27 Old Wagon Rd · Woodstock, NY 12498

$1,275,000

3 bd · 2.0 ba · 1,744 sqft · SingleFamily public records · 15 Days on market

Built 1978 3.50 ac lot $731/sqft · 124% above area Est $1006k · 27% over

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Why this score? — see what drove the F 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).

• Schools +5.2/10.0
• Livability +3.9/5.0
• Cash flow +2.7/30.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0
• ARV discount +0.0/15.0
• Appreciation +0.0/10.0

Listing remarks MLS

Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths measuring 2200 sq. ft. The detached cottage has one bedroom with one full bath measuring 480 sq. ft and the detached studio has another full bath measuring 400 sq ft. The main house is a light-filled classic Woodstock modern home built around the original Woodstock's artist's cabin. Thoughtfully designed to frame the surrounding forest through expansive glass sightlines, allowing for views of deer, birds, and other wildlife throughout the seasons. Inside, the home showcases unique historical details such as chestnut beams in the dining room, a bluestone fireplace, a built-in library, and a mix of slate, Spanish tile, pine, and oak flooring. The multi-level living area features a lofted tongue-and-groove wood ceiling and five architectural skylights that bring the outdoors in. Upon entry, you're greeted by a bright and inviting sunroom that opens into a formal foyer. Just off the foyer is a room that can serve as a home office, reading nook, or playroom, conveniently located next to a full guest bathroom. This level also features a cozy bedroom and a hallway office nook--perfect for remote work or quiet study. The eat-in kitchen includes a charming breakfast nook that offers serene views of the surrounding landscape and seamlessly flows into the dining room, creating a warm and inviting connection between the spaces. The dining area doubles as a music room, enhanced by vintage wide-plank pine flooring and a wood-burning fireplace that adds warmth and character. Step down into the sunken living room, where high ceilings and built-in bookshelves create a bright, welcoming space ideal for relaxing or entertaining. The primary suite features an en-suite bathroom with Parisian influences, including a bidet and a deep, one-person soaking tub with jacuzzi jets. Sliders walk out to the private multi-level deck and your own private atrium. Just off the main area, a newly designed mason-laid bluestone patio features a seamless transition into an expansive deck, offering the perfect setting for quiet evenings or vibrant dinner parties. The second floor features a loft area, ideal as a TV or family room, providing a comfortable space to relax or entertain. Tucked away for privacy, the second primary suite includes a full bath, creating a serene retreat separate from the main living areas. The one-bedroom cottage evokes the feel of an English guesthouse, with wood floors, a full kitchen and bathroom, and its own dedicated utilities, making it a wonderful space for guests or potential rental income. The detached studio, adjoining the three-car garage, feels like a New York City loft, complete with wide-plank floors, an open-concept layout, a bathroom, and a kitchenette. With its own electric and utilities, the space lends itself well to use as an office, yoga or art studio, or another income-producing rental. The garage offers three bays--two for vehicles and one ideal for workshop or storage use. For decades, this special property has been a gathering place for artists, musicians and writers. The home is designed to inspire and connect, all within minutes of Woodstock's vibrant center. It's an exceptional retreat with comfort, character, and potential in every direction. Please see addendum for recent updates and improvements on the home.

Key facts

• One bedroom cottage
• Built in library
• 3.7 acre compound

Tags

• 3.7 ACRE COMPOUND
• ONE BEDROOM COTTAGE
• STUDIO WITH KITCHENETTE
• BUILT IN LIBRARY
• BLUESTONE FIREPLACE
• MULTI LEVEL DECK

Property features AI

Exterior

• Parking: Parking for 6 vehicles; 3-car garage; Driveway; Off-street parking
• Security: Smoke detector(s)
• Utilities: Central Hudson electric service; Septic tank; Cable connected; Phone available
• Home design: Single family residence; Crawl space, partial and unfinished basement (basement present)
• Construction: Frame construction; Wood siding
• Exterior features: Garden; Outdoor lighting; Wood fencing; Garage(s), greenhouse, guest house, outbuilding, shed(s)

Interior

• Kitchen: Dishwasher; Range; Microwave; Refrigerator; Eat-in kitchen
• Bedrooms: Primary suite on main level (master downstairs)
• Flooring: Carpet; Ceramic tile; Tile; Wood
• Bathrooms: 5 full bathrooms
• Heating & cooling: Baseboard heating; Electric heating; Oil heating; Wall/Window cooling units
• Interior features: Beamed ceilings; Bidet; Built-in features; Ceiling fan(s); Eat-in kitchen; Entrance foyer; High ceilings; High speed internet; Storage; Walk-in closet(s); Double pane windows; Insulated windows; Skylight(s); Storm window(s); Deck; Patio
• Laundry & utility: Washer; Dryer; Laundry located in hall; Dehumidifier

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $1.27M.

Deal economics

• At list price, monthly cash flow is $-4k ($-51k/yr) — negative.
• To cash-flow at today's rent, offer at most $519k (59.3% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $485k (61.9% below list).
• Recommended offer: $485k (61.9% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 77/100 on livability (#205 in NY, #3,176 nationally) — a middle-class / working-renter tenant base. Strengths: crime A+, amenities A+, health & safety A+; Watch: employment D, commute F, cost of living F.
• Onteora Central School District (rural): math 58% / reading 59% proficiency, ranked #288 of 755 in NY (top 38%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Woodstock Elementary School (math 75% / reading 75%, grade A, #289 of 2,108 statewide, top 15%, 149 students, 40% FRL); Onteora Middle School (math 10% / reading 30%, grade F, #666 of 729 statewide, top 93%, 171 students, 44% FRL); Onteora High School (math 92% / reading 90%, grade A+, #203 of 1,100 statewide, top 20%, 413 students, 44% FRL).
• Market conditions: 72 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 464 units permitted in Ulster County in 2024 (170 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $9k of loan paydown is wiped out by about $38k of value loss. Plan a longer hold.
• Ulster County population projected at -14% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.

Negotiation context

• It's been on market 15 days — a 2% lower offer ($1.26M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts 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 $70k; list at $1.27M implies a 1721% gain — meaningful room to come down on a strong offer.

Recommended offer $485,158 (61.9% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. Built in 1978 — 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. Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
5. 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?
6. 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.
7. 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.
8. 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: 0.38% ✗
• Cap rate: 2.27%
• Cash-on-cash: -14.38%
• DSCR: 0.36
• GRM: 21.9

CMA / ARV

• ARV (median comp): $1,005,545
• List price: $1,275,000
• Delta: 26.80%
• Verdict: OVERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
28 Pinegrove St	0.25mi	2/2.0 (-1)	1,565 (-10%)	8mo	$729,000	$466	60
12 Library Ln	0.49mi	3/2.5	1,864 (+7%)	6mo	$787,000	$422	58
78 Ratterman Rd	0.52mi	3/2.0	1,548 (-11%)	10mo	$700,000	$452	49
115 Tinker St	0.51mi	3/2.5	1,595 (-8%)	20mo	$760,000	$476	43

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 · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -43.8%
• Equity multiple: -0.34×
• Total profit: $-479,483
• Equity at exit: $190,107

10-year hold

• IRR: -77.9%
• Equity multiple: -1.16×
• Total profit: $-769,890
• Equity at exit: $110,239

Cash invested: $357,000 (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 12498

• Home prices YoY: -21.8%
• Active inventory: 72
• Price-to-rent: 21.9×

Monthly cashflow live

• Estimated rent: $4,852 medium
• Mortgage (P&I): −$6,686
• Tax from tax record: −$894 /mo · $10,729/yr
• Insurance: −$531
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,019
• Net cashflow: $-4,279

Break-even live

Break-even rent $10,268

Max offer price $519,125

Occupancy floor —

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: $318,750
• Closing costs: $38,250
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
36 Northwoods Rd Unit A Woodstock, NY	2.0	1.0	1200	$3,600	$3.00	43d	1	1.20mi
25 Boggs Hill Rd Woodstock, NY	2.0	2.0	1655	$5,900	$3.56	43d	1	1.39mi

Listing history 14 events

1. 2026-05-13
   historical Active Under Contract 3675-char remark

   Show marketing remark (3675 chars)

   Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths measuring 2200 sq. ft. The detached cottage has one bedroom with one full bath measuring 480 sq. ft and the detached studio has another full bath measuring 400 sq ft. The main house is a light-filled classic Woodstock modern home built around the original Woodstock's artist's cabin. Thoughtfully designed to frame the surrounding forest through expansive glass sightlines, allowing for views of deer, birds, and other wildlife throughout the seasons. Inside, the home showcases unique historical details such as chestnut beams in the dining room, a bluestone fireplace, a built-in library, and a mix of slate, Spanish tile, pine, and oak flooring. The multi-level living area features a lofted tongue-and-groove wood ceiling and five architectural skylights that bring the outdoors in. Upon entry, you're greeted by a bright and inviting sunroom that opens into a formal foyer. Just off the foyer is a room that can serve as a home office, reading nook, or playroom, conveniently located next to a full guest bathroom. This level also features a cozy bedroom and a hallway office nook--perfect for remote work or quiet study. The eat-in kitchen includes a charming breakfast nook that offers serene views of the surrounding landscape and seamlessly flows into the dining room, creating a warm and inviting connection between the spaces. The dining area doubles as a music room, enhanced by vintage wide-plank pine flooring and a wood-burning fireplace that adds warmth and character. Step down into the sunken living room, where high ceilings and built-in bookshelves create a bright, welcoming space ideal for relaxing or entertaining. The primary suite features an en-suite bathroom with Parisian influences, including a bidet and a deep, one-person soaking tub with jacuzzi jets. Sliders walk out to the private multi-level deck and your own private atrium. Just off the main area, a newly designed mason-laid bluestone patio features a seamless transition into an expansive deck, offering the perfect setting for quiet evenings or vibrant dinner parties. The second floor features a loft area, ideal as a TV or family room, providing a comfortable space to relax or entertain. Tucked away for privacy, the second primary suite includes a full bath, creating a serene retreat separate from the main living areas. The one-bedroom cottage evokes the feel of an English guesthouse, with wood floors, a full kitchen and bathroom, and its own dedicated utilities, making it a wonderful space for guests or potential rental income. The detached studio, adjoining the three-car garage, feels like a New York City loft, complete with wide-plank floors, an open-concept layout, a bathroom, and a kitchenette. With its own electric and utilities, the space lends itself well to use as an office, yoga or art studio, or another income-producing rental. The garage offers three bays--two for vehicles and one ideal for workshop or storage use. For decades, this special property has been a gathering place for artists, musicians and writers. The home is designed to inspire and connect, all within minutes of Woodstock's vibrant center. It's an exceptional retreat with comfort, character, and potential in every direction. Please see addendum for recent updates and improvements on the home.

2. 2026-05-07
   listed $1,275,000 Active 3674-char remark
3. 2026-05-06
   listed $1,275,000 Active 3675-char remark

   Show marketing remark (3675 chars)

   Just a half mile from the center of Woodstock, this bucolic 3.7-acre compound offers a rare blend of architectural charm, natural beauty, and versatile living. The property includes the main house and two outbuildings, a one-bedroom cottage and a studio with an attached three-bay garage. Bedroom and bath layout described as the primary residence having three bedrooms and three full baths measuring 2200 sq. ft. The detached cottage has one bedroom with one full bath measuring 480 sq. ft and the detached studio has another full bath measuring 400 sq ft. The main house is a light-filled classic Woodstock modern home built around the original Woodstock's artist's cabin. Thoughtfully designed to frame the surrounding forest through expansive glass sightlines, allowing for views of deer, birds, and other wildlife throughout the seasons. Inside, the home showcases unique historical details such as chestnut beams in the dining room, a bluestone fireplace, a built-in library, and a mix of slate, Spanish tile, pine, and oak flooring. The multi-level living area features a lofted tongue-and-groove wood ceiling and five architectural skylights that bring the outdoors in. Upon entry, you're greeted by a bright and inviting sunroom that opens into a formal foyer. Just off the foyer is a room that can serve as a home office, reading nook, or playroom, conveniently located next to a full guest bathroom. This level also features a cozy bedroom and a hallway office nook--perfect for remote work or quiet study. The eat-in kitchen includes a charming breakfast nook that offers serene views of the surrounding landscape and seamlessly flows into the dining room, creating a warm and inviting connection between the spaces. The dining area doubles as a music room, enhanced by vintage wide-plank pine flooring and a wood-burning fireplace that adds warmth and character. Step down into the sunken living room, where high ceilings and built-in bookshelves create a bright, welcoming space ideal for relaxing or entertaining. The primary suite features an en-suite bathroom with Parisian influences, including a bidet and a deep, one-person soaking tub with jacuzzi jets. Sliders walk out to the private multi-level deck and your own private atrium. Just off the main area, a newly designed mason-laid bluestone patio features a seamless transition into an expansive deck, offering the perfect setting for quiet evenings or vibrant dinner parties. The second floor features a loft area, ideal as a TV or family room, providing a comfortable space to relax or entertain. Tucked away for privacy, the second primary suite includes a full bath, creating a serene retreat separate from the main living areas. The one-bedroom cottage evokes the feel of an English guesthouse, with wood floors, a full kitchen and bathroom, and its own dedicated utilities, making it a wonderful space for guests or potential rental income. The detached studio, adjoining the three-car garage, feels like a New York City loft, complete with wide-plank floors, an open-concept layout, a bathroom, and a kitchenette. With its own electric and utilities, the space lends itself well to use as an office, yoga or art studio, or another income-producing rental. The garage offers three bays--two for vehicles and one ideal for workshop or storage use. For decades, this special property has been a gathering place for artists, musicians and writers. The home is designed to inspire and connect, all within minutes of Woodstock's vibrant center. It's an exceptional retreat with comfort, character, and potential in every direction. Please see addendum for recent updates and improvements on the home.

4. 2026-02-01
   historical
5. 2026-01-14
   historical Active Under Contract
6. 2025-10-25
   status Active
7. 2025-10-10
   historical Active Under Contract
8. 2025-10-04
   price $1,295,000
9. 2025-10-04
   price $1,295,000
10. 2025-08-21
    price $1,350,000
11. 2025-08-21
    price $1,350,000
12. 2025-07-10
    listed $1,450,000 Active
13. 2025-07-10
    listed $1,450,000 Active
14. 1985-10-28
    soldstatus $70,000

ⓘ 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: $10,729 · $894/mo
• Projected year-2 tax: $16,138 · $1,345/mo
• Expected delta: +$5,409/yr (+$451/mo · 50.4%)

ⓘ 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 4/10 Moderate
• 🌡 Heat 3/10 Moderate 7 d/yr ≥96°F today · 15 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 7% 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: $58,219
• − Mortgage interest: −$71,420
• − Property taxes: −$10,729
• − Insurance: −$6,375
• − Repairs & maintenance: −$4,658
• − Management: −$4,658
• − Depreciation: −$37,091
• Taxable loss: −$76,711
• Est. tax savings @ 24.0%: +$18,411
• After-tax cash flow: $-32,935/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: Onteora Central School District
• NCES district ID: 3621840
• Math proficiency: 58% ▬ 0.00%
• Reading proficiency: 59% ▼ -3.00%
• Median HH income: $56,997
• Composite: 52.17/100
• National rank: #3482
• State rank: #288 of 755 in NY

Livability — Woodstock

• Score: 77/100
• State rank: #205
• US rank: #3176

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Woodstock, NY
• City population: 4,530
• Population (ZIP): 4,530

Population outlook (Ulster County) Hauer SSP2

• Today (2025): 175,887 people
• By 2030: 171,876 · -2.3%
• By 2040: 161,771 · -8.0%
• By 2050: 151,470 · -13.9%
• By 2075: 133,023 · -24.4%
• By 2100: 113,504 · -35.5%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (84%)
• Race & ethnicity: White 84% Hispanic / Latino 6% Two or more races 5% Asian 3% Black 2%
• Common ancestry: Scotch-Irish 8% Italian 7% Romanian 5%
• Foreign-born: 12% · Canada, China, Jamaica
• Languages at home: 90% English-only · Spanish 3% French/Haitian/Cajun 2% German/W. Germanic 1%

Political lean MEDSL · Ulster

• 2024 margin: D (+18.7) · D 59.3% · R 40.7%
• 2008→2024 swing: -4.9pp toward R · 2008: 23.6pp · 2024: 18.7pp
• All cycles: 2024: D+18.7 2020: D+20.9 2016: D+9.1 2012: D+21.9 2008: D+23.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -96.28%
• Current HPI: 344.8651
• 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

+1721.4% since first listed

16 events — show timeline

• 2026-05-23 Pending — HVCRMLS
• 2026-05-22 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-05-13 Contingent — HVCRMLS
• 2026-05-07 Listed $1,275,000 OneKey® MLS as Distributed by MLS Grid
• 2026-05-06 Listed $1,275,000 HVCRMLS
• 2026-02-01 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2026-01-14 Contingent — HVCRMLS
• 2025-10-25 Relisted — HVCRMLS
• 2025-10-10 Contingent — HVCRMLS
• 2025-10-04 Price Changed $1,295,000 HVCRMLS
• 2025-10-04 Price Changed $1,295,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-21 Price Changed $1,350,000 HVCRMLS
• 2025-08-21 Price Changed $1,350,000 OneKey® MLS as Distributed by MLS Grid
• 2025-07-10 Listed $1,450,000 HVCRMLS
• 2025-07-10 Listed $1,450,000 OneKey® MLS as Distributed by MLS Grid
• 1985-10-28 Sold (Public Records) $70,000 Public Records

Property tax history

+2.0%/yr

Latest (2025): $10,729 · -5.4% YoY. Source: county tax records.