600 Highwood Rd · Southold, NY 11971

$999,999

2 bd · 1.0 ba · 1,954 sqft · SingleFamily · 23 Days on market

Built 1976 1.37 ac lot $512/sqft · 19% below area Est $1228k · 19% 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 +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

Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

Key facts

• 1.37 acre lot
• 2 garage spots
• Built 1976

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $1000k.

Deal economics

• At list price, monthly cash flow is $8k ($102k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($19k rent vs $1000k).
• Recommended offer: $985k (1.5% below list) — sets the bar for market timing.
• Cap rate 16.5% 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+, 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; 4 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 75% 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 $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 ~4 years — after that, you're playing with house money.

Negotiation context

• It's been on market 23 days — a 2% lower offer ($985k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 7y 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 $550k; list at $1000k implies a 82% gain — meaningful room to come down on a strong offer.

Recommended offer $984,999 (1.5% below list)

Questions for the listing agent

1. Built in 1976 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
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. 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.
5. 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.
6. 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: 1.88% ✓
• Cap rate: 16.45%
• Cash-on-cash: 36.29%
• DSCR: 2.61
• GRM: 4.4

CMA / ARV

• ARV (median comp): $1,227,871
• List price: $999,999
• Delta: -18.56%
• 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
800 Goose Creek Ln	0.51mi	3/3.0 (+1)	2,032 (+4%)	7mo	$1,250,000	$615	51
1100 Beachwood Ln	0.64mi	3/2.0 (+1)	2,000 (+2%)	21mo	$1,807,250	$904	40
355 Cedar Dr	0.21mi	3/2.0 (+1)	2,230 (+14%)	23mo	$920,000	$413	38
6060 Main Bayview Rd	0.53mi	3/2.0 (+1)	1,694 (-13%)	12mo	$1,375,000	$812	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: 32.0%
• Equity multiple: 2.35×
• Total profit: $377,211
• Equity at exit: $149,103

10-year hold

• IRR: 39.1%
• Equity multiple: 4.65×
• Total profit: $1,022,684
• Equity at exit: $86,462

Cash invested: $280,000 (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: 4.4×

Monthly cashflow live

• Estimated rent: $18,764 medium
• Mortgage (P&I): −$5,244
• Tax from tax record: −$695 /mo · $8,339/yr
• Insurance: −$417
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,940
• Net cashflow: $8,468

Break-even live

Break-even rent $8,045

Max offer price $999,999

Occupancy floor 50%

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: $250,000
• Closing costs: $30,000
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
1854 N Bayview Rd Southold, NY	2.0	2.5	1750	$15,000	$8.57	43d	1	0.60mi
1265 Brigantine Dr Southold, NY	3.0	2.0	1750	$9,000	$5.14	43d	1	0.86mi
2662 Paradise Shores Rd Southold, NY	3.0	1.5	1300	$25,000	$19.23	24d	1	1.04mi
2845 Hobart Rd Southold, NY	3.0	2.0	1300	$22,000	$16.92	43d	1	1.34mi

Listing history 8 events

1. 2026-05-09
   status Pending 1525-char remark

   Show marketing remark (1525 chars)

   Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

2. 2026-03-20
   listed $999,999 Active 1525-char remark

   Show marketing remark (1525 chars)

   Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

3. 2020-08-24
   soldstatus $550,000
4. 2020-08-11
   soldstatus $550,000
5. 2020-07-27
   soldstatus $550,000 Closed 520-char remark

   Show marketing remark (520 chars)

   Wonderful A-Frame style home with large dramatic windows on a beautiful, well treed half acre lot! Soaring 2 story cathedral ceiling Living Room with sliders to deck, builder's own house with beautifully finished open rafter ceilings, 2 bedrooms, huge 3rd bedroom 2nd story loft with storage. Great lower level with full bath, laundry room and 2-car garage built-in. Convenient access to Southold bay beaches., Additional information: Appearance:Pristine,Business Located At:,Rental Income:,Separate Hotwater Heater:Y

6. 2020-04-27
   price $579,000 520-char remark

   Show marketing remark (520 chars)

   Wonderful A-Frame style home with large dramatic windows on a beautiful, well treed half acre lot! Soaring 2 story cathedral ceiling Living Room with sliders to deck, builder's own house with beautifully finished open rafter ceilings, 2 bedrooms, huge 3rd bedroom 2nd story loft with storage. Great lower level with full bath, laundry room and 2-car garage built-in. Convenient access to Southold bay beaches., Additional information: Appearance:Pristine,Business Located At:,Rental Income:,Separate Hotwater Heater:Y

7. 2020-02-01
   price $599,000 520-char remark

   Show marketing remark (520 chars)

   Wonderful A-Frame style home with large dramatic windows on a beautiful, well treed half acre lot! Soaring 2 story cathedral ceiling Living Room with sliders to deck, builder's own house with beautifully finished open rafter ceilings, 2 bedrooms, huge 3rd bedroom 2nd story loft with storage. Great lower level with full bath, laundry room and 2-car garage built-in. Convenient access to Southold bay beaches., Additional information: Appearance:Pristine,Business Located At:,Rental Income:,Separate Hotwater Heater:Y

8. 2019-10-11
   listed $799,000 New 520-char remark

   Show marketing remark (520 chars)

   Wonderful A-Frame style home with large dramatic windows on a beautiful, well treed half acre lot! Soaring 2 story cathedral ceiling Living Room with sliders to deck, builder's own house with beautifully finished open rafter ceilings, 2 bedrooms, huge 3rd bedroom 2nd story loft with storage. Great lower level with full bath, laundry room and 2-car garage built-in. Convenient access to Southold bay beaches., Additional information: Appearance:Pristine,Business Located At:,Rental Income:,Separate Hotwater Heater:Y

ⓘ 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: $8,339 · $695/mo
• Projected year-2 tax: $12,620 · $1,052/mo
• Expected delta: +$4,280/yr (+$357/mo · 51.3%)

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

Taxation est. · year 1

• Rental income: $225,165
• − Mortgage interest: −$56,015
• − Property taxes: −$8,339
• − Insurance: −$5,000
• − Repairs & maintenance: −$18,013
• − Management: −$18,013
• − Depreciation: −$29,091
• Taxable income: $90,693
• Est. tax owed @ 24.0%: −$21,766
• After-tax cash flow: $79,846/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

+25.2% since first listed

8 events — show timeline

• 2026-05-09 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-03-20 Listed $999,999 OneKey® MLS as Distributed by MLS Grid
• 2020-08-24 Sold (Public Records) $550,000 Public Records
• 2020-08-11 Sold (Public Records) $550,000 Public Records
• 2020-07-27 Sold (MLS) $550,000 OneKey® MLS as Distributed by MLS Grid
• 2020-04-27 Price Changed $579,000 OneKey® MLS as Distributed by MLS Grid
• 2020-02-01 Price Changed $599,000 OneKey® MLS as Distributed by MLS Grid
• 2019-10-11 Listed $799,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+3.4%/yr

Latest (2025): $8,339 · +0.0% YoY. Source: county tax records.