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4408 Old North RoadSouthold, NY 11971

For Sale

$1,385,000

Smart Buyer Rebate $13,850

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

Listed by Kristy B. Naddell

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Douglas Elliman Real Estate

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631-354-8100

Last updated July 18, 2026

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Source: OneKey #1023884

Listing Facts

  • TypeSingle-family
  • NeighborhoodSouthold
  • Bedrooms4
  • Bathrooms3
  • Days on Prevu18
  • Taxes$11,183/year
  • Size2,200 sqft
  • Price per sqft$630

Amenities

  • Private Outdoor Space
  • Washer/Dryer
  • Parking

Location

Mortgage Calculator

Listing History

07/13/2026
Listed by Douglas Elliman Real Estate
$1,385,000

Property Details for 4408 Old North Road

Exterior

Construction

  • Property Condition: Actual
  • Year Built: 2003
  • Architectural Style: Traditional
  • Construction Materials: Frame

Features

  • Other Structures: Shed(s)
  • Patio And Porch Features: Covered, Deck, Patio, Porch, Wrap Around

Measurements

  • Building Area Units: Square Feet
  • Lot Features: See Remarks
  • Lot Size Acres: 2.00
  • Lot Size Square Feet: 8,712,000

Financial

Taxes

  • Parcel Number: 1000-055-00-02-00-008-009
  • Tax Annual Amount: $11,183.00
  • Tax Assessed Value: $7,200.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Dryer, Microwave, Oven, Refrigerator, Washer
  • Fireplace Features: Living Room, Wood Burning
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Hardwood
  • Interior Features: First Floor Bedroom, Ceiling Fan(s), Eat-in Kitchen, Formal Dining, Granite Counters, Stone Counters, Storage, Walk-In Closet(s)

Measurements

  • Living Area: 2,200
  • Living Area Source: CubiCasa

Rooms

  • Basement: Bilco Door(s), Full, Storage Space, Unfinished
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 4
  • Rooms Total: 8

Other

Location

  • Tax Block: 2
  • Tax Lot: 8.9

Parking

Parking

  • Parking Features: Private

Schools

Elementary School

  • Elementary School: Southold Elementary School
  • Elementary School District: Southold

High School

  • High School: Southold Junior-Senior High School
  • High School District: Southold

Middle or Junior School

  • Middle Or Junior School: Southold Junior-Senior High School
  • Middle Or Junior School District: Southold

Utilities

Equipment

  • Heating: Baseboard, Propane
  • Laundry Features: In Basement, Inside
  • Sewer: Cesspool
  • Utilities: Cable Connected, Electricity Connected, Propane, Water Connected
  • Water Source: Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 3 bathrooms in this single-family home at 4408 Old North Road.

What schools are nearby to 4408 Old North Road?

Nearby schools include the Southold Elementary School, Southold Junior-Senior High School, and Southold Junior-Senior High School.

What are the annual taxes for 4408 Old North Road?

Annual taxes for this single-family home are estimated at $11,183.

How does 4408 Old North Road compare to other single-family homes in Southold?

This single-family home is listed 32% below the average price for single-family homes in Southold and has been on the market for 99 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,200 sqft.

4408 Old North Road is a 4-bedroom, 3-bath single-family home for sale in Southold NY 11971. On Prevu for 18 days at $1,385,000. This residence features 2,200 square feet of living space, located in Southold. The median listing price for single-family homes in this area is $1,485,000. Nearby schools include Southold Elementary School, Southold Junior-Senior High School, and Southold Junior-Senior High School. Additional amenities include private outdoor space, parking, and washer/dryer. View other single-family home listings in Suffolk County.

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.