45 Drew Drive presents a rare opportunity to own a beautifully proportioned home set on an expansive lot in one of Eastport's most sought after communities. Offering an exceptional sense of scale and privacy, this property blends timeless comfort with the coveted South Fork lifestyle. The residence features four generously sized bedrooms and two and a half baths, which includes an incredibly spacious primary bedroom En-suite, where sun-filled interiors flow seamlessly throughout the home, creating a warm and inviting atmosphere while offering flexibility for guests, work-from-home spaces, or multi-generational living. Outdoors, the sprawling grounds provide endless potential for resort-style amenities—with an inground pool already in place and outdoor entertaining areas to manicured gardens or future expansion. The size and setting of the lot are truly standout features, offering possibilities rarely found this close to the Hamptons. Perfectly positioned near waterfront access, renowned beaches, marinas, and acclaimed wineries, this home delivers the tranquility of Eastport with easy access to everything the Hamptons have to offer. A refined retreat with room to evolve, 45 Drew Drive is a compelling offering in one of the South Fork’s most desirable gateway communities.
BRAVO - 2150 sq ft, 55+ community - Primary on 1st floor with spacious bath, shower & tub. Nice floor plan for entertaining. Fireplace in Den adjoining kitchen. Large loft area on second floor - possible office, gym, 3rd bedroom. Natural gas, A/C and laundry room. Indoor/Outdoor pools, tennis pickleball courts, fabulous clubhouse. Gated security entrance.
Discover the enchanting charm of this traditional two-story home in the heart of Eastport a prime location known for its proximity to bay beaches and convenient access to New York City and the Hamptons. This turnkey residence is beautifully framed by a clear sunny front lawn and an inviting covered front porch with classic white columns, setting the tone for a warm welcome. Upon entering, you are greeted by a grand entry parlor boasting double-height ceilings and abundant natural light that enhances the beautiful hardwood floors throughout. The home features a well-defined layout including a dedicated dining room for formal meals and a cozy breakfast nook adjacent to a kitchen equipped with granite countertops and premium appliances. The inviting living room, complete with a fireplace and patio egress, ensures a perfect setting for both relaxation and entertainment. Offering four bedrooms and 2.5 baths, this home includes two ensuite bedrooms on the second level, providing ample privacy and comfort. The home office or den area provides a flexible space that can serve as your sunny retreat all year round or be converted into a convenient first-floor bedroom. The unfinished lower level presents a blank canvas awaiting your personal touch to create your dream space-be it a home theater, gym, or additional living quarters. Outside, the bright and sunny backyard is ideal for dining al fresco and enjoying peaceful moments in the open air. The residence is part of a private, gated community, which adds to the allure with resort-like amenities, including tennis courts, a swimming pool, a gym, and a clubhouse. With its serene location and outstanding community features, this home offers luxury and comfort and a lifestyle of ease and elegance, making it a perfect retreat or full-time residence. basic star discount if main residency 1097 rebate check from state
Welcome to Encore Atlantic Shores, a premier 55+ gated community offering an active lifestyle with an array of exceptional amenities. This exquisite Ovation Model boasts one of the most desirable backyards in the community, featuring mature landscaping, a covered porch, and an outdoor patio with an electric awning. Inside, the home offers a variety of inviting living spaces. The separate living and dining rooms create a warm welcome, leading to an open-concept kitchen and great room perfect for casual dining and relaxation. A two-sided fireplace enhances both the dining area and the great room. The first floor features a spacious primary bedroom with two walk-in closets and an ensuite bath complete with dual vanities, a tub, and a shower. Additional first-floor highlights include a den/study, a powder room, and a laundry room that leads to a two-car garage. Upstairs, discover another large bedroom, a full bath, and two versatile loft areas ready to be tailored to your needs. The community amenities are second to none, featuring a clubhouse with a living room, billiards room, ballroom, library, card room, gym, indoor pool, and spa, along with men's and women's locker rooms. Outdoor enthusiasts will appreciate the large pool and spa, tennis courts, pickleball, shuffleboard, and bocce. This remarkable unit offers a unique opportunity for luxurious living in a vibrant community. Don't miss your chance to call this special property home.
Step back in time at this historic, 4 bedroom, 2 bathroom home located in the heart of Eastport. With 278' feet of open bayfront and bulkheading, this one-of-a-kind property offers expansive water views and breathtaking sunsets! Enjoy outdoor living at its finest with wrap around decking and covered porches, perfect for entertaining or relaxing while watching the boats pass by. This timeless treasure blends architectural charm with a premier waterfront location - a rare opportunity for the discerning buyer. The 1.47 acre parcel includes a detached 3 car garage and room for swimming pool.
A rare opportunity to own one of Eastport’s most iconic bayfront properties. Set on 1.47 acres with sweeping, unobstructed water views, this historic residence embodies timeless elegance, old-world craftsmanship, and a sense of place that simply cannot be replicated. From the moment you arrive, the home’s character and charm are unmistakable. With a bulkheaded shoreline stretching along the bay, the property offers a commanding presence and the promise of unforgettable sunsets over shimmering waters. Built with classic proportions and enduring materials, the residence tells a story of a bygone era—yet remains perfectly suited for today’s lifestyle. Inside, gracious living spaces unfold with warmth and distinction. Original details highlight the home’s historic pedigree, while large windows invite natural light and frame the breathtaking vistas beyond. The layout offers an ideal balance of intimacy and grandeur, with rooms designed for both quiet moments and lively gatherings. Outdoors, the expansive grounds provide a private sanctuary rarely found along the South Shore. Mature trees, open lawns, and direct bayfront access create a setting that is as versatile as it is enchanting—whether you envision garden parties by the water, quiet reflection in nature, or future enhancements to create your dream estate. This is more than a property; it is a piece of Eastport’s history—a home where past and present converge to offer a lifestyle defined by elegance, privacy, and the enduring beauty of the bay.
Welcome to your dream home! This stunning new construction boasts over 3,000 square feet of luxurious living space, featuring four spacious bedrooms and three and a half modern bathrooms. The heart of the home is the large kitchen island, perfect for entertaining or family gatherings, complemented by high ceilings that create an open and airy atmosphere. Enjoy the convenience of a well-appointed prep kitchen, making everyday tasks a breeze. With an office/flex space on the first floor, you can tailor this home to suit your lifestyle needs. Step outside to relax on the covered patio, ideal for enjoying morning coffee or evening sunsets. This exquisite property is designed for comfort and style, making it the perfect place to call home! Set on .68 acres, there is plenty of room for a pool. Construction is anticipated to be complete early Summer 2025.
Discover your dream home in this stunning new construction, offering over 3,400 square feet of exquisite living space. This beautifully designed residence features four spacious bedrooms and 3.5 luxurious bathrooms. The open kitchen design boasts high end appliances as well as a large island with quartz countertops, ideal for entertaining or intimate gatherings. This space is complete with a dining area strategically placed for an abundance of natural light and a walk in prep kitchen which adds functionality and storage for the culinary enthusiast. Walking through the home you will enjoy the airy feel of high ceilings and custom finishes. The rest of the first floor features a primary ensuite bedroom with a spacious walk in closet as well as a Den/flex space provides versatility to meet your needs. On the second level, there are 3 genrously sized bedrooms and 2 full bathrooms plus a spacious bonus room. This home is a rare find as it features a full open and unfinished basement with 4 egress windows .Experience modern living at its finest in this exceptional new build! Set on .68 acres, now offered with a covered patio and heated saltwater pool.
To Be Built- Inviting & Warm...Offering Gleaming Hardwood Floors, Granite Kitchen Countertops, Cabinets W/Dove Tail Draws & Soft Touch Close. Pride Of Craftsmanship Throughout! Rendering/Photos Shown Conveys Craftsmanship of Homes Previously Built & To Be Built. Some Optional Features Include Venting Out For Stove, A Fireplace, Tray Ceiling Primary Suite, Shadow-box Molding-- Builder Will Build To Suit- No Models Available To View~ Purchaser To Pay Customary Builders Fees. Prices Subject To Change., Additional information: Appearance:T B B,Separate Hotwater Heater:Tbd
To Be Built- Inviting & Warm...Offering Gleaming Hardwood Floors, Granite Kitchen Countertops, Cabinets W/Dove Tail Draws & Soft Touch Close. Pride Of Craftsmanship Throughout! Rendering/Photos Shown Conveys Craftsmanship of Homes Previously Built & To Be Built. Some Optional Features Include Venting Out For Stove, A Fireplace, Tray Ceiling Primary Suite, Shadow-box Molding-- Builder Will Build To Suit- No Models Available To View~ Purchaser To Pay Customary Builders Fees. Prices Subject To Change., Additional information: Appearance:T B B,Separate Hotwater Heater:O
Welcome to this beautiful shy 1 acre Family Compound or Investors dream nestled in the tranquil and highly sought after Eastport community. Massive tree lined corner lot with Privet hedges features a main house with 3 bedrooms, 2 baths, large kitchen and basement. Walk across the well manicured secluded grounds to an immaculate fully updated artists cottage with private yard space and driveway. Property also features a horse barn and a 3 car detached garage as well as a shed. The grounds feature a beautiful deck and outdoor back yard that's perfect for entertaining with plenty of room for a pool. Walkable boat ramp, as well as many stores, all less then a half mile away. Located just minutes from local beaches, wineries, and the Hamptons. Relaxed country living with easy access to shopping, dinning and entertainment.
Gorgeous 4 Bed, 2.5 Bath Ranch w/finished basement, foyer, open floor plan, hardwood floors, LR, DR, EIK, Fenced Yard, and 2 Car Garage, Appearance is Excellent

Eastport is located in New York. Eastport, New York has a population of 2,095. Eastport is more family-centric than the surrounding county with 36.58% of the households containing married families with children. The county average for households married with children is 32.94%.
The median household income in Eastport, New York is $121,250. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Eastport is 45.3 years.
The average high temperature in July is 82.1 degrees, with an average low temperature in January of 22.2 degrees. The average rainfall is approximately 47.2 inches per year, with 28.5 inches of snow per year.