• Primary Photo - 295 Jackson St
  • Building Photo - 295 Jackson St
    Building Photo - 295 Jackson St
  • Building Photo - 295 Jackson St
    Building Photo - 295 Jackson St
$6,000 / Month

295 Jackson St

,

Southold, NY 11956

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631-897-8451

  • Bedrooms

    3

  • Bathrooms

    2

  • Square Feet

    2,000 sq ft

  • Available

    Available Now

Highlights

  • Water Views
  • Saltbox Architecture
  • Main Floor Bedroom
  • Bathroom on Main Level
295 Jackson St
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About This Home

Available Now

Summer Rental in New Suffolk! Enjoy summer on the North Fork in this well-appointed New Suffolk rental featuring partial water views,a spacious yard,and easy access to local beaches,dining,wineries,breweries,and farm stands. The home offers flexible living spaces,three bedrooms,two full baths,and multiple indoor and outdoor areas for relaxing and entertaining. Amenities include an eat-in kitchen,dining room,outdoor shower,charcoal grill,fire pit,washer/dryer,dishwasher,parking for four vehicles,and a large yard with outdoor seating. The first-floor layout includes a private bedroom,full bath,and adjoining sunroom,while the second floor offers additional bedrooms,a full bath,and a separate lounge area. Conveniently located near New Suffolk waterfront attractions and just minutes from the many vineyards,restaurants,and recreational opportunities throughout the North Fork. Summer 2026 Availability -June (2 week minimum) - $3000 per week,July and August (2 week minimum) - $3000 per week MLS ID KEY1009690 Based on information submitted to the MLS GRID as of [see last changed date above]. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Prices displayed on all Sold listings are the Last Known Listing Price and may not be the actual selling price.

295 Jackson St is a house located in Suffolk County and the 11956 ZIP Code. This area is served by the Mattituck-Cutchogue Union Free School District attendance zone.

* Price shown is base rent. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Home Details

Home Type

Single Family Detached Home

Bedrooms and Bathrooms

Main Floor Bedroom Bathroom on Main Level 2 Full Bathrooms 3 Bedrooms

Home Design

Saltbox Architecture Entry on the 1st floor

Interior Spaces

2,000 Sq Ft Home

Kitchen

Range Dishwasher

Laundry

Dryer Washer

Listing and Financial Details

Assessor Parcel Number 1000-117-00-09-00-002-000

Lot Details

1.25 Acre Lot

Parking

Driveway

Schools

Southold Elementary School Southold Junior-Senior High Middle School Southold Junior-Senior High School

Utilities

Well Heating System Uses Oil Cooling System Mounted To A Wall/Window

Views

Water Views

Community Details

Pet Policy

Call for details about the types of pets allowed

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified. Use the Cost Calculator to determine costs based on your needs.

  • One-Time Basics
    • Due at Move-In
      • Security Deposit - Refundable
        Charged per unit.
        $20

Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

Contact

  • Listed by Natalie Hough | Daniel Gale Sothebys Intl Rlty
  • Phone Number
  • Contact
  • Source
    OneKey® MLS
Information Copyright 2026, OneKey® MLS. All Rights Reserved. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.
Location Get Directions
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Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
City - Southold

Southold, New York sits near the tip of Long Island's North Fork, where vineyards line the back roads and the Long Island Sound is never far from view. This town has a distinct identity shaped by agriculture, maritime heritage, and a slower pace of life that sets it apart from the bustle of metro New York, roughly 80 miles to the west. Unlike the Hamptons to the south, Southold has held onto a grounded character that draws people looking for a more sedate, rooted location.

The town stretches across several hamlets, including Cutchogue, Peconic, and Mattituck, each with its own personality but all connected by a strong sense of place. North Fork wineries and farm stands have brought steady attention to the area, helping fuel a modest but consistent local economy. Stony Brook Southampton and other East End institutions add an educational presence to the broader region.

Rentals here lean toward single-family homes, cottages, and smaller apartment communities tucked within the hamlets.

Learn more about living in Southold 
Education
Colleges & Universities Distance
Colleges & Universities Distance
SUNY Suffolk Co., Eastern
Drive: 34 min 17.2 mi
St Joseph's Coll., Long Island
Drive: 60 min 36.8 mi
SUNY Suffolk Co., Ammerman
Drive: 62 min 37.2 mi
University of Connecticut
Drive: 138 min 44.3 mi
295 Jackson St is within 34 minutes or 17.2 miles from SUNY Suffolk Co., Eastern. It is also near SUNY Suffolk Co., Ammerman and St Joseph's Coll., Long Island.
Schools
Mattituck Cutchogue Elementary School
Public Elementary School
Grades K-5
457 Students
Nearby
Tuckahoe School
Public Elementary & Middle School
Grades PK-8
249 Students
Nearby
Mattituck Junior Senior High School
Public Middle & High School
Grades 6-12
524 Students
Nearby
Peconic Community School
Private Elementary & Middle School
Grades PK-8
115 Students
Nearby
Bishop Mcgann-Mercy Diocesan High School
Private Middle & High School
Grades 6-12
481 Students
Nearby
School data provided by The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

295 Jackson St is near Tweed/New Haven, located 73.4 miles or 172 minutes away.

Commuter Rail Distance
Commuter Rail Distance
Mattituck Station
Drive: 8 min 3.2 mi
Southold Station
Drive: 14 min 6.9 mi
Hampton Bays Station
Drive: 35 min 19.7 mi
Southampton Station
Drive: 49 min 29.4 mi
Bridgehampton Station
Drive: 59 min 34.7 mi
Airports Distance
Airports Distance
Tweed/New Haven
 Drive: 172 min 73.4 mi
Getting Around
Somewhat Walkable
Walkability
20 / 100
Minimal Public Transit
Transit
0 / 100
Exceptionally Drivable
Drivability
90 / 100
Somewhat Bikeable
Bikeability
30 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
-
Soundscore™
- / 100

Traffic

-

Airport

-

Businesses

-

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 295 Jackson St.

Shopping Centers Distance
Shopping Centers Distance
Cutchogue Plaza
Drive: 6 min 2.4 mi
Country Commons
Drive: 6 min 2.7 mi
Angelina Plaza
Drive: 8 min 3.0 mi
295 Jackson St has 3 shopping centers within 3.0 miles, which is about a 8-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Custer Institute Observatory
 Drive: 12 min 5.9 mi
Garden of Eve Farm
 Drive: 18 min 10.2 mi
Sears Bellows County Park
 Drive: 36 min 20.3 mi
Meschutt Beach County Park
 Drive: 41 min 21.9 mi
Elizabeth A. Morton National Wildlife Refuge
 Drive: 63 min 36.3 mi
295 Jackson St has 5 parks within 36.3 miles, including Custer Institute Observatory, Garden of Eve Farm, and Sears Bellows County Park.
Military Bases Distance
Military Bases Distance
Fort Trumbell US Navy
Drive: 131 min 40.1 mi
New London Naval Sub Base
Drive: 139 min 44.1 mi
Eatons Neck CG Station North
Drive: 102 min 57.8 mi
295 Jackson St has 3 military bases within 57.8 miles, the nearest is Fort Trumbell US Navy which is 40.1 miles away and a 131 minute drive.

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