35 Timber Trail Ln · Medford, NY 11763

$499,900

4 bd · 3.0 ba · 1,577 sqft · SingleFamily public records · 29 Days on market

Built 1977 0.34 ac lot $317/sqft · 21% below area Est $633k · 21% under ↓ 8% since listing

---

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
• Cash flow +7.0/30.0
• Schools +5.2/10.0
• Livability +3.5/5.0
• 1% rule +2.8/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +1.2/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Welcome to this spacious 4-bedroom, 2-bath ranch tucked into a quiet Medford neighborhood. The main home features a bright eat-in kitchen, a dedicated dining area, and a comfortable den that provides valuable extra living space. An attached one-car garage opens directly into the den, adding everyday convenience and functionality. A separate garage structure has been converted into a 1-bedroom, 1-bath living area. This conversion is not a legal apartment and will require proper permits with the Town of Brookhaven. The property offers generous outdoor space and sits in a location that provides easy access to the Long Island Expressway, making commuting and travel simple.

Key facts

• Attached garage
• Eat-in kitchen
• Comfortable den

Tags

• EAT-IN KITCHEN
• DEDICATED DINING AREA
• COMFORTABLE DEN
• ATTACHED GARAGE
• SEPARATE GARAGE STRUCTURE
• GENEROUS OUTDOOR SPACE

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $500k.

Deal economics

• At list price, monthly cash flow is $-734 ($-9k/yr) — negative.
• To cash-flow at today's rent, offer at most $370k (25.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $391k (21.7% below list).
• Recommended offer: $370k (25.9% below list) — sets the bar for cash-flow.
• Cap rate 4.5% vs local median 3.5% in Medford — meaningfully above typical; check what's discounted (condition, days-on-market, listing class) to confirm the premium yield is real.

Location & tenants

• Location reads 69/100 on livability (#502 in NY) — a middle-class / working-renter tenant base. Strengths: employment A+, housing A+, health & safety B; Watch: schools C-, amenities F, commute F.
• Longwood Central School District (rural): math 61% / reading 55% proficiency, ranked #235 of 590 in NY (top 40%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 186 active listings in the ZIP; 3 comparable units currently listed for rent nearby; rentals at typical pace (median 21d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• This rent runs 39% of the median local income ($121k/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 $3k of loan paydown is wiped out by about $15k of value loss. Plan a longer hold.
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.

Negotiation context

• It's been on market 29 days — a 2% lower offer ($492k) 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 wind risk, 78% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $370,199 (25.9% 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 1977 — 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. 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?
5. 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.
6. 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.
7. 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: 0.78% ✗
• Cap rate: 4.53%
• Cash-on-cash: -6.29%
• DSCR: 0.72
• GRM: 10.6

CMA / ARV

• ARV (median comp): $632,541
• List price: $499,900
• Delta: -20.97%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 7 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
45 Timber Trail Ln	0.11mi	4/1.5	1,582 (+0%)	0mo	$577,000	$365	88
5 Winged Foot Dr	0.12mi	4/3.5	1,550 (-2%)	18mo	$612,700	$395	75
3 Timber Trail Ln	0.35mi	4/1.0	1,496 (-5%)	1mo	$565,000	$378	66
21 Masem Ct	0.57mi	3/2.0 (-1)	1,690 (+7%)	1mo	$725,000	$429	51
95 Lincoln Rd	0.43mi	3/2.0 (-1)	1,371 (-13%)	5mo	$565,000	$412	45
2809 Heather Ave	0.69mi	3/2.0 (-1)	1,708 (+8%)	0mo	$630,000	$369	44
49 Lincoln Rd	0.49mi	3/2.0 (-1)	1,454 (-8%)	20mo	$530,000	$365	39

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: -27.1%
• Equity multiple: 0.09×
• Total profit: $-127,480
• Equity at exit: $74,537

10-year hold

• IRR: -24.6%
• Equity multiple: -0.21×
• Total profit: $-170,052
• Equity at exit: $43,222

Cash invested: $139,972 (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 11763

• Active inventory: 186
• Price-to-rent: 10.6×

Monthly cashflow live

• Estimated rent: $3,915 medium
• Mortgage (P&I): −$2,622
• Tax from tax record: −$997 /mo · $11,964/yr
• Insurance: −$208
• HOA: −$0
• Vacancy / Maint / Mgmt: −$822
• Net cashflow: $-734

Break-even live

Break-even rent $4,844

Max offer price $370,199

Occupancy floor —

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: $124,975
• Closing costs: $14,997
• Reserves months: —
• Total cash needed: —

Rent comps 3 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
3107 Gull Ave Medford, NY	3.0	1.0	1622	$3,900	$2.40	1d	1	0.82mi
546 Granny Rd Medford, NY	3.0	1.0	1152	$3,500	$3.04	43d	1	1.45mi
546 Granny Rd Medford, NY	3.0	1.0	1152	$3,500	$3.04	20d	1	1.45mi

Listing history 8 events

1. 2026-05-07
   status Pending 679-char remark

   Show marketing remark (679 chars)

   Welcome to this spacious 4-bedroom, 2-bath ranch tucked into a quiet Medford neighborhood. The main home features a bright eat-in kitchen, a dedicated dining area, and a comfortable den that provides valuable extra living space. An attached one-car garage opens directly into the den, adding everyday convenience and functionality. A separate garage structure has been converted into a 1-bedroom, 1-bath living area. This conversion is not a legal apartment and will require proper permits with the Town of Brookhaven. The property offers generous outdoor space and sits in a location that provides easy access to the Long Island Expressway, making commuting and travel simple.

2. 2026-04-08
   listed $499,900 Active 679-char remark

   Show marketing remark (679 chars)

   Welcome to this spacious 4-bedroom, 2-bath ranch tucked into a quiet Medford neighborhood. The main home features a bright eat-in kitchen, a dedicated dining area, and a comfortable den that provides valuable extra living space. An attached one-car garage opens directly into the den, adding everyday convenience and functionality. A separate garage structure has been converted into a 1-bedroom, 1-bath living area. This conversion is not a legal apartment and will require proper permits with the Town of Brookhaven. The property offers generous outdoor space and sits in a location that provides easy access to the Long Island Expressway, making commuting and travel simple.

3. 2025-08-09
   status Pending
4. 2025-08-08
   historical
5. 2025-07-25
   status Active
6. 2025-07-25
   price $499,000
7. 2025-06-10
   status Pending
8. 2025-05-13
   listed $545,000 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: $11,964 · $997/mo
• Projected year-2 tax: $11,964 · $997/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 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥93°F today · 16 d/yr by 30 yrs out
• 💨 Wind 7/10 Severe 78% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $46,976
• − Mortgage interest: −$28,002
• − Property taxes: −$11,964
• − Insurance: −$2,500
• − Repairs & maintenance: −$3,758
• − Management: −$3,758
• − Depreciation: −$14,543
• Taxable loss: −$17,548
• Est. tax savings @ 24.0%: +$4,212
• After-tax cash flow: $-4,599/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: Longwood Central School District
• NCES district ID: 3619230
• Math proficiency: 61% ▬ 0.00%
• Reading proficiency: 55% ▼ -1.00%
• Median HH income: $72,748
• Composite: 51.63/100
• National rank: #1703
• State rank: #235 of 590 in NY

Livability — Medford

• Score: 69/100
• State rank: #502
• US rank: #8793

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Medford, NY
• County: Suffolk County · 679,920 people
• City population: 29,973
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 29,973
• Household income: $120,783
• Rent vs Own: 11.5% rent · 88.5% own
• Severe rent burden: 339.0

Population outlook (Suffolk County) Hauer SSP2

• Today (2025): 1,505,262 people
• By 2030: 1,498,318 · -0.5%
• By 2040: 1,471,101 · -2.3%
• By 2050: 1,424,848 · -5.3%
• By 2075: 1,337,157 · -11.2%
• By 2100: 1,217,720 · -19.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.61)
• Race & ethnicity: White 54% Hispanic / Latino 29% Two or more races 14% Black 11% Asian 2%
• Hispanic origin (detail): Mexican 3% Puerto Rican 6% Dominican 3%
• Common ancestry: Romanian 2% Scotch-Irish 2% Hispanic 2%
• Foreign-born: 17% · Canada, Jamaica
• Languages at home: 70% English-only · Spanish 23% French/Haitian/Cajun 3% Other Indo-European 2%

Political lean MEDSL · Suffolk

• 2024 margin: Lean R (+10.0) · D 45.0% · R 55.0%
• 2008→2024 swing: -16.0pp toward R · 2008: 6.0pp · 2024: -10.0pp
• All cycles: 2024: R+10.0 2020: R+0.0 2016: R+8.2 2012: D+2.9 2008: D+6.0

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -531.78%
• Current HPI: 379.1499
• 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

-8.3% since first listed

8 events — show timeline

• 2026-05-07 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-04-08 Listed $499,900 OneKey® MLS as Distributed by MLS Grid
• 2025-08-09 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-08-08 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-07-25 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-07-25 Price Changed $499,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-10 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-05-13 Listed $545,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+2.7%/yr

Latest (2025): $11,964 · +0.0% YoY. Source: county tax records.