42 Oakwood Ave · Rye, NY 10580

$1,850,000

4 bd · 1.0 ba · 2,316 sqft · SingleFamily public records · 16 Days on market

Built 1914 4,792 sqft lot $799/sqft · 19% below area Est $2273k · 19% under

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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
• Schools +8.6/10.0
• Appreciation +8.3/10.0
• Cash flow +3.5/30.0
• Livability +3.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks

Located in the highly sought-after Rye Gates neighborhood of Rye, this beautifully updated 4-bedroom, 2.5-bath Colonial offers 2,316 square feet of sun-filled living space filled with timeless charm and character. Original moldings and beautiful exposed beams blend seamlessly with modern updates. Spacious rooms, new flooring throughout, and fresh interior and exterior paint create a move-in ready home ideal for today’s lifestyle. A welcoming oversized entrance hall with three double closets provides exceptional mudroom storage, while the stunning large stone fireplace anchors the elegant living space. The home features a large formal dining room and sunny eat-in kitchen with stainless

Key facts

• 4,792 sq ft lot
• Garage
• Built 1914

Property features AI

Exterior

• Parking: Attached garage (1 space)
• Utilities: Electricity connected (Con-Edison); Water connected; Public sewer; Public trash collection
• Home design: Single-family residence
• Construction: Wood siding construction
• Exterior features: Wood siding; Not waterfront

Interior

• Kitchen: Dishwasher; Electric oven; Refrigerator; Stainless steel appliances
• Bedrooms: Total rooms: 8
• Flooring: Hardwood floors
• Bathrooms: 2 full bathrooms; 1 half bathroom
• Heating & cooling: Oil heating; Central air conditioning; Fireplace (1)
• Interior features: Crown molding; Eat-in kitchen; Formal dining room; Open kitchen; Recessed lighting; Walk-in closets; Full unfinished basement with storage space; Walkup attic
• Laundry & utility: Laundry in basement

What this means for you Summary

Snapshot

• This is a 4-bed/1.0-bath single-family listed at $1.85M.

Deal economics

• At list price, monthly cash flow is $-6k ($-67k/yr) — negative.
• To cash-flow at today's rent, offer at most $861k (53.5% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $864k (53.3% below list).
• Recommended offer: $861k (53.5% below list) — sets the bar for cash-flow.
• Cap rate 2.7% vs local median 1.5% in Rye — 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 70/100 on livability (#431 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: amenities F, cost of living F, health & safety F.
• Rye City School District (suburban): math 89% / reading 93% proficiency, ranked #4 of 590 in NY (top 1%) — strong family-tenant draw, lease renewals of 3-5y typical; only 2% free/reduced lunch — higher-income household profile.
• Zoned schools: Milton School (math 95% / reading 95%, grade A+, #5 of 2,108 statewide, top 0%, 349 students, 0% FRL); Rye Middle School (math 77% / reading 92%, grade A+, #13 of 729 statewide, top 2%, 685 students, 0% FRL); Rye High School (math 100% / reading 87%, grade A+, #141 of 1,100 statewide, top 13%, 903 students, 0% FRL) — zoned schools at 0% FRL track the district average.
• Market conditions: 121 active listings in the ZIP; 6 comparable units currently listed for rent nearby; rentals leasing fast (median 5d on market — plan ~1-2 weeks tenant-placement turnaround); high-income renter base; 954 units permitted in Westchester County in 2024 (649 in 5+ unit buildings).
• This rent runs 41% of the median local income ($250k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• In year one you build about $136k of equity ($13k loan paydown + $123k appreciation (6.6% local appreciation)).
• Westchester County population projected at +10% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• By year 2, paydown + projected appreciation supports a ~$217k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 16 days — a 2% lower offer ($1.82M) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1914 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $860,866 (53.5% 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 1914 — 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 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?
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: 0.47% ✗
• Cap rate: 2.66%
• Cash-on-cash: -12.97%
• DSCR: 0.42
• GRM: 17.8

CMA / ARV

• ARV (median comp): $2,272,751
• List price: $1,850,000
• Delta: -18.60%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
9 Bulkley Mnr	0.16mi	4/3.0	2,321 (+0%)	11mo	$1,539,000	$663	75
5 1/2 Oakwood Ave	0.09mi	4/2.0	2,100 (-9%)	4mo	$1,100,000	$524	73
33 Oakwood Ave	0.04mi	4/2.5	2,193 (-5%)	16mo	$2,112,500	$963	70
3 Ormond Pl	0.18mi	3/2.0 (-1)	2,268 (-2%)	13mo	$2,075,000	$915	68
32 Ridgeland Ter	0.10mi	4/2.0	1,978 (-15%)	8mo	$1,104,000	$558	60
5 Redfield St	0.12mi	3/1.5 (-1)	2,006 (-13%)	8mo	$1,675,000	$835	58
306 Oakland Beach Ave	0.29mi	3/2.5 (-1)	2,160 (-7%)	11mo	$1,214,000	$562	55
53 Cowles Ave	0.36mi	3/2.5 (-1)	2,169 (-6%)	12mo	$2,265,000	$1,044	52
5 White Birch Dr	0.53mi	4/3.0	2,394 (+3%)	13mo	$2,500,000	$1,044	51
71 Apawamis Ave	0.45mi	4/2.5	2,597 (+12%)	7mo	$2,320,000	$893	47
39 Sanford St	0.49mi	4/3.0	2,476 (+7%)	15mo	$2,375,500	$959	45
60 Franklin Ave	0.73mi	4/3.5	2,280 (-2%)	14mo	$1,725,000	$757	42

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

6.64% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 6.8%
• Equity multiple: 1.48×
• Total profit: $248,835
• Equity at exit: $1,238,954

10-year hold

• IRR: 8.7%
• Equity multiple: 2.92×
• Total profit: $994,947
• Equity at exit: $2,315,467

Cash invested: $518,000 (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 10580

• Home prices YoY: 2.1%
• Active inventory: 121
• Price-to-rent: 17.8×

Monthly cashflow live

• Estimated rent: $8,640 high
• Mortgage (P&I): −$9,702
• Tax from tax record: −$1,952 /mo · $23,427/yr
• Insurance: −$771
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,814
• Net cashflow: $-5,599

Break-even live

Break-even rent $15,727

Max offer price $860,866

Occupancy floor —

Sensitivity live

Price	-10% $-4,552	-5% $-5,076	+0% $-5,599	+5% $-6,123	+10% $-6,647
Rent	-10% $-6,282	-5% $-5,941	+0% $-5,599	+5% $-5,258	+10% $-4,917
Rate	-1.0pp $-4,668	-0.5pp $-5,129	base $-5,599	+0.5pp $-6,079	+1.0pp $-6,566

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: $462,500
• Closing costs: $55,500
• Reserves months: —
• Total cash needed: —

Rent comps 6 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
9 Marlene Ct Rye, NY	4.0	3.0	1750	$10,500	$6.00	9d	1	0.95mi
150 Theodore Fremd Ave Rye, NY	2.0–4.0	1.0–2.5	1320	$5,795	$4.39	0d	1	1.17mi
124 Maple Ave Rye, NY	3.0	2.5	2615	$9,000	$3.44	5d	1	1.26mi
228 Central Ave Rye, NY	4.0	3.5	2466	$10,000	$4.06	0d	1	1.36mi
228 Central Ave Rye, NY	4.0	3.5	2466	$11,000	$4.46	12d	1	1.36mi
332 Halstead Ave Harrison, NY	1.0–3.0	1.0–3.0	1116	$5,000	$4.48	0d	1	1.46mi

Listing history 2 events

1. 2026-05-14
   listed $1,850,000 Active 1243-char remark
2. 2026-05-11
   historical $1,850,000 1243-char remark

ⓘ 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: $23,427 · $1,952/mo
• Projected year-2 tax: $27,346 · $2,279/mo
• Expected delta: +$3,919/yr (+$327/mo · 16.7%)

ⓘ 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 6/10 Major 7 d/yr ≥98°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 5 unhealthy d/yr today · 7 by 30 yrs out

Taxation est. · year 1

• Rental income: $103,677
• − Mortgage interest: −$103,629
• − Property taxes: −$23,427
• − Insurance: −$9,250
• − Repairs & maintenance: −$8,294
• − Management: −$8,294
• − Depreciation: −$53,818
• Taxable loss: −$103,035
• Est. tax savings @ 24.0%: +$24,728
• After-tax cash flow: $-42,463/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: Rye City School District
• NCES district ID: 3625260
• Math proficiency: 89% ▲ 11.00%
• Reading proficiency: 93% ▲ 12.00%
• Median HH income: $144,848
• Composite: 85.84/100
• National rank: #6
• State rank: #4 of 590 in NY

Livability — Rye

• Score: 70/100
• State rank: #431
• US rank: #7470

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Rye, NY
• County: Westchester County · 709,332 people
• City population: 18,391
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 18,391
• Household income: $250,001
• Rent vs Own: 27.6% rent · 72.4% own
• Severe rent burden: 580.0

Population outlook (Westchester County) Hauer SSP2

• Today (2025): 1,028,035 people
• By 2030: 1,051,636 · +2.3%
• By 2040: 1,098,520 · +6.9%
• By 2050: 1,136,044 · +10.5%
• By 2075: 1,196,925 · +16.4%
• By 2100: 1,175,147 · +14.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (77%)
• Race & ethnicity: White 77% Two or more races 10% Asian 7% Hispanic / Latino 7% Black 2%
• Hispanic origin (detail): Puerto Rican 1%
• Common ancestry: Romanian 5% Italian 3% German 3%
• Foreign-born: 20% · Canada, China, South Korea
• Languages at home: 80% English-only · Spanish 6% Other Indo-European 3% Chinese 2%

Political lean MEDSL · Westchester

• 2024 margin: Strong D (+26.3) · D 63.1% · R 36.9%
• 2008→2024 swing: -1.3pp toward R · 2008: 27.6pp · 2024: 26.3pp
• All cycles: 2024: D+26.3 2020: D+36.3 2016: D+32.8 2012: D+22.2 2008: D+27.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 6.64%
• Current HPI: 321.5777
• Rent YoY: —
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• 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

+0.0% since first listed

3 events — show timeline

• 2026-05-29 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-05-14 Listed $1,850,000 OneKey® MLS as Distributed by MLS Grid
• 2026-05-11 Coming Soon $1,850,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+18.8%/yr

Latest (2025): $23,427 · +3.3% YoY. Source: county tax records.