1665 Glenn Rd · Southold, NY 11971

$2,350,000

4 bd · 4.5 ba · 3,248 sqft · Land · 45 Days on market

Built 2024 0.52 ac lot $724/sqft · 28% above area Est $1836k · 28% over

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Why this score? — see what drove the D 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 +18.8/30.0
• DSCR +5.9/10.0
• 1% rule +5.0/10.0
• Schools +4.8/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• ARV discount +0.0/15.0
• Appreciation +0.0/10.0

Listing remarks

Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a . 52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom and three second-floor ensuite guest rooms. The interior is designed for both comfort and entertaining, with a two-sided gas fireplace, quartz kitchen countertops, Bosch and XO appliances, dimmer lighting throughout, electric shades in key living areas, ceiling fans in all bedrooms, and a first-floo

Key facts

• 98-inch sony screen
• 7 built-in tvs
• 0.52 acre lot

Tags

• TWO-SIDED GAS FIREPLACE
• QUARTZ KITCHEN COUNTERTOPS
• BOSCH AND XO APPLIANCES
• FIRST-FLOOR LAUNDRY ROOM
• 7 BUILT-IN TVS
• 98-INCH SONY SCREEN

Property features AI

Exterior

• Parking: Attached private garage; 2-car garage; Driveway; Garage door opener
• Security: Security system
• Utilities: Septic tank; Utilities: see remarks
• Home design: Single family residence; Living area based on plans
• Construction: Frame construction
• Exterior features: Covered patio and porch; Balcony; Garden; Back yard fencing; Private in-ground saltwater pool; Patio

Interior

• Kitchen: Dishwasher; Gas cooktop; Gas oven; Microwave; Refrigerator; Stainless steel appliances; Energy Star qualified appliances; Wine refrigerator; Exhaust fan
• Bedrooms: Includes a first-floor bedroom
• Flooring: Hardwood floors
• Bathrooms: Four full bathrooms; One half bathroom
• Heating & cooling: Central air; Forced air heating; Propane heating; Smart thermostat
• Interior features: First-floor bedroom; First-floor full bath; Breakfast bar; Built-in features; Ceiling fans; Chef's kitchen; Crown molding; Double vanity; Eat-in kitchen; ENERGY STAR qualified doors; Entertainment cabinets; Kitchen island; Open floorplan; Open kitchen; Primary bathroom; Master on main; Quartz/Quartzite counters; Smart thermostat; Soaking tub; Sound system with speakers; Walk-in closets
• Laundry & utility: Laundry room; Dryer; Gas water heater

What this means for you Summary

Snapshot

• This is a 4-bed/4.5-bath land listed at $2.35M.

Deal economics

• At list price, monthly cash flow is $2k ($29k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($24k rent vs $2.35M).
• Recommended offer: $2.28M (3.0% below list) — sets the bar for market timing.

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 $16k of loan paydown is wiped out by about $70k 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.

Negotiation context

• It's been on market 45 days — a 3% lower offer ($2.28M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 2y 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.

Recommended offer $2,279,500 (3.0% below list)

Questions for the listing agent

1. It's been on market 45 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. 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?
4. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
5. 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.
6. 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.
7. 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: 1.00% ✓
• Cap rate: 7.51%
• Cash-on-cash: 4.35%
• DSCR: 1.19
• GRM: 8.3

CMA / ARV

• ARV (median comp): $1,835,774
• List price: $2,350,000
• Delta: 28.01%
• Verdict: OVERPRICED
• Comps: 20 within 1.0 mi

Projected returns pro-forma

-3.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -9.5%
• Equity multiple: 0.65×
• Total profit: $-228,446
• Equity at exit: $350,393

10-year hold

• IRR: -0.0%
• Equity multiple: 1.00×
• Total profit: $-1,759
• Equity at exit: $203,185

Cash invested: $658,000 (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: 8.3×

Monthly cashflow live

• Estimated rent: $23,578 medium
• Mortgage (P&I): −$12,324
• Tax est. 1.5%: −$2,938 /mo · $35,250/yr
• Insurance: −$979
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,951
• Net cashflow: $2,387

Break-even live

Break-even rent $20,557

Max offer price $2,350,000

Occupancy floor 85%

Sensitivity live

Price	-10% $4,011	-5% $3,199	+0% $2,387	+5% $1,575	+10% $762
Rent	-10% $524	-5% $1,455	+0% $2,387	+5% $3,318	+10% $4,249
Rate	-1.0pp $3,570	-0.5pp $2,984	base $2,387	+0.5pp $1,778	+1.0pp $1,158

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: $587,500
• Closing costs: $70,500
• 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	0.08mi
215 Northfield Ln Southold, NY	4.0	3.0	2300	$13,000	$5.65	19d	1	1.13mi
580 Gin Ln Southold, NY	4.0	4.0	3585	$20,000	$5.58	25d	1	1.30mi
1685 Peconic Ln Peconic, NY	3.0	3.0	3100	$18,000	$5.81	44d	1	1.49mi

Listing history 28 events

1. 2026-06-21
   days on market $2,350,000 Active 45 DOM
2. 2026-06-18
   days on market $2,350,000 Active 43 DOM
3. 2026-06-17
   days on market $2,350,000 Active 42 DOM
4. 2026-06-16
   days on market $2,350,000 Active 41 DOM
5. 2026-06-15
   days on market $2,350,000 Active 40 DOM
6. 2026-06-13
   days on market $2,350,000 Active 38 DOM
7. 2026-06-12
   days on market $2,350,000 Active 37 DOM
8. 2026-06-09
   days on market $2,350,000 Active 34 DOM
9. 2026-06-08
   days on market $2,350,000 Active 33 DOM
10. 2026-06-07
    days on market $2,350,000 Active 32 DOM
11. 2026-06-07
    days on market $2,350,000 Active 31 DOM
12. 2026-06-04
    days on market $2,350,000 Active 28 DOM
13. 2026-06-02
    days on market $2,350,000 Active 27 DOM
14. 2026-06-01
    days on market $2,350,000 Active 26 DOM
15. 2026-05-31
    days on market $2,350,000 Active 25 DOM
16. 2026-05-05
    listed $2,350,000 Active 1626-char remark
17. 2026-04-22
    historical
18. 2025-12-02
    listed $2,395,000 Active
19. 2025-11-19
    historical
20. 2025-10-15
    historical
21. 2025-06-23
    listed $2,650,000 Active
22. 2025-01-16
    soldstatus $2,262,500
23. 2024-10-30
    soldstatus $2,262,500 Closed
24. 2024-10-04
    status Pending
25. 2024-09-28
    status Active
26. 2024-08-28
    listed $2,295,000 Active
27. 2024-08-28
    historical $2,295,000
28. 2024-04-25
    soldstatus $525,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $282,939
• − Mortgage interest: −$131,637
• − Property taxes: −$35,250
• − Insurance: −$11,750
• − Repairs & maintenance: −$22,635
• − Management: −$22,635
• − Depreciation: −$68,364
• Taxable loss: −$9,331
• Est. tax savings @ 24.0%: +$2,239
• After-tax cash flow: $30,878/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

+347.6% since first listed

13 events — show timeline

• 2026-05-05 Listed $2,350,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-22 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-12-02 Listed $2,395,000 OneKey® MLS as Distributed by MLS Grid
• 2025-11-19 Coming Soon — OneKey® MLS as Distributed by MLS Grid
• 2025-10-15 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-06-23 Listed $2,650,000 OneKey® MLS as Distributed by MLS Grid
• 2025-01-16 Sold (Public Records) $2,262,500 Public Records
• 2024-10-30 Sold (MLS) $2,262,500 OneKey® MLS as Distributed by MLS Grid
• 2024-10-04 Pending — OneKey® MLS as Distributed by MLS Grid
• 2024-09-28 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2024-08-28 Listed $2,295,000 OneKey® MLS as Distributed by MLS Grid
• 2024-08-28 Coming Soon $2,295,000 OneKey® MLS as Distributed by MLS Grid
• 2024-04-25 Sold (Public Records) $525,000 Public Records

Property tax history

+2.3%/yr

Latest (2025): $1,229 · +0.0% YoY. Source: county tax records.