Southold Homes with Exp Cape Style

Welcome to Southold, New York, a charming town nestled in the heart of Suffolk County, where coastal beauty meets a vibrant community spirit. Known for its picturesque landscapes and rich history, Southold is not just a great place to live; it’s also home to an exceptional school district that prioritizes education and student success. The Southold School District is dedicated to fostering a nurturing environment, offering a range of academic programs that cater to diverse learning needs. With small class sizes, committed educators, and a strong emphasis on community involvement, students here are equipped with the tools they need to thrive both in and out of the classroom.

For those looking to settle down in this idyllic region, Southold boasts a variety of charming homes, including the beloved Cape Cod style. These Exp Cape homes are a delightful blend of classic New England architecture and modern amenities, featuring spacious layouts that are perfect for families and entertaining. With their distinctive sloped roofs and cozy interiors, these homes provide a warm and inviting atmosphere, often complemented by beautiful gardens and outdoor spaces that capture the essence of Southold’s serene surroundings.

Living in Southold means enjoying not only a strong educational foundation for your children but also a close-knit community where neighbors become friends. Whether you’re exploring the local vineyards, relaxing on the nearby beaches, or enjoying the vibrant arts scene, Southold is a place where you can truly feel at home. Discover your dream Exp Cape home today and become a part of this enchanting community!

Newest Southold Homes with Exp Cape Style

$5,700,000

4 Beds ⋅ 3 Baths ⋅ 1024359 MLS

An Exclusive North Fork Bayfront Retreat in an Unrivaled Private Setting Experience the beauty of one of the North Fork’s most coveted private waterfront locations. Perfectly positioned beside protected land, this exceptional property offers sweeping views of Peconic Bay and a picturesque view of the Little Creek inlet its a setting that can never be replicated. Owned by the same family for generations, this remarkable waterfront property presents a once in a lifetime opportunity to own a truly special piece of North Fork history. Wake to breathtaking sunrises, take in the ever changing views of Peconic Bay and the creek inlet, and enjoy the privacy and serenity that make this one of the North Fork’s premier waterfront settings. A legacy property where protected land, spectacular water views, and unmatched privacy come together. Private. Protected. One of a Kind.

Peconic

$6,550,000

5 Beds ⋅ 5 Baths ⋅ 999173 MLS

Set on a rare south-facing double lot with 200 feet of direct Peconic Bay frontage, a sandy beach, and a protected dock, this exceptional waterfront offering captures the essence of North Fork living. Perfectly positioned to enjoy all-day sunshine, refreshing southerly breezes, and breathtaking sunsets, the property sits at an ideal elevation that enhances the views while maintaining an effortless connection to the shoreline. The broad waterfront and truly usable beach invite days spent swimming, sunbathing, paddleboarding, or simply unwinding at the water's edge. Directly across the street, a separate waterfront parcel features a newly refurbished dock capable of accommodating a mid-twenty-foot boat, offering convenient access to Shelter Island, Sag Harbor, and the Hamptons. Designed to maximize its remarkable setting, the residence is bathed in natural light, with walls of glass and sweeping views that draw the outdoors into everyday life. Bright, inviting interiors and generously scaled gathering spaces create a relaxed coastal atmosphere equally suited for entertaining or quiet retreats. Outside, the waterside terrace provides an exceptional setting for summer barbecues, al fresco dining, and gathering with family and friends. As the day winds down, vibrant sunsets reflect across the bay, creating unforgettable evenings in one of the North Fork's most picturesque waterfront settings.

920 Cedar Point Drive E, Southold

$1,750,000

3 Beds ⋅ 3 Baths ⋅ 951805 MLS

Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 1720 and impeccably maintained in pristine condition. This is not simply a home; it is a rare architectural heirloom, offering authenticity, craftsmanship, and legacy that cannot be replicated. Every historic element has been preserved to perfection, honoring the home’s original character while reflecting a level of care and stewardship that is exceptionally rare. From period details and time-honored construction methods, this residence stands as a living testament to Southold’s rich heritage. The interior offers a gracious and functional layout anchored by an enclosed brick porch, a large formal dining room, a newly renovated expansive eat-in kitchen, a classic parlor room, and a comfortable living room—all thoughtfully arranged for both elegant entertaining and everyday living. Adding to the home’s exceptional character are three stunning fireplaces, each serving as a striking focal point and a reminder of the home’s historic craftsmanship. The residence features three bedrooms and two and a half bathrooms. The first floor includes the primary bedroom and two full bathrooms, allowing for convenient main-level living, while the second floor offers two additional bedrooms and a half bath, providing privacy and flexibility for guests . Outside, the property includes a two-car detached garage and is set on a quiet, peaceful lot in close proximity to Southold Bay, offering the serenity of North Fork living with easy access to the water and surrounding natural beauty. With official historic status, this home carries both distinction and prestige—appealing to discerning buyers who value provenance, integrity, and timeless elegance. Opportunities to own a property of this caliber, condition, and historical significance are exceedingly rare. This is more than a home—it is the stewardship of a true legacy. Lastly, the final photos on this listing demonstrate the secret hatch in the floor and each person to visit between 1750-1800's carved their names into the china cabinet paneling. So interesting to explore all the names. ** NOTE: The legal address for this home is 3500. However, the number on the post outside the home is 3290. CPF Tax/The Peconic Bay Region Community Preservation Fund applies to this listing.**

3500 Pine Neck Road, Southold

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.