19-21 Church St · Highland, NY 12528

$400,000

15 bd · 9.0 ba · 2,700 sqft · MultiFamily · 138 Days on market

Built 1920 Fair condition 4,356 sqft lot $148/sqft · 32% below area Est $586k · 32% 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 +27.8/30.0
• ARV discount +15.0/15.0
• DSCR +9.8/10.0
• 1% rule +7.6/10.0
• Schools +6.3/10.0
• Livability +3.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.2/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 3 units. confirmed

Listing remarks MLS

Village of Highland three family comprised of (2) two bedroom units and (1) one bedroom unit. Spacious apartments with well proportioned rooms. Natural gas for heat & hot water. Separate utilities & off street parking. Centrally located with easy access to village amenities, Route 9W & Mid-Hudson Bridge.

Key facts

• One bedroom unit
• Separate utilities
• Two bedroom units

Tags

• TWO BEDROOM UNITS
• ONE BEDROOM UNIT
• NATURAL GAS
• SEPARATE UTILITIES
• OFF STREET PARKING
• CENTRALLY LOCATED

What this means for you Summary

Snapshot

• This is a 2×2bd/1.0ba + 1×1bd/1.0ba units multifamily listed at $400k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $1k ($15k/yr) — positive. Per door: $406/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $400k).
• Recommended offer: $352k (12.0% below list) — sets the bar for market timing.
• Cap rate 9.9% vs local median 2.6% in Highland — 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 75/100 on livability (#251 in NY, #3,941 nationally) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+, health & safety A+; Watch: amenities F, commute F, cost of living D-.
• Highland Central School District (suburban): math 50% / reading 69% proficiency, ranked #227 of 590 in NY (top 38%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Highland Elementary School (math 46% / reading 67%, grade C+, #899 of 2,108 statewide, top 43%, 638 students, 38% FRL); Highland Middle School (math 27% / reading 57%, grade D-, #379 of 729 statewide, top 54%, 376 students, 42% FRL); Highland High School (math 87% / reading 92%, grade A+, #265 of 1,100 statewide, top 26%, 512 students, 41% FRL).
• Market conditions: 128 active listings in the ZIP; solid renter incomes; 464 units permitted in Ulster County in 2024 (170 in 5+ unit buildings).

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.
• Ulster County population projected at -14% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $112k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 138 days — a 12% lower offer ($352k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1920 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate flood risk; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $352,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 138 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
5. Built in 1920 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
6. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
7. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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 apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 1.26% ✓
• Cap rate: 9.95%
• Cash-on-cash: 13.06%
• DSCR: 1.58
• GRM: 6.6

CMA / ARV

• ARV (median comp): $585,520
• List price: $400,000
• Delta: -31.68%
• Verdict: UNDERPRICED
• Comps: 8 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 3.0%
• Equity multiple: 1.12×
• Total profit: $12,889
• Equity at exit: $59,641

10-year hold

• IRR: 12.6%
• Equity multiple: 2.00×
• Total profit: $111,495
• Equity at exit: $34,585

Cash invested: $112,000 (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 12528

• Home prices YoY: -20.5%
• Active inventory: 128
• Price-to-rent: 18.8×

Monthly cashflow live

• Estimated rent: $5,042 medium
• Mortgage (P&I): −$2,098
• Tax est. 1.5%: −$500 /mo · $6,000/yr
• Insurance: −$167
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,059
• Net cashflow: $1,219

3-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 2× units	2	1	$3,542
1× unit	1	1	$1,500
Total (3 units)			$5,042

Break-even live

Break-even rent $3,499

Max offer price $400,000

Occupancy floor 71%

Sensitivity live

Price	-10% $1,495	-5% $1,357	+0% $1,219	+5% $1,081	+10% $942
Rent	-10% $821	-5% $1,020	+0% $1,219	+5% $1,418	+10% $1,617
Rate	-1.0pp $1,420	-0.5pp $1,321	base $1,219	+0.5pp $1,115	+1.0pp $1,010

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: $100,000
• Closing costs: $12,000
• Club membership (one-time): —
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
23 1/2 Church St Highland, NY	1.0	1.0	—	$1,500	—	93d	1	0.03mi
86 Vineyard Ave Unit 2 Highland, NY	1.0	1.0	800	$1,700	$2.12	93d	1	0.03mi
70 New Paltz Rd Apt 1 Highland, NY	2.0	1.0	900	$2,300	$2.56	93d	1	0.84mi
104 North Rd Highland, NY	3.0	2.5	1550	$3,100	$2.00	93d	1	0.99mi

Listing history 50 events

1. 2026-08-08
   days on market $400,000 Active 138 DOM
2. 2026-08-07
   days on market $400,000 Active 137 DOM
3. 2026-08-06
   days on market $400,000 Active 136 DOM
4. 2026-08-05
   days on market $400,000 Active 135 DOM
5. 2026-08-04
   days on market $400,000 Active 134 DOM
6. 2026-08-03
   days on market $400,000 Active 133 DOM
7. 2026-07-31
   days on market $400,000 Active 130 DOM
8. 2026-07-29
   days on market $400,000 Active 128 DOM
9. 2026-07-27
   days on market $400,000 Active 126 DOM
10. 2026-07-25
    days on market $400,000 Active 124 DOM
11. 2026-07-24
    days on market $400,000 Active 123 DOM
12. 2026-07-23
    days on market $400,000 Active 122 DOM
13. 2026-07-22
    days on market $400,000 Active 121 DOM
14. 2026-07-21
    days on market $400,000 Active 120 DOM
15. 2026-07-20
    days on market $400,000 Active 119 DOM
16. 2026-07-18
    days on market $400,000 Active 117 DOM
17. 2026-07-16
    days on market $400,000 Active 115 DOM
18. 2026-07-15
    days on market $400,000 Active 114 DOM
19. 2026-07-14
    days on market $400,000 Active 113 DOM
20. 2026-07-13
    days on market $400,000 Active 112 DOM
21. 2026-07-12
    days on market $400,000 Active 111 DOM
22. 2026-07-12
    days on market $400,000 Active 110 DOM
23. 2026-07-10
    days on market $400,000 Active 109 DOM
24. 2026-07-09
    days on market $400,000 Active 108 DOM
25. 2026-07-07
    days on market $400,000 Active 106 DOM
26. 2026-07-06
    days on market $400,000 Active 105 DOM
27. 2026-07-05
    days on market $400,000 Active 104 DOM
28. 2026-07-05
    days on market $400,000 Active 103 DOM
29. 2026-07-03
    days on market $400,000 Active 102 DOM
30. 2026-07-03
    days on market $400,000 Active 101 DOM
31. 2026-07-01
    days on market $400,000 Active 100 DOM
32. 2026-06-30
    days on market $400,000 Active 99 DOM
33. 2026-06-29
    days on market $400,000 Active 98 DOM
34. 2026-06-28
    days on market $400,000 Active 97 DOM
35. 2026-06-27
    days on market $400,000 Active 96 DOM
36. 2026-06-26
    days on market $400,000 Active 95 DOM
37. 2026-06-22
    days on market $400,000 Active 91 DOM
38. 2026-06-21
    days on market $400,000 Active 90 DOM
39. 2026-06-21
    days on market $400,000 Active 89 DOM
40. 2026-06-18
    days on market $400,000 Active 87 DOM
41. 2026-06-17
    days on market $400,000 Active 86 DOM
42. 2026-06-16
    days on market $400,000 Active 85 DOM
43. 2026-06-15
    days on market $400,000 Active 84 DOM
44. 2026-06-13
    days on market $400,000 Active 82 DOM
45. 2026-06-12
    days on market $400,000 Active 81 DOM
46. 2026-06-09
    days on market $400,000 Active 78 DOM
47. 2026-06-08
    days on market $400,000 Active 77 DOM
48. 2026-06-07
    days on market $400,000 Active 76 DOM
49. 2026-06-05
    days on market $400,000 Active 74 DOM
50. 2026-06-04
    days on market $400,000 Active 72 DOM

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

Climate risk First Street

• 🌊 Flood 5/10 Major FEMA zone X (unshaded) · 24% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 5/10 Major 7 d/yr ≥98°F today · 16 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 11% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $60,504
• − Mortgage interest: −$22,406
• − Property taxes: −$6,000
• − Insurance: −$2,000
• − Repairs & maintenance: −$4,840
• − Management: −$4,840
• − Depreciation: −$11,636
• Taxable income: $8,781
• Est. tax owed @ 24.0%: −$2,107
• After-tax cash flow: $12,519/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 · 13 photos

Fair 45/100 Moderate rehab Est. rehab $67,500–$121,500 screening

This three-family home requires moderate renovations to improve its condition and increase its value. Key areas for improvement include the kitchen, bathrooms, and HVAC system. Painting and updating these areas can significantly enhance the home's appeal and value.

Repairs flagged

• Major Kitchen cabinets — Older cabinets with visible wear and tear
• Major Bathroom fixtures — Older fixtures with visible wear and tear
• Major HVAC system — Older system with visible wear and tear

Value-add opportunities

• Resale Paint interior walls — Fresh paint can make a significant difference in the home's appearance and value ↑
• Resale Replace kitchen cabinets — Newer cabinets can significantly improve the home's appeal and functionality ↑
• Resale Replace bathroom fixtures — Up-to-date fixtures can make a big difference in the home's appeal and functionality ↑
• Both Replace HVAC system — A new HVAC system can improve comfort and energy efficiency, which is beneficial for both resale and rental value ↑

ⓘ Rehab cost is a screening estimate — Moderate scope × the home's square footage at US $/sqft rules of thumb (the same model as the Flip Finder). Get contractor quotes + a written scope before underwriting.

C Composite school gradezoned avg 63/100

Zoned Schools

Elementary Highland Elementary School C+ NY #899/2,108 Nat'l #9,263/41,679 Middle Highland Middle School D- NY #379/729 Nat'l #5,398/14,009 High Highland High School A+ NY #265/1,100 Nat'l #453/17,239

Schools (NCES district)

• District: Highland Central School District
• NCES district ID: 3614400
• Math proficiency: 50% ▼ -3.00%
• Reading proficiency: 69% ▲ 14.00%
• Median HH income: $63,600
• Composite: 51.89/100
• National rank: #1652
• State rank: #227 of 590 in NY

B Composite livability gradescore 75/100

Livability — Highland

• Score: 75/100
• State rank: #251
• US rank: #3941

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Highland, NY
• County: Ulster · 175,887 people
• Metro: Kingston, NY
• Population (ZIP): 13,818
• Household income: $89,096
• Rent vs Own: 29.9% rent · 70.1% own
• Severe rent burden: 9% of renters

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Population outlook (Ulster County) Hauer SSP2

• Today (2025): 175,887 people
• By 2030: 171,876 · -2.3%
• By 2040: 161,771 · -8.0%
• By 2050: 151,470 · -13.9%
• By 2075: 133,023 · -24.4%
• By 2100: 113,504 · -35.5%

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Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (72%)
• Race & ethnicity: White 72% Hispanic / Latino 10% Two or more races 9% Asian 7% Black 3%
• Hispanic origin (detail): Mexican 4% Puerto Rican 2% Cuban 1% Dominican 1%
• Common ancestry: Romanian 4% Scotch-Irish 2% Slovak 2%
• Foreign-born: 11% · Canada, Vietnam, China
• Languages at home: 81% English-only · Spanish 9% Vietnamese 6% Other Indo-European 2%

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Political lean MEDSL · Ulster

• 2024 margin: D (+18.7) · D 59.3% · R 40.7%
• 2008→2024 swing: -4.9pp toward R · 2008: 23.6pp · 2024: 18.7pp
• All cycles: 2024: D+18.7 2020: D+20.9 2016: D+9.1 2012: D+21.9 2008: D+23.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -84.26%
• Current HPI: 327.3196
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

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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

1 event — show timeline

• 2026-03-23 Listed $400,000 OneKey® MLS as Distributed by MLS Grid