20 Rolling Hill Rd · Old Westbury, NY 11568

$2,499,000

5 bd · 3.0 ba · 4,482 sqft · SingleFamily public records · 405 Days on market

Built 1960 2.10 ac lot $558/sqft · 12% below area Est $2825k · 12% under

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Why this score? — see what drove the D 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).

• ARV discount +12.7/15.0
• Appreciation +10.0/10.0
• Schools +8.5/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Cash flow +2.2/30.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks MLS

HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

Key facts

• 2.1 acre lot
• Garage
• Pool

What this means for you Summary

Snapshot

• This is a 5-bed/3.0-bath single-family listed at $2.50M.

Deal economics

• At list price, monthly cash flow is $-9k ($-108k/yr) — negative.
• To cash-flow at today's rent, offer at most $916k (63.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $1.00M (60.0% below list).
• Recommended offer: $916k (63.3% below list) — sets the bar for cash-flow.

Location & tenants

• Location reads 65/100 on livability (#714 in NY) — a middle-class / working-renter tenant base. Strengths: schools A+, crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Jericho Union Free School District (suburban): math 91% / reading 86% proficiency, ranked #7 of 590 in NY (top 1%) — strong family-tenant draw, lease renewals of 3-5y typical; only 3% free/reduced lunch — higher-income household profile.
• Market conditions: 40 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 824 units permitted in Nassau County in 2024 (153 in 5+ unit buildings).

Forward outlook

• In year one you build about $267k of equity ($17k loan paydown + $250k appreciation (10.0% local appreciation)).
• Nassau County population projected at +7% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• By year 2, paydown + projected appreciation supports a ~$429k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 405 days — a 12% lower offer ($2.20M) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 14y ago; this cycle's ask has dropped $801k (24%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $435k; list at $2.50M implies a 474% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 63% chance of damaging wind over 30y; extreme-heat days projected 7→14/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $915,954 (63.3% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 405 days. Have you received any prior offers? Is the seller open to a 63% concession, seller financing, or rate buy-down credit?
3. Built in 1960 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
8. 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.
9. 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.
10. 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: 0.40% ✗
• Cap rate: 1.99%
• Cash-on-cash: -15.37%
• DSCR: 0.32
• GRM: 20.8

CMA / ARV

• ARV (median comp): $2,824,914
• List price: $2,499,000
• Delta: -11.54%
• Verdict: UNDERPRICED
• Comps: 13 within 1.0 mi

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
24 Rolling Hill Rd	0.11mi	5/5.0	4,700 (+5%)	1mo	$2,350,000	$500	78
10 Rolling Hill Rd	0.18mi	5/3.0	3,810 (-15%)	12mo	$2,400,000	$630	57
31 Wenwood Dr	0.67mi	5/4.5	3,900 (-13%)	9mo	$2,050,000	$526	34

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: 13.6%
• Equity multiple: 2.13×
• Total profit: $790,173
• Equity at exit: $2,251,297

10-year hold

• IRR: 13.7%
• Equity multiple: 4.97×
• Total profit: $2,775,563
• Equity at exit: $4,855,007

Cash invested: $699,720 (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 11568

• Home prices YoY: 4.4%
• Active inventory: 40
• Price-to-rent: 20.8×

Monthly cashflow live

• Estimated rent: $10,000 medium
• Mortgage (P&I): −$13,105
• Tax from tax record: −$2,715 /mo · $32,580/yr
• Insurance: −$1,041
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,100
• Net cashflow: $-8,961

Break-even live

Break-even rent $21,343

Max offer price $915,954

Occupancy floor —

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: $624,750
• Closing costs: $74,970
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
1719 Cedar Swamp Rd Glen Head, NY	6.0	4.5	3031	$10,000	$3.30	1d	1	1.20mi

Listing history 23 events

1. 2026-06-18
   days on market $2,499,000 Active 405 DOM
2. 2026-06-17
   days on market $2,499,000 Active 404 DOM
3. 2026-06-16
   days on market $2,499,000 Active 403 DOM
4. 2026-06-15
   days on market $2,499,000 Active 402 DOM
5. 2026-06-13
   days on market $2,499,000 Active 400 DOM
6. 2026-06-13
   days on market $2,499,000 Active 399 DOM
7. 2026-06-09
   days on market $2,499,000 Active 396 DOM
8. 2026-06-08
   days on market $2,499,000 Active 395 DOM
9. 2026-06-07
   days on market $2,499,000 Active 394 DOM
10. 2026-06-04
    days on market $2,499,000 Active 391 DOM
11. 2026-06-03
    days on market $2,499,000 Active 390 DOM
12. 2026-06-02
    days on market $2,499,000 Active 389 DOM
13. 2026-06-01
    days on market $2,499,000 Active 388 DOM
14. 2026-05-31
    days on market $2,499,000 Active 387 DOM
15. 2026-05-13
    price $2,499,000 647-char remark

    Show marketing remark (647 chars)

    HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

16. 2026-04-30
    price $3,200,000 647-char remark

    Show marketing remark (647 chars)

    HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

17. 2026-04-30
    status Active 647-char remark

    Show marketing remark (647 chars)

    HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

18. 2025-11-04
    status Pending 647-char remark

    Show marketing remark (647 chars)

    HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

19. 2025-04-16
    price $2,999,000 647-char remark

    Show marketing remark (647 chars)

    HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

20. 2024-11-13
    listed $3,300,000 Active 647-char remark

    Show marketing remark (647 chars)

    HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

21. 2023-04-11
    historical
22. 2012-09-24
    listed $1,475,000
23. 1984-03-01
    soldstatus $435,000

ⓘ 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: $32,580 · $2,715/mo
• Projected year-2 tax: $37,406 · $3,117/mo
• Expected delta: +$4,827/yr (+$402/mo · 14.8%)

ⓘ 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 2/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥98°F today · 14 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 63% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 4 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $120,000
• − Mortgage interest: −$139,983
• − Property taxes: −$32,580
• − Insurance: −$12,495
• − Repairs & maintenance: −$9,600
• − Management: −$9,600
• − Depreciation: −$72,698
• Taxable loss: −$156,956
• Est. tax savings @ 24.0%: +$37,669
• After-tax cash flow: $-69,866/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: Jericho Union Free School District
• NCES district ID: 3615810
• Math proficiency: 91% ▼ -1.00%
• Reading proficiency: 86% ▼ -2.00%
• Median HH income: $152,686
• Composite: 84.55/100
• National rank: #11
• State rank: #7 of 590 in NY

Livability — Old Westbury

• Score: 65/100
• State rank: #714
• US rank: #13575

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: Old Westbury, NY
• City population: 4,198
• Population (ZIP): 4,198

Population outlook (Nassau County) Hauer SSP2

• Today (2025): 1,409,302 people
• By 2030: 1,431,482 · +1.6%
• By 2040: 1,471,607 · +4.4%
• By 2050: 1,502,845 · +6.6%
• By 2075: 1,575,403 · +11.8%
• By 2100: 1,554,356 · +10.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (67%)
• Race & ethnicity: White 67% Asian 14% Hispanic / Latino 8% Two or more races 6% Black 5%
• Hispanic origin (detail): Mexican 2% Puerto Rican 1%
• Common ancestry: Romanian 5% Italian 4% Scotch-Irish 2%
• Foreign-born: 22% · China, Canada, South Korea
• Languages at home: 69% English-only · Other Indo-European 12% Spanish 6% Russian/Polish/Slavic 4%

Political lean MEDSL · Nassau

• 2024 margin: Toss-up / Even · D 47.9% · R 52.1%
• 2008→2024 swing: -12.6pp toward R · 2008: 8.4pp · 2024: -4.2pp
• All cycles: 2024: R+4.2 2020: D+9.5 2016: D+5.3 2012: D+6.7 2008: D+8.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 11.54%
• Current HPI: 272.5754
• 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

+474.5% since first listed

9 events — show timeline

• 2026-05-13 Price Changed $2,499,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-30 Price Changed $3,200,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-30 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-11-04 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-04-16 Price Changed $2,999,000 OneKey® MLS as Distributed by MLS Grid
• 2024-11-13 Listed $3,300,000 OneKey® MLS as Distributed by MLS Grid
• 2023-04-11 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2012-09-24 Listed $1,475,000 OneKey® MLS as Distributed by MLS Grid
• 1984-03-01 Sold (Public Records) $435,000 Public Records

Property tax history

+0.4%/yr

Latest (2024): $32,580 · +6.7% YoY. Source: county tax records.