689 Old Rd · Windham, NY 12439

$315,000

2 bd · 2.0 ba · 1,542 sqft · SingleFamily public records · 25 Days on market

Built 1930 1.00 ac lot ↓ 9% since listing

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Why this score? — see what drove the C 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 +19.7/30.0
• ARV discount +7.5/15.0
• DSCR +6.2/10.0
• Appreciation +5.9/10.0
• 1% rule +4.6/10.0
• Schools +4.3/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Step into the charm of this 1930s 2-bedroom, 2-bath ranch, just minutes from the Village of Windham and Windham Mountain. Nestled on a full acre and bordered by 25.5 acres of protected NYC watershed land, the property offers rare privacy and a seamless connection to nature. Wake up to the gentle sounds of a seasonal creek and lush surrounding greenery, a true mountain escape. Outside, a spacious deck invites morning coffee or evening stargazing, while a charming gazebo provides the perfect spot to unwind. A detached garage rounds out the exterior, ideal for storage or a workshop. Inside feel the cozy character of the home with endless potential, whether you're curling up by the fire or host

Key facts

• Charming gazebo
• Seasonal creek
• Renowned hiking

Tags

• SEASONAL CREEK
• SPACIOUS DECK
• CHARMING GAZEBO
• DETACHED GARAGE
• RENOWNED HIKING
• BIKING

Property features AI

Exterior

• Parking: Detached garage (1 car); Asphalt driveway; Paved surfaces; Garage faces side
• Utilities: Private well water; Septic tank sewer; 150 Amp electrical service
• Home design: Single-family house; One level
• Construction: Block foundation; Asphalt shingle roof
• Exterior features: Private yard; Storage; Deck; Patio; Gazebo; Shed(s)

Interior

• Kitchen: Dishwasher; Range; Refrigerator
• Bedrooms: Primary bedroom located on the main level
• Bathrooms: 2 full bathrooms
• Heating & cooling: Baseboard heating; Hot water heat; Oil-fired heating
• Interior features: Main-level primary bedroom; Wood-burning fireplace in the living room; Main-level laundry
• Laundry & utility: Washer and dryer included; Laundry on main level

What this means for you Summary

Snapshot

• This is a 2-bed/2.0-bath single-family listed at $315k.

Deal economics

• At list price, monthly cash flow is $369 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $301k (4.5% below list).
• Recommended offer: $301k (4.5% below list) — sets the bar for 1% rule.
• Cap rate 7.7% vs local median 3.4% in Windham — 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 60/100 on livability (#964 in NY) — a middle-class / working-renter tenant base. Strengths: housing A+, employment B+; Watch: schools C-, crime D+, cost of living D+.
• Windham-Ashland-Jewett Central School District (rural): math 55% / reading 40% proficiency, ranked #517 of 755 in NY (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 2 active listings in the ZIP; 97 units permitted in Greene County in 2024 (0 in 5+ unit buildings).

Forward outlook

• In year one you build about $8k of equity ($2k loan paydown + $6k appreciation (1.8% local appreciation)).
• Greene County population projected at -22% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (1.8% appreciation + 3.0% rent growth), your $88k cash investment doubles in ~6 years — after that, you're playing with house money.
• By year 5, paydown + projected appreciation supports a ~$34k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 25 days — a 2% lower offer ($310k) is reasonable based on typical stale-listing flexibility.
• 8 sale attempts since 3y 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.

Risks & watch-outs

• Watch-outs: built in 1930 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $300,866 (4.5% below list)

Questions for the listing agent

1. Built in 1930 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. 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?
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: 0.96% ✗
• Cap rate: 7.70%
• Cash-on-cash: 5.02%
• DSCR: 1.22
• GRM: 8.7

CMA / ARV

No comps found within radius.

Projected returns pro-forma

1.75% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 8.8%
• Equity multiple: 1.47×
• Total profit: $41,055
• Equity at exit: $120,026

10-year hold

• IRR: 12.1%
• Equity multiple: 2.59×
• Total profit: $139,823
• Equity at exit: $169,655

Cash invested: $88,200 (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 12439

• Home prices YoY: 0.4%
• Active inventory: 2
• Price-to-rent: 8.7×

Monthly cashflow live

• Estimated rent: $3,009 medium
• Mortgage (P&I): −$1,652
• Tax from tax record: −$225 /mo · $2,700/yr
• Insurance: −$131
• HOA: −$0
• Vacancy / Maint / Mgmt: −$632
• Net cashflow: $369

Break-even live

Break-even rent $2,542

Max offer price $315,000

Occupancy floor 83%

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: $78,750
• Closing costs: $9,450
• Reserves months: —
• Total cash needed: —

Listing history 31 events

1. 2026-06-18
   days on market $315,000 Active 25 DOM
2. 2026-06-17
   days on market $315,000 Active 24 DOM
3. 2026-06-16
   days on market $315,000 Active 23 DOM
4. 2026-06-15
   days on market $315,000 Active 22 DOM
5. 2026-06-13
   days on market $315,000 Active 20 DOM
6. 2026-06-12
   days on market $315,000 Active 19 DOM
7. 2026-06-09
   days on market $315,000 Active 16 DOM
8. 2026-06-08
   days on market $315,000 Active 15 DOM
9. 2026-06-07
   days on market $315,000 Active 14 DOM
10. 2026-06-07
    days on market $315,000 Active 13 DOM
11. 2026-06-04
    days on market $315,000 Active 10 DOM
12. 2026-06-02
    days on market $315,000 Active 9 DOM
13. 2026-06-01
    days on market $315,000 Active 8 DOM
14. 2026-05-31
    days on market $315,000 Active 7 DOM
15. 2026-05-24
    listed $315,000 Active
16. 2025-12-25
    historical
17. 2025-09-10
    price $340,000
18. 2025-09-10
    price $340,000
19. 2025-07-18
    status Active
20. 2025-07-18
    status Active
21. 2025-07-10
    status Pending
22. 2025-07-09
    historical Active Under Contract
23. 2025-05-02
    price $343,000
24. 2025-05-02
    price $343,000
25. 2025-04-10
    listed $345,000 Active
26. 2025-03-24
    listed $345,000 Active
27. 2024-08-12
    status Active
28. 2024-07-29
    status Pending
29. 2024-03-18
    status Active
30. 2024-02-04
    historical Accepted (Show)
31. 2023-11-29
    listed $345,000 Active

ⓘ 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: $2,700 · $225/mo
• Projected year-2 tax: $4,012 · $334/mo
• Expected delta: +$1,312/yr (+$109/mo · 48.6%)

ⓘ 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 2/10 Low
• 🌡 Heat 1/10 Low 7 d/yr ≥86°F today · 17 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 3% chance of damaging wind over 30 yrs
• 🫁 Air quality 1/10 Low 0 unhealthy d/yr today · 0 by 30 yrs out

Taxation est. · year 1

• Rental income: $36,104
• − Mortgage interest: −$17,645
• − Property taxes: −$2,700
• − Insurance: −$1,575
• − Repairs & maintenance: −$2,888
• − Management: −$2,888
• − Depreciation: −$9,164
• Taxable loss: −$756
• Est. tax savings @ 24.0%: +$182
• After-tax cash flow: $4,606/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: Windham-Ashland-Jewett Central School District
• NCES district ID: 3631590
• Math proficiency: 55% ▲ 5.00%
• Reading proficiency: 40% ▼ -10.00%
• Median HH income: $46,942
• Composite: 42.57/100
• National rank: #6842
• State rank: #517 of 755 in NY

Livability — Windham

• Score: 60/100
• State rank: #964
• US rank: #18888

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 380

Population outlook (Greene County) Hauer SSP2

• Today (2025): 44,963 people
• By 2030: 43,126 · -4.1%
• By 2040: 38,756 · -13.8%
• By 2050: 34,913 · -22.4%
• By 2075: 28,156 · -37.4%
• By 2100: 22,296 · -50.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (89%)
• Race & ethnicity: White 89% Hispanic / Latino 8% Two or more races 8% Black 3%
• Hispanic origin (detail): Cuban 8%
• Common ancestry: Slovak 7% Lithuanian 3% German 2%
• Foreign-born: 3%
• Languages at home: 82% English-only · Spanish 9% French/Haitian/Cajun 8% Other Indo-European 1%

Political lean MEDSL · Greene

• 2024 margin: R (+17.0) · D 41.5% · R 58.5%
• 2008→2024 swing: -7.1pp toward R · 2008: -9.9pp · 2024: -17.0pp
• All cycles: 2024: R+17.0 2020: R+15.6 2016: R+27.4 2012: R+11.1 2008: R+9.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 1.75%
• Current HPI: 449.8271
• 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

-8.7% since first listed

17 events — show timeline

• 2026-05-24 Listed $315,000 HVCRMLS
• 2025-12-25 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-09-10 Price Changed $340,000 OneKey® MLS as Distributed by MLS Grid
• 2025-09-10 Price Changed $340,000 HVCRMLS
• 2025-07-18 Relisted — HVCRMLS
• 2025-07-18 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-07-10 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-07-09 Contingent — HVCRMLS
• 2025-05-02 Price Changed $343,000 OneKey® MLS as Distributed by MLS Grid
• 2025-05-02 Price Changed $343,000 HVCRMLS
• 2025-04-10 Listed $345,000 OneKey® MLS as Distributed by MLS Grid
• 2025-03-24 Listed $345,000 HVCRMLS
• 2024-08-12 Relisted — HVCRMLS
• 2024-07-29 Pending — HVCRMLS
• 2024-03-18 Relisted — HVCRMLS
• 2024-02-04 Contingent — HVCRMLS
• 2023-11-29 Listed $345,000 HVCRMLS

Property tax history

+4.3%/yr

Latest (2025): $2,700 · +4.6% YoY. Source: county tax records.