110 Hillside Ave · Wingdale, NY 12594

$1,299,000

4 bd · 3.5 ba · 3,770 sqft · SingleFamily public records · 28 Days on market

Built 2008 4.07 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 +26.6/30.0
• DSCR +9.1/10.0
• ARV discount +7.5/15.0
• 1% rule +6.5/10.0
• Appreciation +4.9/10.0
• Schools +4.0/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Set on four beautiful acres with sweeping long range views of the foothills and ridges around Litchfield Hills and The Taconic Mountains, this thoughtfully designed contemporary home offers exceptional privacy, tranquility, and quality throughout. Built by the owners for their own use, no expense was spared, with high end materials and meticulous attention to detail. Incredible natural light fills the home, enhanced by oversized windows that capture the surrounding landscape and bring the outdoors in. A gracious front entry welcomes you into the formal living and dining rooms. The living room features a wood-burning fireplace and beautiful views overlooking the backyard and surrounding land

Key facts

• Large center island
• Sunny eat-in area
• Four acres

Tags

• FOUR ACRES
• LONG-RANGE VIEWS
• OVERSIZED WINDOWS
• WOOD-BURNING FIREPLACE
• LARGE CENTER ISLAND
• SUNNY EAT-IN AREA

Property features AI

Exterior

• Parking: Garage; 2-car garage
• Utilities: Septic tank; Utilities: See remarks
• Home design: Single family residence; Living area reported from public records
• Construction: HardiPlank-type construction; Full attic; Full basement
• Exterior features: HardiPlank-type siding; Barn(s) on the property; Not waterfront

Interior

• Kitchen: Dishwasher; Range; Refrigerator; Stainless steel appliances; Granite counters; Stone and tile counters; Eat-in layout; Pantry
• Bedrooms: Bedroom(s) on the first floor
• Bathrooms: 3 full bathrooms; 1 half bathroom
• Heating & cooling: Oil heating; Central air conditioning; 1 fireplace
• Interior features: First-floor bedroom; First-floor full bathroom; Eat-in kitchen; Entrance foyer; Formal dining room; Granite counters; Natural woodwork; Open kitchen; Pantry; Primary bathroom; Master suite on main level; Stone counters; Tile counters; Walk-in closet(s)
• Laundry & utility: Basement with storage space

What this means for you Summary

Snapshot

• This is a 4-bed/3.5-bath single-family listed at $1.30M.

Deal economics

• At list price, monthly cash flow is $3k ($42k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($15k rent vs $1.30M).
• Recommended offer: $1.28M (1.5% 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.
• Dover Union Free School District (rural): math 44% / reading 48% proficiency, ranked #433 of 590 in NY (top 73%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Zoned schools: Wingdale Elementary School (246 students, 68% FRL); Dover Middle School (math 32% / reading 47%, grade F, #418 of 729 statewide, top 59%, 301 students, 68% FRL); Dover High School (math 92% / reading 74%, grade A, #435 of 1,100 statewide, top 40%, 467 students, 59% FRL) — zoned schools average 65% FRL vs 38% district-wide (27 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Zoned-school proficiency averages 61% at this address vs 46% district-wide (+15 pts) — the actual schools serving this property are materially stronger than the Dover Union Free School District average implies; a family-tenant draw the district grade alone would hide.
• Market conditions: 15 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).

Forward outlook

• In year one you build about $7k of equity ($9k loan paydown + $-2k appreciation (-0.1% local appreciation)).
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-0.1% appreciation + 3.0% rent growth), your $364k cash investment doubles in ~6 years — after that, you're playing with house money.
• By year 8, paydown + projected appreciation supports a ~$83k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 28 days — a 2% lower offer ($1.28M) is reasonable based on typical stale-listing flexibility.
• Current owner paid $98k; list at $1.30M implies a 1232% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

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

Recommended offer $1,279,515 (1.5% below list)

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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.
3. 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.
4. 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: 1.15% ✓
• Cap rate: 9.51%
• Cash-on-cash: 11.51%
• DSCR: 1.51
• GRM: 7.2

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-0.14% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 10.2%
• Equity multiple: 1.48×
• Total profit: $175,137
• Equity at exit: $367,812

10-year hold

• IRR: 15.2%
• Equity multiple: 2.65×
• Total profit: $598,411
• Equity at exit: $434,712

Cash invested: $363,720 (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 12594

• Home prices YoY: -0.1%
• Active inventory: 15
• Price-to-rent: 7.2×

Monthly cashflow live

• Estimated rent: $15,000 medium
• Mortgage (P&I): −$6,812
• Tax from tax record: −$1,009 /mo · $12,113/yr
• Insurance: −$541
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,150
• Net cashflow: $3,487

Break-even live

Break-even rent $10,586

Max offer price $1,299,000

Occupancy floor 72%

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: $324,750
• Closing costs: $38,970
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
209 Cricket Hill Rd Dover Plains, NY	3.0	4.0	4043	$15,000	$3.71	43d	1	0.70mi

Listing history 16 events

1. 2026-06-18
   days on market $1,299,000 Active 28 DOM
2. 2026-06-17
   days on market $1,299,000 Active 27 DOM
3. 2026-06-16
   days on market $1,299,000 Active 26 DOM
4. 2026-06-15
   days on market $1,299,000 Active 25 DOM
5. 2026-06-13
   days on market $1,299,000 Active 23 DOM
6. 2026-06-12
   days on market $1,299,000 Active 22 DOM
7. 2026-06-09
   days on market $1,299,000 Active 19 DOM
8. 2026-06-08
   days on market $1,299,000 Active 18 DOM
9. 2026-06-07
   days on market $1,299,000 Active 17 DOM
10. 2026-06-07
    days on market $1,299,000 Active 16 DOM
11. 2026-06-04
    days on market $1,299,000 Active 13 DOM
12. 2026-06-02
    days on market $1,299,000 Active 12 DOM
13. 2026-06-01
    days on market $1,299,000 Active 11 DOM
14. 2026-05-31
    days on market $1,299,000 Active 10 DOM
15. 2026-05-20
    listed $1,299,000 Active
16. 2003-02-24
    soldstatus $97,500

ⓘ 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: $12,113 · $1,009/mo
• Projected year-2 tax: $17,033 · $1,419/mo
• Expected delta: +$4,920/yr (+$410/mo · 40.6%)

ⓘ 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 5/10 Major
• 🌡 Heat 4/10 Moderate 7 d/yr ≥96°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 17% 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: $180,000
• − Mortgage interest: −$72,764
• − Property taxes: −$12,113
• − Insurance: −$6,495
• − Repairs & maintenance: −$14,400
• − Management: −$14,400
• − Depreciation: −$37,789
• Taxable income: $22,039
• Est. tax owed @ 24.0%: −$5,289
• After-tax cash flow: $36,557/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: Dover Union Free School District
• NCES district ID: 3609210
• Math proficiency: 44% ▼ -8.00%
• Reading proficiency: 48% ▲ 3.00%
• Median HH income: $58,267
• Composite: 40.25/100
• National rank: #3768
• State rank: #433 of 590 in NY

Livability — Wingdale

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

Census & demographics

• Population (ZIP): 3,645

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 (66%)
• Race & ethnicity: White 66% Hispanic / Latino 21% Black 9% Two or more races 4%
• Hispanic origin (detail): Mexican 2% Puerto Rican 10%
• Common ancestry: Romanian 6% Lithuanian 3% Iranian 1%
• Foreign-born: 7% · Canada, South Korea, Guatemala
• Languages at home: 89% English-only · Spanish 11% German/W. Germanic 0%

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: ▼ -0.14%
• Current HPI: 249.3328
• 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

+1232.3% since first listed

2 events — show timeline

• 2026-05-20 Listed $1,299,000 OneKey® MLS as Distributed by MLS Grid
• 2003-02-24 Sold (Public Records) $97,500 Public Records

Property tax history

+0.3%/yr

Latest (2025): $12,113 · -0.3% YoY. Source: county tax records.