20715 Main Road, Southold, NY, 11957
$1,175,000
activeBedrooms
4
Bathrooms
2
Sq Ft
2,000
Lot Size
14,375 sqft
Year Built
1945
Garage
3 car
Type
Single Family
Estimate. Actual payment depends on credit, lender, taxes, and insurance.
You have to come back and see this house with me because it’s got that real “grandma’s classic 1940s winter weekend” energy in the best way that has been on the short list feeling. Picture this: it’s snowing outside, and we’re posted up in the big living room with the granite fireplace going. Knotty pine paneling, bookshelves built in on both sides of the hearth, and that warm glow that makes you feel settled. We’ve got Monopoly spread out on the coffee table, a huge bowl of popcorn (the legit kind made on the stove), and a record playing… then playing again… then somehow playing again because that’s what happens in houses like this. And of course there’s always that one person in our group who breaks out a slide projector, vacation slides from back in the day with the vintage clothing, the hair styles, taking in the moments. This house just fits that vibe perfectly. Then you walk into the sunroom and it changes gears: slate floors under your feet, water views straight out toward the beach, and it becomes the reading and lounging zone. Newspapers, magazines, tuna melts, tomato and rice soup. It’s basically the best relaxing room. Outside, it’s the kind of winter that makes you want to actually do stuff: we can go sledding down Munn Lane, then heading to the Causeway beach to see what the sea rolled in, perfect for seaglass collecting. That whole shoreline exploration where you come back with cold cheeks and a pocket full of little treasures. The layout is great too, wood floors through most of the house, and there’s that first-floor bedroom space (or den) with water views across the street that ties the whole country home feeling. It’s cozy, practical, and somehow still feels special. And the garage… three bays, but it doesn’t feel like “just a garage.” It feels like a workshop where projects are always in motion. The kind of place where sleds, bikes, paddleboards, clam rakes, fishing poles, beach chairs, and coolers all have a home. Here’s the kicker: it comes with two pieces of land, including the waterfront property across the street. So those water views? Protected. There’s about 50 feet of sandy beach, and the path to the water is right across the street, perfect for kayaking or paddleboarding in the summer. And sitting on the hill, the elevation is high enough that you’re not sitting stressing about flood issues. In the summer you’re up on the hill watching fireworks in Orient Village, with views from the living room, sunroom, and that main-floor bedroom/den. It’s peaceful, authentic, and it feels connected to the real local story—ice boat racing off Narrow River Road, oyster farming, clamming, fishing… all of it. This is what relaxation looks like when “country” means coastal, classic, and this is what we wanted.
Listed by Gerald J. Cibulski CBR E-PRO CRS G, Century 21 Albertson Realty
Listings courtesy of OneKey® MLS as distributed by MLS GRIDBased on information submitted to the MLS GRID as of Apr 22, 2026, 3:30 PM UTC (date and time MLS GRID Data was obtained). 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.
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