Southampton Homes with Colonial Style

Welcome to Southampton, NY, a picturesque gem nestled in the heart of Suffolk County. Renowned for its stunning beaches, charming downtown area, and rich history, Southampton is not just a vacation destination; it’s a vibrant community that offers an exceptional quality of life. One of the standout features of this area is its highly regarded school district. The Southampton School District is known for its commitment to academic excellence, providing students with a well-rounded education that fosters both intellectual growth and personal development. With a range of extracurricular activities, dedicated faculty, and a supportive environment, parents can feel confident that their children are receiving the best education possible.

In addition to its educational offerings, Southampton is also celebrated for its architectural beauty, particularly the colonial-style homes that dot the landscape. These charming residences, characterized by their symmetrical facades, gabled roofs, and classic detailing, exude a timeless elegance that appeals to many homebuyers. Imagine living in a beautifully restored colonial home, complete with modern amenities while still retaining its historic charm. The spacious layouts and inviting interiors of these properties offer the perfect backdrop for family gatherings and entertaining friends.

Whether you’re drawn to the area's rich cultural heritage, the top-notch schools, or the allure of colonial architecture, Southampton, NY, is a place where dreams come home. Explore the possibilities today and discover why so many families are proud to call this enchanting community their own.

Newest Southampton Homes with Colonial Style

$5,595,000

5 Beds ⋅ 9 Baths ⋅ 1048083 MLS

Privately set at the end of a long driveway on approximately 2.5 acres in Water Mill, this private Water Mill estate combines scale, privacy and resort-style living with convenient access to Southampton Village, ocean beaches, dining and shopping. Built in 2019, the approximately 7,635-square-foot residence offers 5 bedrooms, 8 full baths and 1 half bath across three finished levels, complemented by two separate pool houses and an oversized 3-car garage. The main level is designed for both everyday living and entertaining, with an expansive gourmet kitchen featuring fully integrated Thermador appliances, oversized paneled refrigeration, wine refrigerator and radiant-heated floors, opening to generous living and dining spaces. Three gas fireplaces add warmth throughout the home. Upstairs, two spacious primary suites each feature private balcony access, dual closets, luxurious baths and radiant-heated floors, joined by two additional bedrooms and a dedicated laundry room. The finished lower level provides substantial additional living space with a large recreation area, fifth bedroom and full bath, ideal for guests, fitness, media or play. Outdoors, the property unfolds into a private Hamptons retreat centered around a heated gunite pool, expansive bluestone patios and multiple areas for lounging, dining and entertaining. Two approximately 370-square-foot accessory pool houses further elevate the setting—one with a full kitchen, lounge, and bath, and the second offering flexible finished space well suited for a home office, gym, yoga studio, art studio or playroom. Additional highlights include an owned rooftop solar system, whole-property fiber-optic Wi-Fi coverage extending to the pool and accessory buildings, bedroom blackout shades, and a dedicated elevator bay designed for future installation. A rare combination of privacy, versatility and Hamptons lifestyle in an exceptional Water Mill setting.

421 Edge of Woods Road, Water Mill

$3,200,000

6 Beds ⋅ 2 Baths ⋅ 1034303 MLS

*601 Watermill Towd Road & 591 Watermill Towd Road Are Being Sold Together* This beautiful, bright six-bedroom, two-full-bath home sits on 1.055a and features a circular driveway, expansive back yard, outdoor shower and charming garden. The entry foyer leads to the sunlit living room featuring a wood burning fireplace, built-ins and dramatic floor-to-ceiling windows. The expansive eat-in kitchen and spacious family room share an open floor plan. Together, they are perfectly designed for dining & entertaining. They boast a wood burning fireplace and 3 sets of french doors which lead out to the oversized deck. A guest bedroom and full bath complete the first floor. The second floor includes the primary bedroom plus 4 additional bedrooms and full bath. *591 WATERMILL TOWD ROAD is also included in this sale. The additional, single & separate .355a buildable lot is perfect for a pool, pool house and/or tennis/pickleball court. The possibilities are endless as paradise awaits you in Southampton!

601 Water Mill Towd Road, Southampton

$3,750,000

6 Beds ⋅ 7 Baths ⋅ 1035855 MLS

SOUTHAMPTON VILLAGE CHARM - IDEAL LOCATION, TIMELESS APPEAL Nestled in the heart of Southampton Village, this recently renovated colonial home seamlessly blends historic charm with modern convenience. Beyond being a stunning residence, this home offers a proven rental history, making it a compelling investment opportunity. Just minutes from the vibrant village center, this property captures the essence of Southampton living. With 6 bedrooms, 7 bathrooms, and a thoughtful layout, this residence is perfectly suited for luxurious living and entertaining. The main level features an inviting open floor plan, highlighted by multiple sunlit living spaces, a cozy fireplace, and a formal dining room. The fully-equipped chef's kitchen is a standout, boasting quartz countertops, a large center island, stainless steel appliances, and a commercial-grade gas stove. Adjacent to the kitchen, a serene sun-room surrounded by lush greenery offers an ideal space for an office or sitting area. The main-floor primary suite is a private retreat, featuring a separate sitting room, en-suite bathroom, and exclusive access to a charming patio adorned with bistro lights. Upstairs, five spacious bedrooms, each with updated en-suite baths, offer comfort and elegance for family and guests. Step outside to your backyard oasis, where relaxation awaits. A pergola-covered deck, stone patio, and sparkling in-ground pool are surrounded by mature landscaping, a picturesque English garden, and sculptural accents. Evenings can be spent gathered around the fire pit or enjoying outdoor activities in this thoughtfully designed space. A true turn-key village home with easy access to the Southampton train and Jitney. The driveway can accommodate up to 10 cars, with extra street parking available.

244 N Main Street, Southampton

$1,744,888

3 Beds ⋅ 4 Baths ⋅ 1019753 MLS

An extraordinary opportunity to create your dream waterfront estate in one of the Hamptons' most coveted locations. Nestled along the tranquil shores of Mill Pond in Water Mill. The home has been thoughtfully taken down to the studs, with an extensive renovation already underway. Architectural plans have been professionally designed to transform the residence into a stunning, modern Hamptons retreat, and the permits are already in place to complete the project. Skip the years of planning, design revisions, permit delays, and uncertainty that come with building new. The vision has been created, the approvals have been secured, and the framework is ready. All that's left is to bring your own style and select the finishes that reflect your personal taste, creating a truly one-of-a-kind waterfront home. The perfect backdrop for effortless indoor-outdoor living and entertaining in one of the East End's most desirable settings. Whether you're seeking a luxurious year-round residence, a spectacular summer escape, or an exceptional investment opportunity, this is a chance that seldom comes to market. Opportunities to customize a waterfront home with approved plans in Water Mill are incredibly rare. Bring your vision to life and enjoy the best of Hamptons living—without the wait. ***Please note there are no bedroom and baths in structure please see attached plans

203 Head Of Pond Road, Water Mill

$10,500,000

7 Beds ⋅ 9 Baths ⋅ 937172 MLS

New Construction | Water Mill South Just completed by boutique custom builder Heartwood Corp, this 7-bedroom, 9-bathroom, 9,600-square-foot Water Mill South estate showcases signature craftsmanship and refined detail. Positioned on prestigious Cobb Road behind a motorized gate and enveloped by mature, professionally designed landscaping, the property offers a private retreat moments from Flying Point Beach and Southampton Village. A soaring two-story foyer introduces the open, light-filled layout, highlighted by architectural floor-to-ceiling millwork on a double-sided gas fireplace shared with the living room. The dining area flows into a fully outfitted butler’s pantry with sink, ice maker, wine refrigerator, and walk-in pantry. The chef’s kitchen blends elegance and performance with custom white oak and painted cabinetry, integrated luxury appliances, and a hybrid waterfall island ideal for entertaining. The first-floor junior suite features a private patio, two walk-in closets, and a large spa-inspired bath with double vanity and privacy-glass shower enclosure that welcomes natural light. The living room, kitchen, foyer, and junior suite all overlook the landscaped grounds and pool, creating seamless indoor-outdoor living. A mudroom with garage access and a powder room complete the main level. Upstairs, the primary suite is a tranquil sanctuary offering two walk-in closets, a luxurious bath with soaking tub, separate vanities, makeup station, and privacy-glass shower and water closet, plus a dedicated office and serene views. Four additional ensuite bedrooms, a bonus room, and a custom-outfitted laundry room complete the second floor. The lower level is designed for recreation, featuring a glass-enclosed wine cellar, den with wet bar and wine cooler, flexible gym/media/game space with exterior access, a private sauna with Bluetooth controls, a full bath with steam shower, powder room, and two guest or staff bedrooms. Outdoors, resort-style amenities include a heated saltwater Gunite pool with integrated spa and sundeck, outdoor shower, stainless-steel kitchen and bar, and a dedicated outdoor powder room for poolside convenience. Expansive patios and lush landscaping set the atmosphere for effortless summer living. With Wi-Fi–enabled smart-home capabilities, custom cabinetry, tailored closet systems, central vacuum, laundry on two levels, and a radiant-heated two-car garage, 158 Cobb Road embodies timeless sophistication, abundant natural light, and modern Hamptons craftsmanship.

158 Cobb Road, Water Mill

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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.