Pending

$1,299,000

Est. $8,512/mo —

•

2,200

sq ft

4408 Old North Rd, Southold, NY 11971

About this home

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!

Single-familyProperty Type

2003Year Built

200 acresLot Size

$590Price/Sq.Ft.

Listing by Kristy Naddell • Douglas Elliman Real Estate

Contact: 631-354-8100

Listing updated: Oct 8, 2026 at 03:04pm

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #1023884

Payment calculator

$8,512 per month

Principal and interest$7,266

Property taxes

$943

HOA dues

Home insurance

$303

Utilities

Add

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Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN FRI, 11AM TO 1PM
$2,700,000
4 beds2.5 baths2,042 sq ft
6 Turtle Pond Rd, Southampton, NY 11968
Listing by Corcoran
OPEN FRI, 5:30PM TO 7PM
$1,745,000
4 beds3.5 baths3,908 sq ft
22 Tuthills Ln, Jamesport, NY 11947
Listing by Douglas Elliman Real Estate
OPEN SAT, 11AM TO 1PM
$999,000
4 beds3.5 baths3,000 sq ft
Main Bayview Main Bayview, Southold, NY 11971
Listing by Corcoran SRG Residential
OPEN SAT, 12PM TO 2PM
$9,600,000
4 beds5.5 baths2,670 sq ft
311 Main St, Sag Harbor, NY 11963
Listing by Douglas Elliman Real Estate
OPEN SAT, 12PM TO 2PM
$2,698,000
4 beds4 baths3,035 sq ft
1430 Bay Haven Ln, Southold, NY 11971
Listing by Compass Greater NY LLC
OPEN SAT, 12PM TO 2PM
$1,149,999
3 beds1.5 baths1,775 sq ft
2000 Westphalia Rd, Mattituck, NY 11952
Listing by Keller Williams Realty Elite
OPEN SAT, 1PM TO 3PM
$3,200,000
6 beds6.5 baths4,760 sq ft
1355 Little Peconic Bay Rd, Cutchogue, NY 11935
Listing by Corcoran
OPEN SAT, 1PM TO 2:30PM
$1,200,000
3 beds2 baths2,100 sq ft
3825 Stars Rd, East Marion, NY 11939
Listing by Corcoran
OPEN SAT, 1PM TO 3PM
$2,350,000
3 beds3.5 baths2,700 sq ft
860 Hillcrest Dr, Orient, NY 11957
Listing by Compass Greater NY LLC
OPEN SAT, 3PM TO 4:30PM
$795,000
3 beds1.5 baths2,000 sq ft
29400 County Road 48, Peconic, NY 11958
Listing by Corcoran

Around this home

Schools

K - 12
Preschool & daycare

Southold Elementary School

Public K-6 • Assigned • 1.4mi

6/10

Southold Junior Senior High School

Public 7-12 • Assigned • 1.4mi

6/10

Provided by GreatSchools

About North

Fork

North Fork, located between Riverhead and Greenport, is a coastal and agricultural Calverton neighborhood with working vineyards and wide-open bayfront views. The mood concentrates around the Sound Avenue corridor near the Calverton hamlet center, where farm stands, tasting rooms, and low-key eateries set a weekend rhythm. Architectural character leans to shingled cottages, ranch homes, and barn-like outbuildings tied to the area’s farming roots. Macari Vineyards, Jamesport Farm Brewery, and Harbes Family Farm act as local pillars for tastings, seasonal events, and market-style shopping. Peconic Bay and the Long Island Sound frame the landscape with beaches, marinas, and long, flat roads made for cycling. The pace stays rural, with small clusters of storefronts separated by fields and rows of vines.

Provided by Walk Score and Local Logic

Offer insights

4408 Old North Rd · $1,299,000

Strong offer

$1.29M and above

75% chance or better to win

Why $1.29M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 31 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
First-floor bedroom
Ceiling fans
Eat-in kitchen
Formal dining
Granite and stone counters
Storage
Walk-in closet(s)

Bedrooms
First-floor bedroom included

Bathrooms
2 full bathrooms
1 half bathroom

Kitchen
Microwave
Oven
Refrigerator
Granite and stone counters

Laundry & utility
Washer
Dryer
Laundry located inside and in basement

Flooring
Hardwood floors

Heating & cooling
Propane heating
Baseboard heating
No central cooling

Sale and tax history for 4408 Old North Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2026

$10,323

$2,100 + $5,100

$7,200

2025

$10,323 (+2.9%)

$2,100 + $5,100

$7,200

2024

$10,030

$2,100 + $5,100

$7,200

2023

$10,038 (+2.9%)

$2,100 + $5,100

$7,200

2022

$9,751

$2,100 + $5,100

$7,200

2021

$9,751 (+3.6%)

$2,100 + $5,100

$7,200

2020

$9,413 (+1.2%)

$2,100 + $5,100

$7,200

2019

$9,306 (+2.8%)

$2,100 + $5,100

$7,200

2018

$9,057 (+2.3%)

$2,100 + $5,100

$7,200

2017

$8,854 (+0.9%)

$2,100 + $5,100

$7,200

2016

$8,772 (+4.9%)

$2,100 + $5,100

$7,200

2015

$8,360 (+3.9%)

$2,100 + $5,100

$7,200

2014

$8,049 (+0.6%)

$2,100 + $5,100

$7,200

2013

$7,998 (−17.8%)

$2,100 + $5,100

$7,200

2012

$9,734 (+1.9%)

$2,100 + $6,800

$8,900

2011

$9,551 (+2.6%)

$2,100 + $6,800

$8,900

2010

$9,306 (+3.4%)

$2,100 + $6,800

$8,900

2009

$9,003

$2,100 + $6,800

$8,900

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

2 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Suffolk County

APN

1000055000200008009

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 21, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 90° expected this year, 19 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Southold, NY • 11971

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

89/ 100

Very good sunlight

Sunscore

This home ranks in the top 24% for direct sun exposure in Southold. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.5 hrs

6.1 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 4408 Old North Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $910,000 and $1,295,000.

Nearby comparable homes

The Redfin Estimate uses 5 recent nearby sales, priced between $910K to $1.3M.

SOLD JUL 28, 2026
$910,000 Last sold price
3 beds2 baths1,500 sq ft
6625 Hortons Ln, Southold, NY 11971
Listing by Signature Premier Properties
$17/sq ft
smaller lot
37 years older
SOLD SEP 18, 2026
$942,500 Last sold price
5 beds2 baths2,238 sq ft
230 Booth Rd, Southold, NY 11971
Listing by Daniel Gale Sothebys Intl Rlty
$169/sq ft
smaller lot
36 years older
SOLD FEB 4, 2026
$1,175,000 Last sold price
4 beds2.5 baths2,400 sq ft
1475 Oaklawn Ave, Southold, NY 11971
Listing by Daniel Gale Sothebys Intl Rlty
$100/sq ft
smaller lot
37 years older
SOLD DEC 6, 2025
$1,295,000 Last sold price
4 beds3 baths1,740 sq ft
1605 Washington Ave, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
$154/sq ft
smaller lot
9 years older
SOLD JUN 16, 2026
$940,000 Last sold price
3 beds1.5 baths1,800 sq ft
506 5th St, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
$68/sq ft
smaller lot
135 years older

This home is pending

The seller has accepted an offer, and this property is now .

Have questions?

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$6,000,000

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New listings for sale in 11971

$2,150,000

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OPEN SAT, 11AM TO 1PM

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Details provided by OneKey® MLS as Distributed by MLS Grid and may not match the public record. Learn more.

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