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.

4004 Old North Rd, Southold

4 Beds, 3 Baths, 2,787 SqFt
Meander down the winding paved driveway to this cleared meadow in the woods with a cape offering a main floor master, double height dining room ceilings, laundry room off the kitchen and stone fireplace. Room for pool in the yard and a bike ride away from Hortons and Southold Town Beach. Great spot if you want to sit on the porch and look at flora and fauna.

1305 Hiawathas Path, Southold

3 Beds, 2 Baths,
A Perfect Beach Retreat located in the Laughing Waters Community with a meticulously landscaped.35 private yard and patio for all your outdoor entertaining. Close to Private Association Beach And two private Marina's this casual 3 bed, 2 bath has what you need for summer fun! Master suite and a large den which overlooks a beautiful fun filled yard with room for a pool.

1380 Oakwood Dr, Southold

4 Beds, 5 Baths, 3,800 SqFt
Welcome to this impeccably maintained Post Modern home. With over 3800 sq.ft. of living space and 92' water front w/dock & direct bay access.This home expemplifies pride in ownership. Contained within are 4 BRs, 4.5 baths including 2 master suites, office, EIK, den w/fireplace & wet bar. Formal LR, Formal DR, three season water view sun room. Expansive upper & lower water view decks. Finished basement, 2 car garage. Professionally

625 Kenneys Rd, Southold

4 Beds, 3 Baths, 2,800 SqFt
Turn Key & Built For Entertaining. This Traditional Style Home Offers Open Living On The Main Level w/ Updated EIK, Living Room & Den All Leading Out To An Impressive Poolside Patio & Deck. Manicured Plantings Established Throughout The Rear & Front Yard w/ Full Sun All Day Long On IG Pool & Expansive Rear Yard. Second Level Features Updated Master Ensuite w/ FB, Laundry Room, 3 Additional Bedrooms & Full Hallway

2150 Paradise Shores Rd, Southold

3 Beds, 3 Baths,
This delightful Southold Victorian home is located on a private street and is just steps away from the private association beach. Relax on the wrap around covered porch. Cook spectacular meals is the large chef's kitchen, enjoy the living room watching a cozy fire burning in the fireplace, enjoy the wonderful sunroom. Upstairs there is a master ensuite and 2 guest bedrooms, a spiral staircase takes you to a 3rd floor attic. Wood floors,

855 Grange Rd, Southold

3 Beds, 2 Baths,
Welcome to Long Islands wine country. This fantastic Ranch style home offers open, bright and airy living space with large bedrooms, a sunken family room with French doors and a country eat in kitchen with plenty of cabinets. Huge basement perfect for additional entertaining space. Deeded beach rights. Ready for summer fun.

49900 County Road 48, Southold

1 Bed, 1 Bath, 592 SqFt
Neat and complete cottage in Southold. Being sold with mls#3137189 which is a 10 acre vacant sub dividable waterfront parcel.

3150 Boisseau Ave, Southold

2 Beds, 2 Baths,
Old North Fork Charmer on 1 acre of manicured property comprised of 3 structures. A 2-bed, 1.5-bath farmhouse with beautiful wide plank pine floors, wood burning fireplace, and many other period details. Large barn with heated work space and hay loft as well as a 1 car garage. Plenty of room for pool. This one is not to be missed!

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. .

1162 N Bayview Road Ext, Southold


2555 Youngs Ave 8b, Southold

2 Beds, 2 Baths, 1,200 SqFt
Light, Bright and Airy Interior Unit In Sought After 55 Plus Community. Partially Finished Basement, Convenient To Shopping, Restaurants, NYC Transportation And North Fork Beaches. Enjoy Your Days At The Community Clubhouse And In-ground Pool!

1210 Hiawathas Path, Southold

3 Beds, 2 Baths, 1,800 SqFt
Step away from the real world and enjoy this meticulously maintained home. Nestled on a beautifully landscaped property, this 3 bedroom, 2 bath ranch is located in the coveted community of Laughing Waters. This Bayside community overlooks Moyle Cove, Corey Creek and the Little Peconic Bay and boasts two private marinas and a beautiful private beach for your summer enjoyment.

50100 County Rd 48, Southold

Rare opportunity to own 10.5 acres of creek front property with development rights intact. Possible compound or subdivision - contact for details

50100 County Rd 48, Southold


48460 County Road 48, Southold

Level 1/2 Acre Buildable Lot in Southold.

2415 Long Creek Dr, Southold

3 Beds, 3 Baths, 1,625 SqFt
Coming soon...



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.