74 Chester St · Bridgehampton, NY 11932

$5,995,000

6 bd · 5.5 ba · 5,450 sqft · SingleFamily · 189 Days on market

Built 2026 Excellent condition 0.29 ac lot $1100/sqft · at area comps Est $6012k · at est. ↓ 5% since listing

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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 +14.8/30.0
• Appreciation +10.0/10.0
• ARV discount +7.6/15.0
• Condition / age +4.8/5.0
• DSCR +4.5/10.0
• Schools +4.3/10.0
• 1% rule +4.1/10.0
• Livability +3.1/5.0
• Rent growth +2.5/5.0

Listing remarks MLS

Masterfully built, blending timeless design with modern comforts and expert craftsmanship, creating an undeniable sense of harmony and place, on a lovely and quiet village street, just a block away from Main Street in Bridgehampton- 74 Chester is the perfect Hamptons house. Clad in classic cedar shingles and anchored by a welcoming covered front porch, this home immediately feels like the perfect Hamptons village home. Inside, uplifting natural light pours through expansive windows, illuminating an elegant foyer and dining room. The kitchen supports both everyday living and effortless entertaining, featuring Taj Mahal countertops, 6 burner Bertazzoni range, double wall ovens, drawer microwave, a 48" Sub-Zero refrigerator, two dishwashers, a generous island, and an adjacent scullery/butler's pantry with a wet bar and exceptional storage. A secondary entry leads into the mudroom featuring a convenient dog-washing station. The first floor also includes a lovely private ensuite bedroom. On the second floor we find the primary suite, a serene sanctuary, featuring an energy-efficient electric fireplace, spacious walk-in closet, and a spa-inspired bath. Two additional guest bedrooms share this level, along with a full laundry room with folding stations and ample storage. This level also provides a flexible bonus room, the ideal setting for a home office, playroom, or additional lounge/recreation space and more. The finished lower level extends the living space with two bedrooms that share a hall bath, plus a large open area that would make a great setting for a gym, sauna, media room, game room, or whatever best suits your wishes and lifestyle. This level also includes a second laundry area and an additional refrigerator. The heated two-car garage is equipped with an electric vehicle charger. Designed for tranquil outdoor enjoyment, the heated gunite saltwater pool features stadium steps and a continuous bench seat with four therapeutic jets. Whisper-quiet filtration equipment ensures peaceful poolside relaxation, while the cool foot natural Madras patio stone keeps surfaces comfortable under the sun. Behind the walls, meticulous construction delivers comfort and efficiency with robust, soundproof insulation between all adjacent walls and floors, and steel beam construction. The home is wired for bedside sconces, wall-mounted televisions, and camera-ready security, and is prewired for a whole-house generator. Environmentally conscious features include energy-efficient electric fireplaces, 9" of formaldehyde-free closed-cell attic insulation, and a mechanical room enclosed in concrete that quietly manages six zones of heating and cooling. The indoor hot water is served by an instant/continuous hot water heater with an 80-gallon tank, and the outdoor shower features its own instant/continuous hot water heater, ensuring consistent and continuous hot water for all. All this and more, in a location that rarely has properties come to market.

Key facts

• Covered front porch
• Two dishwashers
• Double wall ovens

Tags

• COVERED FRONT PORCH
• TAJ MAHAL COUNTERTOPS
• 6 BURNER BERTAZZONI RANGE
• DOUBLE WALL OVENS
• 48 SUB ZERO REFRIGERATOR
• TWO DISHWASHERS

What this means for you Summary

Snapshot

• This is a 6-bed/5.5-bath single-family listed at $6.00M. Condition is rated excellent.

Deal economics

• At list price, monthly cash flow is $2k ($20k/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 $5.45M (9.1% below list).
• Recommended offer: $5.28M (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 62/100 on livability (#874 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, schools B; Watch: amenities F, commute F, cost of living F.
• Bridgehampton Union Free School District (rural): math 50% / reading 40% proficiency, ranked #511 of 755 in NY (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 24 active listings in the ZIP; 2 comparable units currently listed for rent nearby; high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $54,506/mo this rent would consume 377% of the median local household income ($174k/yr) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $641k of equity ($41k loan paydown + $600k appreciation (10.0% local appreciation)).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $1.68M cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$1.03M cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 189 days — a 12% lower offer ($5.28M) is reasonable based on typical stale-listing flexibility.

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 $5,275,600 (12.0% below list)

Questions for the listing agent

1. It's been on market 189 days. Have you received any prior offers? Is the seller open to a 12% 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 B-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: 0.91% ✗
• Cap rate: 6.62%
• Cash-on-cash: 1.16%
• DSCR: 1.05
• GRM: 9.2

CMA / ARV

• ARV (median comp): $6,011,997
• List price: $5,995,000
• Delta: -0.28%
• Verdict: FAIR
• Comps: 7 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
15 West Pond Dr	0.50mi	5/5.5 (-1)	5,800 (+6%)	8mo	$7,350,000	$1,267	55

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 25.1%
• Equity multiple: 3.01×
• Total profit: $3,369,644
• Equity at exit: $5,400,771

10-year hold

• IRR: 22.2%
• Equity multiple: 6.86×
• Total profit: $9,843,066
• Equity at exit: $11,646,966

Cash invested: $1,678,600 (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 11932

• Home prices YoY: 2.9%
• Active inventory: 24
• Price-to-rent: 9.2×

Monthly cashflow live

• Estimated rent: $54,506 medium
• Mortgage (P&I): −$31,438
• Tax est. 1.5%: −$7,494 /mo · $89,925/yr
• Insurance: −$2,498
• HOA: −$0
• Vacancy / Maint / Mgmt: −$11,446
• Net cashflow: $1,630

Break-even live

Break-even rent $52,443

Max offer price $5,995,000

Occupancy floor 92%

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: $1,498,750
• Closing costs: $179,850
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
491 Butter Ln Bridgehampton, NY	5.0	5.0	4800	$30,000	$6.25	44d	1	0.73mi
3 Kellis Way Bridgehampton, NY	5.0	5.5	5100	$75,000	$14.71	22d	1	1.05mi

Listing history 15 events

1. 2026-06-18
   days on market $5,995,000 Active 189 DOM
2. 2026-06-17
   days on market $5,995,000 Active 188 DOM
3. 2026-06-16
   days on market $5,995,000 Active 187 DOM
4. 2026-06-15
   days on market $5,995,000 Active 186 DOM
5. 2026-06-13
   days on market $5,995,000 Active 184 DOM
6. 2026-06-09
   days on market $5,995,000 Active 180 DOM
7. 2026-06-08
   days on market $5,995,000 Active 179 DOM
8. 2026-06-07
   days on market $5,995,000 Active 178 DOM
9. 2026-06-04
   days on market $5,995,000 Active 175 DOM
10. 2026-06-03
    days on market $5,995,000 Active 174 DOM
11. 2026-06-02
    days on market $5,995,000 Active 173 DOM
12. 2026-06-01
    days on market $5,995,000 Active 172 DOM
13. 2026-05-31
    days on market $5,995,000 Active 171 DOM
14. 2026-04-14
    price $5,995,000 2992-char remark

    Show marketing remark (2992 chars)

    Masterfully built, blending timeless design with modern comforts and expert craftsmanship, creating an undeniable sense of harmony and place, on a lovely and quiet village street, just a block away from Main Street in Bridgehampton- 74 Chester is the perfect Hamptons house. Clad in classic cedar shingles and anchored by a welcoming covered front porch, this home immediately feels like the perfect Hamptons village home. Inside, uplifting natural light pours through expansive windows, illuminating an elegant foyer and dining room. The kitchen supports both everyday living and effortless entertaining, featuring Taj Mahal countertops, 6 burner Bertazzoni range, double wall ovens, drawer microwave, a 48" Sub-Zero refrigerator, two dishwashers, a generous island, and an adjacent scullery/butler's pantry with a wet bar and exceptional storage. A secondary entry leads into the mudroom featuring a convenient dog-washing station. The first floor also includes a lovely private ensuite bedroom. On the second floor we find the primary suite, a serene sanctuary, featuring an energy-efficient electric fireplace, spacious walk-in closet, and a spa-inspired bath. Two additional guest bedrooms share this level, along with a full laundry room with folding stations and ample storage. This level also provides a flexible bonus room, the ideal setting for a home office, playroom, or additional lounge/recreation space and more. The finished lower level extends the living space with two bedrooms that share a hall bath, plus a large open area that would make a great setting for a gym, sauna, media room, game room, or whatever best suits your wishes and lifestyle. This level also includes a second laundry area and an additional refrigerator. The heated two-car garage is equipped with an electric vehicle charger. Designed for tranquil outdoor enjoyment, the heated gunite saltwater pool features stadium steps and a continuous bench seat with four therapeutic jets. Whisper-quiet filtration equipment ensures peaceful poolside relaxation, while the cool foot natural Madras patio stone keeps surfaces comfortable under the sun. Behind the walls, meticulous construction delivers comfort and efficiency with robust, soundproof insulation between all adjacent walls and floors, and steel beam construction. The home is wired for bedside sconces, wall-mounted televisions, and camera-ready security, and is prewired for a whole-house generator. Environmentally conscious features include energy-efficient electric fireplaces, 9" of formaldehyde-free closed-cell attic insulation, and a mechanical room enclosed in concrete that quietly manages six zones of heating and cooling. The indoor hot water is served by an instant/continuous hot water heater with an 80-gallon tank, and the outdoor shower features its own instant/continuous hot water heater, ensuring consistent and continuous hot water for all. All this and more, in a location that rarely has properties come to market.

15. 2025-12-11
    listed $6,295,000 Active 2992-char remark

    Show marketing remark (2992 chars)

    Masterfully built, blending timeless design with modern comforts and expert craftsmanship, creating an undeniable sense of harmony and place, on a lovely and quiet village street, just a block away from Main Street in Bridgehampton- 74 Chester is the perfect Hamptons house. Clad in classic cedar shingles and anchored by a welcoming covered front porch, this home immediately feels like the perfect Hamptons village home. Inside, uplifting natural light pours through expansive windows, illuminating an elegant foyer and dining room. The kitchen supports both everyday living and effortless entertaining, featuring Taj Mahal countertops, 6 burner Bertazzoni range, double wall ovens, drawer microwave, a 48" Sub-Zero refrigerator, two dishwashers, a generous island, and an adjacent scullery/butler's pantry with a wet bar and exceptional storage. A secondary entry leads into the mudroom featuring a convenient dog-washing station. The first floor also includes a lovely private ensuite bedroom. On the second floor we find the primary suite, a serene sanctuary, featuring an energy-efficient electric fireplace, spacious walk-in closet, and a spa-inspired bath. Two additional guest bedrooms share this level, along with a full laundry room with folding stations and ample storage. This level also provides a flexible bonus room, the ideal setting for a home office, playroom, or additional lounge/recreation space and more. The finished lower level extends the living space with two bedrooms that share a hall bath, plus a large open area that would make a great setting for a gym, sauna, media room, game room, or whatever best suits your wishes and lifestyle. This level also includes a second laundry area and an additional refrigerator. The heated two-car garage is equipped with an electric vehicle charger. Designed for tranquil outdoor enjoyment, the heated gunite saltwater pool features stadium steps and a continuous bench seat with four therapeutic jets. Whisper-quiet filtration equipment ensures peaceful poolside relaxation, while the cool foot natural Madras patio stone keeps surfaces comfortable under the sun. Behind the walls, meticulous construction delivers comfort and efficiency with robust, soundproof insulation between all adjacent walls and floors, and steel beam construction. The home is wired for bedside sconces, wall-mounted televisions, and camera-ready security, and is prewired for a whole-house generator. Environmentally conscious features include energy-efficient electric fireplaces, 9" of formaldehyde-free closed-cell attic insulation, and a mechanical room enclosed in concrete that quietly manages six zones of heating and cooling. The indoor hot water is served by an instant/continuous hot water heater with an 80-gallon tank, and the outdoor shower features its own instant/continuous hot water heater, ensuring consistent and continuous hot water for all. All this and more, in a location that rarely has properties come to market.

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

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 3 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $654,070
• − Mortgage interest: −$335,813
• − Property taxes: −$89,925
• − Insurance: −$29,975
• − Repairs & maintenance: −$52,326
• − Management: −$52,326
• − Depreciation: −$174,400
• Taxable loss: −$80,694
• Est. tax savings @ 24.0%: +$19,367
• After-tax cash flow: $38,921/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 · 12 photos

Excellent 95/100 None rehab

This pristine new construction in Bridgehampton is move-in ready with excellent condition and modern design, making it an ideal investment property.

Value-add opportunities

• Both landscaping — enhances curb appeal and adds value
• Both interior paint — fresh paint can make a home more appealing
• Both window treatments — improves energy efficiency and aesthetics

Renovation cost estimate screening

Value-add ROI direction

• Both landscaping — enhances curb appeal and adds value ↑
• Both interior paint — fresh paint can make a home more appealing ↑
• Both window treatments — improves energy efficiency and aesthetics ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Bridgehampton Union Free School District
• NCES district ID: 3605370
• Math proficiency: 50% ▼ -10.00%
• Reading proficiency: 40% ▼ -10.00%
• Median HH income: $69,915
• Composite: 42.79/100
• National rank: #6761
• State rank: #511 of 755 in NY

Livability — Bridgehampton

• Score: 62/100
• State rank: #874
• US rank: #16891

Category grades

Amenities F Commute F Cost of living F Crime A+ Employment A+ Housing B- Health & safety F User ratings A

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Bridgehampton, NY
• County: Suffolk County · 679,920 people
• City population: 725
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 725
• Household income: $173,672
• Rent vs Own: 10.7% rent · 89.3% own

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 (68%)
• Race & ethnicity: White 68% Hispanic / Latino 22% Black 10% Two or more races 6%
• Hispanic origin (detail): Mexican 12% Dominican 10%
• Common ancestry: Italian 5% Romanian 3% Scotch-Irish 3%
• Foreign-born: 32% · Canada, China
• Languages at home: 71% English-only · Spanish 17% Russian/Polish/Slavic 6% French/Haitian/Cajun 6%

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: ▲ 15.37%
• Current HPI: 546.5294
• Rent YoY: —
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• 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

-4.8% since first listed

2 events — show timeline

• 2026-04-14 Price Changed $5,995,000 OneKey® MLS as Distributed by MLS Grid
• 2025-12-11 Listed $6,295,000 OneKey® MLS as Distributed by MLS Grid