3475 Oaklawn Ave · Southold, NY 11971

$1,200,000

3 bd · 1.5 ba · 2,000 sqft · SingleFamily · 135 Days on market

Built 1909 0.50 ac lot $600/sqft · at area comps Est $1218k · at est.

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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 +28.2/30.0
• DSCR +10.0/10.0
• ARV discount +8.2/15.0
• 1% rule +7.0/10.0
• Schools +4.8/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence features three bedrooms, one full bath, and one half bath, along with building plans for a potential second full bathroom on the second floor, allowing the next owner to enhance comfort while preserving the home’s original charm. Original wood flooring and original moldings combined with new windows throughout, updated kitchen featuring granite and marble countertops high end appliances and updated roof lends itself to nostalgic beauty while enjoying modern-day functionality and efficiency. The home has new I-A septic technology. The expansive 4 car garage is an excellent opportunity for car lovers. Ideally situated just moments from the Peconic Bay and Southold’s waterfront, the home provides easy access to beaches, boating, and tranquil coastal living. Downtown Southold Village is also nearby, offering shops, restaurants, wineries, farm stands, and marinas—all within easy reach. With its classic farmhouse proportions, intimate scale, and timeless appeal, this property is perfectly suited as a year-round residence, weekend retreat, or investment opportunity. Set in one of Southold’s most desirable locations, it offers a rare chance to own a piece of North Fork history while thoughtfully planning for the future. A true farmhouse gem—cozy, historic, and ideally located.

Key facts

• High end appliances
• Updated kitchen
• Updated roof

Tags

• CIRCA 1909 FARMHOUSE
• ORIGINAL WOOD FLOORING
• UPDATED KITCHEN
• GRANITE AND MARBLE COUNTERTOPS
• HIGH END APPLIANCES
• UPDATED ROOF

What this means for you Summary

Snapshot

• This is a 3-bed/1.5-bath single-family listed at $1.20M.

Deal economics

• At list price, monthly cash flow is $4k ($46k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($14k rent vs $1.20M).
• Recommended offer: $1.06M (12.0% below list) — sets the bar for market timing.
• Cap rate 10.1% vs local median 6.9% in Southold — 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 67/100 on livability (#583 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, schools A-; Watch: amenities F, commute F, cost of living F.
• Southold Union Free School District (town): math 46% / reading 59% proficiency, ranked #298 of 590 in NY (top 50%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 17% free/reduced lunch — higher-income household profile.
• Market conditions: 79 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 88% of comp listings sitting > 30 days — soft ceiling on asking rent; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $8k of loan paydown is wiped out by about $36k 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.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $336k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• It's been on market 135 days — a 12% lower offer ($1.06M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 6y 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 $999k; 20% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1909 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,056,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 135 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1909 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
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: 1.20% ✓
• Cap rate: 10.10%
• Cash-on-cash: 13.61%
• DSCR: 1.61
• GRM: 7.0

CMA / ARV

• ARV (median comp): $1,218,440
• List price: $1,200,000
• Delta: -1.51%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 10 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
2505 Wells Ave	0.33mi	3/2.0	2,000 (0%)	16mo	$1,575,000	$788	69
1100 Beachwood Ln	0.41mi	3/2.0	2,000 (0%)	21mo	$1,807,250	$904	62
265 Custer Ave	0.33mi	3/1.5	1,800 (-10%)	9mo	$800,000	$444	61
800 Goose Creek Ln	0.66mi	3/3.0	2,032 (+2%)	7mo	$1,250,000	$615	55
730 Pine Neck Rd	0.35mi	4/2.0 (+1)	2,200 (+10%)	7mo	$985,000	$448	54
200 Breitstadt Ct	0.23mi	4/2.5 (+1)	1,925 (-4%)	23mo	$1,200,000	$623	54
2300 Pine Neck Rd	0.07mi	4/2.0 (+1)	2,300 (+15%)	20mo	$915,000	$398	48
555 Oakwood Dr	0.32mi	4/2.5 (+1)	2,300 (+15%)	11mo	$899,000	$391	42
2740 Main Bayview Rd	0.72mi	3/2.5	2,100 (+5%)	22mo	$1,505,000	$717	35
205 Pine Ave	0.69mi	4/3.0 (+1)	2,280 (+14%)	10mo	$1,205,000	$529	25

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: 3.7%
• Equity multiple: 1.14×
• Total profit: $48,030
• Equity at exit: $178,924

10-year hold

• IRR: 13.2%
• Equity multiple: 2.05×
• Total profit: $353,345
• Equity at exit: $103,754

Cash invested: $336,000 (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 11971

• Home prices YoY: -15.8%
• Active inventory: 79
• Price-to-rent: 7.0×

Monthly cashflow live

• Estimated rent: $14,347 high
• Mortgage (P&I): −$6,293
• Tax from tax record: −$730 /mo · $8,756/yr
• Insurance: −$500
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,013
• Net cashflow: $3,811

Break-even live

Break-even rent $9,522

Max offer price $1,200,000

Occupancy floor 68%

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: $300,000
• Closing costs: $36,000
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
110 Sleepy Hollow Ln Southold, NY	4.0	3.0	2900	$25,000	$8.62	44d	1	0.43mi
1854 N Bayview Rd Southold, NY	2.0	2.5	1750	$15,000	$8.57	44d	1	0.61mi
1235 Youngs Ave Southold, NY	2.0	1.5	1462	$4,000	$2.74	44d	1	0.82mi
425 Old Shipyard Ln Southold, NY	3.0	1.5	1578	$10,000	$6.34	44d	1	0.88mi
215 Northfield Ln Southold, NY	4.0	3.0	2300	$13,000	$5.65	18d	1	0.90mi
275 Maier Pl Southold, NY	3.0	2.0	2000	$10,000	$5.00	44d	1	1.17mi
3400 Youngs Ave Southold, NY	4.0	2.0	2000	$7,500	$3.75	44d	1	1.22mi
1265 Brigantine Dr Southold, NY	3.0	2.0	1750	$9,000	$5.14	44d	1	1.33mi

Listing history 28 events

1. 2026-06-18
   days on market $1,200,000 Active 135 DOM
2. 2026-06-17
   days on market $1,200,000 Active 134 DOM
3. 2026-06-16
   days on market $1,200,000 Active 133 DOM
4. 2026-06-15
   days on market $1,200,000 Active 132 DOM
5. 2026-06-13
   days on market $1,200,000 Active 130 DOM
6. 2026-06-12
   days on market $1,200,000 Active 129 DOM
7. 2026-06-09
   days on market $1,200,000 Active 126 DOM
8. 2026-06-08
   days on market $1,200,000 Active 125 DOM
9. 2026-06-07
   days on market $1,200,000 Active 124 DOM
10. 2026-06-07
    days on market $1,200,000 Active 123 DOM
11. 2026-06-04
    days on market $1,200,000 Active 120 DOM
12. 2026-06-02
    days on market $1,200,000 Active 119 DOM
13. 2026-06-01
    days on market $1,200,000 Active 118 DOM
14. 2026-05-31
    days on market $1,200,000 Active 117 DOM
15. 2026-02-03
    listed $1,200,000 Active 1717-char remark

    Show marketing remark (1717 chars)

    Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, Southold, a circa-1909 farmhouse rich in warmth, character, and North Fork authenticity. This charming home, situated on a 1/2 acre, captures the essence of early-20th-century farmhouse living, offering a cozy, inviting atmosphere paired with thoughtful functionality and future potential. The residence features three bedrooms, one full bath, and one half bath, along with building plans for a potential second full bathroom on the second floor, allowing the next owner to enhance comfort while preserving the home’s original charm. Original wood flooring and original moldings combined with new windows throughout, updated kitchen featuring granite and marble countertops high end appliances and updated roof lends itself to nostalgic beauty while enjoying modern-day functionality and efficiency. The home has new I-A septic technology. The expansive 4 car garage is an excellent opportunity for car lovers. Ideally situated just moments from the Peconic Bay and Southold’s waterfront, the home provides easy access to beaches, boating, and tranquil coastal living. Downtown Southold Village is also nearby, offering shops, restaurants, wineries, farm stands, and marinas—all within easy reach. With its classic farmhouse proportions, intimate scale, and timeless appeal, this property is perfectly suited as a year-round residence, weekend retreat, or investment opportunity. Set in one of Southold’s most desirable locations, it offers a rare chance to own a piece of North Fork history while thoughtfully planning for the future. A true farmhouse gem—cozy, historic, and ideally located.

16. 2025-03-25
    price $999,000
17. 2025-02-20
    status Active
18. 2025-02-14
    listed $1,100,000 Active
19. 2025-02-11
    historical
20. 2025-02-11
    soldstatus $999,000
21. 2024-12-19
    soldstatus $999,000 Closed
22. 2024-10-25
    status Pending
23. 2024-09-05
    listed $999,000 Active
24. 2024-09-01
    historical $999,000
25. 2020-11-10
    soldstatus $649,000
26. 2020-10-08
    soldstatus $649,000 Closed
27. 2020-07-02
    listed $649,000 Active
28. 2006-05-15
    soldstatus $485,000

ⓘ 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: $8,756 · $730/mo
• Projected year-2 tax: $14,518 · $1,210/mo
• Expected delta: +$5,762/yr (+$480/mo · 65.8%)

ⓘ 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 5/10 Major 7 d/yr ≥90°F today · 19 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% 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: $172,159
• − Mortgage interest: −$67,219
• − Property taxes: −$8,756
• − Insurance: −$6,000
• − Repairs & maintenance: −$13,773
• − Management: −$13,773
• − Depreciation: −$34,909
• Taxable income: $27,730
• Est. tax owed @ 24.0%: −$6,655
• After-tax cash flow: $39,079/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: Southold Union Free School District
• NCES district ID: 3627620
• Math proficiency: 46% ▼ -10.00%
• Reading proficiency: 59% ▲ 6.00%
• Median HH income: $78,622
• Composite: 47.54/100
• National rank: #2269
• State rank: #298 of 590 in NY

Livability — Southold

• Score: 67/100
• State rank: #583
• US rank: #10545

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Southold, NY
• City population: 6,507
• Population (ZIP): 6,507

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: Predominantly White (78%)
• Race & ethnicity: White 78% Hispanic / Latino 14% Two or more races 5% Asian 4%
• Hispanic origin (detail): Mexican 3% Puerto Rican 1% Dominican 3%
• Common ancestry: Romanian 6% Italian 2% Slovak 2%
• Foreign-born: 14% · Canada, China, Dominican Republic
• Languages at home: 83% English-only · Spanish 11% Russian/Polish/Slavic 2% 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: ▼ -74.14%
• Current HPI: 396.5481
• 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

+147.4% since first listed

14 events — show timeline

• 2026-02-03 Listed $1,200,000 OneKey® MLS as Distributed by MLS Grid
• 2025-03-25 Price Changed $999,000 OneKey® MLS as Distributed by MLS Grid
• 2025-02-20 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-02-14 Listed $1,100,000 OneKey® MLS as Distributed by MLS Grid
• 2025-02-11 Coming Soon — OneKey® MLS as Distributed by MLS Grid
• 2025-02-11 Sold (Public Records) $999,000 Public Records
• 2024-12-19 Sold (MLS) $999,000 OneKey® MLS as Distributed by MLS Grid
• 2024-10-25 Pending — OneKey® MLS as Distributed by MLS Grid
• 2024-09-05 Listed $999,000 OneKey® MLS as Distributed by MLS Grid
• 2024-09-01 Coming Soon $999,000 OneKey® MLS as Distributed by MLS Grid
• 2020-11-10 Sold (Public Records) $649,000 Public Records
• 2020-10-08 Sold (MLS) $649,000 OneKey® MLS as Distributed by MLS Grid
• 2020-07-02 Listed $649,000 OneKey® MLS as Distributed by MLS Grid
• 2006-05-15 Sold (Public Records) $485,000 Public Records

Property tax history

+3.0%/yr

Latest (2025): $8,756 · +0.0% YoY. Source: county tax records.