240 Lisa Dr · Southold, NY 11971

$949,000

4 bd · 2.5 ba · 1,862 sqft · SingleFamily · 61 Days on market

Built 1992 0.58 ac lot $510/sqft · 22% below area Est $1217k · 22% under

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Why this score? — see what drove the C 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
• ARV discount +15.0/15.0
• DSCR +5.9/10.0
• Schools +4.8/10.0
• 1% rule +4.3/10.0
• 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

Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage, and a full basement with 8-foot ceilings offering excellent storage and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is just moments from public beaches, scenic trails, wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

Key facts

• Open-concept kitchen
• Formal living room
• Welcoming front yard

Tags

• CORNER LOT
• WELCOMING FRONT YARD
• GENEROUSLY SIZED BACKYARD
• OPEN-CONCEPT KITCHEN
• FORMAL LIVING ROOM
• CONVENIENT LAUNDRY ROOM

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $949k.

Deal economics

• At list price, monthly cash flow is $947 ($11k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $885k (6.7% below list).
• Recommended offer: $885k (6.7% below list) — sets the bar for 1% rule.

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; 7 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 $7k of loan paydown is wiped out by about $28k 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 61 days — a 6% lower offer ($892k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $460k; list at $949k implies a 106% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→20/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $885,279 (6.7% below list)

Questions for the listing agent

1. It's been on market 61 days. Have you received any prior offers? Is the seller open to a 7% concession, seller financing, or rate buy-down credit?
2. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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: 0.93% ✗
• Cap rate: 7.49%
• Cash-on-cash: 4.28%
• DSCR: 1.19
• GRM: 8.9

CMA / ARV

• ARV (median comp): $1,216,938
• List price: $949,000
• Delta: -22.02%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
57020 Route 25	0.50mi	3/3.0 (-1)	2,100 (+13%)	6mo	$750,000	$357	43
5535 Old North Rd	0.54mi	3/1.0 (-1)	1,760 (-6%)	15mo	$775,000	$440	42
1490 Long Creek Dr	0.55mi	3/2.0 (-1)	1,600 (-14%)	15mo	$875,000	$547	32
2415 Long Creek Dr	0.74mi	3/2.5 (-1)	1,625 (-13%)	20mo	$1,150,000	$708	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: -9.6%
• Equity multiple: 0.65×
• Total profit: $-93,616
• Equity at exit: $141,499

10-year hold

• IRR: -0.2%
• Equity multiple: 0.98×
• Total profit: $-4,553
• Equity at exit: $82,052

Cash invested: $265,720 (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 →

ZIP-level market 11971

• Home prices YoY: -15.8%
• Active inventory: 79
• Price-to-rent: 8.9×

Monthly cashflow live

• Estimated rent: $8,853 high
• Mortgage (P&I): −$4,977
• Tax from tax record: −$674 /mo · $8,090/yr
• Insurance: −$395
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,859
• Net cashflow: $947

Break-even live

Break-even rent $7,653

Max offer price $949,000

Occupancy floor 84%

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: $237,250
• Closing costs: $28,470
• Reserves months: —
• Total cash needed: —

Rent comps 7 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
275 Maier Pl Southold, NY	3.0	2.0	2000	$10,000	$5.00	43d	1	0.16mi
3400 Youngs Ave Southold, NY	4.0	2.0	2000	$7,500	$3.75	43d	1	0.33mi
425 Old Shipyard Ln Southold, NY	3.0	1.5	1578	$10,000	$6.34	43d	1	0.70mi
215 Leon Rd Southold, NY	4.0	4.0	1800	$6,000	$3.33	43d	1	0.72mi
2845 Hobart Rd Southold, NY	3.0	2.0	1300	$22,000	$16.92	43d	1	0.94mi
13595 Soundview Ave Southold, NY	4.0	2.5	1600	$4,800	$3.00	43d	1	1.24mi
485 Pine Rd Southold, NY	3.0	2.5	2000	$12,000	$6.00	43d	1	1.33mi

Listing history 18 events

1. 2026-06-18
   days on market $949,000 Active 61 DOM
2. 2026-06-17
   days on market $949,000 Active 60 DOM
3. 2026-06-16
   days on market $949,000 Active 59 DOM
4. 2026-06-15
   days on market $949,000 Active 58 DOM
5. 2026-06-13
   days on market $949,000 Active 56 DOM
6. 2026-06-12
   days on market $949,000 Active 55 DOM
7. 2026-06-09
   days on market $949,000 Active 52 DOM
8. 2026-06-08
   days on market $949,000 Active 51 DOM
9. 2026-06-07
   days on market $949,000 Active 50 DOM
10. 2026-06-07
    days on market $949,000 Active 49 DOM
11. 2026-06-04
    days on market $949,000 Active 46 DOM
12. 2026-06-02
    days on market $949,000 Active 45 DOM
13. 2026-06-01
    days on market $949,000 Active 44 DOM
14. 2026-05-31
    days on market $949,000 Active 43 DOM
15. 2026-05-05
    price $949,000 1041-char remark

    Show marketing remark (1041 chars)

    Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage, and a full basement with 8-foot ceilings offering excellent storage and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is just moments from public beaches, scenic trails, wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

16. 2026-04-08
    listed $999,000 Active 1041-char remark

    Show marketing remark (1041 chars)

    Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage, and a full basement with 8-foot ceilings offering excellent storage and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is just moments from public beaches, scenic trails, wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

17. 2005-08-16
    soldstatus $460,000
18. 1999-11-19
    soldstatus $192,500

ⓘ 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: $8,090 · $674/mo
• Projected year-2 tax: $12,064 · $1,005/mo
• Expected delta: +$3,974/yr (+$331/mo · 49.1%)

ⓘ 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 · 20 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $106,233
• − Mortgage interest: −$53,159
• − Property taxes: −$8,090
• − Insurance: −$4,745
• − Repairs & maintenance: −$8,499
• − Management: −$8,499
• − Depreciation: −$27,607
• Taxable loss: −$4,365
• Est. tax savings @ 24.0%: +$1,048
• After-tax cash flow: $12,417/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

+393.0% since first listed

4 events — show timeline

• 2026-05-05 Price Changed $949,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-08 Listed $999,000 OneKey® MLS as Distributed by MLS Grid
• 2005-08-16 Sold (Public Records) $460,000 Public Records
• 1999-11-19 Sold (Public Records) $192,500 Public Records

Property tax history

+2.6%/yr

Latest (2025): $8,090 · +0.0% YoY. Source: county tax records.