All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
Refine your search to less than 500 properties to save.
Click on the map to draw your polygon search.
Click on the map to draw your radius search.
Search only mappable listings within the map's bounds.

54180 Route 25, Southold

2,200 SqFt
2200 Sq.Ft Of Newly Renovated Commercial Space In Prime Retail Shopping District. Ideal For Upscale Retail, Farm To Table, Take-Out, And Other Retail. Amazing Outdoor Square Area. Possible Storage In New Basement.

49200 Route 25, Southold

422 SqFt
422 Sq.Ft. Of Storage/Garage Space

55000 Main Rd, Southold

Prominent And Picturesque Office Building With Various Configurations/Costs Ranging From $500 To $1,500 Or More. Off Street Parking. See Attachment For Various Office Configurations And Their Costs.

53740 Route 25, Southold

1 Bath,
Updated Office Space Ideal For A Professional. 5 Rooms Plus a Bath. Municipal Parking Lot Nearby.

53740 Route 25, Southold

Updated Office Space Ideal For A Professional On Second Floor. 5 Rooms Plus A Bath. Annual Lease @ $1,600/month. Tenant is Responsible For Heat and Electricity. Municipal Parking Lot Nearby.

120 E Richmond Rd Rear, Southold

2 Beds, 1 Bath,
Clean and cute! Let this prototypical North Fork cottage be your happy summer getaway; just 300 feet to sandy Town Beach, too! ZILLOW/TRULIA users: THIS IS A SUMMER RENTAL ONLY!

490 Victoria Dr, Southold

3 Beds, 2 Baths,
Adorable and Affordable Ranch with updated kitchen and baths. SEASONAL RENTAL to enjoy for Various Weeks or Months this SUMMER. Located Near Fabulous Beaches and Close to Shopping, Vineyard, and Restaurants.

400 Meadow Ct 31, Southold

3 Beds, 3 Baths,
Spacious 3 bedroom, 2 1/2 bath townhome at The Cove in Southold. Furnishings not included, unit will be empty. Features a main level master suite with en suite bath, 2 additional bedrooms plus loft, front and rear decks, laundry, 1 car garage, and basement. Community tennis courts, pool, and water access for kayaking, paddle boarding, etc. Close to North Fork wineries, dining, beaches, and more.

125 Hill Top Path, Southold

3 Beds, 3 Baths,
Dine Outdoors On The Roof Terrace Overlooking The Li Sound.. Flexible Rental All Year Long (Min Stay 2 Weeks Per Town Code), Monthly, Or For Summer 2018 Season. Private 1.5 Acre Sunset Knolls Beach At Your Doorstop! Home Features Contemporary Living Close To The Village: Lr W/Gas Fireplace, Dr, Eik, Master Suite W/Bath And Terrace; 2 Additional Br's & Full Bath, Den, Pw

655 W Shore Dr, Southold

3 Beds, 2 Baths,
Beautiful, Bright, Airy Contemporary Farm House In Reydon Shores Private Beach Community. Vaulted Ceilings, Large Windows Fill The Rooms w/ Sunlight. Screened In Front Porch W/Water Views, Serene Backyard, Slate Patio, Fire Pit For Smores & Herb Garden To Enjoy. Water Access Diagonally Across The Street. Sandy Beach Feet Away. 3 Bedrms + private Den w/ Pull-Out Couch, Comfortably Sleeps 8. Dog & Cat friendly.

170 Lake Dr, Southold

3 Beds, 2 Baths,
A Great Front Beach Cottage A Short Distance To Kenny's Beach. 3 Beds, 2 Baths, Dining Room, Living Room With Sliders To Back Deck Facing Long Island Sound. 1 Queen Bed, 1 Full Bed And 2 Twin Beds .Near Vineyards, Shopping And Restaurants.

1425 Paradise Point Rd, Southold

2 Beds, 2 Baths,
Escape to this stylish North Fork getaway situated on a lush 5 acre property. The tranquil setting is perfect for a summer stay or year round residency. 2 bed, 2 baths, plenty of living space and close to all the North Fork has to offer. Walking distance to coveted Cedar Beach. Available for June, July, August and year round rental, $3000 per month.

12, Southold

3 Beds, 3 Baths,
Be Prepared To Be Enchanted From This Waterfront End Unit In The Private Community Of The Cove. Views From All Rooms. 2 Waterfront Private Decks. Newly Renovated Tennis Courts. Ig Pool Is Heated. Launch Area For Paddle Boards, Kayaks. Minutes To Bay. Spacious 3 Bedroom, 2.5 Bath Located Smack In The Middle Of Foodie And Winey Heaven, Surrounded By Sandy Beaches. Paradise. Flexible rental dates, mimum of 3 months up to 12 months starting

1605 Old Shipyard Ln, Southold

4 Beds, 4 Baths,
Spacious and sophisticated home in Founders Landing. One Block from Beach and Marina. Room for the Whole Family and more to enjoy. Perfect Summer Getaway! Complimentry bicycles included. .

870 Bay Home Rd, Southold

4 Beds, 4 Baths,
Charming North Fork Waterfront home with magnificent, private sugar sand beach on the open Bay. Open plan first floor living / dining room, with screened porch. Fully equipped kitchen, large garden with outdoor dining, shower, BBQ, Concierge Services. Renovated plumbing and electric, while retaining many original features. Central AC in 4 double bedrooms, 2 full baths, Master Bedroom en-suite with half bath. Close to restaurants, farm stands,

2125 Hyatt Rd, Southold

3 Beds, 2 Baths,
Easy, Breezy, Fully Renovated Home With Access To Private Long Island Sound Beach Across The Way. Very Private Location For Your Summer Retreat.



Nowhere in Southold Town is there a more rich history than in its namesake hamlet of Southold.

Southold was the first English settlement in the future New York State, founded by Puritans from New Haven, Connecticut, in the summer of 1640, on land purchased from the Corchaug Indians. The Indian name for the land that would become Southold was Yenicott. Southold remained under the jurisdiction of Connecticut until 1674.

The name Southold is believed by some to be a misspelling of Southwold, which is a coastal town in the corresponding English county of Suffolk. This claim is debatable, but John Youngs, one of the town’s founding fathers, was born and raised in Southwold.

A portion of this historic hamlet is a federally recognized historic district and there are many homes and structures dating back to the 17th Century.

Southold has long been a vibrant community which continues to evolve with each passing year. The hamlet of Southold features miles of both bay and sound front beaches, sprawling vineyards, boutique wineries, farm stands, museums, an observatory, and unlimited recreational activities. There are a number of quaint home décor shops in Southold’s downtown, as well as a good number of casual eateries and coffee shops. Most of Southold Town's government buildings are also located in the hamlet of Southold.

Southold students attend the elementary, middle and senior high school centrally located on a single sprawling campus on Oaklawn Avenue.

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.

Information Copyright 2019, Multiple Listing Service of Long Island, Inc. All Rights Reserved.