NEW 8 HRS AGO

For sale

$1,350,000

Est. $8,385/mo —

•

2,400

sq ft

39595 Main Rd, Orient, NY 11957

About this home

This Traditional 4-bedroom, 2.5-bath home sits near Orient State Park and the Cross Sound Ferry. The private, landscaped backyard has a pool and patio, plus a large deck with glass doors to the open-plan kitchen and family room, making it ideal for entertaining. The first floor is completed with a private living room, a dining room, laundry, and a powder room. Upstairs, the primary ensuite has a full bath with views of the backyard and pool. Three more bedrooms and a full bath complete the second floor. The finished lower level offers a large recreation space. This home is ideal year-round living or for enjoying North Fork summers.

Single-familyProperty Type

2005Year Built

0.45 acresLot Size

$563Price/Sq.Ft.

2 car garageParking

Listing by Janet Markarian • Daniel Gale Sothebys Intl Rlty

Contact: 631-477-0013

Listing updated: Oct 16, 2026 at 02:08pm

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #1061683

Payment calculator

$8,385 per month

Principal and interest$7,459

Property taxes

$544

HOA dues

Home insurance

$383

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN SAT TO 2PM
$1,189,000
4 beds3.5 baths3,000 sq ft
25105 Main Rd N, Orient, NY 11957
Listing by Douglas Elliman Real Estate
OPEN SAT, 11AM TO 1PM
$1,890,000
3 beds2.5 baths1,690 sq ft
845 Orchard St, Orient, NY 11957
Listing by Daniel Gale Sothebys Intl Rlty
OPEN SAT, 11AM TO 12:30PM
$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 2PM3D WALKTHROUGH
$699,000
3 beds1 bath— sq ft
430 Grove Rd, Southold, NY 11971
Listing by Compass Greater NY LLC
OPEN SAT, 12PM TO 2PM
$1,575,000
4 beds3.5 baths3,766 sq ft
21-1 Haywagon Dr, Old Lyme, CT 06371
OPEN SAT, 12PM TO 2PM
$699,000
2 beds1 bath1,200 sq ft
216 Broad St, Greenport, NY 11944
Listing by Compass Greater NY LLC
OPEN SAT, 12PM TO 2PM
$1,675,000
3 beds3.5 baths3,457 sq ft
225 Marion Ln, East Marion, NY 11939
Listing by Howard Hanna Coach
OPEN SAT, 1PM TO 2:30PM
$1,349,000
3 beds2 baths1,232 sq ft
66 Sycamore Dr, East Hampton, NY 11937
Listing by Brown Harris Stevens Hamptons
OPEN SUN, 11AM TO 12:30PM
$2,795,000
7 beds6.5 baths4,562 sq ft
1050 Tasker Ln, Greenport, NY 11944
Listing by Douglas Elliman Real Estate
OPEN SUN, 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

Around this home

Schools

K - 12
Preschool & daycare

Oysterponds Elementary School

Public PreK-6 • Assigned • 2.8mi

4/10

Greenport High School

Public 7-12 • Assigned • 7.3mi

5/10

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

Market insights

39595 Main Rd · $1,350,000

DAYS ON MARKET

The average home goes pending in 31 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

LIST PRICE

Median sale price in this area is $733,483. (46% lower than this home)

PRICE DROP

15% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Formal dining
Kitchen island
Primary bathroom
Finished full basement

Bathrooms
2 full bathrooms
1 half bathroom

Kitchen
Dishwasher
Microwave
Range
Refrigerator

Laundry & utility
Washer
Dryer
Washer/dryer hookup

Heating & cooling
Forced-air heating
Central air conditioning

Sale and tax history for 39595 Main Rd

Sale History
Tax History

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #1061683

Oct 16, 2026

Listed

$1,350,000

$563/sq ft

ONEKEY #962793

Jun 25, 2026

Rental Removed

$25,000

$10/sq ft

Feb 20, 2026

Listed for Rent

$25,000

$10/sq ft

ONEKEY #877059

Oct 1, 2025

Rental Removed

$12,000

$5/sq ft

Jun 14, 2025

Listed for Rent

$12,000

$5/sq ft

Public Records

Mar 26, 2021

Sold

$755,000

$315/sq ft

OneKey® MLS as Distributed by MLS Grid #L3200387

Nov 6, 2020

Sold

$755,000

$315/sq ft

Sep 15, 2020

Listing Removed

—

Feb 16, 2020

Listed

$750,000

$313/sq ft

In the heart of Orient's country setting rests this traditional 4 bed 2.5 bath home.Enter property via horseshoe d-way leading to large front porch which flows into inviting foyer, FDR, den & open EIK/LR combo. Large deck off rear of the house enjoys privacy of meticulously landscaped yard compliments of established 10' privet.Second level features 3 guest bedrooms, 1 FB & Master En-suite with additional private bath.Commercial Marina and Orient State Park just around the corner. Room for pool!, Additional information: Appearance:Pristine,Business Located At:,Rental Income:

Public Records

Nov 20, 2007

Sold

$517,250

$216/sq ft

Public Records

Jan 8, 2004

Sold

$170,000

$71/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$6,524

$700 + $5,900

$6,600

2025

$6,524 (+3.2%)

$700 + $5,900

$6,600

2024

$6,320 (+20.1%)

$700 + $5,900

$6,600

2023

$5,261 (+0.8%)

$700 + $5,300

$6,000

2022

$5,222

$700 + $5,300

$6,000

2021

$5,222 (+4.7%)

$700 + $5,300

$6,000

2020

$4,988 (−5.4%)

$700 + $5,200

$5,900

2019

$5,273 (+2.2%)

$700 + $5,200

$5,900

2018

$5,161 (+1.7%)

$700 + $5,200

$5,900

2017

$5,075 (−1.6%)

$700 + $5,200

$5,900

2016

$5,157 (+5.4%)

$700 + $5,200

$5,900

2015

$4,893 (+2.6%)

$700 + $5,200

$5,900

2014

$4,771 (+1.6%)

$700 + $5,200

$5,900

2013

$4,698 (+1.8%)

$700 + $5,200

$5,900

2012

$4,616 (+1.3%)

$700 + $5,200

$5,900

2011

$4,556 (+2.0%)

$700 + $5,200

$5,900

2010

$4,465 (−3.4%)

$700 + $5,200

$5,900

2009

$4,624

$700 + $5,200

$5,900

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.45 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Suffolk County

APN

1000015000800016000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 21, 2026.

Climate risks

3/10 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 92° expected this year, 18 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

5/10 Air Factor

6 unhealthy days expected this year, 8 days in 30 years

Provided by First Street

Historical weather

Orient, NY • 11957

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

88/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Orient. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.7 hrs

6.1 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 39595 Main Rd

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

Nearby homes have recently sold between $1,215,000 and $1,500,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.2M to $1.5M.

SOLD APR 25, 2026
$1,470,000 Last sold price
5 beds3.5 baths2,400 sq ft
155 Bridge St, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
$50/sq ft
smaller lot
16 years newer
SOLD MAY 8, 2026
$1,260,000 Last sold price
4 beds2 baths2,075 sq ft
275 Munn Ln, Orient, NY 11957
Listing by Signature Premier Properties
$44/sq ft
larger lot
65 years older
SOLD SEP 29, 2026
$1,215,000 Last sold price
3 beds2 baths1,600 sq ft
575 Willow Dr, East Marion, NY 11939
Listing by Corcoran
$196/sq ft
larger lot
20 years older
SOLD JUN 18, 2026
$1,295,000 Last sold price
3 beds2 baths1,800 sq ft
3190 The Long Way Ln, East Marion, NY 11939
Listing by Compass Greater NY LLC
$156/sq ft
larger lot
17 years older
SOLD AUG 12, 2026
$1,415,000 Last sold price
4 beds2.5 baths2,300 sq ft
619 Bailey Ave, Greenport, NY 11944
Listing by Daniel Gale Sothebys Intl Rlty
$52/sq ft
smaller lot
80 years older
BOUGHT WITH REDFIN APR 24, 2026
$1,500,000 Last sold price
4 beds3 baths2,800 sq ft
980 The Greenway, East Marion, NY 11939
Listing by Signature Premier Properties
$27/sq ft
larger lot
7 years older

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