164 Highland St · Port Chester, NY 10573

$669,000

3 bd · 2.0 ba · 1,565 sqft · MultiFamily public records · 19 Days on market

Built 1890 9,345 sqft lot Est $667k · at est.

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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).

• Cash flow +15.2/30.0
• ARV discount +7.3/15.0
• 1% rule +4.8/10.0
• DSCR +4.7/10.0
• Schools +4.1/10.0
• Livability +3.7/5.0
• Condition / age +2.5/5.0
• Rent growth +2.1/5.0
• Appreciation +0.0/10.0

Multi-family units

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

Listing remarks

Opportunity Awaits! Strong Upside Potential! Large multifamily property offering exceptional space, flexibility, and future potential. Featuring 5 bedrooms and 2 full bathrooms, this unique property includes duplex style units ideal for owner occupancy, multigenerational living, or investment income. Large entry Sunporch on front plus Bright enclosed sunroom that overlooks the spacious backyard, creating additional living space filled with natural light. With Easy walkout to the backyard and side yard, it offers added convenience and privacy. Generous outdoor areas offer room for entertaining, gardening, or relaxation. Expansive Attic presents tremendous potential for future expansion. C

Key facts

• Large entry sunporch
• Spacious backyard
• Duplex style units

Tags

• MULTIFAMILY PROPERTY
• DUPLEX STYLE UNITS
• LARGE ENTRY SUNPORCH
• BRIGHT ENCLOSED SUNROOM
• SPACIOUS BACKYARD
• GENEROUS OUTDOOR AREAS

What this means for you Summary

Snapshot

• This is a 2 × 2-bed/?-bath units multifamily listed at $669k.

Deal economics

• At list price, monthly cash flow is $230 ($3k/yr) — positive. Per door: $115/mo.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $658k (1.7% below list).
• Recommended offer: $658k (1.7% below list) — sets the bar for 1% rule.
• Cap rate 6.7% vs local median 4.3% in Port Chester — 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 73/100 on livability (#315 in NY) — a middle-class / working-renter tenant base. Strengths: commute A+, employment A+, health & safety A; Watch: amenities D, cost of living F.
• Port Chester-Rye Union Free School District (suburban): math 44% / reading 49% proficiency, ranked #428 of 590 in NY (top 72%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: King Street School (math 22% / reading 47%, grade F, #1,577 of 2,108 statewide, top 77%, 412 students, 60% FRL); Port Chester Middle School (math 20% / reading 43%, grade F, #522 of 729 statewide, top 73%, 971 students, 75% FRL); Port Chester Senior High School (math 88% / reading 92%, grade A+, #238 of 1,100 statewide, top 23%, 1,555 students, 73% FRL).
• Market conditions: Rents soft (-1.7%/yr); 144 active listings in the ZIP; 40 comparable units currently listed for rent nearby; rentals at typical pace (median 24d on market — plan ~3-4 weeks tenant-placement turnaround); solid renter incomes; 954 units permitted in Westchester County in 2024 (649 in 5+ unit buildings).
• At $6,575/mo this rent would consume 75% of the median local household income ($106k/yr) (locally 1362% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $5k of loan paydown is wiped out by about $20k of value loss. Plan a longer hold.
• Westchester County population projected at +10% by 2050 — modest demand growth; plan on rents tracking national, not racing it.

Negotiation context

• It's been on market 19 days — a 2% lower offer ($659k) is reasonable based on typical stale-listing flexibility.
• 8 sale attempts since 21y 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 $505k; 32% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1890 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 55% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $657,500 (1.7% below list)

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 1890 — 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. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
6. 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?
7. 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.
8. 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.
9. 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: 0.98% ✗
• Cap rate: 6.70%
• Cash-on-cash: 1.47%
• DSCR: 1.07
• GRM: 8.5

CMA / ARV

• ARV (on-the-fly): $666,690
• Comps found: 8

Show comp detail 8 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
280 Locust Ave	0.24mi	3/2.0	1,554 (-1%)	9mo	$645,000	$415	80
37 Washington St	0.44mi	3/2.0	1,590 (+2%)	13mo	$675,000	$425	66
558 Locust Ave	0.58mi	3/2.0	1,656 (+6%)	7mo	$705,000	$426	57
43 Washington St	0.45mi	4/3.0 (+1)	1,452 (-7%)	6mo	$665,000	$458	53
412 W William St	0.73mi	3/2.0	1,566 (+0%)	17mo	$680,000	$434	52
332 Locust Ave	0.34mi	4/3.0 (+1)	1,480 (-5%)	19mo	$610,000	$412	51
40 Exchange Pl	0.37mi	4/2.0 (+1)	1,716 (+10%)	19mo	$830,000	$484	46
312 William St	0.61mi	4/2.0 (+1)	1,718 (+10%)	14mo	$730,000	$425	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 · 0.0% rent growth · sell at horizon

5-year hold

• IRR: -17.6%
• Equity multiple: 0.40×
• Total profit: $-112,748
• Equity at exit: $99,750

10-year hold

• IRR: -17.3%
• Equity multiple: 0.19×
• Total profit: $-152,565
• Equity at exit: $57,843

Cash invested: $187,320 (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 10573

• Rents YoY: -1.7%
• Active inventory: 144
• Price-to-rent: 17.0×

Monthly cashflow live

• Estimated rent: $6,575 high
• Mortgage (P&I): −$3,508
• Tax from tax record: −$1,178 /mo · $14,132/yr
• Insurance: −$279
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,381
• Net cashflow: $230

Break-even live

Break-even rent $6,284

Max offer price $669,000

Occupancy floor 92%

Sensitivity live

Price	-10% $608	-5% $419	+0% $230	+5% $40	+10% $-149
Rent	-10% $-290	-5% $-30	+0% $230	+5% $489	+10% $749
Rate	-1.0pp $566	-0.5pp $400	base $230	+0.5pp $56	+1.0pp $-120

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

Units	Beds	Baths	Est. rent
▸ 2× units	2	—	$6,574
Total (2 units)			$6,575

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: $167,250
• Closing costs: $20,070
• Reserves months: —
• Total cash needed: —

Rent comps 40 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
201 Willett Ave Port Chester, NY	2.0	1.0–2.0	817	$4,691	$5.74	8d	1	0.09mi
169 N Main St Port Chester, NY	2.0	1.0–2.0	799	$4,652	$5.82	2d	43	0.13mi
21 Willett Ave Port Chester, NY	2.0–3.0	1.0–2.0	1199	$4,950	$4.13	2d	1	0.19mi
20 Church St W Unit A24 Greenwich, CT	3.0	2.0	1578	$10,500	$6.65	3d	1	0.30mi
88 S Water St #107 Greenwich, CT	2.0	2.0	1256	$6,300	$5.02	2d	1	0.32mi
19 Edison Pl Unit 2 Port Chester, NY	3.0	2.0	1500	$3,800	$2.53	13d	1	0.39mi
Westchester Ave Unit A Port Chester, NY	2.0	2.0	1102	$3,015	$2.74	25d	1	0.39mi
5 Wellington Pl Unit B Greenwich, CT	3.0	2.0	1152	$4,500	$3.91	44d	1	0.45mi
11 Madison Ave Unit 2nd Fl Port Chester, NY	3.0	1.0	1200	$3,700	$3.08	25d	1	0.46mi
144 Pine St Unit D Greenwich, CT	2.0	1.5	1120	$2,950	$2.63	15d	1	0.47mi
10 Prospect St W Greenwich, CT	4.0	2.0	1784	$7,495	$4.20	2d	1	0.51mi
82 Putnam Ave Port Chester, NY	3.0	1.0	1200	$3,600	$3.00	44d	1	0.53mi
347 Delavan Ave Unit A Greenwich, CT	3.0	2.5	2158	$5,500	$2.55	19d	1	0.54mi
71 Byram Rd Unit 2 Greenwich, CT	3.0	2.0	1200	$3,400	$2.83	24d	1	0.54mi
89 View St W Unit 2nd floor Greenwich, CT	3.0	2.0	1870	$5,450	$2.91	19d	1	0.55mi
411 Westchester Ave Port Chester, NY	2.0	2.0	1250	$3,015	$2.41	17d	1	0.60mi
98 Byram Shore Rd Greenwich, CT	3.0	2.0	2000	$6,950	$3.48	2d	1	0.63mi
321 Olivia St Apt 1 Port Chester, NY	4.0	3.0	2040	$4,500	$2.21	44d	1	0.74mi
70 Riverdale Ave #1001 Greenwich, CT	2.0	2.5	1960	$5,500	$2.81	15d	1	0.78mi
124 Ritch Ave W Greenwich, CT	1.0–3.0	1.0–2.0	1238	$8,750	$7.07	2d	3	0.90mi
9 1/2 Putnam Grn Greenwich, CT	1.0–3.0	1.0–2.5	1234	$6,577	$5.33	2d	19	0.91mi
494 W William St Unit 1st Floor Rye Brook, NY	2.0	2.0	1244	$3,685	$2.96	44d	1	0.94mi
494 W William St Port Chester, NY	2.0	2.0	1370	$3,685	$2.69	44d	1	0.94mi
68 Pemberwick Rd Unit 1 Greenwich, CT	3.0	1.5	1300	$4,000	$3.08	44d	1	1.01mi
83 Grant St Unit 2 Port Chester, NY	2.0	1.0	1200	$3,000	$2.50	25d	1	1.02mi
108 Monica Rd Unit 4 Greenwich, CT	3.0	1.5	1364	$3,775	$2.77	22d	1	1.03mi
34 Windy Knls Unit A Greenwich, CT	3.0	3.0	2146	$7,500	$3.49	3d	1	1.03mi
250 S Ridge St Unit 2 Rye Brook, NY	3.0	1.0	1350	$3,800	$2.81	25d	1	1.05mi
81 Pemberwick Rd Unit A Greenwich, CT	2.0	3.5	2092	$4,950	$2.37	44d	1	1.07mi
42 Tower Hill Dr Port Chester, NY	4.0	1.5	1864	$5,100	$2.74	44d	1	1.10mi
22 Wyman St Rye Brook, NY	3.0	1.0	1193	$3,500	$2.93	44d	1	1.14mi
45 Moshier St Unit A Greenwich, CT	3.0	2.0	1373	$5,000	$3.64	11d	1	1.24mi
2 Grange St Unit 2 Greenwich, CT	3.0	1.0	1092	$3,800	$3.48	22d	1	1.25mi
2 Grange St Unit 2 Greenwich, CT	3.0	1.0	1092	$3,800	$3.48	24d	1	1.25mi
38 Gerry St Unit 2 Greenwich, CT	2.0	1.0	1100	$2,995	$2.72	22d	1	1.31mi
37 Gerry St Unit A Greenwich, CT	3.0	2.0	1700	$4,975	$2.93	44d	1	1.32mi
147 Holly Hill Ln #9 Greenwich, CT	2.0	2.5	2200	$9,000	$4.09	24d	1	1.35mi
147 Holly Hill Ln #2 Greenwich, CT	2.0	2.5	2200	$12,000	$5.45	24d	1	1.35mi
147 Holly Hill Ln Greenwich, CT	2.0	2.5	1611	$11,000	$6.83	44d	2	1.35mi
16 Harold Ave Apt 2 Greenwich, CT	3.0	1.0	1686	$2,800	$1.66	44d	1	1.41mi

Listing history 23 events

1. 2026-03-16
   status Pending
2. 2026-02-25
   listed $669,000 Active
3. 2026-01-14
   soldstatus $505,000
4. 2018-08-31
   historical
5. 2017-10-08
   historical Pending
6. 2016-11-17
   price $399,000
7. 2016-11-17
   status Active
8. 2016-05-05
   historical Pending
9. 2016-01-29
   listed $299,000 Active
10. 2012-02-19
    historical
11. 2011-07-07
    historical Pending
12. 2011-02-18
    listed Active
13. 2010-11-07
    historical
14. 2010-10-11
    status Active
15. 2010-10-08
    historical
16. 2010-08-09
    price
17. 2010-05-07
    listed Active
18. 2006-12-27
    soldstatus $555,000
19. 2006-11-01
    soldstatus $525,000
20. 2006-11-01
    price $579,500
21. 2006-02-20
    listed $525,000
22. 2005-12-21
    historical
23. 2005-09-23
    listed

ⓘ 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: $14,132 · $1,178/mo
• Projected year-2 tax: $14,132 · $1,178/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 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥98°F today · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 55% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 5 unhealthy d/yr today · 7 by 30 yrs out

Taxation est. · year 1

• Rental income: $78,900
• − Mortgage interest: −$37,474
• − Property taxes: −$14,132
• − Insurance: −$3,345
• − Repairs & maintenance: −$6,312
• − Management: −$6,312
• − Depreciation: −$19,462
• Taxable loss: −$8,137
• Est. tax savings @ 24.0%: +$1,953
• After-tax cash flow: $4,707/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: Port Chester-Rye Union Free School District
• NCES district ID: 3623460
• Math proficiency: 44% ▲ 2.00%
• Reading proficiency: 49% ▲ 6.00%
• Median HH income: $58,362
• Composite: 40.67/100
• National rank: #3676
• State rank: #428 of 590 in NY

Livability — Port Chester

• Score: 73/100
• State rank: #315
• US rank: #5245

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Port Chester, NY
• County: Westchester County · 709,332 people
• City population: 40,786
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 40,786
• Household income: $105,686
• Rent vs Own: 44.7% rent · 55.3% own
• Severe rent burden: 1362.0

Population outlook (Westchester County) Hauer SSP2

• Today (2025): 1,028,035 people
• By 2030: 1,051,636 · +2.3%
• By 2040: 1,098,520 · +6.9%
• By 2050: 1,136,044 · +10.5%
• By 2075: 1,196,925 · +16.4%
• By 2100: 1,175,147 · +14.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.61)
• Race & ethnicity: Hispanic / Latino 48% White 40% Two or more races 16% Black 5% Asian 4%
• Hispanic origin (detail): Mexican 7% Puerto Rican 6% Dominican 3%
• Common ancestry: Romanian 3% Scotch-Irish 2% Italian 1%
• Foreign-born: 37% · Canada, Jamaica, China
• Languages at home: 50% English-only · Spanish 41% Other Indo-European 5% Chinese 1%

Political lean MEDSL · Westchester

• 2024 margin: Strong D (+26.3) · D 63.1% · R 36.9%
• 2008→2024 swing: -1.3pp toward R · 2008: 27.6pp · 2024: 26.3pp
• All cycles: 2024: D+26.3 2020: D+36.3 2016: D+32.8 2012: D+22.2 2008: D+27.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -389.46%
• Current HPI: 258.9227
• Rent YoY: ▼ -1.70%
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• 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

+27.4% since first listed

23 events — show timeline

• 2026-03-16 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-02-25 Listed $669,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-14 Sold (Public Records) $505,000 Public Records
• 2018-08-31 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2017-10-08 Contingent — OneKey® MLS as Distributed by MLS Grid
• 2016-11-17 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2016-11-17 Price Changed $399,000 OneKey® MLS as Distributed by MLS Grid
• 2016-05-05 Contingent — OneKey® MLS as Distributed by MLS Grid
• 2016-01-29 Listed $299,000 OneKey® MLS as Distributed by MLS Grid
• 2012-02-19 Delisted — HGMLS
• 2011-07-07 Contingent — HGMLS
• 2011-02-18 Listed — HGMLS
• 2010-11-07 Delisted — HGMLS
• 2010-10-11 Relisted — HGMLS
• 2010-10-08 Delisted — HGMLS
• 2010-08-09 Price Changed — HGMLS
• 2010-05-07 Listed — HGMLS
• 2006-12-27 Sold (Public Records) $555,000 Public Records
• 2006-11-01 Price Changed $579,500 HGMLS
• 2006-11-01 Sold (MLS) $525,000 HGMLS
• 2006-02-20 Listed $525,000 HGMLS
• 2005-12-21 Delisted — HGMLS
• 2005-09-23 Listed — HGMLS

Property tax history

+0.4%/yr

Latest (2025): $14,132 · +9.1% YoY. Source: county tax records.