41 County Road 39 · Round Top, NY 12473

$289,000

15 bd · 8.0 ba · 5,542 sqft · MultiFamily · 120 Days on market

Built 1890 Fair condition 2.40 ac 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
• Appreciation +6.9/10.0
• Schools +3.8/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.2/5.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 5 units. estimate disagrees with records

Listing remarks MLS

Exceptional opportunity to own a historic lodge property in the Catskills, formerly operated as the well-known Woodlands Lodge. Situated on approximately 2.4 acres in desirable Round Top, New York, this expansive property offers incredible potential for a bed & breakfast, boutique inn, wedding venue, retreat center, or private estate. The main residence features multiple levels of bedrooms and baths, showcasing original character throughout, including beautiful woodwork, pocket doors, and a grand staircase in the impressive entry foyer. The first floor offers a spacious prep kitchen with pantry and office area, bar room, double parlor, large sun-filled dining room, and an additional sitting room created from enclosed porch space. A rear staircase and separate exterior entrance provide convenient access to guest accommodations. The second floor includes five bedrooms and six bathrooms, while the third floor offers seven additional bedrooms with sinks and two full baths. A rear addition provides four more bedrooms with baths, creating substantial capacity for guests or extended living arrangements. Additional features include a laundry area and staff quarters off the kitchen. The Property is being sold As-Is and Cash offer preferred because of low asking price. The back cottage is gutted and is approximately 1024 square feet. The property is ideally located near popular ski resorts, golf courses, hiking trails, and outdoor recreation, with convenient access to the New York State Thruway, making travel from the New York City metro area easy. With vision and renovation, this property presents tremendous potential to restore it to an active hospitality destination or create a one-of-a-kind private compound. The property has been successfully subdivided, and taxes will be based on the 2.4-acre parcel. Most furnishings and contents associated with former lodge operations are included in the sale, with limited personal exclusions.

Key facts

• Guest accommodations
• Double parlor
• Expansive property

Tags

• HISTORIC LODGE PROPERTY
• EXPANSIVE PROPERTY
• SPACIOUS PREP KITCHEN
• DOUBLE PARLOR
• SUN-FILLED DINING ROOM
• GUEST ACCOMMODATIONS

What this means for you Summary

Snapshot

• This is a 5 × 3-bed/?-bath units multifamily listed at $289k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $3k ($41k/yr) — positive. Per door: $679/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($7k rent vs $289k).
• Recommended offer: $263k (9.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Cairo-Durham Central School District (rural): math 41% / reading 48% proficiency, ranked #470 of 590 in NY (top 80%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Cairo-Durham Elementary School (math 27% / reading 42%, grade F, #1,577 of 2,108 statewide, top 77%, 439 students, 60% FRL); Cairo-Durham Middle School (math 27% / reading 47%, grade F, #448 of 729 statewide, top 63%, 256 students, 62% FRL); Cairo-Durham High School (math 92% / reading 90%, grade A+, #203 of 1,100 statewide, top 20%, 325 students, 59% FRL) — zoned schools average 60% FRL vs 40% district-wide (20 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 11 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 $13k of equity ($2k loan paydown + $11k appreciation (3.8% 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 (3.8% appreciation + 3.0% rent growth), your $81k cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$32k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 120 days — a 9% lower offer ($263k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1890 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $262,990 (9.0% below list)

Questions for the listing agent

1. It's been on market 120 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
5. Built in 1890 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
6. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
7. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
8. 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.
9. 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.
10. 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: 2.36% ✓
• Cap rate: 20.39%
• Cash-on-cash: 50.35%
• DSCR: 3.24
• GRM: 3.5

CMA / ARV

No comps found within radius.

Projected returns pro-forma

3.75% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 56.4%
• Equity multiple: 4.25×
• Total profit: $262,805
• Equity at exit: $142,327

10-year hold

• IRR: 55.3%
• Equity multiple: 8.65×
• Total profit: $618,732
• Equity at exit: $229,498

Cash invested: $80,920 (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 12473

• Home prices YoY: 0.9%
• Active inventory: 11
• Price-to-rent: 17.6×

Monthly cashflow live

• Estimated rent: $6,826 medium
• Mortgage (P&I): −$1,516
• Tax est. 1.5%: −$361 /mo · $4,335/yr
• Insurance: −$120
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,433
• Net cashflow: $3,395

Break-even live

Break-even rent $2,528

Max offer price $289,000

Occupancy floor 45%

Sensitivity live

Price	-10% $3,595	-5% $3,495	+0% $3,395	+5% $3,295	+10% $3,196
Rent	-10% $2,856	-5% $3,126	+0% $3,395	+5% $3,665	+10% $3,935
Rate	-1.0pp $3,541	-0.5pp $3,469	base $3,395	+0.5pp $3,320	+1.0pp $3,244

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

Units	Beds	Baths	Est. rent
▸ 5× units	3	—	$6,825
Total (5 units)			$6,826

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: $72,250
• Closing costs: $8,670
• Reserves months: —
• Total cash needed: —

Listing history 17 events

1. 2026-06-22
   days on market $289,000 Active 120 DOM
2. 2026-06-18
   days on market $289,000 Active 117 DOM
3. 2026-06-17
   days on market $289,000 Active 116 DOM
4. 2026-06-16
   days on market $289,000 Active 115 DOM
5. 2026-06-15
   days on market $289,000 Active 114 DOM
6. 2026-06-14
   days on market $289,000 Active 112 DOM
7. 2026-06-10
   days on market $289,000 Active 109 DOM
8. 2026-06-09
   days on market $289,000 Active 108 DOM
9. 2026-06-08
   days on market $289,000 Active 107 DOM
10. 2026-06-07
    days on market $289,000 Active 106 DOM
11. 2026-06-05
    days on market $289,000 Active 103 DOM
12. 2026-06-03
    days on market $289,000 Active 102 DOM
13. 2026-06-02
    days on market $289,000 Active 101 DOM
14. 2026-06-01
    days on market $289,000 Active 100 DOM
15. 2026-05-31
    days on market $289,000 Active 99 DOM
16. 2026-05-31
    days on market $289,000 Active 98 DOM
17. 2026-02-21
    listed $289,000 Active 1963-char remark

    Show marketing remark (1963 chars)

    Exceptional opportunity to own a historic lodge property in the Catskills, formerly operated as the well-known Woodlands Lodge. Situated on approximately 2.4 acres in desirable Round Top, New York, this expansive property offers incredible potential for a bed & breakfast, boutique inn, wedding venue, retreat center, or private estate. The main residence features multiple levels of bedrooms and baths, showcasing original character throughout, including beautiful woodwork, pocket doors, and a grand staircase in the impressive entry foyer. The first floor offers a spacious prep kitchen with pantry and office area, bar room, double parlor, large sun-filled dining room, and an additional sitting room created from enclosed porch space. A rear staircase and separate exterior entrance provide convenient access to guest accommodations. The second floor includes five bedrooms and six bathrooms, while the third floor offers seven additional bedrooms with sinks and two full baths. A rear addition provides four more bedrooms with baths, creating substantial capacity for guests or extended living arrangements. Additional features include a laundry area and staff quarters off the kitchen. The Property is being sold As-Is and Cash offer preferred because of low asking price. The back cottage is gutted and is approximately 1024 square feet. The property is ideally located near popular ski resorts, golf courses, hiking trails, and outdoor recreation, with convenient access to the New York State Thruway, making travel from the New York City metro area easy. With vision and renovation, this property presents tremendous potential to restore it to an active hospitality destination or create a one-of-a-kind private compound. The property has been successfully subdivided, and taxes will be based on the 2.4-acre parcel. Most furnishings and contents associated with former lodge operations are included in the sale, with limited personal exclusions.

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 3/10 Moderate 7 d/yr ≥93°F today · 16 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 5% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $81,912
• − Mortgage interest: −$16,188
• − Property taxes: −$4,335
• − Insurance: −$1,445
• − Repairs & maintenance: −$6,553
• − Management: −$6,553
• − Depreciation: −$8,407
• Taxable income: $38,430
• Est. tax owed @ 24.0%: −$9,223
• After-tax cash flow: $31,521/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.

Condition & rehab AI · 13 photos

Fair 45/100 Extensive rehab

This historic property requires extensive repairs and updates to improve its condition and increase its resale and rental value.

Repairs flagged

• Major roof — The roof appears to be in poor condition and may need replacement.
• Major exterior siding — The exterior siding is peeling and requires repainting.
• Major porch railings — The porch railings are damaged and need repair.
• Major flooring — The flooring in the kitchen and living areas needs replacement.
• Major interior walls — The interior walls show signs of wear and tear and need repainting.
• Major bathrooms — The bathrooms are outdated and need updates.
• Major HVAC system — The HVAC system appears to be old and may need replacement.

Value-add opportunities

• Resale New roof — A new roof will significantly improve the home's appearance and reduce the risk of leaks.
• Resale Exterior painting — Repainting the exterior siding will improve the home's curb appeal and increase its resale value.
• Resale Porch railings repair — Repairing the damaged porch railings will improve the home's safety and appearance.
• Resale Flooring replacement — Replacing the old flooring in the kitchen and living areas will improve the home's appearance and increase its resale value.
• Resale Interior wall repainting — Repainting the interior walls will improve the home's appearance and increase its resale value.
• Resale Bathroom updates — Updating the bathrooms will improve the home's appearance and increase its resale value.
• Resale HVAC replacement — Replacing the old HVAC system will improve the home's comfort and energy efficiency, increasing its resale value.

Renovation cost estimate screening

Repair item	Severity	Est. cost
roof · The roof appears to be in poor condition and may need replacement.	Major	$15,000–50,000
exterior siding · The exterior siding is peeling and requires repainting.	Major	$15,000–50,000
porch railings · The porch railings are damaged and need repair.	Major	$15,000–50,000
flooring · The flooring in the kitchen and living areas needs replacement.	Major	$15,000–50,000
interior walls · The interior walls show signs of wear and tear and need repainting.	Major	$15,000–50,000
bathrooms · The bathrooms are outdated and need updates.	Major	$15,000–50,000
HVAC system · The HVAC system appears to be old and may need replacement.	Major	$15,000–50,000
Total estimated repair cost · 7 items		$105,000–350,000

Value-add ROI direction

• Resale New roof — A new roof will significantly improve the home's appearance and reduce the risk of leaks. ↑
• Resale Exterior painting — Repainting the exterior siding will improve the home's curb appeal and increase its resale value. ↑
• Resale Porch railings repair — Repairing the damaged porch railings will improve the home's safety and appearance. ↑
• Resale Flooring replacement — Replacing the old flooring in the kitchen and living areas will improve the home's appearance and increase its resale value. ↑
• Resale Interior wall repainting — Repainting the interior walls will improve the home's appearance and increase its resale value. ↑
• Resale Bathroom updates — Updating the bathrooms will improve the home's appearance and increase its resale value. ↑
• Resale HVAC replacement — Replacing the old HVAC system will improve the home's comfort and energy efficiency, increasing its resale value. ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Cairo-Durham Central School District
• NCES district ID: 3606160
• Math proficiency: 41% ▼ -3.00%
• Reading proficiency: 48% ▲ 8.00%
• Median HH income: $46,192
• Composite: 37.84/100
• National rank: #4330
• State rank: #470 of 590 in NY

Livability — Round Top

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• Census place: Round Top, NY
• City population: 1,344
• Population (ZIP): 693

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 (96%)
• Race & ethnicity: White 96% Two or more races 4% Hispanic / Latino 1%
• Common ancestry: Scotch-Irish 5% Romanian 5% Lithuanian 4%
• Foreign-born: 2%
• Languages at home: 96% English-only · German/W. Germanic 4%

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: ▲ 3.75%
• Current HPI: 424.2436
• 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

1 event — show timeline

• 2026-02-21 Listed $289,000 HVCRMLS