Southold Homes with Contemporary Style

Welcome to Southold, a picturesque gem nestled on the North Fork of Long Island, New York. Known for its stunning coastal views, charming vineyards, and a rich tapestry of history, Southold offers a unique blend of tranquility and vibrancy that appeals to homebuyers seeking a serene lifestyle. With easy access to the sparkling waters of the Long Island Sound, residents can enjoy a variety of outdoor activities, from boating and fishing to leisurely beach strolls.

In Southold, contemporary-style homes are redefining the local real estate landscape. These modern residences are designed with an emphasis on open spaces, natural light, and sleek lines, seamlessly blending with the area's natural beauty. Many contemporary homes feature eco-friendly materials and cutting-edge technology, making them not only stylish but also sustainable. Imagine sipping your morning coffee on a sun-drenched patio or hosting friends in a spacious, airy living room that connects effortlessly to the outdoors.

The community is rich with amenities, including boutique shops, farm-to-table dining, and renowned wineries, making it an ideal location for those who appreciate a slower pace of life without sacrificing modern conveniences. Southold’s strong sense of community and commitment to preserving its natural surroundings further enhance its appeal.

Whether you’re looking for a full-time residence or a peaceful getaway, Southold’s contemporary homes offer the perfect blend of style, comfort, and sophistication. Discover the beauty of Southold and find your dream home in this enchanting corner of New York.

Newest Southold Homes with Contemporary Style

$1,849,000

4 Beds ⋅ 4 Baths ⋅ 1008927 MLS

This turnkey opportunity in Southold, bordering beautiful Goose Creek, offers a private dock and is perfect for those seeking a North Fork beach house with a boater's lifestyle. Situated on more than two-thirds of an acre, this contemporary home features modern lines, abundant natural light, and a stunning yard ideal for outdoor entertaining. Upon arrival, you are welcomed by a spacious driveway leading to an inviting entrance and foyer. The open floor plan, vaulted ceilings, and coastal color palette create a warm atmosphere, enhanced by sunlight flooding in through the windows that showcase the mature, landscaped backyard. The living room, anchored by a wood-burning fireplace, provides a generous seating area, while the formal dining area is elegantly situated in the center. The expansive chef's kitchen is equipped with high-end appliances and custom cabinetry, offering ample storage space, sleek lines, side island seating, and a cozy hostess nook. On the main floor, there is also a guest bedroom and a well-appointed full bathroom. Upstairs, the primary bedroom is located on one side, while a catwalk leads to two additional bedrooms and a full, spa-inspired bathroom. The lower level features a finished recreation space complete with a lounge, bar, and pool table. A bathroom, extra closets, and a bonus room complete this level. Outdoors, the two-tier entertaining area includes a spacious deck and a lower-level patio immersed in a well-landscaped yard with specimen plantings. The property also has an approval for a waterside pool, permit in hand. The dock is in excellent condition and has electric and water, providing direct access to Peconic Bay. This wonderful location is perfect for paddling, kayaking, and boating, and is close to everything the beautiful East End has to offer, including wineries, farm stands, the Southold town village, dining options, and the picturesque Goose Creek beach—just a short paddle away.

2100 Glenn Road, Southold

$935,000

3 Beds ⋅ 2 Baths ⋅ 1004231 MLS

Just a stone's throw from the sands of Town Sound Beach, this bright and airy retreat offers the perfect blend of coastal proximity and quiet privacy. Freshly painted inside and out, the home feels crisp and modern, anchored by a stunning living room featuring cathedral ceilings, a cozy wood-burning fireplace, and oversized windows that flood the space with natural light. The layout is designed for easy flow, boasting a large open kitchen and a formal dining room where sliders lead out to a brand-new deck—perfect for morning coffee or evening hosting. Three strategically placed skylights ensure the interior stays sun-drenched all day long. For those working from home, the dedicated office provides a quiet, professional sanctuary. The primary suite serves as a true escape with its own ensuite bath, complemented by two additional spacious bedrooms and a second full bathroom. Downstairs, the massive basement with 10-foot ceilings and Bilco doors offers incredible potential for a gym, media room, or extra storage. Outside, the .78-acre property is a total dream. The manicured gardens and park-like setting create a lush backdrop for the expansive wood deck, offering a serene environment to relax after a day at the beach. It’s a rare find that perfectly balances large-scale rooms with a warm, inviting soul.

100 Bayberry Lane, Southold

$1,445,000

3 Beds ⋅ 2 Baths ⋅ 975344 MLS

Boaters Dream! Located in Southold, this 3-bedroom, 2-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen includes modern appliances and ample counter space. Large windows provide natural light and water views, with direct access to the rear deck. The outdoor space includes a spacious deck with room for seating and dining, along with a gas grill setup. The dock provides convenient access for boating, kayaking, and other activities. The home includes three bedrooms and two bathrooms, offering flexible space for a variety of living arrangements. Additional features include well-maintained interiors and updated elements throughout. Conveniently located near local wineries, restaurants, and shops, with access to all that the North Fork has to offer.

470 Windy Point Lane, Southold

$2,399,000

3 Beds ⋅ 2 Baths ⋅ 943087 MLS

Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporary home offers open water views, beautiful sunrises and sunsets, and a seamless indoor–outdoor flow. The light-filled main level features a newly built modern kitchen that opens directly to the outdoor entertaining area, along with a waterside first-floor primary suite. Large windows invite the views in, creating a relaxed, airy atmosphere throughout the home. Outside, the property lives like a private shoreline retreat. Enjoy the new heated saltwater pool with automatic cover, an enclosed outdoor shower, and generous patio space perfect for lounging or hosting. The private dock provides more than just waterfront enjoyment—there’s direct boating access to Southold Bay and Peconic Bay, with easy routes to Greenport, Shelter Island, and even Sag Harbor for dining, marinas, and day trips. A turnkey waterfront residence that blends comfort, modern updates, spectacular views and the best of coastal living!!!

470 Goose Creek Lane, Southold

$1,499,000

3 Beds ⋅ 4 Baths ⋅ 924424 MLS

Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to own this exceptional property: Option 1: New Construction Package – $3,300,000 Partner with the highly regarded North Fork Building Company to create a custom 2,900 sq ft modern waterfront home, expertly designed to showcase water views and deliver a luxurious coastal lifestyle. Planned Features Include: 3 en suite bedrooms, additional full bath off the mudroom, main-floor flex room (ideal for a 4th bedroom, home office, or den), Heated waterside pool, covered outdoor living room with kitchen and wood-burning fireplace, private dock + floating swim dock, detached two-car garage with unfinished attic space and breezeway. Interior Highlights: Gourmet kitchen with custom cabinetry, quartz countertops, Thermador appliances, gas fireplace in the living room with custom built-in bookcases, 10’ ceilings on the main level, 9’ ceilings upstairs, white oak flooring throughout, Kohler fixtures, Andersen windows, and recessed lighting. Custom molding package, Walk-in closets in all bedrooms and upstairs laundry room. With final plan approvals nearing completion and permits ready to issue, now is the ideal time to customize your finishes and build your North Fork dream home. Option 2: Purchase As-Is with Approved Plans – $1,499,000 Prefer to build on your own schedule or with your own team? The existing home is also available as-is . This includes: Fully approved architectural plans, ready-to-issue building permits, .37-acre lot on a quiet canal with private dock. Prime opportunity to invest in a trophy location with a head start on construction. Whether you're ready to break ground now or planning for the future, 535 Bay Home Road is a rare chance to own one of the North Fork’s most prestigious waterfront streets — just steps to a private beach and directly across from a scenic vineyard.

535 Bay Home Road, Southold

Start Your Search

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.