89 Deer Pond Rd · Millbrook, NY 12585

$575,000

4 bd · 1.5 ba · 2,112 sqft · SingleFamily public records · 164 Days on market

Built 1960 3.99 ac lot $272/sqft · 5% below area Est $749k · 23% under ↓ 4% since listing

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

• ARV discount +15.0/15.0
• Appreciation +7.3/10.0
• Schools +5.8/10.0
• Cash flow +4.5/30.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.5/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor primary suite with walk-in closet, two additional closets and large ensuite bathroom. Second floor includes media room w/balcony, four additional bedrooms and full bathroom. Two car garage plus carport for abundant storage. Three bay barn with furnace is ideal for contractor, auto enthusiast, hobbyist or studio space. Quiet & private yet minutes to Village of Millbrook, Route 44, Route 55, Taconic State Park, dining, shopping and area attractions. Ideal as a primary residence or weekend retreat. Sold as-is. Cash or renovation loan only. Inquire for details on alterations necessary to secure certificate of occupancy.

Key facts

• Balcony
• Stocked pond
• Inground pool

Tags

• STOCKED POND
• INGROUND POOL
• THREE BAY BARN
• SUNROOM ANNEX
• MEDIA ROOM
• BALCONY

What this means for you Summary

Snapshot

• This is a 4-bed/1.5-bath single-family listed at $575k.

Deal economics

• At list price, monthly cash flow is $-1k ($-18k/yr) — negative.
• To cash-flow at today's rent, offer at most $312k (45.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $313k (45.5% below list).
• Recommended offer: $312k (45.7% below list) — sets the bar for cash-flow.
• Cap rate 3.2% vs local median 2.0% in Millbrook — 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 68/100 on livability (#524 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A; Watch: amenities F, commute F, cost of living F.
• Millbrook Central School District (rural): math 65% / reading 63% proficiency, ranked #198 of 755 in NY (top 26%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 17% free/reduced lunch — higher-income household profile.
• Zoned schools: Elm Drive Elementary School (192 students, 22% FRL); Millbrook Middle School (math 42% / reading 67%, grade B-, #214 of 729 statewide, top 31%, 202 students, 37% FRL); Millbrook High School (math 87%, 271 students, 34% FRL).
• Market conditions: 9 active listings in the ZIP; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).

Forward outlook

• In year one you build about $31k of equity ($4k loan paydown + $27k appreciation (4.7% local appreciation)).
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• By year 2, paydown + projected appreciation supports a ~$49k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 164 days — a 12% lower offer ($506k) is reasonable based on typical stale-listing flexibility.
• 3 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.

Risks & watch-outs

• Climate carrying-cost: major wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $312,165 (45.7% 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. It's been on market 164 days. Have you received any prior offers? Is the seller open to a 46% concession, seller financing, or rate buy-down credit?
3. Built in 1960 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. Schools are A-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?
7. 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?
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 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: 0.55% ✗
• Cap rate: 3.19%
• Cash-on-cash: -11.09%
• DSCR: 0.51
• GRM: 15.3

CMA / ARV

• ARV (median comp): $748,705
• List price: $575,000
• Delta: -23.20%
• Verdict: UNDERPRICED
• Comps: 4 within 1.0 mi

Projected returns pro-forma

4.65% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 2.6%
• Equity multiple: 1.16×
• Total profit: $26,265
• Equity at exit: $313,564

10-year hold

• IRR: 5.7%
• Equity multiple: 2.04×
• Total profit: $167,199
• Equity at exit: $531,278

Cash invested: $161,000 (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 12585

• Home prices YoY: 2.0%
• Active inventory: 9
• Price-to-rent: 15.3×

Monthly cashflow live

• Estimated rent: $3,134 medium
• Mortgage (P&I): −$3,015
• Tax from tax record: −$709 /mo · $8,507/yr
• Insurance: −$240
• HOA: −$0
• Vacancy / Maint / Mgmt: −$658
• Net cashflow: $-1,488

Break-even live

Break-even rent $5,018

Max offer price $312,165

Occupancy floor —

Sensitivity live

Price	-10% $-1,162	-5% $-1,325	+0% $-1,488	+5% $-1,651	+10% $-1,813
Rent	-10% $-1,735	-5% $-1,612	+0% $-1,488	+5% $-1,364	+10% $-1,240
Rate	-1.0pp $-1,198	-0.5pp $-1,342	base $-1,488	+0.5pp $-1,637	+1.0pp $-1,788

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: $143,750
• Closing costs: $17,250
• Reserves months: —
• Total cash needed: —

Listing history 22 events

1. 2026-06-22
   days on market $575,000 Active 164 DOM
2. 2026-06-21
   days on market $575,000 Active 163 DOM
3. 2026-06-21
   days on market $575,000 Active 162 DOM
4. 2026-06-18
   days on market $575,000 Active 160 DOM
5. 2026-06-17
   days on market $575,000 Active 159 DOM
6. 2026-06-16
   days on market $575,000 Active 158 DOM
7. 2026-06-15
   days on market $575,000 Active 157 DOM
8. 2026-06-13
   days on market $575,000 Active 155 DOM
9. 2026-06-12
   days on market $575,000 Active 154 DOM
10. 2026-06-09
    days on market $575,000 Active 151 DOM
11. 2026-06-08
    days on market $575,000 Active 150 DOM
12. 2026-06-07
    days on market $575,000 Active 149 DOM
13. 2026-06-07
    days on market $575,000 Active 148 DOM
14. 2026-06-04
    days on market $575,000 Active 145 DOM
15. 2026-06-02
    days on market $575,000 Active 144 DOM
16. 2026-06-01
    days on market $575,000 Active 143 DOM
17. 2026-05-31
    days on market $575,000 Active 142 DOM
18. 2026-02-05
    status Active 1035-char remark

    Show marketing remark (1035 chars)

    Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor primary suite with walk-in closet, two additional closets and large ensuite bathroom. Second floor includes media room w/balcony, four additional bedrooms and full bathroom. Two car garage plus carport for abundant storage. Three bay barn with furnace is ideal for contractor, auto enthusiast, hobbyist or studio space. Quiet & private yet minutes to Village of Millbrook, Route 44, Route 55, Taconic State Park, dining, shopping and area attractions. Ideal as a primary residence or weekend retreat. Sold as-is. Cash or renovation loan only. Inquire for details on alterations necessary to secure certificate of occupancy.

19. 2026-02-05
    price $575,000 1035-char remark

    Show marketing remark (1035 chars)

    Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor primary suite with walk-in closet, two additional closets and large ensuite bathroom. Second floor includes media room w/balcony, four additional bedrooms and full bathroom. Two car garage plus carport for abundant storage. Three bay barn with furnace is ideal for contractor, auto enthusiast, hobbyist or studio space. Quiet & private yet minutes to Village of Millbrook, Route 44, Route 55, Taconic State Park, dining, shopping and area attractions. Ideal as a primary residence or weekend retreat. Sold as-is. Cash or renovation loan only. Inquire for details on alterations necessary to secure certificate of occupancy.

20. 2026-01-02
    listed $599,000 Active 1035-char remark

    Show marketing remark (1035 chars)

    Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor primary suite with walk-in closet, two additional closets and large ensuite bathroom. Second floor includes media room w/balcony, four additional bedrooms and full bathroom. Two car garage plus carport for abundant storage. Three bay barn with furnace is ideal for contractor, auto enthusiast, hobbyist or studio space. Quiet & private yet minutes to Village of Millbrook, Route 44, Route 55, Taconic State Park, dining, shopping and area attractions. Ideal as a primary residence or weekend retreat. Sold as-is. Cash or renovation loan only. Inquire for details on alterations necessary to secure certificate of occupancy.

21. 2026-01-01
    historical
22. 2025-08-29
    listed $599,000 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: $8,507 · $709/mo
• Projected year-2 tax: $9,112 · $759/mo
• Expected delta: +$605/yr (+$50/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 6/10 Major
• 🌡 Heat 3/10 Moderate 7 d/yr ≥96°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 13% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $37,611
• − Mortgage interest: −$32,209
• − Property taxes: −$8,507
• − Insurance: −$2,875
• − Repairs & maintenance: −$3,009
• − Management: −$3,009
• − Depreciation: −$16,727
• Taxable loss: −$28,726
• Est. tax savings @ 24.0%: +$6,894
• After-tax cash flow: $-10,960/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: Millbrook Central School District
• NCES district ID: 3619380
• Math proficiency: 65% ▲ 1.00%
• Reading proficiency: 63% ▲ 5.00%
• Median HH income: $77,504
• Composite: 58.47/100
• National rank: #2061
• State rank: #198 of 755 in NY

Livability — Millbrook

• Score: 68/100
• State rank: #524
• US rank: #9248

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 1,252

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 (82%)
• Race & ethnicity: White 82% Two or more races 11% Hispanic / Latino 6% Asian 5%
• Hispanic origin (detail): Dominican 5%
• Common ancestry: Romanian 8% Subsaharan African 4% Serbian 2%
• Foreign-born: 12% · China, Canada
• Languages at home: 87% English-only · Spanish 6% Chinese 5% Other Indo-European 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: ▲ 4.65%
• Current HPI: 235.0339
• 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

-4.0% since first listed

5 events — show timeline

• 2026-02-05 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-02-05 Price Changed $575,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-02 Listed $599,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-01 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-08-29 Listed $599,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+0.4%/yr

Latest (2025): $8,507 · +2.5% YoY. Source: county tax records.