1476 County Route 5 · East Nassau, NY 12029

$449,000

3 bd · 2.0 ba · 2,324 sqft · SingleFamily public records · 238 Days on market

Built 1960 3.10 ac lot $193/sqft · 33% below area Est $667k · 33% under

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Why this score? — see what drove the A- 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
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +4.4/10.0
• Appreciation +4.2/10.0
• Livability +2.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Escape to this lovely 3-bedroom ranch set on three peaceful acres with long views of the Berkshire Hills along a country road in Canaan, New York. The open floor plan provides a seamless flow for everyday living and entertaining. The living room centers around a wood-burning fireplace and is adjacent to a dining area and a large year-round sunroom -- with wet bar - that opens to a large back yard with barn and pastoral views. The private, in-ground swimming pool off the large deck is perfectly positioned to capture the landscape. Skylights brighten the well-appointed kitchen which has plenty of storage and counter space -- perfect for gathering with family or friends. A flexible home office or studio space located over the garage provides room for work, creativity, or quiet retreat. The primary suite has lots of natural light also opens to the pool area for easy indoor-outdoor living. Its bathroom features both a soaking tub and shower with body jets. Two additional bedrooms and abundant storage ensure space and comfort for everyone. The barn, in the back yard is set for horses or your creative ideas. The 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also 10 minutes to the charming Village of Chatham and less than 30 minutes from Hudson or Albany, and just over two hours from NYC or Boston. This property blends country charm and plenty of room to breathe. Come see for yourself!

Key facts

• In-ground pool
• Open floor plan
• Soaking tub

Tags

• IN-GROUND POOL
• OPEN FLOOR PLAN
• WOOD-BURNING FIREPLACE
• FLEXIBLE HOME OFFICE
• PRIMARY SUITE
• SOAKING TUB

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $449k.

Deal economics

• At list price, monthly cash flow is $5k ($57k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($10k rent vs $449k).
• Recommended offer: $395k (12.0% below list) — sets the bar for market timing.
• Cap rate 19.0% vs local median 2.1% in East Nassau — 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 56/100 on livability (#1,099 in NY) — a working-class tenant base; expect higher turnover. Strengths: housing A-, cost of living B; Watch: schools D+, crime D-, amenities F.
• Chatham Central School District (rural): math 48% / reading 53% proficiency, ranked #353 of 590 in NY (top 60%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 29 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 136 units permitted in Columbia County in 2024 (0 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-1.5%/yr); year-one equity from $3k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Columbia County population projected at -22% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-1.5% appreciation + 3.0% rent growth), your $126k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• It's been on market 238 days — a 12% lower offer ($395k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 7y ago; this cycle's ask has dropped $146k (25%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $285k; list at $449k implies a 58% gain — meaningful room to come down on a strong offer.

Recommended offer $395,120 (12.0% below list)

Questions for the listing agent

1. It's been on market 238 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1960 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
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. Crime grade is D in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
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 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: 2.23% ✓
• Cap rate: 18.99%
• Cash-on-cash: 45.34%
• DSCR: 3.02
• GRM: 3.7

CMA / ARV

• ARV (median comp): $666,821
• List price: $449,000
• Delta: -32.67%
• Verdict: UNDERPRICED
• Comps: 4 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
72 Old Queechy Rd	0.69mi	3/2.0	2,400 (+3%)	10mo	$880,000	$367	54

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-1.54% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 44.5%
• Equity multiple: 3.05×
• Total profit: $257,986
• Equity at exit: $96,778

10-year hold

• IRR: 49.0%
• Equity multiple: 6.09×
• Total profit: $640,531
• Equity at exit: $92,035

Cash invested: $125,720 (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 12029

• Home prices YoY: -0.4%
• Active inventory: 29
• Price-to-rent: 3.7×

Monthly cashflow live

• Estimated rent: $10,000 medium
• Mortgage (P&I): −$2,355
• Tax from tax record: −$608 /mo · $7,301/yr
• Insurance: −$187
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,100
• Net cashflow: $4,750

Break-even live

Break-even rent $3,987

Max offer price $449,000

Occupancy floor 48%

Sensitivity live

Price	-10% $5,004	-5% $4,877	+0% $4,750	+5% $4,623	+10% $4,496
Rent	-10% $3,960	-5% $4,355	+0% $4,750	+5% $5,145	+10% $5,540
Rate	-1.0pp $4,976	-0.5pp $4,864	base $4,750	+0.5pp $4,634	+1.0pp $4,515

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: $112,250
• Closing costs: $13,470
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
77 Vandenburg Rd Canaan, NY	3.0	3.5	2800	$10,000	$3.57	24d	1	1.48mi

Listing history 27 events

1. 2026-06-19
   days on market $449,000 Active 238 DOM
2. 2026-06-18
   price $449,000 Active 237 DOM
3. 2026-06-18
   days on market $499,000 Active 237 DOM
4. 2026-06-17
   days on market $499,000 Active 236 DOM
5. 2026-06-16
   days on market $499,000 Active 235 DOM
6. 2026-06-15
   days on market $499,000 Active 234 DOM
7. 2026-06-14
   days on market $499,000 Active 232 DOM
8. 2026-06-12
   days on market $499,000 Active 231 DOM
9. 2026-06-09
   days on market $499,000 Active 228 DOM
10. 2026-06-08
    days on market $499,000 Active 227 DOM
11. 2026-06-07
    days on market $499,000 Active 226 DOM
12. 2026-06-04
    days on market $499,000 Active 222 DOM
13. 2026-06-02
    days on market $499,000 Active 221 DOM
14. 2026-06-01
    days on market $499,000 Active 220 DOM
15. 2026-05-31
    days on market $499,000 Active 219 DOM
16. 2026-05-31
    days on market $499,000 Active 218 DOM
17. 2026-05-04
    price $499,000 1519-char remark

    Show marketing remark (1519 chars)

    Escape to this lovely 3-bedroom ranch set on three peaceful acres with long views of the Berkshire Hills along a country road in Canaan, New York. The open floor plan provides a seamless flow for everyday living and entertaining. The living room centers around a wood-burning fireplace and is adjacent to a dining area and a large year-round sunroom -- with wet bar - that opens to a large back yard with barn and pastoral views. The private, in-ground swimming pool off the large deck is perfectly positioned to capture the landscape. Skylights brighten the well-appointed kitchen which has plenty of storage and counter space -- perfect for gathering with family or friends. A flexible home office or studio space located over the garage provides room for work, creativity, or quiet retreat. The primary suite has lots of natural light also opens to the pool area for easy indoor-outdoor living. Its bathroom features both a soaking tub and shower with body jets. Two additional bedrooms and abundant storage ensure space and comfort for everyone. The barn, in the back yard is set for horses or your creative ideas. The 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also 10 minutes to the charming Village of Chatham and less than 30 minutes from Hudson or Albany, and just over two hours from NYC or Boston. This property blends country charm and plenty of room to breathe. Come see for yourself!

18. 2026-03-27
    price $549,000 1519-char remark

    Show marketing remark (1519 chars)

    Escape to this lovely 3-bedroom ranch set on three peaceful acres with long views of the Berkshire Hills along a country road in Canaan, New York. The open floor plan provides a seamless flow for everyday living and entertaining. The living room centers around a wood-burning fireplace and is adjacent to a dining area and a large year-round sunroom -- with wet bar - that opens to a large back yard with barn and pastoral views. The private, in-ground swimming pool off the large deck is perfectly positioned to capture the landscape. Skylights brighten the well-appointed kitchen which has plenty of storage and counter space -- perfect for gathering with family or friends. A flexible home office or studio space located over the garage provides room for work, creativity, or quiet retreat. The primary suite has lots of natural light also opens to the pool area for easy indoor-outdoor living. Its bathroom features both a soaking tub and shower with body jets. Two additional bedrooms and abundant storage ensure space and comfort for everyone. The barn, in the back yard is set for horses or your creative ideas. The 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also 10 minutes to the charming Village of Chatham and less than 30 minutes from Hudson or Albany, and just over two hours from NYC or Boston. This property blends country charm and plenty of room to breathe. Come see for yourself!

19. 2025-12-21
    price $579,000 1519-char remark

    Show marketing remark (1519 chars)

    Escape to this lovely 3-bedroom ranch set on three peaceful acres with long views of the Berkshire Hills along a country road in Canaan, New York. The open floor plan provides a seamless flow for everyday living and entertaining. The living room centers around a wood-burning fireplace and is adjacent to a dining area and a large year-round sunroom -- with wet bar - that opens to a large back yard with barn and pastoral views. The private, in-ground swimming pool off the large deck is perfectly positioned to capture the landscape. Skylights brighten the well-appointed kitchen which has plenty of storage and counter space -- perfect for gathering with family or friends. A flexible home office or studio space located over the garage provides room for work, creativity, or quiet retreat. The primary suite has lots of natural light also opens to the pool area for easy indoor-outdoor living. Its bathroom features both a soaking tub and shower with body jets. Two additional bedrooms and abundant storage ensure space and comfort for everyone. The barn, in the back yard is set for horses or your creative ideas. The 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also 10 minutes to the charming Village of Chatham and less than 30 minutes from Hudson or Albany, and just over two hours from NYC or Boston. This property blends country charm and plenty of room to breathe. Come see for yourself!

20. 2025-09-24
    listed $595,000 Active 1519-char remark

    Show marketing remark (1519 chars)

    Escape to this lovely 3-bedroom ranch set on three peaceful acres with long views of the Berkshire Hills along a country road in Canaan, New York. The open floor plan provides a seamless flow for everyday living and entertaining. The living room centers around a wood-burning fireplace and is adjacent to a dining area and a large year-round sunroom -- with wet bar - that opens to a large back yard with barn and pastoral views. The private, in-ground swimming pool off the large deck is perfectly positioned to capture the landscape. Skylights brighten the well-appointed kitchen which has plenty of storage and counter space -- perfect for gathering with family or friends. A flexible home office or studio space located over the garage provides room for work, creativity, or quiet retreat. The primary suite has lots of natural light also opens to the pool area for easy indoor-outdoor living. Its bathroom features both a soaking tub and shower with body jets. Two additional bedrooms and abundant storage ensure space and comfort for everyone. The barn, in the back yard is set for horses or your creative ideas. The 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also 10 minutes to the charming Village of Chatham and less than 30 minutes from Hudson or Albany, and just over two hours from NYC or Boston. This property blends country charm and plenty of room to breathe. Come see for yourself!

21. 2019-09-23
    soldstatus $285,000 1035-char remark

    Show marketing remark (1035 chars)

    Step through the front door of this turn-key home and your eye will instantly be drawn to the sight of meadows, trees, and Berkshire hills in the distance. This 3-bedroom home features an Open Floor Plan that provides multiple opportunities to enjoy the views. There's a wood-burning Fireplace & skylight in the Living Room. The Spacious Kitchen, w/ another skylight, is designed for cooks, family gatherings, or entertaining friends. An addition to the original house is the light-filled, Year Round Sunroom/Family Room w/ wet-bar, Cast Iron Stove, wall of windows & 3 more Skylights. The large Master Bedroom has an updated en-suite bathroom w/ large tub and shower w/ body jets to complement the overhead faucet. Outside, an Azek deck leads to hot tub area & in-ground pool. There's a 2-horse barn on the property & detached 2-story garage w/ finished/heated space. 15 minutes away from The Berkshires' towns & attractions, 30 Minutes to Hudson or Albany & a little over 2 hours to NYC or Boston.

22. 2019-09-23
    soldstatus $285,000

    Show marketing remark (1035 chars)

    Step through the front door of this turn-key home and your eye will instantly be drawn to the sight of meadows, trees, and Berkshire hills in the distance. This 3-bedroom home features an Open Floor Plan that provides multiple opportunities to enjoy the views. There's a wood-burning Fireplace & skylight in the Living Room. The Spacious Kitchen, w/ another skylight, is designed for cooks, family gatherings, or entertaining friends. An addition to the original house is the light-filled, Year Round Sunroom/Family Room w/ wet-bar, Cast Iron Stove, wall of windows & 3 more Skylights. The large Master Bedroom has an updated en-suite bathroom w/ large tub and shower w/ body jets to complement the overhead faucet. Outside, an Azek deck leads to hot tub area & in-ground pool. There's a 2-horse barn on the property & detached 2-story garage w/ finished/heated space. 15 minutes away from The Berkshires' towns & attractions, 30 Minutes to Hudson or Albany & a little over 2 hours to NYC or Boston.

23. 2019-09-23
    soldstatus $285,000

    Show marketing remark (1035 chars)

    Step through the front door of this turn-key home and your eye will instantly be drawn to the sight of meadows, trees, and Berkshire hills in the distance. This 3-bedroom home features an Open Floor Plan that provides multiple opportunities to enjoy the views. There's a wood-burning Fireplace & skylight in the Living Room. The Spacious Kitchen, w/ another skylight, is designed for cooks, family gatherings, or entertaining friends. An addition to the original house is the light-filled, Year Round Sunroom/Family Room w/ wet-bar, Cast Iron Stove, wall of windows & 3 more Skylights. The large Master Bedroom has an updated en-suite bathroom w/ large tub and shower w/ body jets to complement the overhead faucet. Outside, an Azek deck leads to hot tub area & in-ground pool. There's a 2-horse barn on the property & detached 2-story garage w/ finished/heated space. 15 minutes away from The Berkshires' towns & attractions, 30 Minutes to Hudson or Albany & a little over 2 hours to NYC or Boston.

24. 2019-04-01
    listed $298,000 1035-char remark

    Show marketing remark (1035 chars)

    Step through the front door of this turn-key home and your eye will instantly be drawn to the sight of meadows, trees, and Berkshire hills in the distance. This 3-bedroom home features an Open Floor Plan that provides multiple opportunities to enjoy the views. There's a wood-burning Fireplace & skylight in the Living Room. The Spacious Kitchen, w/ another skylight, is designed for cooks, family gatherings, or entertaining friends. An addition to the original house is the light-filled, Year Round Sunroom/Family Room w/ wet-bar, Cast Iron Stove, wall of windows & 3 more Skylights. The large Master Bedroom has an updated en-suite bathroom w/ large tub and shower w/ body jets to complement the overhead faucet. Outside, an Azek deck leads to hot tub area & in-ground pool. There's a 2-horse barn on the property & detached 2-story garage w/ finished/heated space. 15 minutes away from The Berkshires' towns & attractions, 30 Minutes to Hudson or Albany & a little over 2 hours to NYC or Boston.

25. 2019-04-01
    listed $298,000

    Show marketing remark (1035 chars)

    Step through the front door of this turn-key home and your eye will instantly be drawn to the sight of meadows, trees, and Berkshire hills in the distance. This 3-bedroom home features an Open Floor Plan that provides multiple opportunities to enjoy the views. There's a wood-burning Fireplace & skylight in the Living Room. The Spacious Kitchen, w/ another skylight, is designed for cooks, family gatherings, or entertaining friends. An addition to the original house is the light-filled, Year Round Sunroom/Family Room w/ wet-bar, Cast Iron Stove, wall of windows & 3 more Skylights. The large Master Bedroom has an updated en-suite bathroom w/ large tub and shower w/ body jets to complement the overhead faucet. Outside, an Azek deck leads to hot tub area & in-ground pool. There's a 2-horse barn on the property & detached 2-story garage w/ finished/heated space. 15 minutes away from The Berkshires' towns & attractions, 30 Minutes to Hudson or Albany & a little over 2 hours to NYC or Boston.

26. 2004-06-10
    soldstatus $315,000
27. 2002-08-02
    soldstatus $243,000

ⓘ 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: $7,301 · $608/mo
• Projected year-2 tax: $7,445 · $620/mo
• Expected delta: +$143/yr (+$12/mo · 2.0%)

ⓘ 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 · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 2/10 Low 7 d/yr ≥92°F today · 16 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 8% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $120,000
• − Mortgage interest: −$25,151
• − Property taxes: −$7,301
• − Insurance: −$2,245
• − Repairs & maintenance: −$9,600
• − Management: −$9,600
• − Depreciation: −$13,062
• Taxable income: $53,041
• Est. tax owed @ 24.0%: −$12,730
• After-tax cash flow: $44,269/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: Chatham Central School District
• NCES district ID: 3607110
• Math proficiency: 48% ▼ -12.00%
• Reading proficiency: 53% ▲ 1.00%
• Median HH income: $61,460
• Composite: 44.28/100
• National rank: #2835
• State rank: #353 of 590 in NY

Livability — East Nassau

• Score: 56/100
• State rank: #1099
• US rank: #22410

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 1,723
• Population (ZIP): 1,017

Population outlook (Columbia County) Hauer SSP2

• Today (2025): 58,662 people
• By 2030: 56,557 · -3.6%
• By 2040: 51,324 · -12.5%
• By 2050: 45,790 · -21.9%
• By 2075: 35,232 · -39.9%
• By 2100: 25,846 · -55.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (91%)
• Race & ethnicity: White 91% Black 5% Two or more races 3%
• Common ancestry: Slovak 8% Romanian 4% Lithuanian 2%
• Foreign-born: 4% · Canada
• Languages at home: 97% English-only · Other Asian/Pacific 1% Other Indo-European 1% German/W. Germanic 1%

Political lean MEDSL · Columbia

• 2024 margin: D (+14.7) · D 57.4% · R 42.6%
• 2008→2024 swing: +1.3pp toward D · 2008: 13.4pp · 2024: 14.7pp
• All cycles: 2024: D+14.7 2020: D+16.7 2016: D+1.4 2012: D+11.7 2008: D+13.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -1.54%
• Current HPI: 384.886
• 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

+105.3% since first listed

11 events — show timeline

• 2026-05-04 Price Changed $499,000 HVCRMLS
• 2026-03-27 Price Changed $549,000 HVCRMLS
• 2025-12-21 Price Changed $579,000 HVCRMLS
• 2025-09-24 Listed $595,000 HVCRMLS
• 2019-09-23 Sold (Public Records) $285,000 Public Records
• 2019-09-23 Sold (MLS) $285,000 Global MLS
• 2019-09-23 Sold (MLS) $285,000 HVCRMLS
• 2019-04-01 Listed $298,000 Global MLS
• 2019-04-01 Listed $298,000 HVCRMLS
• 2004-06-10 Sold (Public Records) $315,000 Public Records
• 2002-08-02 Sold (Public Records) $243,000 Public Records

Property tax history

+0.4%/yr

Latest (2025): $7,301 · -1.9% YoY. Source: county tax records.