150 Baywater Ave · Southold, NY 11971

$850,000

3 bd · 4.0 ba · 2,100 sqft · SingleFamily · 65 Days on market

Built 1900 1.05 ac lot $405/sqft · 26% below area Est $1156k · 26% under

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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 +30.0/30.0
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• 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

Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and the charming village of Southold, with its shops, waterfront, and access to the Long Island Sound. The land at 150 Baywater Avenue is tied to the remarkable story of Maltby Freeman, a formerly enslaved man who earned his freedom in 1807 and, through extraordinary determination, came to own this very property along Bayview near South Harbor Road. Maltby and his wife, Dorcus Benjamin, began with a single-room structure, gradually expanding it into a family homestead in the early 1800s. Their descendants continued to acquire land, eventually owning a house and 30 acres. The Freeman family’s story is one of the earliest documented examples of Black land ownership and upward mobility on Long Island, and this property stands as a tangible connection to that chapter of American history. The property is offered strictly as-is, presenting a rare opportunity for a developer, preservationist, or visionary owner-builder. Included in the sale is a complete set of fully approved architectural and construction plans, a process that required two years of review by the Historic Preservation Commission, Town Planning Department, and Building Department. This extensive approval represents significant time, cost, and expertise that the next owner will not need to replicate. With permits and plans already secured, construction can begin immediately upon closing. For those seeking a property defined by history, character, and forward potential, 150 Baywater Avenue is ready for its next chapter.

Key facts

• 1.05 acre parcel
• 1.05 acre lot
• Built 1900

Tags

• 1.05 ACRE PARCEL
• MOMENTS FROM SANDY BAY BEACHES
• ACCESS TO LONG ISLAND SOUND

What this means for you Summary

Snapshot

• This is a 3-bed/4.0-bath single-family listed at $850k.

Deal economics

• At list price, monthly cash flow is $22k ($260k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($34k rent vs $850k).
• Recommended offer: $799k (6.0% below list) — sets the bar for market timing.
• Cap rate 36.9% 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; 3 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% 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 $6k of loan paydown is wiped out by about $26k 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 $238k cash investment doubles in ~1 year — after that, you're playing with house money.

Negotiation context

• It's been on market 65 days — a 6% lower offer ($799k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 3y 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 $700k; 21% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1900 — 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 $799,000 (6.0% below list)

Questions for the listing agent

1. It's been on market 65 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Built in 1900 — 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: 4.04% ✓
• Cap rate: 36.93%
• Cash-on-cash: 109.41%
• DSCR: 5.87
• GRM: 2.1

CMA / ARV

• ARV (median comp): $1,156,291
• List price: $850,000
• Delta: -26.49%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
2865 S Harbor Rd	0.06mi	3/3.0	2,250 (+7%)	11mo	$1,150,000	$511	72
2740 Main Bayview Rd	0.24mi	3/2.5	2,100 (0%)	22mo	$1,505,000	$717	64
730 Pine Neck Rd	0.68mi	4/2.0 (+1)	2,200 (+5%)	7mo	$985,000	$448	42
265 Custer Ave	0.67mi	3/1.5	1,800 (-14%)	9mo	$800,000	$444	28
200 Breitstadt Ct	0.70mi	4/2.5 (+1)	1,925 (-8%)	23mo	$1,200,000	$623	23

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: —
• Equity multiple: 6.23×
• Total profit: $1,244,590
• Equity at exit: $126,738

10-year hold

• IRR: —
• Equity multiple: 13.04×
• Total profit: $2,864,429
• Equity at exit: $73,492

Cash invested: $238,000 (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: 2.1×

Monthly cashflow live

• Estimated rent: $34,353 medium
• Mortgage (P&I): −$4,457
• Tax from tax record: −$627 /mo · $7,527/yr
• Insurance: −$354
• HOA: −$0
• Vacancy / Maint / Mgmt: −$7,214
• Net cashflow: $21,700

Break-even live

Break-even rent $6,885

Max offer price $850,000

Occupancy floor 32%

Sensitivity live

Price	-10% $22,181	-5% $21,940	+0% $21,700	+5% $21,459	+10% $21,219
Rent	-10% $18,986	-5% $20,343	+0% $21,700	+5% $23,057	+10% $24,414
Rate	-1.0pp $22,128	-0.5pp $21,916	base $21,700	+0.5pp $21,480	+1.0pp $21,256

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: $212,500
• Closing costs: $25,500
• Reserves months: —
• Total cash needed: —

Rent comps 3 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	0.50mi
1854 N Bayview Rd Southold, NY	2.0	2.5	1750	$15,000	$8.57	44d	1	1.27mi
3375 Indian Neck Ln Peconic, NY	4.0	4.5	1525	$80,000	$52.46	44d	1	1.27mi

Listing history 21 events

1. 2026-06-21
   days on market $850,000 Active 65 DOM
2. 2026-06-18
   days on market $850,000 Active 63 DOM
3. 2026-06-17
   days on market $850,000 Active 62 DOM
4. 2026-06-16
   days on market $850,000 Active 61 DOM
5. 2026-06-15
   days on market $850,000 Active 60 DOM
6. 2026-06-13
   days on market $850,000 Active 58 DOM
7. 2026-06-12
   days on market $850,000 Active 57 DOM
8. 2026-06-09
   days on market $850,000 Active 54 DOM
9. 2026-06-08
   days on market $850,000 Active 53 DOM
10. 2026-06-07
    days on market $850,000 Active 52 DOM
11. 2026-06-07
    days on market $850,000 Active 51 DOM
12. 2026-06-04
    days on market $850,000 Active 48 DOM
13. 2026-06-02
    days on market $850,000 Active 47 DOM
14. 2026-06-01
    days on market $850,000 Active 46 DOM
15. 2026-05-31
    days on market $850,000 Active 45 DOM
16. 2026-04-15
    listed $850,000 Active 1915-char remark

    Show marketing remark (1915 chars)

    Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and the charming village of Southold, with its shops, waterfront, and access to the Long Island Sound. The land at 150 Baywater Avenue is tied to the remarkable story of Maltby Freeman, a formerly enslaved man who earned his freedom in 1807 and, through extraordinary determination, came to own this very property along Bayview near South Harbor Road. Maltby and his wife, Dorcus Benjamin, began with a single-room structure, gradually expanding it into a family homestead in the early 1800s. Their descendants continued to acquire land, eventually owning a house and 30 acres. The Freeman family’s story is one of the earliest documented examples of Black land ownership and upward mobility on Long Island, and this property stands as a tangible connection to that chapter of American history. The property is offered strictly as-is, presenting a rare opportunity for a developer, preservationist, or visionary owner-builder. Included in the sale is a complete set of fully approved architectural and construction plans, a process that required two years of review by the Historic Preservation Commission, Town Planning Department, and Building Department. This extensive approval represents significant time, cost, and expertise that the next owner will not need to replicate. With permits and plans already secured, construction can begin immediately upon closing. For those seeking a property defined by history, character, and forward potential, 150 Baywater Avenue is ready for its next chapter.

17. 2024-03-27
    soldstatus $700,000
18. 2024-03-27
    soldstatus $700,000
19. 2024-01-22
    soldstatus $700,000 Closed 565-char remark

    Show marketing remark (565 chars)

    Charming Antique Fixer Upper/Project Home Set on One Acre. Bring Your Contractor. This Circa 1663 Home Offers 3 Bedrooms, 2.5 Baths, 2 Fireplaces and So Much More. Large Grounds with Good Size Barn (has partial basement) and Shed. One of the Best Bay Beaches a Short Distance Away! Award Winning Winery 8 Houses Away. Don't Miss This Opportunity! This Property is Part of Southold Park District which allows Special Privileges at Several Nearby Beaches. Please Do Not Walk Grounds Unattended., Additional information: Appearance:Fair,Interior Features:Lr/Dr

20. 2023-04-28
    status Pending 565-char remark

    Show marketing remark (565 chars)

    Charming Antique Fixer Upper/Project Home Set on One Acre. Bring Your Contractor. This Circa 1663 Home Offers 3 Bedrooms, 2.5 Baths, 2 Fireplaces and So Much More. Large Grounds with Good Size Barn (has partial basement) and Shed. One of the Best Bay Beaches a Short Distance Away! Award Winning Winery 8 Houses Away. Don't Miss This Opportunity! This Property is Part of Southold Park District which allows Special Privileges at Several Nearby Beaches. Please Do Not Walk Grounds Unattended., Additional information: Appearance:Fair,Interior Features:Lr/Dr

21. 2023-03-13
    listed $699,000 Active 565-char remark

    Show marketing remark (565 chars)

    Charming Antique Fixer Upper/Project Home Set on One Acre. Bring Your Contractor. This Circa 1663 Home Offers 3 Bedrooms, 2.5 Baths, 2 Fireplaces and So Much More. Large Grounds with Good Size Barn (has partial basement) and Shed. One of the Best Bay Beaches a Short Distance Away! Award Winning Winery 8 Houses Away. Don't Miss This Opportunity! This Property is Part of Southold Park District which allows Special Privileges at Several Nearby Beaches. Please Do Not Walk Grounds Unattended., Additional information: Appearance:Fair,Interior Features:Lr/Dr

ⓘ 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: $7,527 · $627/mo
• Projected year-2 tax: $10,946 · $912/mo
• Expected delta: +$3,419/yr (+$285/mo · 45.4%)

ⓘ 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 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $412,235
• − Mortgage interest: −$47,613
• − Property taxes: −$7,527
• − Insurance: −$4,250
• − Repairs & maintenance: −$32,979
• − Management: −$32,979
• − Depreciation: −$24,727
• Taxable income: $262,159
• Est. tax owed @ 24.0%: −$62,918
• After-tax cash flow: $197,480/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

+21.6% since first listed

6 events — show timeline

• 2026-04-15 Listed $850,000 OneKey® MLS as Distributed by MLS Grid
• 2024-03-27 Sold (Public Records) $700,000 Public Records
• 2024-03-27 Sold (Public Records) $700,000 Public Records
• 2024-01-22 Sold (MLS) $700,000 OneKey® MLS as Distributed by MLS Grid
• 2023-04-28 Pending — OneKey® MLS as Distributed by MLS Grid
• 2023-03-13 Listed $699,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+1.6%/yr

Latest (2025): $7,527 · +0.0% YoY. Source: county tax records.