5045 Main Bayview Rd · Southold, NY 11971

$999,000

4 bd · 2.5 ba · 3,000 sqft · SingleFamily · 93 Days on market

Built 1984 Good condition 0.34 ac lot Garage $333/sqft · 48% below area Est $1.934M · 48% 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
• Condition / age +3.8/5.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Welcome to this charming residence nestled in the heart of Southold. This gem boasts 4 spacious bedrooms, 2 full bathrooms, along with an additional half bath for your convenience. Step inside to be greeted by a formal dining room, perfect for hosting memorable gatherings. The primary bathroom offers a private sanctuary, while the walk-through kitchen is equipped with stainless steel appliances including a dishwasher, oven, range, and refrigerator, ready to inspire your culinary creativity. Experience the warmth of this gem with cozy carpeting, elegant hardwood, and a welcoming fireplace, not to mention the indoor hot tub.

Key facts

• 0.34 acre lot
• Garage
• Pool

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $999k. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $10k ($118k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $999k).
• Recommended offer: $909k (9.0% below list) — sets the bar for market timing.
• Cap rate 18.1% vs local median 6.3% 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: 99 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals lingering (median 74d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% 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).
• At $20,447/mo this rent would consume 198% of the median local household income ($124k/yr) (locally 22% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $7k of loan paydown is wiped out by about $30k 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 $280k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• It's been on market 93 days — a 9% lower offer ($909k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $10k; list at $999k implies a 9890% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $56/mo.
• Climate carrying-cost: severe flood risk; 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 $909,090 (9.0% below list)

Questions for the listing agent

1. It's been on market 93 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
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: 2.05% ✓
• Cap rate: 18.13%
• Cash-on-cash: 42.29%
• DSCR: 2.88
• GRM: 4.1

CMA / ARV

• ARV (median comp): $1,933,698
• List price: $999,000
• Delta: -45.75%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 6 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
5805 Main Bayview Rd	0.12mi	4/3.0	3,253 (+8%)	7mo	$2,700,000	$830	72
2335 Minnehaha Blvd	0.54mi	4/2.5	2,800 (-7%)	10mo	$2,750,000	$982	56
480 N Bayview Road Ext	0.62mi	3/3.0 (-1)	2,936 (-2%)	8mo	$1,175,000	$400	54
4015 Main Bayview Rd	0.21mi	3/3.5 (-1)	3,377 (+13%)	18mo	$1,925,000	$570	45
1305 Cedar Dr	0.52mi	4/3.5	3,233 (+8%)	19mo	$999,999	$309	42
8355 Main Bayview Rd	0.66mi	4/3.0	2,662 (-11%)	17mo	$1,800,000	$676	34

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: 38.7%
• Equity multiple: 2.65×
• Total profit: $462,411
• Equity at exit: $148,954

10-year hold

• IRR: 45.2%
• Equity multiple: 5.31×
• Total profit: $1,206,448
• Equity at exit: $86,375

Cash invested: $279,720 (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 →

Active competition Active MLS

• For sale now: 7 active · 4 under contract
• Median asking: $2,250,000 ($693/sqft)
• Median days on market: 58 d
• This list price: lowest-priced of the active set
• ARV vs active asking: -7.0% 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: 99
• Price-to-rent: 4.1×

Monthly cashflow live

• Estimated rent: $20,447 high
• Mortgage (P&I): −$5,239
• Tax from tax record: −$640 /mo · $7,677/yr
• Insurance: −$416
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,294
• Net cashflow: $9,802

Break-even live

Break-even rent $8,039

Max offer price $999,000

Occupancy floor 47%

Sensitivity live

Price	-10% $10,368	-5% $10,085	+0% $9,802	+5% $9,520	+10% $9,237
Rent	-10% $8,187	-5% $8,995	+0% $9,802	+5% $10,610	+10% $11,418
Rate	-1.0pp $10,306	-0.5pp $10,057	base $9,802	+0.5pp $9,544	+1.0pp $9,280

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: $249,750
• Closing costs: $29,970
• Club membership (one-time): —
• Reserves months: —
• Total cash needed: —

Rent comps 5 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	93d	1	0.42mi
580 Gin Ln Southold, NY	4.0	4.0	3585	$20,000	$5.58	74d	1	1.10mi
215 Northfield Ln Southold, NY	4.0	3.0	2300	$13,000	$5.65	67d	1	1.23mi
1000 Rambler Rd Southold, NY	4.0	3.0	2700	$15,000	$5.56	38d	1	1.27mi
1685 Peconic Ln Peconic, NY	3.0	3.0	3100	$18,000	$5.81	93d	1	1.47mi

Property features AI

Exterior

• Parking: Attached garage1 garage spaceNo carport
• Utilities: Cesspool sewerElectricity connected
• Home design: Single family residence
• Construction: Frame construction
• Exterior features: Private poolSpaFrame constructionNot waterfront

Interior

• Kitchen: DishwasherMicrowaveOvenRangeRefrigeratorStainless steel appliances
• Bedrooms: 10 total rooms (bedroom counts not specified)
• Flooring: CarpetHardwoodWoodOther
• Bathrooms: 2 full bathrooms1 half bathroom
• Heating & cooling: Baseboard heatingOil heatingWall/window air conditioning units
• Interior features: Formal diningPrimary bathroomWalk-through kitchenCovered porch
• Laundry & utility: WasherDryer

Listing history 50 events

1. 2026-08-08
   days on market $999,000 Active 93 DOM
2. 2026-08-07
   days on market $999,000 Active 92 DOM
3. 2026-08-06
   days on market $999,000 Active 91 DOM
4. 2026-08-05
   price $999,000 Active 90 DOM
5. 2026-08-05
   days on market $1,049,000 Active 90 DOM
6. 2026-08-04
   days on market $1,049,000 Active 89 DOM
7. 2026-08-03
   days on market $1,049,000 Active 88 DOM
8. 2026-07-31
   days on market $1,049,000 Active 85 DOM
9. 2026-07-30
   days on market $1,049,000 Active 84 DOM
10. 2026-07-29
    days on market $1,049,000 Active 83 DOM
11. 2026-07-27
    days on market $1,049,000 Active 81 DOM
12. 2026-07-25
    days on market $1,049,000 Active 79 DOM
13. 2026-07-24
    days on market $1,049,000 Active 78 DOM
14. 2026-07-23
    days on market $1,049,000 Active 77 DOM
15. 2026-07-22
    days on market $1,049,000 Active 76 DOM
16. 2026-07-21
    days on market $1,049,000 Active 75 DOM
17. 2026-07-20
    days on market $1,049,000 Active 74 DOM
18. 2026-07-18
    days on market $1,049,000 Active 72 DOM
19. 2026-07-16
    days on market $1,049,000 Active 70 DOM
20. 2026-07-15
    days on market $1,049,000 Active 69 DOM
21. 2026-07-14
    days on market $1,049,000 Active 68 DOM
22. 2026-07-13
    days on market $1,049,000 Active 67 DOM
23. 2026-07-12
    days on market $1,049,000 Active 66 DOM
24. 2026-07-12
    days on market $1,049,000 Active 65 DOM
25. 2026-07-10
    days on market $1,049,000 Active 64 DOM
26. 2026-07-09
    days on market $1,049,000 Active 63 DOM
27. 2026-07-07
    days on market $1,049,000 Active 61 DOM
28. 2026-07-06
    days on market $1,049,000 Active 60 DOM
29. 2026-07-05
    days on market $1,049,000 Active 59 DOM
30. 2026-07-05
    days on market $1,049,000 Active 58 DOM
31. 2026-07-03
    days on market $1,049,000 Active 57 DOM
32. 2026-07-02
    days on market $1,049,000 Active 56 DOM
33. 2026-07-01
    days on market $1,049,000 Active 55 DOM
34. 2026-06-30
    days on market $1,049,000 Active 54 DOM
35. 2026-06-29
    days on market $1,049,000 Active 53 DOM
36. 2026-06-28
    days on market $1,049,000 Active 52 DOM
37. 2026-06-27
    days on market $1,049,000 Active 51 DOM
38. 2026-06-26
    days on market $1,049,000 Active 50 DOM
39. 2026-06-23
    price $1,049,000 Active 46 DOM
40. 2026-06-22
    days on market $1,099,000 Active 46 DOM
41. 2026-06-21
    days on market $1,099,000 Active 45 DOM
42. 2026-06-21
    days on market $1,099,000 Active 44 DOM
43. 2026-06-18
    days on market $1,099,000 Active 42 DOM
44. 2026-06-17
    days on market $1,099,000 Active 41 DOM
45. 2026-06-16
    days on market $1,099,000 Active 40 DOM
46. 2026-06-15
    days on market $1,099,000 Active 39 DOM
47. 2026-06-13
    days on market $1,099,000 Active 37 DOM
48. 2026-06-12
    days on market $1,099,000 Active 36 DOM
49. 2026-06-09
    days on market $1,099,000 Active 33 DOM
50. 2026-06-08
    days on market $1,099,000 Active 32 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: $7,677 · $640/mo
• Projected year-2 tax: $12,280 · $1,023/mo
• Expected delta: +$4,603/yr (+$384/mo · 60.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone X (shaded) · 99% 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: $245,360
• − Mortgage interest: −$55,960
• − Property taxes: −$7,677
• − Insurance: −$5,662
• − Repairs & maintenance: −$19,629
• − Management: −$19,629
• − Depreciation: −$29,062
• Taxable income: $107,743
• Est. tax owed @ 24.0%: −$25,858
• After-tax cash flow: $91,771/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 · 10 photos

Good 75/100 Cosmetic rehab Est. rehab $15,000–$45,000 screening

This well-maintained single-family home with a pool and spacious yard offers a good investment opportunity with minor cosmetic updates to enhance its curb appeal and rental value.

Value-add opportunities

• Resale Paint exterior siding — Fresh paint enhances curb appeal and property value. ↑
• Rental Upgrade pool equipment — Modern pool equipment improves rental appeal and tenant satisfaction. ↑
• Resale Replace outdated wallpaper — Fresh, modern wallpaper enhances the aesthetic and marketability of the home. ↑

ⓘ Rehab cost is a screening estimate — Cosmetic 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

Exterior

• Parking: Attached garage1 garage spaceNo carport
• Utilities: Cesspool sewerElectricity connected
• Home design: Single family residence
• Construction: Frame construction
• Exterior features: Private poolSpaFrame constructionNot waterfront

Interior

• Kitchen: DishwasherMicrowaveOvenRangeRefrigeratorStainless steel appliances
• Bedrooms: 10 total rooms (bedroom counts not specified)
• Flooring: CarpetHardwoodWoodOther
• Bathrooms: 2 full bathrooms1 half bathroom
• Heating & cooling: Baseboard heatingOil heatingWall/window air conditioning units
• Interior features: Formal diningPrimary bathroomWalk-through kitchenCovered porch
• Laundry & utility: WasherDryer

Price history

+10890.0% since first listed

3 events — show timeline

• 2026-05-27 Price Changed $1,099,000 OneKey® MLS as Distributed by MLS Grid
• 2025-12-09 Listed $1,175,000 OneKey® MLS as Distributed by MLS Grid
• 1983-10-03 Sold (Public Records) $10,000 Public Records

Property tax history

-0.3%/yr

Latest (2025): $7,677 · +0.0% YoY. Source: county tax records.