7786 S Main St · Pine Plains, NY 12567

$499,000

4 bd · 1.5 ba · 3,072 sqft · SingleFamily public records · 36 Days on market

Built 1903 0.47 ac lot $162/sqft · 9% below area Est $546k · 9% 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 +11.4/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Appreciation +10.0/10.0
• Schools +4.8/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details. Once home to both the town pharmacy and library, this unique property blends rich local history with classic Hudson Valley charm. Inside, you’ll find stunning original woodwork and trim, oversized rooms, high ceilings, and beautiful hardwood floors throughout — long protected beneath carpeting for many years and now ready to shine once again. T

Key facts

• Colonial style home
• Center of town
• Original woodwork

Tags

• COLONIAL STYLE HOME
• ORIGINAL WOODWORK
• LARGE BARN
• WALKABLE TO LOCAL RESTAURANTS
• CENTER OF TOWN

Property features AI

Exterior

• Parking: Driveway; Off-street parking; 2-car garage
• Utilities: Cesspool sewer; Electricity connected; Propane available; Water connected
• Home design: Single family residence; Living area reported from public records
• Construction: Vinyl siding construction
• Exterior features: Vinyl siding; Not waterfront

Interior

• Kitchen: Gas range; Microwave; Refrigerator; Stainless steel appliances
• Bedrooms: Total of 9 rooms (bedroom count not specified)
• Bathrooms: 1 full bathroom; 1 half bathroom
• Heating & cooling: Oil heating; Other heating; Wall/window air conditioning units
• Interior features: Original details and natural woodwork; Unfinished basement; Full attic
• Laundry & utility: Washer; Dryer

What this means for you Summary

Snapshot

• This is a 4-bed/1.5-bath single-family listed at $499k.

Deal economics

• At list price, monthly cash flow is $6k ($72k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($12k rent vs $499k).
• Recommended offer: $484k (3.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 64/100 on livability (#746 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment B+; Watch: cost of living D+, amenities F, commute F.
• Pine Plains Central School District (rural): math 55% / reading 50% proficiency, ranked #372 of 755 in NY (top 49%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Seymour Smith Intermediate Learning Center (math 24% / reading 75%, grade D+, #1,057 of 2,108 statewide, top 51%, 201 students, 40% FRL); Stissing Mountain Junior/Senior High School (math 92% / reading 75%, grade A, #409 of 1,100 statewide, top 39%, 460 students, 36% FRL).
• Zoned-school proficiency averages 67% at this address vs 52% district-wide (+14 pts) — the actual schools serving this property are materially stronger than the Pine Plains Central School District average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 39 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).

Forward outlook

• In year one you build about $53k of equity ($3k loan paydown + $50k appreciation (10.0% local appreciation)).
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $140k cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$86k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 36 days — a 3% lower offer ($484k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 2y 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 $110k; list at $499k implies a 354% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1903 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $484,030 (3.0% below list)

Questions for the listing agent

1. It's been on market 36 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1903 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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.
5. 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.
6. 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: 2.40% ✓
• Cap rate: 20.82%
• Cash-on-cash: 51.87%
• DSCR: 3.31
• GRM: 3.5

CMA / ARV

• ARV (median comp): $546,029
• List price: $499,000
• Delta: -8.61%
• Verdict: FAIR
• Comps: 18 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
30 N Main St	0.23mi	4/2.5	3,180 (+4%)	6mo	$520,000	$164	75

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

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 65.2%
• Equity multiple: 5.70×
• Total profit: $656,603
• Equity at exit: $449,539

10-year hold

• IRR: 58.8%
• Equity multiple: 12.68×
• Total profit: $1,631,445
• Equity at exit: $969,447

Cash invested: $139,720 (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 12567

• Home prices YoY: 18.7%
• Active inventory: 39
• Price-to-rent: 3.5×

Monthly cashflow live

• Estimated rent: $12,000 medium
• Mortgage (P&I): −$2,617
• Tax from tax record: −$616 /mo · $7,389/yr
• Insurance: −$208
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,520
• Net cashflow: $6,039

Break-even live

Break-even rent $4,355

Max offer price $499,000

Occupancy floor 45%

Sensitivity live

Price	-10% $6,322	-5% $6,181	+0% $6,039	+5% $5,898	+10% $5,757
Rent	-10% $5,091	-5% $5,565	+0% $6,039	+5% $6,513	+10% $6,987
Rate	-1.0pp $6,291	-0.5pp $6,166	base $6,039	+0.5pp $5,910	+1.0pp $5,779

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: $124,750
• Closing costs: $14,970
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
231 Lake Rd Pine Plains, NY	4.0	4.0	3029	$12,000	$3.96	24d	1	1.21mi

Listing history 25 events

1. 2026-06-18
   days on market $499,000 Active 36 DOM
2. 2026-06-17
   days on market $499,000 Active 35 DOM
3. 2026-06-16
   days on market $499,000 Active 34 DOM
4. 2026-06-15
   days on market $499,000 Active 33 DOM
5. 2026-06-14
   days on market $499,000 Active 31 DOM
6. 2026-06-10
   days on market $499,000 Active 28 DOM
7. 2026-06-09
   days on market $499,000 Active 27 DOM
8. 2026-06-08
   days on market $499,000 Active 26 DOM
9. 2026-06-07
   days on market $499,000 Active 25 DOM
10. 2026-06-05
    days on market $499,000 Active 22 DOM
11. 2026-06-03
    days on market $499,000 Active 21 DOM
12. 2026-06-02
    days on market $499,000 Active 20 DOM
13. 2026-06-01
    days on market $499,000 Active 19 DOM
14. 2026-05-31
    days on market $499,000 Active 18 DOM
15. 2026-05-30
    days on market $499,000 Active 17 DOM
16. 2026-05-13
    listed $499,000 Active 1615-char remark
17. 2026-02-16
    historical
18. 2025-11-14
    price $499,000
19. 2025-11-14
    price $499,000
20. 2025-06-06
    price $509,000
21. 2025-06-06
    price $509,000
22. 2025-04-23
    price $525,000
23. 2024-09-04
    listed $550,000 Active
24. 2024-08-27
    listed $525,000 Active
25. 2017-12-05
    soldstatus $110,000

ⓘ 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: $7,389 · $616/mo
• Projected year-2 tax: $7,911 · $659/mo
• Expected delta: +$522/yr (+$43/mo · 7.1%)

ⓘ 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 4/10 Moderate 7 d/yr ≥95°F today · 17 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 · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $144,000
• − Mortgage interest: −$27,952
• − Property taxes: −$7,389
• − Insurance: −$2,495
• − Repairs & maintenance: −$11,520
• − Management: −$11,520
• − Depreciation: −$14,516
• Taxable income: $68,607
• Est. tax owed @ 24.0%: −$16,466
• After-tax cash flow: $56,008/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: Pine Plains Central School District
• NCES district ID: 3623040
• Math proficiency: 55% ▬ 0.00%
• Reading proficiency: 50% ▲ 1.00%
• Median HH income: $66,189
• Composite: 48.33/100
• National rank: #4688
• State rank: #372 of 755 in NY

Livability — Pine Plains

• Score: 64/100
• State rank: #746
• US rank: #14240

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Pine Plains, NY
• City population: 2,498
• Population (ZIP): 2,498

Population outlook (Dutchess County) Hauer SSP2

• Today (2025): 291,768 people
• By 2030: 287,131 · -1.6%
• By 2040: 274,881 · -5.8%
• By 2050: 259,971 · -10.9%
• By 2075: 235,366 · -19.3%
• By 2100: 208,786 · -28.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (85%)
• Race & ethnicity: White 85% Two or more races 8% Hispanic / Latino 7% Pacific Islander 2% Asian 2%
• Hispanic origin (detail): Mexican 4%
• Common ancestry: Iranian 3% Scotch-Irish 2% Romanian 2%
• Foreign-born: 5% · Canada
• Languages at home: 95% English-only · Spanish 3% Tagalog/Filipino 1%

Political lean MEDSL · Dutchess

• 2024 margin: Lean D (+5.4) · D 52.7% · R 47.3%
• 2008→2024 swing: -3.2pp toward R · 2008: 8.6pp · 2024: 5.4pp
• All cycles: 2024: D+5.4 2020: D+9.6 2016: R+1.1 2012: D+6.6 2008: D+8.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 50.77%
• Current HPI: 322.2342
• 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

+353.6% since first listed

10 events — show timeline

• 2026-05-13 Listed $499,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-16 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-11-14 Price Changed $499,000 HVCRMLS
• 2025-11-14 Price Changed $499,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-06 Price Changed $509,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-06 Price Changed $509,000 HVCRMLS
• 2025-04-23 Price Changed $525,000 OneKey® MLS as Distributed by MLS Grid
• 2024-09-04 Listed $550,000 OneKey® MLS as Distributed by MLS Grid
• 2024-08-27 Listed $525,000 HVCRMLS
• 2017-12-05 Sold (Public Records) $110,000 Public Records

Property tax history

+3.5%/yr

Latest (2025): $7,389 · +30.5% YoY. Source: county tax records.