15 Roosevelt Ave · Rye, NY 10580

$1,469,999

4 bd · 1.0 ba · 1,545 sqft · SingleFamily public records · 61 Days on market

Built 1923 5,227 sqft lot $951/sqft · 15% below area Est $1726k · 15% 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 +14.2/15.0
• Schools +8.6/10.0
• Appreciation +8.3/10.0
• Cash flow +4.8/30.0
• Livability +3.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.3/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Great Oppotunity. Colonial In Need Of Work In Darling Neighborhood. Walk To Oakland Beach On The Long Island Sound.

Key facts

• Access to garden
• Livingroom fireplace
• Unfinished basement

Tags

• YARD WITH MANY FLOWERS
• LIVINGROOM FIREPLACE
• DEN
• EAT-IN KITCHEN
• UNFINISHED BASEMENT
• ACCESS TO GARDEN

Property features AI

Exterior

• Parking: Driveway; 5 total parking spaces; 2-car garage
• Utilities: Public sewer; Cable available
• Home design: Single family residence
• Construction: Frame construction
• Exterior features: Frame construction; Partial fencing; Deck; Porch; Not waterfront

Interior

• Kitchen: Gas range; Dishwasher; Microwave; Refrigerator
• Bedrooms: Total rooms: 9
• Flooring: Wood flooring; Tile flooring
• Bathrooms: 1 full bathroom; 1 half bathroom
• Heating & cooling: Oil heating; Central air conditioning; Zoned cooling
• Interior features: Formal dining room; High ceilings; Natural woodwork; Original details; Washer/dryer hookup; Unfinished basement
• Laundry & utility: Washer; Dryer; Washer/dryer hookup

What this means for you Summary

Snapshot

• This is a 4-bed/1.0-bath single-family listed at $1.47M.

Deal economics

• At list price, monthly cash flow is $-4k ($-43k/yr) — negative.
• To cash-flow at today's rent, offer at most $838k (43.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $777k (47.1% below list).
• Recommended offer: $777k (47.1% below list) — sets the bar for 1% rule.
• Cap rate 3.4% 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: Midland School (math 82% / reading 98%, grade A+, #37 of 2,108 statewide, top 2%, 460 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; 4 comparable units currently listed for rent nearby; rentals at typical pace (median 19d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 954 units permitted in Westchester County in 2024 (649 in 5+ unit buildings).

Forward outlook

• In year one you build about $108k of equity ($10k loan paydown + $98k 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 ~$172k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 61 days — a 6% lower offer ($1.38M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 22y ago 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 $572k; list at $1.47M implies a 157% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1923 — 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 $777,446 (47.1% 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 61 days. Have you received any prior offers? Is the seller open to a 47% concession, seller financing, or rate buy-down credit?
3. Built in 1923 — 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: 0.53% ✗
• Cap rate: 3.37%
• Cash-on-cash: -10.42%
• DSCR: 0.54
• GRM: 15.8

CMA / ARV

• ARV (median comp): $1,726,280
• List price: $1,469,999
• Delta: -14.85%
• 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
44 Tyler Cir	0.33mi	4/2.5	1,604 (+4%)	15mo	$893,000	$557	60
12 Fenton St	0.61mi	4/2.0	1,554 (+1%)	9mo	$1,623,028	$1,044	59
108 Midland Ave	0.35mi	3/1.0 (-1)	1,379 (-11%)	9mo	$1,331,000	$965	53
343 Rye Beach Ave	0.44mi	3/2.0 (-1)	1,703 (+10%)	3mo	$1,705,000	$1,001	51
444 Milton Rd	0.58mi	3/2.0 (-1)	1,439 (-7%)	3mo	$885,000	$615	50
23 Elmwood Ave	0.39mi	4/1.5	1,716 (+11%)	19mo	$1,800,000	$1,049	46
346 Milton Rd	0.56mi	3/2.0 (-1)	1,485 (-4%)	21mo	$1,195,000	$805	41
13 Waters Edge	0.67mi	3/2.0 (-1)	1,605 (+4%)	17mo	$250,000	$156	39
319 Oakland Beach Ave	0.68mi	4/2.0	1,601 (+4%)	24mo	$995,000	$621	38
62 Hill St	0.66mi	4/2.5	1,612 (+4%)	22mo	$1,325,000	$822	38
5 Fernwood Ave	0.51mi	3/2.5 (-1)	1,718 (+11%)	11mo	$1,610,000	$937	38
9 Fenton St	0.59mi	3/2.0 (-1)	1,428 (-8%)	19mo	$1,430,000	$1,001	35

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: 8.7%
• Equity multiple: 1.62×
• Total profit: $253,289
• Equity at exit: $984,465

10-year hold

• IRR: 10.2%
• Equity multiple: 3.21×
• Total profit: $910,287
• Equity at exit: $1,839,857

Cash invested: $411,600 (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 10580

• Home prices YoY: 2.1%
• Active inventory: 121
• Price-to-rent: 15.8×

Monthly cashflow live

• Estimated rent: $7,774 medium
• Mortgage (P&I): −$7,709
• Tax from tax record: −$1,396 /mo · $16,751/yr
• Insurance: −$612
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,633
• Net cashflow: $-3,575

Break-even live

Break-even rent $12,300

Max offer price $838,384

Occupancy floor —

Sensitivity live

Price	-10% $-2,743	-5% $-3,159	+0% $-3,575	+5% $-3,991	+10% $-4,408
Rent	-10% $-4,190	-5% $-3,883	+0% $-3,575	+5% $-3,268	+10% $-2,961
Rate	-1.0pp $-2,835	-0.5pp $-3,202	base $-3,575	+0.5pp $-3,956	+1.0pp $-4,344

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: $367,500
• Closing costs: $44,100
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
9 Fenton St Rye, NY	3.0	2.0	1428	$8,800	$6.16	19d	1	0.57mi
9 Marlene Ct Rye, NY	4.0	3.0	1750	$10,500	$6.00	9d	1	1.06mi
27-29 Purchase St Rye, NY	3.0	1.0	1081	$4,600	$4.26	21d	1	1.08mi
150 Theodore Fremd Ave Rye, NY	2.0–4.0	1.0–2.5	1320	$5,795	$4.39	0d	1	1.12mi

Listing history 41 events

1. 2026-06-21
   days on market $1,469,999 Active 61 DOM
2. 2026-06-18
   days on market $1,469,999 Active 58 DOM
3. 2026-06-17
   days on market $1,469,999 Active 57 DOM
4. 2026-06-16
   days on market $1,469,999 Active 56 DOM
5. 2026-06-15
   days on market $1,469,999 Active 55 DOM
6. 2026-06-13
   days on market $1,469,999 Active 53 DOM
7. 2026-06-13
   days on market $1,469,999 Active 52 DOM
8. 2026-06-09
   days on market $1,469,999 Active 49 DOM
9. 2026-06-08
   days on market $1,469,999 Active 48 DOM
10. 2026-06-07
    days on market $1,469,999 Active 47 DOM
11. 2026-06-04
    days on market $1,469,999 Active 44 DOM
12. 2026-06-03
    days on market $1,469,999 Active 43 DOM
13. 2026-06-02
    days on market $1,469,999 Active 42 DOM
14. 2026-06-01
    days on market $1,469,999 Active 41 DOM
15. 2026-05-31
    days on market $1,469,999 Active 40 DOM
16. 2026-05-13
    price $1,469,999 308-char remark
17. 2026-04-21
    listed $1,499,999 Active 308-char remark
18. 2025-12-10
    historical $6,350
19. 2025-12-10
    historical
20. 2025-10-31
    price $1,279,500
21. 2025-10-30
    price $6,350
22. 2025-10-21
    price $6,550
23. 2025-10-02
    status Active
24. 2025-09-18
    price $1,299,950
25. 2025-09-17
    price $6,750
26. 2025-09-06
    price $6,975
27. 2025-08-26
    price $7,275
28. 2025-08-24
    price $1,345,000
29. 2025-08-19
    price $7,375
30. 2025-08-12
    price $7,750
31. 2025-08-07
    price $1,375,500
32. 2025-07-18
    price $1,399,500
33. 2025-07-10
    listed $7,950
34. 2025-07-10
    listed $1,575,000 Active
35. 2025-07-08
    price $1,575,000
36. 2025-07-08
    historical
37. 2006-05-01
    soldstatus $571,550
38. 2006-01-26
    soldstatus $555,000

    Show marketing remark (115 chars)

    Great Oppotunity. Colonial In Need Of Work In Darling Neighborhood. Walk To Oakland Beach On The Long Island Sound.

39. 2004-04-09
    historical

    Show marketing remark (115 chars)

    Great Oppotunity. Colonial In Need Of Work In Darling Neighborhood. Walk To Oakland Beach On The Long Island Sound.

40. 2004-04-09
    price $585,000

    Show marketing remark (115 chars)

    Great Oppotunity. Colonial In Need Of Work In Darling Neighborhood. Walk To Oakland Beach On The Long Island Sound.

41. 2004-03-19
    listed $555,000

    Show marketing remark (115 chars)

    Great Oppotunity. Colonial In Need Of Work In Darling Neighborhood. Walk To Oakland Beach On The Long Island Sound.

ⓘ 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: $16,751 · $1,396/mo
• Projected year-2 tax: $20,797 · $1,733/mo
• Expected delta: +$4,046/yr (+$337/mo · 24.2%)

ⓘ 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: $93,294
• − Mortgage interest: −$82,343
• − Property taxes: −$16,751
• − Insurance: −$7,350
• − Repairs & maintenance: −$7,463
• − Management: −$7,463
• − Depreciation: −$42,764
• Taxable loss: −$70,841
• Est. tax savings @ 24.0%: +$17,002
• After-tax cash flow: $-25,903/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

+164.9% since first listed

26 events — show timeline

• 2026-05-13 Price Changed $1,469,999 OneKey® MLS as Distributed by MLS Grid
• 2026-04-21 Listed $1,499,999 OneKey® MLS as Distributed by MLS Grid
• 2025-12-10 Rental Removed $6,350 ONEKEY
• 2025-12-10 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-10-31 Price Changed $1,279,500 OneKey® MLS as Distributed by MLS Grid
• 2025-10-30 Price Changed $6,350 ONEKEY
• 2025-10-21 Price Changed $6,550 ONEKEY
• 2025-10-02 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-09-18 Price Changed $1,299,950 OneKey® MLS as Distributed by MLS Grid
• 2025-09-17 Price Changed $6,750 ONEKEY
• 2025-09-06 Price Changed $6,975 ONEKEY
• 2025-08-26 Price Changed $7,275 ONEKEY
• 2025-08-24 Price Changed $1,345,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-19 Price Changed $7,375 ONEKEY
• 2025-08-12 Price Changed $7,750 ONEKEY
• 2025-08-07 Price Changed $1,375,500 OneKey® MLS as Distributed by MLS Grid
• 2025-07-18 Price Changed $1,399,500 OneKey® MLS as Distributed by MLS Grid
• 2025-07-10 Listed for Rent $7,950 ONEKEY
• 2025-07-10 Listed $1,575,000 OneKey® MLS as Distributed by MLS Grid
• 2025-07-08 Price Changed $1,575,000 OneKey® MLS as Distributed by MLS Grid
• 2025-07-08 Coming Soon — OneKey® MLS as Distributed by MLS Grid
• 2006-05-01 Sold (Public Records) $571,550 Public Records
• 2006-01-26 Sold (MLS) $555,000 HGMLS
• 2004-04-09 Price Changed $585,000 HGMLS
• 2004-04-09 Delisted — HGMLS
• 2004-03-19 Listed $555,000 HGMLS

Property tax history

+18.8%/yr

Latest (2025): $16,751 · +3.3% YoY. Source: county tax records.