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!
Pending
Price cut: $86K (9/1)
$1,299,000
4408 Old North Rd, Southold, NY 11971
4beds
2,200sqft
Single Family Residence
Built in 2001
2 Acres Lot
$1,280,100 Zestimate®
$590/sqft
$-- HOA
What's special
Abundant natural lightQuintessential cedar shake farmhouseScreened-in side porchUpdated bathHardwood floors throughoutJacuzzi tubWood-burning fireplace
- 92 days
- 1,421
- 64
Zillow last checked:
Listed by:
Douglas Elliman Real Estate 631-354-8100,
Kristy B. Naddell - Associate Real Estate Broker 631-905-8584
Source: Out East,MLS#: 396741
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Family Room, Office
Features
- Basement: Yes
- Has fireplace: Yes
Interior area
- Total structure area: 2,200
- Total interior livable area: 2,200 sqft
Property
Parking
- Parking features: None
Features
- Stories: 2
- Pool features: Room for a Pool
Lot
- Size: 2 Acres
Details
- Parcel number: 1000055000200008009
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 2001
Community & HOA
Community
- Features: Room for a Tennis Court
Location
- Region: Southold
Financial & listing details
- Price per square foot: $590/sqft
- Tax assessed value: $1,309,091
- Date on market: 7/13/2026
- Lease term: Contact For Details
Estimated market value
$1,280,100
$1.22M - $1.34M
$6,560/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/8/2026 | Pending sale | $1,299,000$590/sqft |
Source: | ||
| 9/1/2026 | Price change | $1,299,000-6.2%$590/sqft |
Source: | ||
| 7/13/2026 | Listed for sale | $1,385,000+1219%$630/sqft |
Source: Out East #396741 Report a problem | ||
| 10/29/1999 | Sold | $105,000$48/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $7,200 |
| 2024 | -- | $7,200 |
| 2023 | -- | $7,200 |
| 2022 | -- | $7,200 |
| 2021 | -- | $7,200 |
| 2020 | -- | $7,200 |
| 2019 | -- | $7,200 |
| 2018 | -- | $7,200 |
| 2017 | $9,057 | $7,200 |
| 2016 | -- | $7,200 |
| 2015 | -- | $7,200 |
| 2014 | -- | $7,200 |
| 2013 | -- | $7,200 |
| 2012 | -- | $7,200 -19.1% |
| 2011 | -- | $8,900 |
| 2010 | -- | $8,900 |
| 2009 | -- | $8,900 |
| 2008 | -- | $8,900 |
| 2007 | $8,536 +19.8% | $8,900 |
| 2005 | $7,127 +4.9% | $8,900 |
| 2004 | $6,796 +4.4% | $8,900 |
| 2003 | $6,511 -3.2% | $8,900 |
| 2002 | $6,726 | $8,900 |
| 2001 | -- | $8,900 |
Find assessor info on the county website




