Southold Homes with Cape Cod Style

Welcome to Southold, New York, a charming coastal town nestled in the heart of Suffolk County. Known for its picturesque landscapes and rich maritime heritage, Southold offers a unique blend of small-town charm and modern amenities. One of the standout features of this delightful community is its exceptional school district, which is dedicated to fostering a nurturing and stimulating environment for students.

The Southold School District is highly regarded for its commitment to academic excellence and holistic development. With a focus on personalized education, small class sizes, and a dedicated faculty, students here receive the attention they deserve. The district's curriculum is designed to inspire creativity and critical thinking, ensuring that each child is well-prepared for the challenges of tomorrow. Beyond academics, Southold schools emphasize the importance of character development, community involvement, and extracurricular activities, creating well-rounded individuals who thrive both inside and outside the classroom.

In addition to its outstanding education system, Southold is renowned for its beautiful Cape Cod-style homes. These charming residences, characterized by their steeply pitched roofs, symmetrical facades, and inviting porches, evoke a sense of warmth and nostalgia. Many of these homes are nestled among lush greenery and offer stunning views of the surrounding landscapes, making them perfect for families and individuals seeking tranquility and beauty.

Whether you’re drawn to Southold for its exceptional schools or its enchanting Cape Cod architecture, this community offers a welcoming atmosphere that feels like home. Come explore the beauty and charm of Southold—your dream home awaits!

Newest Southold Homes with Cape Cod Style

$985,000

5 Beds ⋅ 2 Baths ⋅ 1017107 MLS

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

230 Booth Road, Southold

$949,000

4 Beds ⋅ 3 Baths ⋅ 982950 MLS

Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a welcoming front yard and a generously sized backyard with ample room for a pool and outdoor entertaining. Inside, the home features an open-concept kitchen with new refrigerator, and dining area ideal for everyday living and gatherings, complemented by a formal living room for added versatility. Additional highlights include a convenient laundry room, a two-car attached garage with brand new doors, and a full basement with 8-foot ceilings offering excellent storage and a new hot water heater, gas heat, and potential for future finishing. Perfectly situated to enjoy the North Fork lifestyle, this home is in the Founders Park and Beach Park District, with direct access to a sugar sand beach, park and playground and is just moments from wineries, farm stands, the hamlet, train station, Jitney stop and a variety of shops and restaurants. Easy access to Greenport and Mattituck makes this location both convenient and desirable. A wonderful opportunity to make this home your own and enjoy all that the North Fork has to offer.

240 Lisa Drive, Southold

$950,000

3 Beds ⋅ 2 Baths ⋅ 964309 MLS

Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private escape that backs directly onto protected woodlands. One of the home’s standout features is an expansive four-season sunroom, which serves as a light-filled bridge between the indoors and your own quiet backyard sanctuary. Whether you are hosting a summer brunch or enjoying a morning coffee, the surrounding nature ensures a level of privacy that is truly rare. Additionally, the backyard features ample room for a pool, complete with an already approved pool permit to fast-track your summer dreams. Inside, the residence is designed for effortless living and is flooded with natural light. The main level offers the ultimate convenience of a primary bedroom with an ensuite bath and a dedicated laundry room, anchored by a spacious living area perfect for relaxing. Upstairs, you will find two additional oversized bedrooms—one featuring a generous walk-in closet—along with easy access to the attic. Modern essentials are seamlessly integrated throughout, including a full-house generator for peace of mind, a zoned irrigation sprinkler system, and a built-in Sonos system to set the mood for any occasion. This property places the very best of the North Fork right at your fingertips, situated just minutes from the stunning waters of Goose Creek, the sands of Cedar Beach, and Southold’s vibrant main street known for boutique shopping and fine dining. With renowned farmstands and vineyards only a short drive away, this home represents a rare opportunity to enjoy a secluded coastal lifestyle in one of the area’s most sought-after locations.

5845 N Bayview Road, 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

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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.