Greenport Homes with Colonial Style

Greenport Homes with Colonial Style

Welcome to Greenport, a picturesque village nestled in the heart of Suffolk County, New York, where charming coastal living meets a vibrant community spirit. Known for its rich maritime history and stunning waterfront views, Greenport is not only a desirable destination for residents but also an ideal place for families seeking quality education. The Greenport School District is highly regarded for its commitment to academic excellence and holistic development, offering a range of programs that cater to diverse learning needs. With dedicated teachers and a strong sense of community, students thrive in an environment that encourages curiosity and creativity.

As you explore the real estate options in Greenport, you'll discover a delightful selection of Colonial-style homes that perfectly complement the area's historic charm. These timeless residences boast classic architectural features, such as symmetrical facades, grand entryways, and inviting porches, making them a favorite among homebuyers who appreciate elegance and tradition. Many Colonial homes in Greenport are set on generous lots, providing ample outdoor space for family gatherings and summer barbecues, while their spacious interiors are ideal for both entertaining and everyday living.

Living in Greenport means enjoying a harmonious blend of small-town charm and modern conveniences. From local shops and eateries to scenic parks and beaches, residents have access to a wealth of amenities that enhance their quality of life. Whether you're drawn to the area's exceptional school district or the allure of Colonial architecture, Greenport offers a unique lifestyle that is sure to captivate you. Come and experience the warmth and community spirit that makes Greenport a truly special place to call home!

Newest Greenport Homes with Colonial Style

$2,249,000
4 Beds ⋅ 4 Baths ⋅ 1032350 MLS
Welcome to this amazing compound, short walk to private deed beach and dock Fit for entertaining large gatherings. Outdoor covered built in bar and kitchen Quite, Peaceful surrounding. Low taxes. Ready to move in. Will consider selling furnished

705 Gus Drive, East Marion
$799,000
3 Beds ⋅ 1 Baths ⋅ 1028101 MLS
Super Cute Greenport Village home packed with charm and character. Walking distance to downtown. 3 bedrooms, 1 bath, diving area, kitchen and living area all on 1st floor with 3 bedrooms and a full bathroom above. Full walk out Basement and fenced in yard. Close to downtown Greenport, Marinas, Golf, restuarants and wineries.

308 Monsell Place, Greenport
$1,249,000
3 Beds ⋅ 4 Baths ⋅ 1028434 MLS
Stylish Heritage Farmhouse: Dating to approximately 1910, this beautifully reimagined Queen Anne–inspired country home preserves a tangible connection to East Marion’s past. Set along the historic route once known as Kings Highway and Sunset Trail—today’s Main Road—and near Marion Lake, the residence was built when the hamlet still reflected its longstanding agricultural and maritime heritage while emerging as a sought-after North Fork summer retreat. Comprehensively renewed for contemporary living, the home pairs early-20th-century character and gracious proportions with refined interiors and exceptional outdoor potential. All major systems have been updated, offering the comfort, convenience and confidence of a modern residence within a home of enduring character. Privately situated behind stylish gates on a level, sun-filled half-acre, the property offers turnkey living in a thoughtfully landscaped setting. A welcoming wraparound porch opens to a beautifully appointed kitchen featuring stainless-steel appliances, quality finishes and sophisticated details. The open-concept living and dining areas flow naturally from the kitchen and extend to an open-air deck overlooking the expansive backyard. An existing pool permit provides an exciting opportunity to create a private outdoor retreat, while one of the property’s two substantial sheds could potentially be converted into a pool house, subject to applicable permits and approvals. The first-floor primary suite includes a beautifully finished bath with a soaking tub, while a separate powder room serves guests. Upstairs, two additional en-suite bedrooms each feature a thoughtfully designed full bath. Generous proportions continue throughout the home, with the basement providing abundant storage and a spacious laundry room. Propane heat and new central air conditioning ensure year-round comfort. The home’s flexible layout and peaceful yet convenient location also create an ideal live-work environment for remote professionals, digital nomads and those seeking a sophisticated country escape without sacrificing modern connectivity or convenience. Low East Marion taxes, two large sheds and mature landscaping further distinguish the offering. Ideally located minutes from Long Island Sound and Peconic Bay beaches, Marion Lake for kayaking and birdwatching, and the shops, restaurants and waterfront attractions of Greenport Village—with ferry connections to Shelter Island and the Hamptons—this stylish heritage farmhouse presents a rare opportunity to embrace four-season North Fork living and establish your own enduring North Fork legacy.

East Marion
$4,250,000
4 Beds ⋅ 5 Baths ⋅ 1007919 MLS
Orient, North Fork - For buyers ready to trade city noise for salt air, open sky, and space to truly exhale, 1640 Grand View Drive in Orient offers the kind of North Fork escape that feels both elevated and completely livable. Set above the shoreline with sweeping, cinematic views over Long Island Sound, this Nantucket-inspired coastal estate combines privacy, scale, craftsmanship, and direct waterfront beauty in one rare offering. With approximately 130 feet of private beach and more than 5,000 square feet of upscale, finely crafted living space, the home is designed around what city life often lacks: light, quiet, room to gather, room to work, and a constant connection to nature. From nearly every principal living area, the setting frames wide-open views of water, sky, and shoreline, creating an everyday backdrop that feels more like a retreat than a residence. A spacious covered porch entry opens to a gracious foyer and sets the tone for the home’s relaxed coastal character. The dramatic living room, with soaring vaulted ceilings, clerestory windows, and expansive Sound views, is made for both slow weekends and effortless entertaining. It is the kind of room that can host a holiday dinner, a laid-back summer gathering, or a quiet night in with multiple fireplaces, a record playing, and the water just beyond the glass. The large dining room offers an elegant setting for dinners with friends and family, while the immaculate kitchen with breakfast area overlooks the lush landscape of this private coastal retreat. The open-plan family room, complete with a gas fireplace, flows naturally to the waterside terrace, blurring the line between indoors and out. Morning coffee, golden-hour cocktails, long summer lunches, and late-night conversations all find their place here, with the Sound as the view. The main level includes a thoughtfully designed owner’s suite with fireplace, sunroom/sitting room, and serene private spaces that make the most of the home’s waterfront orientation. A dedicated home office with private en suite bath adds the flexibility modern buyers want, whether used as a true work-from-home setup, creative studio, guest suite, or potentially a fifth bedroom. Upstairs, the home continues to offer room for everyone and everything: a large sitting room, billiard/family room, sewing or craft room, junior owner’s suite with full bath, and two additional bedrooms connected by a Jack-and-Jill bath. The layout is ideal for hosting weekend guests, extended family, or friends escaping the city for beach days, dinners outside, and slower mornings. Immaculate and exceptionally well-maintained, the estate includes a wine cellar, full-house generator, outdoor shower, and many quality details throughout. The grounds also offer room for a potential waterside pool (permits required), adding the possibility of creating a full resort-style experience at home. For city-area buyers looking for a more grounded way to live without sacrificing style, comfort, or design, 1640 Grand View Drive offers a rare balance: sophisticated coastal architecture, true privacy, direct beach access, and the natural beauty of the North Fork. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life.

1640 Grandview Drive, Orient
$1,297,000
4 Beds ⋅ 2 Baths ⋅ 980655 MLS
Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this versatile property features a porch, deck, patio, and 1-car garage, along with additional outdoor amenities including a cabana and hot tub, all conveniently located near local restaurants, shopping, and transportation.

407 Wiggins Street, Greenport
$1,297,000
4 Beds ⋅ 2 Baths ⋅ 980657 MLS
Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this flexible property offers central air conditioning, front porch, deck, and patio, all conveniently close to local restaurants, shopping, and transportation. Turnkey appeal and income-producing potential enhance this compelling offering.

401 Wiggins Street, Greenport
$1,529,000
4 Beds ⋅ 3 Baths ⋅ 961091 MLS
Experience the beauty of coastal living with this young Colonial built in 2006 and set on 1.2 verdant level acres of privacy and seclusion. The expansive front yard, complemented by a grand circular driveway, creates a lasting first impression. The welcoming covered front porch is perfect for sipping your morning coffee while the equally expansive rear yard is ideal for star gazing on warm summer evenings or hosting large gatherings. An open floor plan connects the living, dining and kitchen spaces offering seamless daily living and makes entertaining a breeze. Four generously-sized bedrooms including a substantial primary ensuite with jacuzzi and an additional hall bath, complete the second floor. There is unfinished attic space above the attached two-car garage and a full unfinished lower level with high ceilings which may provide a blank slate for even more living space. Located just down the road from renowned Rocky Point Rd. Beach, a fresh vegetable stand and fragrant lavender farm, this home is also just a stone's throw from convenient ferries, a myriad of wineries and acclaimed Greenport with world class dining. This gem offers a fantastic opportunity to enjoy all the North Fork is so well known for and more!

2655 Rocky Point Road, East Marion
$2,150,000
4 Beds ⋅ 4 Baths ⋅ 915982 MLS
This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up! Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom adds convenience and flexibility. High ceilings and expansive windows frame the water views, filling the space with natural light. The custom chef’s kitchen features top-of-the-line appliances and flows easily into both formal and informal dining areas. The large living room includes a gas fireplace, game area, and a striking marine-lacquered wet bar complete with fridge/freezer adjacent to both pool and living areas. An additional den with water views offers a quiet retreat or extra space for guests. Outdoors, cedar fencing encloses a private backyard with a heated saltwater pool, areas for al fresco dining, and space to relax. Upstairs features two guest bedrooms sharing a well-appointed designer bath, tub shower combo. The primary suite has stunning water views, cathedral-ceiling, a separate sitting room/office, spacious dressing room, and a spa-like bath with soaking tub, large shower, and separate water closet with bidet. Stone steps lead through beach grass to a private dock—perfect for boating, kayaking, or paddle boarding. Located a few blocks outside Greenport village, yet tucked away from the crowds, and near one of the North Fork’s best bay beaches, this home offers the ideal balance of serenity and convenience. Also available furnished.

980 Manhanset Avenue, Greenport
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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.