53 Main St · Highland, NY 12528

$529,000

7 bd · 5.0 ba · 3,970 sqft · MultiFamily public records · 12 Days on market

Built 1900 5,227 sqft lot

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Schools +5.2/10.0
• Livability +3.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 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

Some properties ask you to be patient. This one puts money in your pocket from closing day. Fully occupied and cash flowing, this commercial-residential multi-family sits on Main Street in the heart of Highland, steps from the Walkway Over the Hudson, one of the most visited destinations in the entire Hudson Valley. Two tenanted units. Month-to-month leases. Current rents below market value. A new owner inherits immediate income with a clear and near-term path to increased returns, no waiting, no buildout, no guesswork. The lower unit offers 3 bedrooms, 2 full baths, a private primary suite with deck access overlooking a secluded backyard, wood-burning fireplace, custom kitchen with stainle

Key facts

• Custom kitchen
• Two tenanted units
• 5,227 sq ft lot

Tags

• TWO TENANTED UNITS
• PRIVATE PRIMARY SUITE
• WOOD-BURNING FIREPLACE
• CUSTOM KITCHEN
• FULL UNFINISHED BASEMENT
• GENEROUSLY SIZED BEDROOMS

Property features AI

Exterior

• Parking: Driveway parking; Off-street parking; 2-car garage
• Utilities: Public sewer; Cable connected; Electricity connected
• Home design: Duplex
• Construction: Frame construction
• Exterior features: Back yard; Near public transit; Partially wooded lot; Shed(s)

Interior

• Kitchen: Eat-in kitchen; Pantry
• Bedrooms: Includes a main-level master bedroom
• Flooring: Other flooring types
• Bathrooms: Full bathroom on the first floor; Primary bathroom
• Heating & cooling: Hot water heating; Wall/window air conditioning units
• Interior features: First-floor bedroom; First-floor full bathroom; Ceiling fans; Eat-in kitchen; Entrance foyer; Formal dining room; High ceilings; Pantry; Primary bathroom; Master bedroom on main level; Storage
• Laundry & utility: Laundry located in the basement

What this means for you Summary

Snapshot

• This is a 3 × 2-bed/?-bath units multifamily listed at $529k.

Deal economics

• At list price, monthly cash flow is $2k ($30k/yr) — positive. Per door: $831/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($8k rent vs $529k).
• Cap rate 12.0% 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: 107 active listings in the ZIP; 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 $4k of loan paydown is wiped out by about $16k 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 $148k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• Only 12 days on market — expect competitive offers; lowballing is unlikely to land.
• 6 sale attempts since 9y ago 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.
• Current owner paid $200k; list at $529k implies a 164% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $529,000

Questions for the listing agent

1. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
2. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
3. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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 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: 1.54% ✓
• Cap rate: 11.95%
• Cash-on-cash: 20.21%
• DSCR: 1.90
• GRM: 5.4

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: 12.5%
• Equity multiple: 1.50×
• Total profit: $73,430
• Equity at exit: $78,876

10-year hold

• IRR: 21.4%
• Equity multiple: 2.82×
• Total profit: $269,679
• Equity at exit: $45,738

Cash invested: $148,120 (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: 107
• Price-to-rent: 16.3×

Monthly cashflow live

• Estimated rent: $8,130 medium
• Mortgage (P&I): −$2,774
• Tax from tax record: −$934 /mo · $11,207/yr
• Insurance: −$220
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,707
• Net cashflow: $2,494

Break-even live

Break-even rent $4,973

Max offer price $529,000

Occupancy floor 64%

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

Units	Beds	Baths	Est. rent
▸ 3× units	2	—	$8,130
Total (3 units)			$8,130

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: $132,250
• Closing costs: $15,870
• Reserves months: —
• Total cash needed: —

Listing history 10 events

1. 2026-06-18
   days on market $529,000 Active 12 DOM
2. 2026-06-17
   days on market $529,000 Active 11 DOM
3. 2026-06-16
   days on market $529,000 Active 10 DOM
4. 2026-06-15
   days on market $529,000 Active 9 DOM
5. 2026-06-13
   days on market $529,000 Active 7 DOM
6. 2026-06-12
   days on market $529,000 Active 6 DOM
7. 2026-06-09
   days on market $529,000 Active 3 DOM
8. 2026-06-08
   days on market $529,000 Active 2 DOM
9. 2026-06-07
   remarks 699-char remark
10. 2026-06-07
    listed $529,000 Active 1 DOM

ⓘ 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: $11,207 · $934/mo
• Projected year-2 tax: $11,207 · $934/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 ≥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: $97,560
• − Mortgage interest: −$29,632
• − Property taxes: −$11,207
• − Insurance: −$2,645
• − Repairs & maintenance: −$7,805
• − Management: −$7,805
• − Depreciation: −$15,389
• Taxable income: $23,077
• Est. tax owed @ 24.0%: −$5,539
• After-tax cash flow: $24,393/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: 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

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
• Population (ZIP): 13,818

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%

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%

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

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

+487.8% since first listed

12 events — show timeline

• 2026-06-05 Listed $529,000 OneKey® MLS as Distributed by MLS Grid
• 2024-02-03 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-02-03 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2021-06-12 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2021-04-19 Listed $455,000 OneKey® MLS as Distributed by MLS Grid
• 2021-04-17 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2020-07-17 Listed $455,000 OneKey® MLS as Distributed by MLS Grid
• 2020-07-17 Listed $475,000 OneKey® MLS as Distributed by MLS Grid
• 2017-08-08 Listed $325,000 OneKey® MLS as Distributed by MLS Grid
• 2017-08-08 Listed $325,000 HVCRMLS
• 2003-10-03 Sold (Public Records) $200,000 Public Records
• 1995-06-09 Sold (Public Records) $90,000 Public Records

Property tax history

+1.1%/yr

Latest (2025): $11,207 · +3.6% YoY. Source: county tax records.