Southold Homes with Traditional Style

Welcome to Southold, NY, a picturesque gem nestled in the heart of Suffolk County. Known for its stunning coastal views and rich agricultural heritage, Southold is not just a beautiful place to live; it’s also home to a highly regarded school district that prioritizes the educational needs of its community. The Southold School District is committed to fostering a nurturing environment, where students are encouraged to explore their interests and excel academically. With a strong emphasis on individualized attention, small class sizes, and a dedicated faculty, parents can feel confident that their children are receiving a top-notch education.

As you explore the charming neighborhoods of Southold, you’ll discover a variety of homes that embody traditional style. These residences are characterized by their timeless architectural details, inviting front porches, and warm, welcoming interiors. Many of these homes are set amidst lush landscapes, providing a perfect backdrop for family gatherings and outdoor activities.

Living in Southold means enjoying the best of both worlds: a serene, small-town atmosphere with access to quality education and the vibrant, cultural experiences that come from being near the beautiful North Fork. Whether you’re sipping wine at a local vineyard or taking a stroll along the waterfront, you’ll find that Southold is more than just a place to call home; it’s a lifestyle that embraces community, tradition, and the beauty of nature. Come discover the charm of Southold and envision your future in one of its lovely traditional-style homes!

Newest Southold Homes with Traditional Style

$2,695,000

5 Beds ⋅ 4 Baths ⋅ 1031524 MLS

This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and exceptional East End retreat Stunning carpentry, high-end appliances, and designer fixtures carry throughout. The custom-built kitchen features bespoke cabinetry and hardware, flowing seamlessly into a dining area and a light-filled living room anchored by a wood-burning fireplace. Oversized windows and a vaulted ceiling define the dining room, which connects to an oversized back deck overlooking the sprawling backyard. Outside, a gunite, heated, saltwater pool complements the cedar-shingled accessory structure, which combines a pool house with its own bathroom, a garage, a covered outdoor patio with a gas fireplace, and an outdoor shower. Back inside, two additional guest bedrooms share a full bath on the second floor, while downstairs, two large recreation rooms offer further customization and flexibility. The location is just as compelling as the house itself, minutes from Goose Creek Beach, Cedar Beach, Croteaux Vineyards, and the many shops and restaurants of Southold Hamlet. This is a special property with a real point of view that you'll look forward to walking into each time you return home.

605 Cedar Drive, Southold

$1,525,000

5 Beds ⋅ 3 Baths ⋅ 1031207 MLS

Welcome to your North Fork escape in the charming hamlet of New Suffolk. Tucked away on a quiet property surrounded by mature trees, this spacious 5-bedroom, 3-bath home offers the perfect blend of privacy, comfort, and coastal living. Start your mornings with a stroll to the beach, spend the afternoon boating or fishing on the bay, then enjoy dinner at one of the North Fork's celebrated restaurants or visit nearby wineries and farm stands. Everything you love about the East End is just minutes away. Inside, the home is warm, comfortable, and filled with natural light. The eat-in kitchen is the heart of the home, perfect for gathering and preparing delicious meals. A first-floor bedroom and full bath, provide flexibility for guests, a home office, or first-floor living. Upstairs, the spacious primary suite features a private bath and walk-in closet, while three additional bedrooms and full bath offer plenty of room for all. Outside, the expansive backyard is a peaceful retreat. Surrounded by mature landscaping for exceptional privacy, there is plenty of room to relax, entertain, play, or simply enjoy the quiet setting. Whether you're looking for a year-round residence or the perfect weekend getaway, this is your opportunity to enjoy the best of North Fork living in one of its most sought-after seaside communities.

705 Fanning Road, New Suffolk

$2,650,000

4 Beds ⋅ 4 Baths ⋅ 1023134 MLS

This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

195 Williamsburg Drive, Southold

$2,150,000

3 Beds ⋅ 3 Baths ⋅ 1022803 MLS

Perfectly sited on a protected inlet on West Lake, with direct access to the pristine waters of the Little Peconic Bay, this exceptional waterfront retreat embodies the effortless elegance of North Fork living. Thoughtfully designed to embrace its spectacular setting, the home is filled with natural light and showcases captivating water views from its principal living spaces. The main level offers an inviting open-concept design, where a gracious living room with a gas fireplace, elegant dining area, and beautifully appointed chef's kitchen with premium finishes flow seamlessly onto an expansive waterfront deck, creating an ideal setting for both intimate gatherings and grand-scale entertaining. A private staircase leads to the large dock, with room for multiple boats and a permitted kayak launch, offering immediate access to some of the East End's finest boating, sailing, and fishing. Above, the rooftop observation deck captures sweeping panoramic vistas across Little Peconic Bay, Robins Island, and the ever-changing coastal landscape beyond. The finished lower level encompasses an additional 1,675 square feet of living space and features a spacious family room, two bedrooms, a bathroom, another fireplace, a wine cellar, and walls of sliding glass doors that blur the line between indoors and out, inviting the waterfront into every moment. Complete with private beach access, this is more than a home-it is a rare opportunity to embrace an extraordinary waterfront lifestyle where sunrise boat-rides, paddles, afternoons on the bay, and unforgettable sunsets become part of everyday life.

2245 Little Peconic Bay Lane, Southold

$1,385,000

4 Beds ⋅ 3 Baths ⋅ 1023884 MLS

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

4408 Old North Road, Southold

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 1016523 MLS

Southold – Goose Creek- Located along a quiet private lane leading to Goose Creek Beach, this beautifully crafted and completely renovated cedar shingled two story home offers the perfect blend of charm, privacy, and North Fork living. The first floor features an open, sun filled layout highlighted by a spacious living room with a wood burning stove, a bright and airy kitchen with an expansive dining area framed by walls of windows, and a dining area with doors opening to the pool and patio. A first floor sitting room with an adjacent full bath provides a flexible space that can be easily converted into a first floor primary en-suite. Upstairs, the generous primary en-suite offers creek views, accompanied by two additional guest bedrooms and a full guest bath. Privacy surrounds the heated saltwater in ground pool and patio, creating a peaceful retreat for relaxation or entertaining. This exceptional property captures the essence of the North Fork lifestyle — a short stroll to beautiful Goose Creek Bay beach, yet tucked away in a quiet, coveted location. With creek access you can launch a kayak or paddleboard and enjoy the serene waters of Goose Creek. f you are interested in a "real" North Fork experience, this house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

1195 Goose Creek Lane, Southold

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 1000846 MLS

Explore a prime location in Southold, perfect for a beach getaway, featuring the highly sought-after Kenneys Beach—one of the most picturesque beaches on the North Fork. This traditional-style home is built with meticulous attention to detail and quality craftsmanship. Upon entering, you are greeted by a cathedral ceiling that highlights a stunning stone staircase with iron railings. The spacious living room boasts a cozy fireplace and an open floor plan that seamlessly connects to the dining room, which is filled with natural light and provides direct access to the backyard patio. The chef's kitchen is equipped with a center island, granite countertops, custom cabinetry, high-end appliances, and a built-in pantry. The breezeway leading to the side yard offers access to the garage, a full bathroom, and a laundry room. Upstairs, the generous primary bedroom features two walk-in closets and an ensuite bathroom finished in marble, complete with radiant heated flooring. Three additional bedrooms share a full marble bathroom. A dedicated alcove space serves as both an office and a casual lounge. The backyard is a private retreat, ideal for al fresco dining and entertaining, featuring a large patio and mature landscaping. There is ample space to incorporate a pool or lawn games. This residence includes an outdoor shower, a two-car attached garage, and a generator. Conveniently located near all that the East End has to offer, residents can enjoy wineries, farms, local shopping, dining options, and the beautiful landscape the region is known for. This listing includes images that have been digitally altered.

2015 Kenneys Road, Southold

$4,000,000

3 Beds ⋅ 4 Baths ⋅ 997738 MLS

Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision. The grounds are equally compelling. A tennis court is already in place, and the oversized detached three-car garage adds flexibility for storage, studio space, or future accessory use, leaving ample room to site a pool. Centrally located with easy access to the North Fork’s vineyards, farm stands, restaurants, and marinas, the setting strikes a balance between privacy and convenience. Offerings with this combination of land, beach quality, and potential are increasingly rare, presenting a clear opportunity to create a premier waterfront compound.

1480 Old Wood Path, Southold

$3,450,000

5 Beds ⋅ 4 Baths ⋅ 995842 MLS

Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of luxury, comfort, and location. Just across the street from the shores of Kenney’s Beach, this 2009-built residence features 5 spacious bedrooms and 3.5 beautifully appointed baths, including a serene first-floor primary suite. Set on nearly a full acre, the property is an entertainer’s dream with a heated saltwater pool, outdoor shower, and a screened-in porch ideal for summer evenings. The home also boasts a 3-car garage, whole-house sound system, security system, elevator, and a full irrigation system that keeps the grounds lush and green. Gorgeous landscaping with landscape lighting throughout. High-end construction materials and thoughtful design elevate the entire living experience, with 8-foot ceilings in the basement offering the perfect opportunity to create a media room or home gym. Enjoy spectacular sunsets, unbeatable beach access, and the potential to easily add a pool house—water and electric are already in place. This is coastal living at its finest.

790 N Sea Drive, Southold

$2,250,000

4 Beds ⋅ 5 Baths ⋅ 990099 MLS

Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a .52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom and three second-floor ensuite guest rooms. The interior is designed for both comfort and entertaining, with a two-sided gas fireplace, quartz kitchen countertops, Bosch and XO appliances, dimmer lighting throughout, electric shades in key living areas, ceiling fans in all bedrooms, and a first-floor laundry room. Home includes 7 built-in TVs, a 98-inch Sony screen and home theater with blackout shades, creating an impressive entertainment space. Since purchasing, the owner has elevated the property, including full front and rear landscaping, new lawns, extensive plantings, 73 trees, a new front walkway and steps, a rear sprinkler system, outdoor accent lighting, and a limestone patio surrounding the pool. The exterior is anchored by an 18x36 gated heated saltwater pool with a 500-gallon inground propane tank for the pool heater, a rear porch, dog run, retaining wall, and roof deck with water views. Additional features include a Sonos music system inside and out, alarm system, 2-car attached garage with shelving, additional refrigerator, and electric car hookup. Ideally located in Southold, this move-in-ready home combines new construction ease with substantial post-purchase improvements already completed.

1665 Glenn Road, Southold

$2,895,000

5 Beds ⋅ 6 Baths ⋅ 990263 MLS

North Fork living, refined. Welcome to Wildberry. A newly constructed residence where design, light, and landscape converge - set against sweeping, sunset vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its surroundings. Luxury finishes have been selected and wired for full smart home capability. Intuitively designed for both everyday living and elevated entertaining. Offering 5 bedrooms and 5 full bathrooms and one half bathroom, the layout balances scale and comfort, providing a private retreat while accommodating guests with ease. Featuring two primary en-suite bedrooms on both the first and second floors, three guest bedrooms and a full cabana-style bathroom in the walk-out basement for pool party guests. Salt water pool is 18x36 and surrounded by patio with outdoor kitchen. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork. Home is expected to be completed July 2026, photo is artist rendering, landscape design is rendering not actual, additional photography and information coming soon.

1135 Wildberry 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.