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3400 & 3500 Sound Drive, Greenport
$4,600,000
3 Beds ⋅ 2 Baths ⋅ 825540 MLS
Presenting an exceptionally rare waterfront offering on the stunning Long Island Sound. This remarkable opportunity features two separate parcels totaling just shy of two acres: 3500 Sound Drive showcases a meticulously crafted mid-century modern single-family residence, boasting completely unobstructed coastal views that stretch for miles along the Long Island Sound. With a northwestern exposure, you’ll be treated to breathtaking sunsets that transform the sky into a magnificent display of colors each evening. 3400 Sound Drive is a pristine vacant parcel, offering versatile possibilities. This land can be seamlessly integrated into a grand estate or serve as a prime location for an additional single-family home, also featuring direct water views to the north and captivating vistas to the west. Both parcels present an impressive 250 feet of waterfront combined or 125' each, positioned approximately 25 feet above sea level, enhancing the panoramic views and ensuring a serene waterfront experience. Whether you are looking for a dual-residence opportunity or a trophy property to design your forever home, this unique package provides endless possibilities for waterfront living at its finest! Don’t miss your chance to own this exceptional slice of paradise.

3400 & 3500 Sound Drive, Greenport
250 Osprey Nest Road, Greenport
$2,900,000
4 Beds ⋅ 7 Baths ⋅ 968387 MLS
"Precision In Every Detail. Elevated Living Throughout" - Set within a private enclave moments from the Peconic Bay, this newly constructed home delivers a refined living experience defined by custom craftsmanship, scale, and seamless indoor-outdoor flow. Every element has been thoughtfully curated, blending clean architectural lines with bespoke materials and elevated finishes throughout. At the heart of the home, a striking chef’s kitchen anchors the main living space—appointed with quartz countertops, custom white oak cabinetry with lighting, Kohler workstation sink and a full suite of Miele appliances. Designed for both everyday living and elevated entertaining, the open-concept layout transitions effortlessly into expansive living and dining areas, where soaring ceilings, abundant natural light, solid white oak wood 6" plank floors and a custom stone fireplace anchored by bookcases create a warm yet sophisticated atmosphere. Bedrooms and bathrooms are designed as private retreats, featuring refined finishes, generous proportions, and a calm, modern aesthetic. A first floor primary ensuite offers the ultimate in convenience and privacy, creating a true main level retreat with exceptional finishes, flawless primary bathroom, expansive custom finished walk in closet and all with a well proportioned layout. The outdoor setting is equally compelling, offering a resort-inspired setting complete with a heated saltwater pool with custom waterfall, expansive bluestone slate patio, and built-in fireplace—ideal for hosting or unwinding in total privacy. The offering is further elevated by private association beach access to the Peconic Bay, perfectly suited for effortless trips by golf cart, which is included, creating a seamless connection between home and shoreline. Every detail, from the curated landscaping to the integrated lighting, enhances both ambiance and usability from day to evening. The home is equipped with a fully integrated custom home automation system, delivering intuitive control over lighting, climate, sound, and security. A generator hook up will ensure uninterrupted comfort, while thoughtful additions such as a golf cart—perfect for easy access to nearby waterfront and community amenities—further elevate the lifestyle offering. Each space reflects the same level of detail and intention found throughout the home. An unmatched opportunity to own a turnkey, showstopping residence where design, technology, and lifestyle converge—crafted for those who value both precision and presence. This listing may include images that have been digitally altered or virtually staged.

250 Osprey Nest Road, Greenport
340 Robinson Road, Greenport
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 935398 MLS
Presenting a rare waterfront property in Greenport, for the serious boater. This remarkable home features over 150 feet of waterfront on protected Stirling Harbor, offering the deep water dock space you've been waiting for. The luxury floating dock can easily accommodate oversized vessels, making it ideal for large yachts. Less than 3 years old, it has both 85 feet and 30 feet deep-water sides and is fully serviced with 200 amps of power and internet. Plenty of space for multiple boats, kayaks and friends to pull up waterside. Stirling Harbor offers big-boat access with an 8 foot maintained channel and calm water protection. Also perfect for quick runs to Gardiners Bay and Shelter Island. This very spacious 4-bedroom, 3-full bath home is in excellent condition and boasts wood floors throughout, an open floor plan, fireplace and central air conditioning. At the heart of the home is a sleek chef's kitchen with stainless steel appliances, kitchen island and a separate sunken dining room with direct water views. Step into the modern living room with fireplace, offering seamless indoor outdoor living with a large waterfront deck perfect for al fresco dining. First floor also boasts 3 large guest bedrooms with closets, 2 spa bathrooms, a laundry room and an oversized garage. The spacious second floor primary suite includes a living area, ensuite bathroom, walk-in closet and private walk-out balcony, perfect for enjoying the serene harbor views. Master suite could also double as a separate guest quarters, offering plenty of space for a large family. Beyond the unparalleled boating amenities, the property offers a prime Greenport location. You can easily bike to sandy beaches, award-winning vineyards or take a leisurely stroll into the charming Greenport Village full of restaurants, galleries, movie theater, fitness studios, fine shopping and ferry to Shelter Island and Hamptons. Greenport offers an easy commute (99 miles) to NYC via LIRR train or Hampton Jitney bus. Room for a future in-ground pool. This property offers a unique opportunity for those seeking a luxurious waterfront lifestyle with direct access to superb boating. Schedule a private viewing before this rare opportunity has left the dock!

340 Robinson Road, Greenport
2375 Sound Drive, Greenport
$2,150,000
5 Beds ⋅ 6 Baths ⋅ 975661 MLS
Perched atop the bluffs of the Long Island Sound, this carefully designed showstopper is located within the desirable Eastern Stirling Shores community, offering private beach access just a short walk away. The rear yard provides a true resort-style setting, where you can bask in full sun poolside beside the natural gas–heated, in-ground saltwater pool with electric cover, all while enjoying exceptional privacy created by mature privet hedges surrounding the property. Inside, the home features beautiful white oak floors throughout and a stunning chef’s kitchen anchored by a dramatic waterfall stone island. The main level offers one of two primary en-suite bedrooms complete with dual walk-in closets, along with a full-size laundry room with sink, pantry, half bath, and multiple living spaces centered around a gas fireplace. The second floor features a second primary en-suite bedroom with a spacious walk-in closet, private bathroom, and a balcony capturing water views of the Long Island Sound. This level also includes an additional stacked laundry area and three more en-suite bedrooms, each with its own private bathroom and balcony access. Completing the home is a large attached two-car garage that flows seamlessly into the main living area, as well as a third garage located beneath the main level. A spacious walk-out basement with high ceilings offers the opportunity to easily finish over 1,000 additional square feet of living space. Offering an exceptional blend of location, amenities, and turnkey condition, this impressive home delivers the very best of North Fork coastal living.

2375 Sound Drive, Greenport
3200 Sound Drive, Greenport
$2,142,500
4 Beds ⋅ 3 Baths ⋅ 951049 MLS
Set directly on the Long Island Sound, this waterfront home offers a rare opportunity to create something truly special in an exceptional location. Enjoy spectacular sunsets and water views from this gracious residence featuring 4 bedrooms and 3 full baths, including a primary suite on the first floor. The open floor plan is anchored by a spacious great room with a wood-burning fireplace, ideal for relaxed coastal living and entertaining. A full basement with high ceilings provides excellent potential for additional finished living space. Additional highlights include a generator, roof replaced in 2015, and deeded beach rights with beach access just a stone’s throw away. With vision and updates, this sound-front property can be transformed into an extraordinary waterfront retreat.

3200 Sound Drive, Greenport
3200 Bay Shore Road, Greenport
$2,025,000
4 Beds ⋅ 4 Baths ⋅ 853979 MLS
Ideally located just minutes from the heart of historic Greenport, this beautifully crafted home offers the perfect blend of coastal elegance and modern comfort. Enjoy access to the serene shores of Peconic Bay where tranquil waters and scenic views invite daily relaxation. Entertain and impress your guests from the bricked patio, and heated saltwater pool. Professional, lush landscaped grounds and local produce from the farm around the road completes the Farm to Table setting! Experience the perfect blend of comfort and classic charm in this stunning 2-year-old farmhouse with expansive water views from multiple rooms. This beauty is located in the coveted Peconic Bay Estates. Meticulously designed and ready for immediate enjoyment, custom details, 4-bedroom, 3.5-bathroom home offers spacious, light-filled living crafted for both relaxation and sophistication. A bright and airy home office offers sweeping views of Greenport’s waterways truly an inspiring place to work or create. Whether you’re strolling the quaint streets of Greenport or enjoying the natural beauty right outside your door, this property offers a lifestyle rich in charm and convenience.

3200 Bay Shore Road, Greenport
435 Maple Lane, Greenport
$1,900,000
4 Beds ⋅ 5 Baths ⋅ 915141 MLS
Welcome to this brand-new coastal retreat that epitomizes North Fork luxury. This exquisite property offers 4,500 square feet of meticulously designed living space across three levels, including a full walkout basement. This home seamlessly blends upscale entertaining with relaxed everyday living. Stroll outside to your private oasis, where a 20 x 40 heated, saltwater inground pool is the focal point, surrounded by an expansive patio, cozy fire pit, and lush landscaping. The 500 square-foot pool house enhances the outdoor experience with a wet bar, half bath, covered patio, and outdoor shower-ideal for rinsing off after enjoying your deeded Peconic Bay beach rights, located just moments away. Inside, high ceilings and open living spaces create a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, while the 5 spa-inspired bathrooms and 4 generous bedrooms offer comfort and style. The walkout lower level provides versatile space, perfect for a home theater, gym, or guest suite. An attached two-car garage offers convenience and ample storage for beach or golf gear. Situated in the coveted Cleaves Point Community, this property is just one minute from the beautiful Islands End Golf Course and three minutes from historic Greenport Village. This location combines coastal serenity with village convenience, making it an ideal full-time residence or luxurious weekend escape. This rare North Fork find is now available for sale, offering a unique opportunity to own a piece of paradise in one of New York's most sought-after locations. Could be You!

435 Maple Lane, Greenport
131 6th Street Unit #G7, Greenport
$1,687,500
3 Beds ⋅ 3 Baths ⋅ 862399 MLS
Experience the best of North Fork coastal living in this beautifully appointed 3-bedroom, 2.5-bath waterfront condo with breathtaking views of Peconic Bay and Shelter Island. Enjoy your morning coffee as the sun rises or set sail from your dock just steps from your door. With spacious, light-filled interiors, two fireplaces and seamless indoor-outdoor flow, this home is designed for effortless living and entertaining by the sea. A rare offering in a coveted location-just a few minutes from all that Greenport has to offer; boating, shopping, dining, tasting rooms, art and more!

131 6th Street Unit #G7, Greenport
426 Clark Street, Greenport
$1,645,000
3 Beds ⋅ 3 Baths ⋅ 941986 MLS
Okay, so I went to this house and it actually just works. You come in and there's this built in coat rack with cubbies for shoes (like finally, a spot for beach stuff). The first floor is totally open, living, dining, kitchen are all connected so everyone can hang out while you cook. Off the kitchen there's a deck set up for sitting and eating, and it looks right out to a cute backyard. The mudroom is clutch, storage cabinets, laundry, and a half bath, and a door straight outside. Plus there's a detached garage that's basically your beach gear locker, and the beach is literally a block away. It's just been completely renovated but still feels like Greenport Village, and with the low maintenance coastal siding, new windows, insulation, roof, furnace already done, we don't have to do any work. Also, you're like .3 miles to the shops, LIRR, Hampton Jitney and Shelter Island Ferry, so weekends are super easy for adventures. This is a Holiday Home that can work for us.

426 Clark Street, Greenport
123 Sterling Avenue Unit #4, Greenport
$1,600,000
2 Beds ⋅ 3 Baths ⋅ 961095 MLS
Welcome to an exceptional waterfront includes 2 units, 2-bedroom, 2.5-bath luxury condo offering sweeping panoramic views of Greenport Harbor and Stirling Basin. Located in one of Greenport’s most sought-after luxury buildings, this rare residence includes your own private boat slip and delivers an unmatched North Fork lifestyle. The home features a chef’s kitchen outfitted with state-of-the-art stainless steel appliances, an integrated refrigerator and dishwasher, and a built-in wine cooler. The open-concept kitchen, dining, and living area is designed for effortless entertaining, enhanced by soaring high ceilings and dramatic double doors that open onto a wrap-around balcony with breathtaking water views. Sunlight pours in throughout the day, brightening the entire space and framing breathtaking panoramic water views. The spacious primary suite is a private retreat, complete with balcony access, a custom walk-in closet with built-ins, and a spa-like en suite bath. A well-appointed second bedroom and additional full bath provide comfort and privacy for guests, while a convenient half bath serves the main living area. A unique bonus space adds incredible flexibility and can be used as an entertainment lounge, office, storage area, or private retreat — a rare feature that sets this unit apart. Additional highlights include in-unit laundry, dedicated indoor parking, and an additional outdoor parking space. Whether enjoying sunrise coffee on the balcony, docking your boat steps from home, or entertaining with harbor views as your backdrop, this residence captures the very best of waterfront living in the heart of Greenport.

123 Sterling Avenue Unit #4, Greenport
130 Sunset Lane, Greenport
$1,475,000
4 Beds ⋅ 5 Baths ⋅ 880117 MLS
Stunning Greenport New Construction Colonial w/ Heated In-ground pool! Step into a seamless blend of turn-of-the-century elegance and contemporary comfort in this exquisite new construction Colonial. Designed with classic architectural details and high-end finishes throughout, this 4-bedroom, 4.5-bathroom residence offers 2,900 sq. ft. of thoughtfully crafted living space and includes a 10x20 heated in-ground salt water pool. From the moment you arrive, the crushed stone driveway and detached 1-car garage set the tone for the timeless appeal of this home. Inside, you’ll find gleaming hardwood floors throughout, complemented by custom millwork that adds warmth and character to every room. The open floor plan is anchored by a spacious Great Room with a stately fireplace, creating a cozy yet sophisticated gathering space. The gourmet kitchen opens effortlessly to the dining and living areas, ideal for entertaining. The main-level primary suite is a serene retreat, featuring a spa-like en-suite bathroom and ample closet space. A charming laundry/mudroom with custom red brick flooring offers both function and style. Downstairs, the fully finished basement expands the living space with a second fireplace, a wet bar, a full bathroom, and a dedicated media room—perfect for movie nights or game-day entertaining. Enjoy outdoor living on the poolside private patio, ideal for morning coffee or summer barbecues. Every inch of this home reflects a perfect balance of traditional craftsmanship and modern convenience. A rare opportunity to own a new home with historic character in every detail that is in close proximity to Greenport Village, walk to 67 Steps Beach along the LI Sound and direct access to all that the North Fork has to offer!

130 Sunset Lane, Greenport
155 Bridge Street, Greenport
$1,470,000
5 Beds ⋅ 4 Baths ⋅ 969483 MLS
Welcome to 155 Bridge St, a custom-built stunner within walking distance to Greenport Village’s thriving water-front district and close proximity to North Fork farm-stands and world renown beaches. This well-appointed and thoughtfully designed home is truly turnkey, offering everything you could ask for and more. The open floor plan great-room is airy and flush with natural light, compliments of high-vaulted ceilings in the kitchen and perfectly balanced by the wide plank white oak floors throughout. As you walk-through the home, you’ll admire custom mill work, built-in shelving, a gas fireplace anchoring the first-floor great room and chic finishes that were perfectly selected and executed. The main level offers a convenient first floor en-suite bedroom, while the second floor features a generously sized primary bedroom with private en-suite bathroom and 2 additional guest bedrooms sharing a full hallway bathroom. The lower level provides a huge bonus with a second living-room/media room, conveniently located 1/2 bathroom, dry bar, laundry room, fifth bedroom, utility room for storage and owner’s closets. Finally, the rear yard provides a private resort-like experience with its bluestone patio, 10x20 heated saltwater pool, 8-foot high hedges and outdoor shower. This offering boasts outstanding rental history over the last five years, plus the option of coming fully furnished (down to the pool floats!), making this an ideal turnkey investment as well as your East End retreat!

155 Bridge Street, Greenport
1000 Green Hill Lane, Greenport
$1,450,000
4 Beds ⋅ 3 Baths ⋅ 899283 MLS
This beautiful custom built 2 story home is located minutes from a deeded beach and downtown Greenport with shops, wineries, boating, and golf. This classic style home blends style and comfort. Features include first floor primary bedroom with its own full bathroom and walk in closet, chef's style eat in kitchen with sub zero fridge, Jenn Air oven, and center island, wide plank flooring, living room that shares a two sided gas fireplace with the den, sun filled sunroom/dining room, laundry room, and half bathroom. The second floor features 3 bedrooms, one of which is huge and could be used for entertaining, and a full bathroom. The home has a full basement with an inside and outside entrance. Extras include a generator, central vac, central a/c, and rear patio.

1000 Green Hill Lane, Greenport
619 Bailey Avenue, Greenport
$1,415,000
4 Beds ⋅ 3 Baths ⋅ 990609 MLS
Welcome to 619 Bailey Avenue, a fully restored and move-in ready farmhouse located on the fringe of Greenport Village. Originally part of a larger North Fork farm and estate, this incredibly well appointed circa 1900 residence has been thoughtfully re-imagined to blend modern conveniences with preserved period details. Original features such as hardwood floors, detailed millwork/moldings, and classic architectural elements have been carefully maintained, while updates throughout provide comfort and functionality. The custom kitchen is a standout, featuring a 48" range, oversized center island, custom cabinetry, and an 8-foot bi-fold glass door that opens to the rear yard, creating seamless indoor-outdoor living. The first floor offers a well-balanced layout with a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, the second level includes two guest bedrooms and a full hallway bath, along with a primary suite featuring vaulted ceilings, a large walk-in closet, and an en-suite bathroom with double vanity and a walk-in shower with a dual shower head system. The rear yard is expansive and private, complemented by a detached one-car garage. Not to mention, there is also an active permit in place for a 16' x 32' in-ground pool, a perfect opportunity to take this rare offering one step further. Conveniently located near Greenport Village's business district, Kontokosta Vineyard, Bay/Sound Beaches and Sep's Farm-stand, this amazing offering is sure not to last!

619 Bailey Avenue, Greenport
123 Sterling Avenue Unit #8, Greenport
$1,330,000
3 Beds ⋅ 3 Baths ⋅ 813226 MLS
Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 8 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan. Additional information: Appearance: New.

123 Sterling Avenue Unit #8, Greenport
604 Main Street, Greenport
$1,300,000
3 Beds ⋅ 4 Baths ⋅ 861088 MLS
This c.1890 Greenport Village gem boasts 3 bedrooms, 2.5 baths plus a detached studio apartment. Set in the heart of the historic district, it merges many distinctive original details with thoughtful modern updates. A beautifully planted enclosed rear garden with deck and patio, perfect for relaxing and entertaining, leads to a renovated barn which features a 2-car garage and the spacious studio apartment. The main residence's generous ground floor living spaces include a front parlor and living room with original pocket doors, dining room, powder room, and a large renovated kitchen centered on a 48" Capital gas range. Upstairs there are three bedrooms and two full bathrooms, including one en suite. Refinished original wood floors add warmth and character throughout. The restaurants, shops and waterfront of the maritime village are just a few blocks away from this refined and peaceful retreat.

604 Main Street, Greenport
1605 Washington Avenue, Greenport
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 813518 MLS
Located just moments away from the vibrant heart of Greenport Village, this stylish and fully updated residence offers a perfect blend of modern amenities and coastal charm. Nestled on a generous ½-acre lot, the property will feature a captivating 12x24 heated, salt-water inground pool and a spacious patio, ideal for entertaining or relaxing in the sun (pool pictures are renderings as pool will be installed this Spring). step inside, you'll discover a bright and inviting interior adorned with beautiful white oak floors throughout. The open-concept first floor is designed for easy living, anchored by a crisp white kitchen that incorporates contemporary touches for a sleek aesthetic. Conveniently, you’ll find a cozy first-floor bedroom, perfect for guests or a home office. Venture to the second level, where two additional guest rooms share a well-appointed full bathroom. The highlight of this level is the stunning primary en-suite bedroom, featuring soaring sunlit ceilings and a luxurious private bathroom, creating a serene retreat. With its prime location and impeccable features, 1605 Washington Ave is the perfect blend of comfort and style. Don’t miss your chance to make this remarkable property your new home!

1605 Washington Avenue, Greenport
55 Brown Street, Greenport
$1,294,000
3 Beds ⋅ 3 Baths ⋅ 950921 MLS
Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

55 Brown Street, Greenport
58425 Route 48, Greenport
$1,240,000
3 Beds ⋅ 2 Baths ⋅ L3587738 MLS
Views that never end! Welcome to your picturesque beachfront retreat along the Long Island Sound, where breathtaking water views and private beach access create a serene escape. Enjoy year-round sunsets that will take your breath away. This charming home features a fantastic layout with sun-soaked, high ceilings in the great room, seamlessly connecting the eat-in kitchen, living room, and dining area. The large elevated waterside deck offers easy access, perfect for entertaining or simply soaking in the beauty of your surroundings. The main level accommodates two spacious bedrooms and a full bathroom, while the second level is dedicated entirely to a luxurious primary bedroom complete with an ensuite bathroom and a private waterside balcony-ideal for enjoying quiet moments overlooking the water. Don't miss this incredible opportunity to own your slice of heaven on the North Fork!

58425 Route 48, Greenport
175 AKA 611 Maple Street, Greenport
$1,215,000
3 Beds ⋅ 2 Baths ⋅ 999868 MLS
Some houses get a coat of paint and call it a day, 611 aka 175 Maple Street got a full designer renovation! This charming house is just a short stroll from Greenport Village waterfront restaurants, boutiques & beaches. This home delivers the warmth of classic architecture with a modern flair. Enter through the front door and the character hits first: hardwood floors throughout, recessed lighting overhead, and high-end finishes that make every room feel curated rather than constructed. The first floor flows easily between a thoughtfully designed living space and a kitchen equipped with stainless steel high end appliances and clean lines. Enjoy a cozy sun-room overlooking the backyard and a bonus space off the kitchen, which could have many uses including an office or flex space. Up-stairs, the entire second floor is dedicated to a spacious primary suite removed from the rest of the home in the best way possible! The primary suite spans the full upper level...a genuine retreat with vaulted ceilings with wood beams and its own en-suite bathroom including radiant heat in the floors and designer finishes. Two additional bedrooms on the main floor keep family and guests comfortable without compromise. Outside, the transformation continues. Bluestone pavers trace the front walkway and wrap the back patio. There is a detached cedar shake garage that is also freshly renovated. The ample driveway, which is crushed natural stone handles guests effortlessly- a rare feature for Greenport! Every system, the electric, plumbing, HVAC is brand new. Truly a turnkey getaway in one of the best locations in Greenport!

175 AKA 611 Maple Street, Greenport
1111 Main Street, Greenport
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 892479 MLS
A Creative Sanctuary in the Heart of Greenport. Tucked away on a tree-lined street in one of the “prettiest towns in America” (Forbes), this Cape Cod-style, wood-shingled home offers a rare blend of charm, privacy, and proximity to everything that makes Greenport so desirable. Perfectly situated on a full acre of land, the backyard abuts 8 acres of preserved open space owned by the Town of Southold — a rare buffer that offers both tranquility and an enduring sense of privacy. It’s less than a 15-minute stroll to 67 Steps Beach on the Long Island Sound and the vibrant heart of the village — including shops, galleries, restaurants, the North Fork Arts Center / movie theater, and the Greenport LIRR. Just a short bike ride away are Norman Klipp Park/Gull Pond Beach, 5th Street Beach, and the waterfront Kontokosta Winery. You’ll also find several nearby noteworthy wineries and farm stands that define the North Fork lifestyle. Inside, the home features three spacious bedrooms and two recently-updated full bathrooms, along with a wood-burning fireplace and original 1956 details that exude character. A separate 400 sq ft studio/office with vaulted ceilings, skylight, and radiant heated floors offers the ideal space for creative work, yoga, or lounging. Out back, the private garden and gravel patio were designed by Manscapers NY and feel like an outdoor room — complete with lounge chairs, shaded dining under mature trees, string lights, and layers of thoughtfully placed perennials, ferns, and herbs. It’s the perfect spot to gather with friends, grill, or unwind and watch the sunset. Whether year-round or as a weekend retreat, this is a home that invites creativity, connection, and calm — all just minutes from Greenport Village and the sea.

1111 Main Street, Greenport
145 Osprey Nest Road, Greenport
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 990436 MLS
Newly Reduced Price! Welcome to 145 Osprey Nest Road, a gem nestled in the heart of the charming Cleaves Point Beach Community. This home, with its resort-like atmosphere, offers an enticing blend of comfort and convenience. As a member of the Community, this property affords use of a private Bay Beach, in addition to having a community marina with some private docks and mooring lots, in a protected inlet off the Peconic Bay. This spacious home boasts four bedrooms and three bathrooms, designed with a modern aesthetic and an open, airy layout. The primary suite offers a private retreat, while three additional guest bedrooms share a full bath. The home's generous windows and soaring ceiling heights invite an abundance of natural light, creating a warm and inviting atmosphere. The home's living spaces are equally impressive. A cozy family room, a formal living room, and a dining area that flows into an eat-in kitchen, provide ample space for entertaining or relaxing. A wood-burning fireplace adds a touch of rustic charm, and a conveniently located full bath off the kitchen houses a washer/dryer for easy laundry days. The property's exterior is equally impressive. It sits on a generous 1/3 acre corner lot, surrounded by mature hedges for added privacy. The large mahogany deck, with a built-in Endless Pool Swim Spa, is the perfect place to relax and soak in the sun. Before returning indoors, the adjacent outdoor shower is available for your use. Just a stone's throw away, you'll find the bustling Village of Greenport, home to boutique shops, top-rated restaurants, and the Greenport marina in Mitchell Park. The nearby Island’s End Golf & Country Club, vineyards, farms, and beaches, along with the Orient Beach State Park, offer a plethora of leisure activities. 145 Osprey Nest Road is more than just a home; it's a lifestyle. Experience the best of coastal living in a community that welcomes everyone. Don't miss out on this opportunity. Schedule your viewing today!

145 Osprey Nest Road, Greenport
217 Center Street, Greenport
$1,075,000
3 Beds ⋅ 2 Baths ⋅ 1021578 MLS
Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport.

217 Center Street, Greenport
1105 August Lane, Greenport
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 988365 MLS
Welcome to this charming abode. This beautiful residence features three spacious bedrooms and two well-appointed bathrooms, perfect for comfortable living. The house is thoughtfully designed with additional features that add to its allure. Hard wood floors throughout. Buckets of room for a pool on this shy acre. Nestled in the heart of Greenport, the community environment is vibrant and welcoming. The area boasts of various local amenities, including parks, shopping centers, and eateries, ensuring a balanced and enjoyable lifestyle. The property is in excellent condition, offering a blend of comfort and modernity. Its neutral palette and inclusive design make it an ideal choice for anyone looking for a peaceful retreat in the midst of a thriving community. Experience a unique blend of tranquility and convenience here at your North Fork retreat. This property is not just a house, but a place you can truly call home. Reserve your private showing today!

1105 August Lane, Greenport
1705 Kerwin Boulevard, Greenport
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 949504 MLS
Opportunities like this in August Acres are few and far between. This 4-bedroom, 2.5-bath Colonial with deeded beach rights delivers the rare combination buyers wait for—location, efficiency, and long-term value—without compromise. From the moment you arrive, the home feels both welcoming and solid. A cozy fireplace anchors the main living space, while tilt-in Andersen windows fill the home with natural light and simplify maintenance. Behind the scenes, major investments have already been made: solar panels, a new roof, and central vacuum offer peace of mind and lower carrying costs—features buyers wish for but rarely find already done. The radiant-heated basement and garage elevate everyday living and future potential, providing comfort and flexibility that set this home apart from others in the neighborhood. Step outside to the bluestone patio, where summer evenings, entertaining, and quiet mornings become part of daily life. With beach access, meaningful upgrades, and a highly desirable neighborhood, this is the kind of home buyers regret missing. A rare chance to secure not just a property—but a lifestyle—in August Acres.

1705 Kerwin Boulevard, Greenport
609 1st Street, Greenport
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 912884 MLS
A true gem in the heart of Greenport's charming maritime village! Charming 4-bedroom home on a picturesque tree-lined street with water glimpses as you go. This beautifully preserved home is full of character and charm, and ideally located just moments from the waterfront, dining, shops, convenient transportation, beaches and everything that makes Greenport village so special. This gem of a home has a welcoming front porch, inviting foyer/parlor, eat-in kitchen, formal dining room, spacious living room, full walk-up attic offering expansion potential or creative space, full basement for storage or workshop use, and a one car detached garage. Whether you're seeking a year-round residence, a weekend retreat, or a piece of Greenport's rich history, this property offers unmatched character and location.

609 1st Street, Greenport
450 Maple Lane, Greenport
$999,999
3 Beds ⋅ 3 Baths ⋅ 1002141 MLS
Welcome to North Fork living at its finest! This beautifully maintained 3-bedroom 2 1/2-bath home offers the perfect blend of coastal charm and comfort, ideally located just moments from the golf course and with private beach access. Surrounded by stunning, professionally landscaped grounds, the property features an inviting deck and spacious patio-perfect for outdoor entertaining or relaxing in a peaceful setting. Inside you will find a layout designed for both everyday living and weekend getaways. Whether you're seeking a year-round residence or a serene retreat, this exceptional home captures the best of the North Fork lifestyle

450 Maple Lane, Greenport
285 Sandy Beach Road, Greenport
$999,999
4 Beds ⋅ 4 Baths ⋅ 960148 MLS
Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

285 Sandy Beach Road, Greenport
216 North Street, Greenport
$999,000
3 Beds ⋅ 4 Baths ⋅ 961348 MLS
CHIC. STYLISH. SOPHISTICATED. This Brooklyn Brownstone-inspired beauty brings big-city edge to North Fork living. 3 Beds | 3.5 Baths. Stunning new construction. Entertainer's dream kitchen. EV charging ready. Chic studio shed. Fenced + professionally landscaped backyard. Sun-drenched. Designer-finished. MINT+++. Stroll to farmers markets, restaurants, bars, boutiques, and the waterfront. This is Greenport living at its most irresistible.

216 North Street, Greenport
168 Bay Avenue, Greenport
$999,000
3 Beds ⋅ 2 Baths ⋅ 934918 MLS
Historic Italianate home located within the Greenport Village Historic District, this timeless residence captures classic Greenport charm just one block from the Village’s best shops, restaurants, and harborfront attractions. The home spans approximately 2600 square feet on a generous lot. The first floor offers a kitchen with moveable island and full appliance suite, a light-filled living room with sterno fireplace and ceiling speakers, and front and back parlor rooms that open for easy flow and entertaining. A formal dining room, large ADA-compliant full bath, half bath, and laundry nook complete the main level. Upstairs are three bedrooms—including one with possible surround sound and TV setup—a full bathroom with steam shower, and an additional storage room. An unfinished attic and basement provide potential for expansion or creative use. Additional highlights include hardwood floors throughout, HardiePlank siding, wooden storm doors, an inground sprinkler system, and a gated driveway with space for two cars. Mechanical updates include a 2024 oil furnace, electric hot water heater, and modernized systems with cast iron radiators and electric baseboard heat. Village sewer and electric service, plus a private well with filtration, water softener, and reverse osmosis systems, ensure comfort and efficiency. A rare opportunity to own a true piece of Greenport’s history—filled with character, warmth, and an unbeatable in-town location.

168 Bay Avenue, Greenport

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