33 Thompson St · Red Hook, NY 12571

$345,000

3 bd · 1.0 ba · 1,496 sqft · SingleFamily public records · 196 Days on market

Built 1900 $231/sqft · 35% below area Est $535k · 35% under

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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 +15.5/30.0
• ARV discount +15.0/15.0
• Schools +5.1/10.0
• 1% rule +4.9/10.0
• DSCR +4.8/10.0
• Livability +4.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

Key facts

• Huge attic space
• Brand new oil tank
• Water heater

Tags

• CORNER LOT
• HUGE ATTIC SPACE
• 3 PARKING SPOTS AVAILABLE
• BRAND NEW OIL TANK
• WATER HEATER
• ELECTRICAL PANEL

What this means for you Summary

Snapshot

• This is a 3-bed/1.0-bath single-family listed at $345k.

Deal economics

• At list price, monthly cash flow is $140 ($2k/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 $341k (1.2% below list).
• Recommended offer: $304k (12.0% below list) — sets the bar for market timing.
• Cap rate 6.8% vs local median 2.7% in Red Hook — 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 89/100 on livability (#5 in NY, #113 nationally) — a professional / high-income tenant draw. Strengths: crime A+, commute A+, employment A+; Watch: cost of living D-.
• Red Hook Central School District (town): math 58% / reading 57% proficiency, ranked #245 of 590 in NY (top 42%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 16% free/reduced lunch — higher-income household profile.
• Market conditions: 70 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals at typical pace (median 15d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).
• This rent runs 34% of the median local income ($119k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $10k of value loss. Plan a longer hold.
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.

Negotiation context

• It's been on market 196 days — a 12% lower offer ($304k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $54k (14%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $15k; list at $345k implies a 2200% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $303,600 (12.0% below list)

Questions for the listing agent

1. It's been on market 196 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 1900 — 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 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?
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: 0.99% ✗
• Cap rate: 6.78%
• Cash-on-cash: 1.74%
• DSCR: 1.08
• GRM: 8.4

CMA / ARV

• ARV (median comp): $534,748
• List price: $345,000
• Delta: -35.48%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 11 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
20 Prince St	0.36mi	3/1.0	1,440 (-4%)	10mo	$492,000	$342	68
39 Thompson St	0.04mi	3/2.0	1,384 (-8%)	18mo	$400,000	$289	67
11 Cambridge Dr	0.61mi	3/1.0	1,400 (-6%)	2mo	$389,500	$278	60
14 Fisk St	0.22mi	2/1.5 (-1)	1,372 (-8%)	21mo	$525,000	$383	52
14 Fisk St	0.22mi	2/1.5 (-1)	1,372 (-8%)	21mo	$525,000	$383	52
9 Cambridge Dr	0.56mi	3/1.5	1,400 (-6%)	15mo	$417,000	$298	48
7365 S Broadway	0.52mi	3/1.5	1,650 (+10%)	11mo	$525,000	$318	48
27 Prince St	0.41mi	3/2.0	1,612 (+8%)	21mo	$437,000	$271	47
8 Willow Dr	0.73mi	4/2.0 (+1)	1,592 (+6%)	4mo	$394,050	$248	43
3 Holt Rd	0.75mi	3/2.0	1,350 (-10%)	9mo	$475,000	$352	38
333 Norton Rd	0.53mi	3/3.0	1,716 (+15%)	19mo	$967,000	$564	27

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: -13.5%
• Equity multiple: 0.52×
• Total profit: $-46,831
• Equity at exit: $51,441

10-year hold

• IRR: -4.5%
• Equity multiple: 0.70×
• Total profit: $-28,667
• Equity at exit: $29,829

Cash invested: $96,600 (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 12571

• Home prices YoY: -15.6%
• Active inventory: 70
• Price-to-rent: 8.4×

Monthly cashflow live

• Estimated rent: $3,408 medium
• Mortgage (P&I): −$1,809
• Tax from tax record: −$599 /mo · $7,193/yr
• Insurance: −$144
• HOA: −$0
• Vacancy / Maint / Mgmt: −$716
• Net cashflow: $140

Break-even live

Break-even rent $3,231

Max offer price $345,000

Occupancy floor 91%

Sensitivity live

Price	-10% $335	-5% $238	+0% $140	+5% $42	+10% $-55
Rent	-10% $-129	-5% $5	+0% $140	+5% $275	+10% $409
Rate	-1.0pp $314	-0.5pp $228	base $140	+0.5pp $51	+1.0pp $-40

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: $86,250
• Closing costs: $10,350
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
33 W Market St Unit 2A Red Hook, NY	3.0	1.0	1000	$3,400	$3.40	24d	1	0.34mi
46 W Market St Red Hook, NY	4.0	2.0	1600	$4,200	$2.62	15d	1	0.38mi
10 Smith St Red Hook, NY	3.0	1.5	1148	$2,700	$2.35	15d	1	0.72mi

Listing history 9 events

1. 2026-05-05
   status Pending 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

2. 2026-03-23
   price $345,000 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

3. 2026-02-27
   price $359,000 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

4. 2026-01-16
   price $379,000 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

5. 2026-01-08
   status Active 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

6. 2026-01-08
   price $439,000 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

7. 2025-11-09
   price $369,000 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

8. 2025-10-04
   listed $399,000 Active 888-char remark

   Show marketing remark (888 chars)

   This charming home has been loved by the same owner for 50 years who is ready to give the opportunity for someone else to make it their own. Endless possibilities await with the good bones of this classic home. Desirable location on a Corner lot walking distance to all Village amenities. You will love the wood detail throughout, the multitude of windows for lots of natural light, and a huge attic space for someone to finish or just have for storage. Cozy kitchen with pellet stove. Lovely Backyard Space with Shed. 3 Parking Spots Available which is so rare in the Village. House needs TLC but Roof is 10YO, Brand New Furnace, Water Heater & Electrical Panel. Walking distance to Bard Shuttle, Red Hook Library, Shopping Boutiques & Restaurants. Red Hook New York is a magical town. Come see for Yourself and Book your Showing Today. Contractor Quote Available for Renovation.

9. 1975-05-16
   soldstatus $15,000

ⓘ 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: $7,193 · $599/mo
• Projected year-2 tax: $7,193 · $599/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 4/10 Moderate 7 d/yr ≥98°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 10% 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: $40,898
• − Mortgage interest: −$19,325
• − Property taxes: −$7,193
• − Insurance: −$1,725
• − Repairs & maintenance: −$3,272
• − Management: −$3,272
• − Depreciation: −$10,036
• Taxable loss: −$3,926
• Est. tax savings @ 24.0%: +$942
• After-tax cash flow: $2,623/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: Red Hook Central School District
• NCES district ID: 3624240
• Math proficiency: 58% ▼ -4.00%
• Reading proficiency: 57% ▼ -8.00%
• Median HH income: $69,040
• Composite: 50.84/100
• National rank: #1801
• State rank: #245 of 590 in NY

Livability — Red Hook

• Score: 89/100
• State rank: #5
• US rank: #113

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Red Hook, NY
• County: Dutchess County · 188,048 people
• City population: 10,108
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• Population (ZIP): 10,108
• Household income: $118,967
• Rent vs Own: 19.9% rent · 80.1% own
• Severe rent burden: 241.0

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 7% Hispanic / Latino 4% Black 2% Asian 2%
• Common ancestry: Italian 5% Romanian 4% Iranian 4%
• Foreign-born: 6% · Canada, China
• Languages at home: 94% English-only · Spanish 2% Other Indo-European 1% Russian/Polish/Slavic 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: ▼ -61.80%
• Current HPI: 333.5841
• Rent YoY: —
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• 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

+2200.0% since first listed

9 events — show timeline

• 2026-05-05 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-03-23 Price Changed $345,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-27 Price Changed $359,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-16 Price Changed $379,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-08 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-01-08 Price Changed $439,000 OneKey® MLS as Distributed by MLS Grid
• 2025-11-09 Price Changed $369,000 OneKey® MLS as Distributed by MLS Grid
• 2025-10-04 Listed $399,000 OneKey® MLS as Distributed by MLS Grid
• 1975-05-16 Sold (Public Records) $15,000 Public Records

Property tax history

+2.5%/yr

Latest (2025): $7,193 · +3.3% YoY. Source: county tax records.