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3500 Pine Neck Road, Southold, NY, 11971

3beds
3baths
2,000sqft
$1,750,000
$875price/sqft
$12,468/moest. monthly cost
$498,720/yrincome needed

About This Home

Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection, honoring the home’s original character while reflecting a level of care and stewardship that is exceptionally rare. From period details and time-honored construction methods, this residence stands as a living testament to Southold’s rich heritage. The interior offers a gracious and functional layout anchored by an enclosed brick porch, a large formal dining room, a newly renovated expansive eat-in kitchen, a classic parlor room, and a comfortable living room—all thoughtfully arranged for both elegant entertaining and everyday living. Adding to the home’s exceptional character are three stunning fireplaces, each serving as a striking focal point and a reminder of the home’s historic craftsmanship. The residence features three bedrooms and two and a half bathrooms. The first floor includes the primary bedroom and two full bathrooms, allowing for convenient main-level living, while the second floor offers two additional bedrooms and a half bath, providing privacy and flexibility for guests . Outside, the property includes a two-car detached garage and is set on a quiet, peaceful lot in close proximity to Southold Bay, offering the serenity of North Fork living with easy access to the water and surrounding natural beauty. With official historic status, this home carries both distinction and prestige—appealing to discerning buyers who value provenance, integrity, and timeless elegance. Opportunities to own a property of this caliber, condition, and historical significance are exceedingly rare. This is more than a home—it is the stewardship of a true legacy. Lastly, the final photos on this listing demonstrate the secret hatch in the floor and each person to visit between 1750-1800's carved their names into the china cabinet paneling. So interesting to explore all the names. ** NOTE: The legal address for this home is 3500. However, the number on the post outside the home is 3290. CPF Tax/The Peconic Bay Region Community Preservation Fund applies to this listing.**

Getting Around

9
WalkingCar-Dependent
0
TransitVery Limited Transit
30
BikeSomewhat Bikeable

Schools

6/10

Construction

Condition

  • Year built: 1720

Materials

  • Construction materials: Shingle Siding

Type & Style

  • Home type: SingleFamily
  • Architectural style: Exp Cape
  • Property subType: Single Family Residence,Residential

Interior

Appliances

  • Appliances included: Gas Cooktop,Gas Oven,Gas Range,Refrigerator
  • Laundry features: Washer/Dryer Hookup

Basement

  • Has basement: Yes
  • Basement: Crawl Space

Bathroom1

  • Level: First

Bathroom2

  • Level: Second

Bedroom1

  • Level: First

Bedroom2

  • Level: Second

Bedroom3

  • Level: Second

Bedrooms & Bathrooms

  • Bedrooms: 3
  • Bathrooms: 3
  • Full bathrooms: 2
  • 1/2 bathrooms: 1

Features

  • First Floor Bedroom,Eat-in Kitchen,Formal Dining,Natural Woodwork,Original Details,Primary Bathroom
  • Number of fireplaces: 3
  • Fireplace: Yes
  • Attic: Partial

Heating & Cooling

  • Heating features: Baseboard,Oil,See Remarks
  • Cooling features: Central Air

Interior Area

  • Total structure area: 2,000
  • Total interior livable area: 2,000 sqft

Kitchen

  • Level: First

Living Room

  • Level: First

Property

Details

  • Parcel number: 1000070001200003000
  • Special condition: None

Lot

  • Lot size: 0.57 Acres
  • Features: Back Yard,Front Yard,Historic District,Sprinklers In Front,Sprinklers In Rear

Parking

  • Total spaces: 2
  • Parking features: Detached,Driveway
  • Has garage: Yes
  • Attached garage spaces: 2
  • Covered spaces: 2
  • Has uncovered spaces: Yes

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Coastal Flooding
    Coastal FloodingRelatively High
  • Hurricane
    HurricaneModerate
  • Winter Weather
    Winter WeatherModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Coastal Flooding
Hurricane
Winter Weather
Tsunami

FEMA Declared Disasters in Suffolk County and New York

Flood
Severe Storm
Snowstorm
Straight Line Winds
Tropical Storm
Winter Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $8,848$106,176
Home Insurance *$928$11,136
Property Taxes $2,362$28,344
Electricity $330$3,966
Total$12,468$149,616
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$427,474/yr
40% on housing$374,040/yr
45% on housing$332,480/yr

New York FAIR Plan Programs

New York Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 20,669Commercial: 1,556
Total Premiums$32.27M
Total Exposure$7.63B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 4.6%
4.6%
0%30.0%
Electricity Growth Rate10-year average: 7.1%
7.1%
0%15.0%
Property Taxes Growth Rate2-year average: 1.0%
1.0%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$875This listing

vs Other Active Listings

Avg $/sqft

ZIP 11971$811
Suffolk County$724

vs Homes Sold Last Month

Median $/sqft

ZIP 11971$542
Suffolk County$412

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-01-22Listed for sale$1,999,000
1998-12-11Sold$280,000

For Sale by Agent

AgentTrish Bergin
BrokerageSignature Premier Properties

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