Southold Homes with Exp Cape Style

Welcome to Southold, a picturesque gem nestled in the heart of Suffolk County, New York. Known for its stunning waterfront views and charming small-town atmosphere, Southold offers a perfect blend of coastal living and rich history. With its roots dating back to the 17th century, this quaint town is steeped in tradition while embracing modern comforts, making it an ideal location for families, retirees, and everyone in between.

One of the most sought-after home styles in Southold is the Expansive Cape Cod. These homes are characterized by their classic charm and versatile layouts, making them perfect for both cozy family gatherings and entertaining guests. With their inviting gabled roofs and spacious interiors, Exp Cape Style homes often feature large living areas, multiple bedrooms, and ample outdoor space, allowing residents to enjoy the serene beauty of their surroundings. Many of these homes are situated near the stunning beaches, vineyards, and parks that Southold is renowned for, offering a lifestyle that seamlessly blends relaxation and recreation.

In addition to the captivating architecture, Southold boasts a vibrant community filled with local shops, farm stands, and artisanal eateries. Outdoor enthusiasts will appreciate the abundance of recreational activities available, from boating and fishing to hiking and cycling. With its friendly atmosphere and breathtaking landscapes, Southold is not just a place to live; it’s a place to thrive. If you’re considering making Southold your home, the Exp Cape Style houses here offer a perfect backdrop for creating lasting memories in this enchanting corner of New York.

Newest Southold Homes with Exp Cape Style

$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.