36 Weygant Hl · Woodbury, NY 10930

$399,000

3 bd · 3.0 ba · 1,779 sqft · SingleFamily public records · 66 Days on market

Built 1900 0.40 ac lot $224/sqft · 32% below area Est $587k · 32% 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 +15.0/15.0
• Cash flow +9.5/30.0
• Schools +5.0/10.0
• 1% rule +3.6/10.0
• Livability +3.3/5.0
• DSCR +2.7/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Welcome to 36 Weygant Hill Road – a Charming Cape Cod Gem in Highland Mills! Discover this wonderful Cape Cod–style home nestled in the heart of Highland Mills. Situated on a spacious 0.40-acre lot (17,424 sq. ft.), this property offers plenty of room to enjoy the outdoors, complete with a detached garage for added convenience. Step inside to find a warm and inviting kitchen, a cozy living room, and a spacious dining area perfect for gatherings. The home features three comfortable bedrooms and three full bathrooms, providing ample space for guests. Located just minutes from Route 17, I-87, Woodbury Commons, and Bear Mountain, this home combines charm, comfort, and convenience in one great package. Don’t miss this exceptional opportunity – schedule your private showing today!

Key facts

• 0.4 acre lot
• Garage
• Built 1900

What this means for you Summary

Snapshot

• This is a 3-bed/3.0-bath single-family listed at $399k.

Deal economics

• At list price, monthly cash flow is $-279 ($-3k/yr) — negative.
• To cash-flow at today's rent, offer at most $350k (12.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $344k (13.9% below list).
• Recommended offer: $344k (13.9% below list) — sets the bar for 1% rule.
• Cap rate 5.5% vs local median 1.8% in Woodbury — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 66/100 on livability (#663 in NY) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Monroe-Woodbury Central School District (suburban): math 50% / reading 56% proficiency, ranked #250 of 590 in NY (top 42%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 15% free/reduced lunch — higher-income household profile.
• Zoned schools: Smith Clove Elementary School (458 students, 56% FRL); Monroe-Woodbury Middle School (math 28% / reading 50%, grade F, #433 of 729 statewide, top 60%, 1,584 students, 40% FRL); Monroe-Woodbury High School (math 98% / reading 95%, grade A+, #56 of 1,100 statewide, top 5%, 2,353 students, 33% FRL) — zoned schools average 43% FRL vs 15% district-wide (28 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Zoned-school proficiency averages 68% at this address vs 53% district-wide (+15 pts) — the actual schools serving this property are materially stronger than the Monroe-Woodbury Central School District average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 82 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals at typical pace (median 23d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 1,746 units permitted in Orange County in 2024 (1,265 in 5+ unit buildings).
• This rent runs 34% of the median local income ($120k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $12k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 66 days — a 6% lower offer ($375k) is reasonable based on typical stale-listing flexibility.
• 6 sale attempts since 5y ago; this cycle's ask has dropped $50k (11%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $280k; 42% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $343,677 (13.9% 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 66 days. Have you received any prior offers? Is the seller open to a 14% concession, seller financing, or rate buy-down credit?
3. Built in 1900 — 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: 0.86% ✗
• Cap rate: 5.45%
• Cash-on-cash: -2.99%
• DSCR: 0.87
• GRM: 9.7

CMA / ARV

• ARV (median comp): $586,661
• List price: $399,000
• Delta: -31.99%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
15 Cherry Ct	0.45mi	3/3.0	1,786 (+0%)	5mo	$449,900	$252	74
9 Cherry Ct	0.43mi	3/3.0	1,807 (+2%)	5mo	$430,000	$238	73
13 Butternut Ct	0.36mi	3/2.5	1,704 (-4%)	2mo	$435,000	$255	72
3 Laurel Ct	0.23mi	3/2.5	1,575 (-12%)	3mo	$429,900	$273	66
10 Ironwood Dr	0.35mi	3/2.5	1,614 (-9%)	5mo	$420,000	$260	62
17 Hickory St	0.15mi	4/1.5 (+1)	1,546 (-13%)	2mo	$399,000	$258	58
93 Weygant Hl	0.24mi	3/2.0	1,512 (-15%)	3mo	$445,000	$294	57
8 Ledger View Ct	0.46mi	3/2.5	1,569 (-12%)	6mo	$500,000	$319	52
7 Sycamore Ct	0.40mi	3/2.0	1,518 (-15%)	4mo	$455,000	$300	49
10 Cliffside Ct	0.50mi	3/2.5	1,569 (-12%)	10mo	$485,000	$309	47
4 Cliffside Ct	0.52mi	3/2.5	1,569 (-12%)	10mo	$450,000	$287	46
3 Stanford Dr	0.71mi	4/2.0 (+1)	1,908 (+7%)	8mo	$565,000	$296	39

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: -21.2%
• Equity multiple: 0.26×
• Total profit: $-82,213
• Equity at exit: $59,492

10-year hold

• IRR: -14.6%
• Equity multiple: 0.16×
• Total profit: $-93,652
• Equity at exit: $34,498

Cash invested: $111,720 (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 10930

• Home prices YoY: -15.8%
• Active inventory: 82
• Price-to-rent: 9.7×

Monthly cashflow live

• Estimated rent: $3,437 medium
• Mortgage (P&I): −$2,092
• Tax from tax record: −$735 /mo · $8,822/yr
• Insurance: −$166
• HOA: −$0
• Vacancy / Maint / Mgmt: −$722
• Net cashflow: $-279

Break-even live

Break-even rent $3,790

Max offer price $349,753

Occupancy floor —

Sensitivity live

Price	-10% $-53	-5% $-166	+0% $-279	+5% $-392	+10% $-505
Rent	-10% $-550	-5% $-415	+0% $-279	+5% $-143	+10% $-7
Rate	-1.0pp $-78	-0.5pp $-177	base $-279	+0.5pp $-382	+1.0pp $-487

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: $99,750
• Closing costs: $11,970
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
19 Mountainview Dr Highland Mills, NY	4.0	1.5	1622	$3,500	$2.16	25d	1	0.18mi
468 State Route 32 Highland Mills, NY	3.0	2.5	1722	$2,250	$1.31	23d	1	0.41mi
8 Fillmore Ct Highland Mills, NY	3.0	1.5	1836	$3,300	$1.80	23d	1	0.49mi
665 State Route 32 Highland Mills, NY	4.0	2.0	2500	$3,595	$1.44	15d	1	0.62mi

Listing history 38 events

1. 2026-06-21
   days on market $399,000 Active 66 DOM
2. 2026-06-18
   days on market $399,000 Active 63 DOM
3. 2026-06-17
   days on market $399,000 Active 62 DOM
4. 2026-06-16
   days on market $399,000 Active 61 DOM
5. 2026-06-15
   days on market $399,000 Active 60 DOM
6. 2026-06-14
   days on market $399,000 Active 58 DOM
7. 2026-06-10
   days on market $399,000 Active 55 DOM
8. 2026-06-09
   days on market $399,000 Active 54 DOM
9. 2026-06-08
   days on market $399,000 Active 53 DOM
10. 2026-06-07
    days on market $399,000 Active 52 DOM
11. 2026-06-05
    days on market $399,000 Active 49 DOM
12. 2026-06-03
    days on market $399,000 Active 48 DOM
13. 2026-06-02
    days on market $399,000 Active 47 DOM
14. 2026-06-01
    days on market $399,000 Active 46 DOM
15. 2026-05-31
    days on market $399,000 Active 45 DOM
16. 2026-05-30
    days on market $399,000 Active 44 DOM
17. 2026-05-05
    price $399,000 809-char remark

    Show marketing remark (809 chars)

    Welcome to 36 Weygant Hill Road – a Charming Cape Cod Gem in Highland Mills! Discover this wonderful Cape Cod–style home nestled in the heart of Highland Mills. Situated on a spacious 0.40-acre lot (17,424 sq. ft.), this property offers plenty of room to enjoy the outdoors, complete with a detached garage for added convenience. Step inside to find a warm and inviting kitchen, a cozy living room, and a spacious dining area perfect for gatherings. The home features three comfortable bedrooms and three full bathrooms, providing ample space for guests. Located just minutes from Route 17, I-87, Woodbury Commons, and Bear Mountain, this home combines charm, comfort, and convenience in one great package. Don’t miss this exceptional opportunity – schedule your private showing today!

18. 2026-04-15
    listed $449,000 Active 809-char remark

    Show marketing remark (809 chars)

    Welcome to 36 Weygant Hill Road – a Charming Cape Cod Gem in Highland Mills! Discover this wonderful Cape Cod–style home nestled in the heart of Highland Mills. Situated on a spacious 0.40-acre lot (17,424 sq. ft.), this property offers plenty of room to enjoy the outdoors, complete with a detached garage for added convenience. Step inside to find a warm and inviting kitchen, a cozy living room, and a spacious dining area perfect for gatherings. The home features three comfortable bedrooms and three full bathrooms, providing ample space for guests. Located just minutes from Route 17, I-87, Woodbury Commons, and Bear Mountain, this home combines charm, comfort, and convenience in one great package. Don’t miss this exceptional opportunity – schedule your private showing today!

19. 2025-12-22
    listed $449,000 Active
20. 2025-12-05
    soldstatus $280,000
21. 2025-10-27
    soldstatus $280,000 Closed
22. 2025-09-12
    soldstatus $375,000
23. 2025-08-29
    status Pending
24. 2025-07-31
    price $358,500
25. 2025-06-25
    price $368,500
26. 2025-05-25
    listed $374,900 Active
27. 2022-09-27
    soldstatus $250,000
28. 2022-09-27
    soldstatus $675,000
29. 2022-02-25
    price $1,189,900
30. 2021-11-01
    historical
31. 2021-11-01
    status Active
32. 2021-11-01
    price $1,250,000
33. 2021-08-09
    historical
34. 2021-06-25
    price $435,000
35. 2021-06-06
    status Active
36. 2021-06-06
    price $1,325,000
37. 2021-06-05
    historical
38. 2021-06-04
    listed $400,000 Active

ⓘ 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: $8,822 · $735/mo
• Projected year-2 tax: $8,822 · $735/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 5/10 Major 7 d/yr ≥96°F today · 17 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 17% 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: $41,241
• − Mortgage interest: −$22,350
• − Property taxes: −$8,822
• − Insurance: −$1,995
• − Repairs & maintenance: −$3,299
• − Management: −$3,299
• − Depreciation: −$11,607
• Taxable loss: −$10,132
• Est. tax savings @ 24.0%: +$2,432
• After-tax cash flow: $-914/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: Monroe-Woodbury Central School District
• NCES district ID: 3619650
• Math proficiency: 50% ▼ -17.00%
• Reading proficiency: 56% ▼ -1.00%
• Median HH income: $104,681
• Composite: 50.48/100
• National rank: #1855
• State rank: #250 of 590 in NY

Livability — Woodbury

• Score: 66/100
• State rank: #663
• US rank: #11975

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Woodbury, NY
• County: Orange County · 267,004 people
• City population: 9,402
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• Population (ZIP): 9,569
• Household income: $120,098
• Rent vs Own: 9.8% rent · 90.2% own
• Severe rent burden: 104.0

Population outlook (Orange County) Hauer SSP2

• Today (2025): 379,830 people
• By 2030: 378,955 · -0.2%
• By 2040: 375,444 · -1.2%
• By 2050: 369,311 · -2.8%
• By 2075: 354,233 · -6.7%
• By 2100: 318,150 · -16.2%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.64)
• Race & ethnicity: White 52% Hispanic / Latino 27% Two or more races 16% Black 10% Asian 6%
• Hispanic origin (detail): Mexican 6% Puerto Rican 14% Dominican 5%
• Common ancestry: Romanian 7% Scandinavian 2% Slovak 2%
• Foreign-born: 14% · Canada, China, Jamaica
• Languages at home: 81% English-only · Spanish 11% German/W. Germanic 4% Other Indo-European 2%

Political lean MEDSL · Orange

• 2024 margin: Lean R (+8.4) · D 45.8% · R 54.2%
• 2008→2024 swing: -12.5pp toward R · 2008: 4.1pp · 2024: -8.4pp
• All cycles: 2024: R+8.4 2020: R+0.2 2016: R+6.5 2012: D+5.2 2008: D+4.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -50.76%
• Current HPI: 271.431
• Rent YoY: —
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• 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

-0.2% since first listed

22 events — show timeline

• 2026-05-05 Price Changed $399,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-15 Listed $449,000 OneKey® MLS as Distributed by MLS Grid
• 2025-12-22 Listed $449,000 OneKey® MLS as Distributed by MLS Grid
• 2025-12-05 Sold (Public Records) $280,000 Public Records
• 2025-10-27 Sold (MLS) $280,000 OneKey® MLS as Distributed by MLS Grid
• 2025-09-12 Sold (Public Records) $375,000 Public Records
• 2025-08-29 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-07-31 Price Changed $358,500 OneKey® MLS as Distributed by MLS Grid
• 2025-06-25 Price Changed $368,500 OneKey® MLS as Distributed by MLS Grid
• 2025-05-25 Listed $374,900 OneKey® MLS as Distributed by MLS Grid
• 2022-09-27 Sold (Public Records) $675,000 Public Records
• 2022-09-27 Sold (Public Records) $250,000 Public Records
• 2022-02-25 Price Changed $1,189,900 OneKey® MLS as Distributed by MLS Grid
• 2021-11-01 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2021-11-01 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2021-11-01 Price Changed $1,250,000 OneKey® MLS as Distributed by MLS Grid
• 2021-08-09 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2021-06-25 Price Changed $435,000 OneKey® MLS as Distributed by MLS Grid
• 2021-06-06 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2021-06-06 Price Changed $1,325,000 OneKey® MLS as Distributed by MLS Grid
• 2021-06-05 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2021-06-04 Listed $400,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+0.4%/yr

Latest (2025): $8,822 · -0.4% YoY. Source: county tax records.