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  1. Building Photo - 53995 NY-25
    1 BED, 1 BATH
    $2,500

    53995 NY-25

    53995 NY-25, Southold, NY 11971
  6. 3 BEDS, 2 BATHS
    $3,500

    315 Lake Dr

    315 Lake Dr, Southold, NY 11971
  12. 4 BEDS, 4 BATHS
    $5,000

    215 Leon Rd

    215 Leon Rd, Southold, NY 11971
  22. 3 BEDS, 2 BATHS
    $8,000

    400 Hill Rd

    400 Hill Rd, Southold, NY 11971
  28. 3 BEDS, 2.5 BATHS
    $10,000

    485 Pine Rd

    485 Pine Rd, Southold, NY 11971
  36. 3 BEDS, 2 BATHS
    $10,000

    275 Maier Pl

    275 Maier Pl, Southold, NY 11971
  40. 3 BEDS, 2 BATHS
    $12,500

    455 Fred St

    455 Fred St, Southold, NY 11956
Showing 42 of 70 results, Page 1 of 2

Southold at a Glance

Average Rent

N/A
(All bedrooms and property types)
7

School Rating

out of 10 Rating
Learn more about
Schools in Southold
0

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Southold
46

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Southold

Southold, NY Houses for Rent

Southold, NY, is a delightful blend of scenic beauty and rich history, nestled on the North Fork of Long Island. This charming town offers a variety of rental options, from cozy apartments to quaint cottages, making it an appealing choice for those seeking a comfortable home. Residents can revel in stunning views of the Long Island Sound and the nearby Peconic Bay, perfect for outdoor enthusiasts. Parks similar to Goldsmith's Inlet Park and Cedar Beach County Park provide ample opportunities for relaxation, picnicking, and recreational activities, while local farmers' markets showcase the region's agricultural heritage.

The culinary scene is vibrant, with popular spots such as Claudio's Tavern & Grill and Lucharitos serving up delicious meals. For waterfront dining, Claudio's Waterfront and The Halyard Restaurant offer breathtaking views alongside their exquisite menus. Cafes similar to Aldo's Coffee Company and North Fork Roasting Co. invite locals to savor a warm cup of coffee, while Encanto Crepes & Cafe and Stars Cafe provide delightful treats for a casual outing.

Cultural events and community gatherings enrich the town's atmosphere, with annual festivals similar to the Southold Historical Society's Strawberry Festival celebrating local traditions and fostering a sense of belonging. Museums such as the Horton Point Lighthouse Nautical Museum and the East End Seaport Museum and Marine Foundation offer fascinating insights into the area's maritime history. The Railroad Museum of Long Island and the Shelter Island Historical Society further contribute to the cultural tapestry, making Southold a place where history comes alive.

With its friendly atmosphere, access to beautiful natural surroundings, and proximity to local universities, Southold presents an inviting environment for those looking to enjoy a fulfilling lifestyle. Notable landmarks, including the historic Southold Lighthouse and the charming village center, create a picturesque backdrop for daily life, while the nearby parks, shopping centers similar to Dina Multicervicios, and diverse dining options ensure that there’s always something to explore.

Getting Around Southold

Transportation

42

Car-Dependent

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
46

Somewhat Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
0

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

GreatSchools Rating
Southold Elementary School

Public Elementary School

Public
Grades K-6
317 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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