2100 Glenn Rd · Southold, NY 11971

$1,925,000

4 bd · 3.5 ba · 2,850 sqft · SingleFamily · 9 Days on market

Built 1984 0.64 ac lot

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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 +28.8/30.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• 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

Waterfront With Dock In The Heart Of Wine Country! Extremely Low Taxes & Gorgeous Views, This Charming & Well Adorned Residence Rests Peacefully On Goose Creek. Features An Open, Airy Floor Plan. Spacious Great/Family Room w Fireplace Overlooking Sensational Landscaping & Newly Redone Waterfront Dock. Chef's Kitchen w Quartz Countertops & Thermador Appliances, Andersen Windows, Ductless AC Units, And A Tremendous Basement. This Special Southold Home Is Truly A Must See. Don't Wait, This Won't Last!, Additional information: Appearance:Diamond++,Separate Hotwater Heater:Yes

Key facts

• 0.64 acre lot
• 2 garage spots
• Built 1984

Property features AI

Exterior

• Parking: Driveway; 2-car garage
• Utilities: Electric service by PSEG; Cesspool for sewer; Other utilities — see remarks
• Home design: Single family residence; Three or more stories/levels
• Construction: HardiPlank-type exterior
• Exterior features: Dock; Waterfront property

Interior

• Kitchen: Chef's kitchen with stainless steel appliances
• Bedrooms: Includes a bedroom on the first floor
• Bathrooms: Three full bathrooms; One half bathroom
• Heating & cooling: Forced air heating (oil); Ductless cooling
• Interior features: First-floor bedroom; First-floor full bath; Cathedral ceilings; Ceiling fans; Chef's kitchen; Entrance foyer; Formal dining room; Finished full basement; 12 total rooms; Three or more levels
• Laundry & utility: Laundry located in a bathroom

What this means for you Summary

Snapshot

• This is a 4-bed/3.5-bath single-family listed at $1.93M.

Deal economics

• At list price, monthly cash flow is $6k ($78k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($23k rent vs $1.93M).
• Cap rate 10.3% 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+, 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: 79 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 45d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% 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 $13k of loan paydown is wiped out by about $58k 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 $539k cash investment doubles in ~9 years — after that, you're playing with house money.

Negotiation context

• Only 9 days on market — expect competitive offers; lowballing is unlikely to land.
• 4 sale attempts since 11y ago; this cycle's ask is 34% above the opening price — seller raised mid-cycle; expect resistance to lowballs.
• Current owner paid $1.44M; 34% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• 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 $1,925,000

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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?
3. 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.
4. 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.
5. 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: 10.32%
• Cash-on-cash: 14.39%
• DSCR: 1.64
• GRM: 6.9

CMA / ARV

• ARV (on-the-fly): $1,271,100
• Comps found: 5

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
5805 Main Bayview Rd	0.32mi	4/3.0	3,253 (+14%)	5mo	$2,700,000	$830	55
480 N Bayview Road Ext	0.61mi	3/3.0 (-1)	2,936 (+3%)	6mo	$1,175,000	$400	54
3295 Pine Neck Rd	0.60mi	3/2.5 (-1)	2,971 (+4%)	19mo	$1,325,000	$446	40
8355 Main Bayview Rd	0.72mi	4/3.0	2,662 (-7%)	16mo	$1,800,000	$676	40
1305 Cedar Dr	0.50mi	4/3.5	3,233 (+13%)	18mo	$999,999	$309	40

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: 4.8%
• Equity multiple: 1.18×
• Total profit: $99,249
• Equity at exit: $287,024

10-year hold

• IRR: 14.2%
• Equity multiple: 2.14×
• Total profit: $614,347
• Equity at exit: $166,439

Cash invested: $539,000 (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: 6.9×

Monthly cashflow live

• Estimated rent: $23,160 medium
• Mortgage (P&I): −$10,095
• Tax from tax record: −$934 /mo · $11,214/yr
• Insurance: −$802
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,864
• Net cashflow: $6,465

Break-even live

Break-even rent $14,977

Max offer price $1,925,000

Occupancy floor 67%

Sensitivity live

Price	-10% $7,554	-5% $7,009	+0% $6,465	+5% $5,920	+10% $5,375
Rent	-10% $4,635	-5% $5,550	+0% $6,465	+5% $7,379	+10% $8,294
Rate	-1.0pp $7,434	-0.5pp $6,954	base $6,465	+0.5pp $5,966	+1.0pp $5,458

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: $481,250
• Closing costs: $57,750
• Reserves months: —
• Total cash needed: —

Rent comps 4 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	0.18mi
1160 Goose Creek Ln Southold, NY	5.0	3.0	2000	$50,000	$25.00	44d	1	0.67mi
215 Northfield Ln Southold, NY	4.0	3.0	2300	$13,000	$5.65	19d	1	1.04mi
580 Gin Ln Southold, NY	4.0	4.0	3585	$20,000	$5.58	25d	1	1.17mi

Listing history 12 events

1. 2026-06-21
   days on market $1,925,000 Active 9 DOM
2. 2026-06-18
   days on market $1,925,000 Active 7 DOM
3. 2026-06-17
   days on market $1,925,000 Active 6 DOM
4. 2026-06-16
   days on market $1,925,000 Active 5 DOM
5. 2026-06-15
   days on market $1,925,000 Active 4 DOM
6. 2026-06-13
   days on market $1,925,000 Active 2 DOM
7. 2026-06-12
   statusdays on market $1,925,000 Active 1 DOM
8. 2026-06-09
   days on market $1,925,000 Coming Soon 4 DOM
9. 2026-06-08
   days on market $1,925,000 Coming Soon 3 DOM
10. 2026-06-07
    days on market $1,925,000 Coming Soon 2 DOM
11. 2026-06-07
    remarks 699-char remark
12. 2026-06-07
    listed $1,925,000 Coming Soon 1 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: $11,214 · $934/mo
• Projected year-2 tax: $21,873 · $1,823/mo
• Expected delta: +$10,659/yr (+$888/mo · 95.1%)

ⓘ 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: $277,916
• − Mortgage interest: −$107,830
• − Property taxes: −$11,214
• − Insurance: −$9,625
• − Repairs & maintenance: −$22,233
• − Management: −$22,233
• − Depreciation: −$56,000
• Taxable income: $48,781
• Est. tax owed @ 24.0%: −$11,707
• After-tax cash flow: $65,868/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

+6109.7% since first listed

16 events — show timeline

• 2026-06-05 Coming Soon $1,925,000 OneKey® MLS as Distributed by MLS Grid
• 2021-12-15 Sold (Public Records) $1,435,000 Public Records
• 2021-10-20 Sold (MLS) $1,435,000 OneKey® MLS as Distributed by MLS Grid
• 2021-09-15 Sold (Public Records) $1,350,000 Public Records
• 2021-08-23 Pending — OneKey® MLS as Distributed by MLS Grid
• 2021-08-05 Listed $1,435,000 OneKey® MLS as Distributed by MLS Grid
• 2020-12-27 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2019-11-18 Listed $1,290,000 OneKey® MLS as Distributed by MLS Grid
• 2016-05-17 Sold (Public Records) $545,000 Public Records
• 2016-04-29 Sold (MLS) $545,000 OneKey® MLS as Distributed by MLS Grid
• 2016-04-29 Sold (MLS) $545,000 MLSLI
• 2016-03-29 Pending — MLSLI
• 2015-09-28 Price Changed $599,000 MLSLI
• 2015-06-18 Listed $650,000 MLSLI
• 2015-06-18 Listed $599,000 OneKey® MLS as Distributed by MLS Grid
• 1981-08-21 Sold (Public Records) $31,000 Public Records

Property tax history

+2.5%/yr

Latest (2025): $11,214 · +0.0% YoY. Source: county tax records.