• List price: $2,499,999
• Delta: -2.64%
• Verdict: FAIR
• Comps: 3 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
555 Grandview Dr	0.37mi	4/4.5 (-1)	4,300 (+2%)	22mo	$2,075,000	$483	53

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

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 26.7%
• Equity multiple: 3.13×
• Total profit: $1,488,439
• Equity at exit: $2,252,197

10-year hold

• IRR: 23.4%
• Equity multiple: 7.12×
• Total profit: $4,281,110
• Equity at exit: $4,856,948

Cash invested: $700,000 (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 11957

• Home prices YoY: 6.6%
• Active inventory: 25
• Price-to-rent: 9.5×

Monthly cashflow live

• Estimated rent: $21,998 medium
• Mortgage (P&I): −$13,110
• Tax from tax record: −$1,221 /mo · $14,652/yr
• Insurance: −$1,042
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,619
• Net cashflow: $2,005

Break-even live

Break-even rent $19,459

Max offer price $2,499,999

Occupancy floor 86%

Sensitivity live

Price	-10% $3,420	-5% $2,713	+0% $2,005	+5% $1,298	+10% $590
Rent	-10% $267	-5% $1,136	+0% $2,005	+5% $2,874	+10% $3,743
Rate	-1.0pp $3,264	-0.5pp $2,641	base $2,005	+0.5pp $1,357	+1.0pp $698

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: $625,000
• Closing costs: $75,000
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
2055 Grandview Dr Orient, NY	4.0	5.0	5000	$18,000	$3.60	45d	1	0.58mi
1080 Lands End Rd Orient, NY	4.0	3.0	4000	$32,000	$8.00	45d	1	1.36mi
300 Latham Ln Orient, NY	4.0	4.0	3800	$20,000	$5.26	45d	1	1.44mi

Listing history 31 events

1. 2026-06-22
   days on market $2,499,999 Active 481 DOM
2. 2026-06-21
   days on market $2,499,999 Active 480 DOM
3. 2026-06-21
   days on market $2,499,999 Active 479 DOM
4. 2026-06-18
   days on market $2,499,999 Active 477 DOM
5. 2026-06-17
   days on market $2,499,999 Active 476 DOM
6. 2026-06-16
   days on market $2,499,999 Active 475 DOM
7. 2026-06-15
   days on market $2,499,999 Active 474 DOM
8. 2026-06-13
   days on market $2,499,999 Active 472 DOM
9. 2026-06-12
   days on market $2,499,999 Active 471 DOM
10. 2026-06-09
    days on market $2,499,999 Active 468 DOM
11. 2026-06-08
    days on market $2,499,999 Active 467 DOM
12. 2026-06-07
    days on market $2,499,999 Active 466 DOM
13. 2026-06-07
    days on market $2,499,999 Active 465 DOM
14. 2026-06-04
    days on market $2,499,999 Active 462 DOM
15. 2026-06-02
    days on market $2,499,999 Active 461 DOM
16. 2026-06-01
    days on market $2,499,999 Active 460 DOM
17. 2026-05-31
    days on market $2,499,999 Active 459 DOM
18. 2026-03-26
    price $2,499,999 1580-char remark

    Show marketing remark (1580 chars)

    This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you're greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef's dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it's perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you're lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you'll find serenity and relaxation at every turn. Beyond the property's boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there's something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you're seeking a tranquil retreat or a sophisticated entertainer's paradise, this custom-built home is sure to exceed your expectations.

19. 2026-02-27
    status Active 1580-char remark

    Show marketing remark (1580 chars)

    This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you're greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef's dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it's perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you're lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you'll find serenity and relaxation at every turn. Beyond the property's boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there's something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you're seeking a tranquil retreat or a sophisticated entertainer's paradise, this custom-built home is sure to exceed your expectations.

20. 2026-02-26
    historical 1580-char remark

    Show marketing remark (1580 chars)

    This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you're greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef's dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it's perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you're lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you'll find serenity and relaxation at every turn. Beyond the property's boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there's something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you're seeking a tranquil retreat or a sophisticated entertainer's paradise, this custom-built home is sure to exceed your expectations.

21. 2025-02-25
    listed $2,699,000 Active 1580-char remark

    Show marketing remark (1580 chars)

    This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you're greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef's dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it's perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you're lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you'll find serenity and relaxation at every turn. Beyond the property's boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there's something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you're seeking a tranquil retreat or a sophisticated entertainer's paradise, this custom-built home is sure to exceed your expectations.

22. 2025-02-23
    historical
23. 2024-10-02
    historical
24. 2024-07-31
    price $2,699,000
25. 2024-06-18
    price $3,150,000
26. 2024-03-07
    listed $3,499,999 Active
27. 2024-02-23
    historical
28. 2024-02-23
    listed $2,699,000 Active
29. 2017-06-02
    soldstatus $300,000
30. 2007-12-17
    soldstatus $340,000
31. 2002-06-04
    soldstatus $165,000

ⓘ 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: $14,652 · $1,221/mo
• Projected year-2 tax: $28,451 · $2,371/mo
• Expected delta: +$13,799/yr (+$1,150/mo · 94.2%)

ⓘ 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 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥91°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: $263,971
• − Mortgage interest: −$140,039
• − Property taxes: −$14,652
• − Insurance: −$12,500
• − Repairs & maintenance: −$21,118
• − Management: −$21,118
• − Depreciation: −$72,727
• Taxable loss: −$18,182
• Est. tax savings @ 24.0%: +$4,364
• After-tax cash flow: $28,426/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: Oysterponds Union Free School District
• NCES district ID: 3621930
• Math proficiency: 30% ▼ -10.00%
• Reading proficiency: 60% ▲ 20.00%
• Median HH income: $71,948
• Composite: 42.9/100
• National rank: #6712
• State rank: #506 of 755 in NY

Livability — Orient

• Score: 57/100
• State rank: #1080
• US rank: #21725

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Orient, NY
• Population (ZIP): 1,152

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 (96%)
• Race & ethnicity: White 96% Hispanic / Latino 2%
• Common ancestry: Romanian 5% Scotch-Irish 3% Iranian 3%
• Foreign-born: 17% · Canada, China
• Languages at home: 85% English-only · Other Asian/Pacific 5% Russian/Polish/Slavic 3% 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: ▲ 16.41%
• Current HPI: 265.16
• 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

+1415.2% since first listed

14 events — show timeline

• 2026-03-26 Price Changed $2,499,999 OneKey® MLS as Distributed by MLS Grid
• 2026-02-27 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-02-26 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-02-25 Listed $2,699,000 OneKey® MLS as Distributed by MLS Grid
• 2025-02-23 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-10-02 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-07-31 Price Changed $2,699,000 OneKey® MLS as Distributed by MLS Grid
• 2024-06-18 Price Changed $3,150,000 OneKey® MLS as Distributed by MLS Grid
• 2024-03-07 Listed $3,499,999 OneKey® MLS as Distributed by MLS Grid
• 2024-02-23 Coming Soon — OneKey® MLS as Distributed by MLS Grid
• 2024-02-23 Listed $2,699,000 OneKey® MLS as Distributed by MLS Grid
• 2017-06-02 Sold (Public Records) $300,000 Public Records
• 2007-12-17 Sold (Public Records) $340,000 Public Records
• 2002-06-04 Sold (Public Records) $165,000 Public Records

Property tax history

+17.1%/yr

Latest (2025): $14,652 · +0.0% YoY. Source: county tax records.