150 Baywater Ave · Southold, NY 11971

$850,000

3 bd · 4.0 ba · 2,100 sqft · SingleFamily · 160 Days on market

Built 1900 Poor condition 1.05 ac lot $405/sqft · 29% below area Est $1.195M · 29% 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 +5.1/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +1.0/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

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.

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. Condition is rated poor.

Deal economics

• At list price, monthly cash flow is $7k ($78k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($15k rent vs $850k).
• Recommended offer: $748k (12.0% below list) — sets the bar for market timing.
• Cap rate 15.5% vs local median 6.6% 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+, health & safety B+; 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.
• Zoned schools: Southold Elementary School (math 37% / reading 62%, grade D, #1,085 of 2,108 statewide, top 56%, 317 students, 35% FRL); Southold Junior-Senior High School (math 52% / reading 52%, grade D+, #946 of 1,100 statewide, top 88%, 380 students, 40% FRL) — zoned schools average 38% FRL vs 17% district-wide (21 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 118 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals leasing fast (median 2d on market — plan ~1-2 weeks tenant-placement turnaround); 40% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 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 ~4 years — after that, you're playing with house money.

Negotiation context

• It's been on market 160 days — a 12% lower offer ($748k) 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 $748,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 160 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
3. Built in 1900 — 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. 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.
8. 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.
9. 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: 1.78% ✓
• Cap rate: 15.51%
• Cash-on-cash: 32.90%
• DSCR: 2.46
• GRM: 4.7

CMA / ARV

• ARV (median comp): $1,195,496
• List price: $850,000
• Delta: -28.90%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 11 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%)	14mo	$1,150,000	$511	69
2300 Glenn Rd	0.55mi	3/3.0	2,500 (+19%)	1mo	$1,935,000	$774	45
730 Pine Neck Rd	0.68mi	4/2.0 (+1)	2,200 (+5%)	10mo	$985,000	$448	39
205 Pine Ave	0.98mi	4/3.0 (+1)	2,280 (+9%)	13mo	$1,205,000	$529	31
1100 Beachwood Ln	1.08mi	3/2.0	2,000 (-5%)	24mo	$1,807,250	$904	29
6060 Main Bayview Rd	0.56mi	3/2.0	1,694 (-19%)	15mo	$1,375,000	$812	29
265 Custer Ave	0.67mi	3/1.5	1,800 (-14%)	12mo	$800,000	$444	25
605 aka 565 Cedar Dr	0.88mi	4/2.0 (+1)	1,911 (-9%)	16mo	$950,000	$497	24
585 Peconic Ln	0.99mi	3/2.0	1,700 (-19%)	10mo	$650,000	$382	24
2300 Pine Neck Rd	0.87mi	4/2.0 (+1)	2,300 (+10%)	23mo	$915,000	$398	17
344 Terry Ct	1.10mi	3/2.0	1,700 (-19%)	24mo	$1,175,000	$691	12

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: 28.1%
• Equity multiple: 2.17×
• Total profit: $277,861
• Equity at exit: $126,738

10-year hold

• IRR: 35.5%
• Equity multiple: 4.26×
• Total profit: $776,996
• 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 →

Buyer's market Market conditions within 1.0 mi — comparable homes for sale

Active competition Active MLS

• For sale now: 5 active · 3 under contract
• Months of supply: 30.0 mo (3%/mo absorbed)
• Median asking: $1,550,000 ($903/sqft)
• Median days on market: 117 d
• This list price: lowest-priced of the active set
• ARV vs active asking: -37.0% vs current asking $/sqft

Closed sales set the value; these active listings set current market conditions and a practical price ceiling.

ZIP-level market 11971

• Home prices YoY: -15.8%
• Active inventory: 118
• Price-to-rent: 4.7×

Monthly cashflow live

• Estimated rent: $15,145 medium
• Mortgage (P&I): −$4,457
• Tax from tax record: −$627 /mo · $7,527/yr
• Insurance: −$354
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,181
• Net cashflow: $6,526

Break-even live

Break-even rent $6,885

Max offer price $850,000

Occupancy floor 52%

Sensitivity live

Price	-10% $7,007	-5% $6,766	+0% $6,526	+5% $6,285	+10% $6,045
Rent	-10% $5,329	-5% $5,928	+0% $6,526	+5% $7,124	+10% $7,722
Rate	-1.0pp $6,954	-0.5pp $6,742	base $6,526	+0.5pp $6,306	+1.0pp $6,082

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
• Club membership (one-time): —
• Reserves months: —
• Total cash needed: —

Rent comps 5 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
2380 S Harbor Rd Southold, NY	3.0	1.0	1500	$15,500	$10.33	1d	1	0.06mi
4525 S Harbor Rd Southold, NY	3.0	2.0	1693	$14,000	$8.27	1d	1	0.38mi
110 Sleepy Hollow Ln Southold, NY	4.0	3.0	2900	$12,000	$4.14	1d	1	0.50mi
1854 N Bayview Rd Southold, NY	2.0	2.5	1750	$15,000	$8.57	139d	1	1.27mi
3375 Indian Neck Ln Peconic, NY	4.0	4.5	1525	$80,000	$52.46	139d	1	1.27mi

Property features AI

Finance

Exterior

• Parking: DrivewayNo carport
• Utilities: Sewer: Cesspool or septic tankUtilities: see remarks
• Home design: Single family residence
• Construction: Built with other construction materialsOther foundation
• Exterior features: Other construction materialsOther foundation detailsNot waterfront

Interior

• Kitchen: Other kitchen appliances (see remarks)
• Bathrooms: 4 full bathrooms
• Heating & cooling: No central coolingHeating described as 'See Remarks' / Other
• Interior features: Other interior features (see remarks)Attic details available (see remarks)8 total rooms

Listing history 50 events

1. 2026-09-23
   days on market $850,000 Active 160 DOM
2. 2026-09-21
   days on market $850,000 Active 158 DOM
3. 2026-09-20
   days on market $850,000 Active 157 DOM
4. 2026-09-19
   days on market $850,000 Active 156 DOM
5. 2026-09-19
   days on market $850,000 Active 155 DOM
6. 2026-09-17
   days on market $850,000 Active 154 DOM
7. 2026-09-17
   days on market $850,000 Active 153 DOM
8. 2026-09-16
   days on market $850,000 Active 152 DOM
9. 2026-09-14
   days on market $850,000 Active 151 DOM
10. 2026-09-13
    days on market $850,000 Active 150 DOM
11. 2026-09-12
    days on market $850,000 Active 149 DOM
12. 2026-09-11
    days on market $850,000 Active 148 DOM
13. 2026-09-05
    days on market $850,000 Active 142 DOM
14. 2026-09-04
    days on market $850,000 Active 141 DOM
15. 2026-09-03
    days on market $850,000 Active 140 DOM
16. 2026-09-02
    days on market $850,000 Active 139 DOM
17. 2026-08-30
    days on market $850,000 Active 136 DOM
18. 2026-08-29
    days on market $850,000 Active 135 DOM
19. 2026-08-28
    days on market $850,000 Active 134 DOM
20. 2026-08-27
    days on market $850,000 Active 133 DOM
21. 2026-08-26
    days on market $850,000 Active 132 DOM
22. 2026-08-25
    days on market $850,000 Active 131 DOM
23. 2026-08-24
    days on market $850,000 Active 130 DOM
24. 2026-08-23
    days on market $850,000 Active 129 DOM
25. 2026-08-22
    days on market $850,000 Active 128 DOM
26. 2026-08-21
    days on market $850,000 Active 127 DOM
27. 2026-08-20
    days on market $850,000 Active 126 DOM
28. 2026-08-19
    days on market $850,000 Active 125 DOM
29. 2026-08-18
    days on market $850,000 Active 124 DOM
30. 2026-08-17
    days on market $850,000 Active 123 DOM
31. 2026-08-16
    days on market $850,000 Active 122 DOM
32. 2026-08-15
    days on market $850,000 Active 121 DOM
33. 2026-08-14
    days on market $850,000 Active 120 DOM
34. 2026-08-13
    days on market $850,000 Active 119 DOM
35. 2026-08-12
    days on market $850,000 Active 118 DOM
36. 2026-08-11
    days on market $850,000 Active 117 DOM
37. 2026-08-10
    days on market $850,000 Active 116 DOM
38. 2026-08-09
    days on market $850,000 Active 115 DOM
39. 2026-08-08
    days on market $850,000 Active 114 DOM
40. 2026-08-07
    days on market $850,000 Active 113 DOM
41. 2026-08-06
    days on market $850,000 Active 112 DOM
42. 2026-08-05
    days on market $850,000 Active 111 DOM
43. 2026-08-04
    days on market $850,000 Active 110 DOM
44. 2026-08-03
    days on market $850,000 Active 109 DOM
45. 2026-07-31
    days on market $850,000 Active 106 DOM
46. 2026-07-30
    days on market $850,000 Active 105 DOM
47. 2026-07-29
    days on market $850,000 Active 104 DOM
48. 2026-07-27
    days on market $850,000 Active 102 DOM
49. 2026-07-25
    days on market $850,000 Active 100 DOM
50. 2026-07-24
    days on market $850,000 Active 99 DOM

ⓘ 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: $181,744
• − Mortgage interest: −$47,613
• − Property taxes: −$7,527
• − Insurance: −$4,250
• − Repairs & maintenance: −$14,539
• − Management: −$14,539
• − Depreciation: −$24,727
• Taxable income: $68,547
• Est. tax owed @ 24.0%: −$16,451
• After-tax cash flow: $61,859/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.

Condition & rehab AI · 5 photos

Poor 20/100 Extensive rehab Est. rehab $105,000–$189,000 screening

The property is in poor condition with significant repairs and maintenance needed, including landscaping, fencing, and exterior and interior painting. A comprehensive renovation is required to improve its value and make it move-in ready.

Repairs flagged

• Major Landscaping — Overgrown vegetation and lack of landscaping.
• Major Fencing — No visible fencing.
• Major Exterior Painting — No visible exterior paint condition.
• Major Roof Inspection — No visible roof condition, but the satellite image shows a pitched roof structure.
• Major Interior Painting — No visible interior paint condition.
• Major Systems Inspection — No visible systems condition, but the satellite image shows a pitched roof structure.

Value-add opportunities

• Both Landscaping and Fencing — Enhances curb appeal and property value. ↑
• Both Exterior Painting — Improves the home's appearance and value. ↑
• Both Roof Inspection and Repairs — Ensures structural integrity and protects against water damage. ↑
• Both Interior Painting — Enhances the home's appearance and value. ↑
• Both Systems Inspection and Repairs — Ensures the home's systems are functioning properly and safely. ↑

ⓘ Rehab cost is a screening estimate — Extensive scope × the home's square footage at US $/sqft rules of thumb (the same model as the Flip Finder). Get contractor quotes + a written scope before underwriting.

D Composite school gradezoned avg 51/100

Zoned Schools

Elementary Southold Elementary School D NY #1,085/2,108 Nat'l #12,785/41,679 High Southold Junior-Senior High School D+ NY #946/1,100 Nat'l #5,016/17,239

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

C Composite livability gradescore 67/100

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
• County: Suffolk · 1,505,262 people
• City population: 6,507
• Metro: New York-Newark-Jersey City, NY-NJ
• Population (ZIP): 6,507
• Household income: $124,097
• Rent vs Own: 15.2% rent · 84.8% own
• Severe rent burden: 22% of renters

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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%

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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%

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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

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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

Property features AI

Finance

Exterior

• Parking: DrivewayNo carport
• Utilities: Sewer: Cesspool or septic tankUtilities: see remarks
• Home design: Single family residence
• Construction: Built with other construction materialsOther foundation
• Exterior features: Other construction materialsOther foundation detailsNot waterfront

Interior

• Kitchen: Other kitchen appliances (see remarks)
• Bathrooms: 4 full bathrooms
• Heating & cooling: No central coolingHeating described as 'See Remarks' / Other
• Interior features: Other interior features (see remarks)Attic details available (see remarks)8 total rooms

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.