The 30 Best Cottages in Southold, New York

Welcome to Kimberly Krupski, your trusted real estate agent at Daniel Gale Sotheby’s International Realty, located in Cutchogue, New York. Situated at 28080 Main Road, our office is deeply rooted in the heart of the North Fork community. Kim Krupski is not just a real estate agent; she is a 5th generation farmer who grew up on her family's farm in Cutchogue and continues to live there with her husband, Brandon. Her family's land has been a part of the community since 1909, showcasing her deep connections and commitment to the area. Kim is a proud graduate of Mattituck High School and SUNY Geneseo, where she earned a degree in Accounting. Her professional journey took her to the US Department of Agriculture, where she worked for five years, further strengthening her ties to the local community. Currently, she volunteers on the Southold Town Land Preservation Committee, reflecting her passion for preserving the unique character of the North Fork.

Welcome to Mary Lentini's Real Estate Services at Daniel Gale Sotheby’s International Realty, located at 70 Love Lane, Mattituck, New York. With nearly three decades of real estate expertise, Mary Lentini is a premier agent on the East End of Long Island. Her passion for real estate and caring nature are the driving forces behind her successful career. Mary is a real estate broker with hundreds of successful transactions and holds several specialist certifications. She has earned the prestigious Gold Circle of Excellence award from Daniel Gale Sotheby’s International Realty, reflecting her commitment to excellence. As a longstanding resident of Southold Town, Mary possesses extensive personal and professional knowledge of the area. Her journey began as a medical transcriptionist in Queens, NY, which provided the flexibility to care for her young family. Transitioning into real estate, Mary has become a full-time professional known for her honesty, integrity, and perseverance. She is skilled in negotiating deals and dedicated to ensuring customer satisfaction.

Welcome to White Blossom House Inn, a charming retreat nestled in the heart of Southold, New York. Located at 695 Pine Neck Road, our delightful inn offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a romantic getaway, a peaceful weekend, or a base for exploring the beautiful North Fork of Long Island, White Blossom House Inn provides the perfect setting. Our inn features elegantly appointed rooms that blend classic charm with modern comforts. Each room is thoughtfully designed to ensure a restful and rejuvenating stay, complete with plush bedding, private bathrooms, and complimentary Wi-Fi. Guests can enjoy a leisurely breakfast in our inviting dining area or unwind in our lush garden, which offers a tranquil space to relax and reflect.

Welcome to Vine Sand, your serene escape nestled in the heart of Southold, New York. Located at 47100 New York 25, our charming lodging offers a perfect blend of comfort and tranquility, ideal for those looking to unwind and explore the captivating beauty of the North Fork. At Vine Sand, we pride ourselves on providing a warm and inviting atmosphere, where guests can enjoy modern amenities amidst a picturesque setting. Each of our thoughtfully designed rooms offers a cozy retreat, ensuring a restful stay. Wake up to the gentle sounds of nature and start your day with a fresh, locally-sourced breakfast that highlights the best of the region.

Welcome to Southampton Village Motel Nestled in the heart of Southampton, New York, Southampton Village Motel offers a quintessential Hamptons experience, blending timeless elegance with modern luxury. Located at 315 New York 27A, our newly renovated motel provides the perfect retreat for those seeking a serene and exclusive getaway.