luxury real estate for sale Greenport, United States

Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

Welcome to 550 Madison Avenue in Greenport, a thoughtfully designed New Construction farmhouse that feels comfortable from the moment you arrive. The covered front porch is more than an architectural detail. There is actually room for a chair and side table, creating the perfect spot for a quiet morning coffee. Inside, wide 6-inch oak floors connect the bright, open living spaces. The powder room is conveniently located near the front entrance, but it is tucked far enough away from the open living room, dining area, and kitchen to give everyone a little privacy when the house is full. The custom kitchen design brings together the features buyers keep asking for, including a paneled refrigerator, a full pantry closet, open shelving, generous cabinetry, and a kitchen sink positioned beneath a window overlooking the backyard. Even doing the dishes comes with a view of the established maple trees. A full glass slider in the dining area fills the back of the home with natural light and creates an easy connection to the outdoor entertaining spaces and grill. The backyard views can also be enjoyed from the living room, making the surrounding landscape feel like part of the interior design. Upstairs, the primary bedroom features a peaceful en-suite bathroom with distinctive tile flooring and calm, carefully selected finishes. Even the first-floor powder room has beautiful wallpaper, adding personality and making this New Construction home feel intentional rather than predictable. The fully fenced backyard is surrounded by established maple trees, creating a quiet and private setting that feels like a hidden corner of Greenport. The newly installed stone patio includes an outdoor cushioned conversation area, a separate outdoor dining patio, and a dedicated fire pit for evenings under the trees. There is also room to explore the possibility of adding a pool without making the yard feel crowded. The location brings the North Fork lifestyle within easy reach. The Greenport LIRR station and Hampton Jitney stop are approximately half a mile away for convenient transportation to New York City. Aldo’s Coffee is about a three-minute bike ride or a ten-minute walk, with Greenport Village shops, restaurants, waterfront destinations, and local beaches all close enough to enjoy without always getting back into the car. New Construction, a custom kitchen, paneled appliances, wide oak floors, en-suite bathrooms, a fenced backyard, mature trees, outdoor entertaining spaces, and easy access to Greenport Village. This might be the one you have been waiting for. You really need to come see it. In the evening it sparks with fireflies to capture summer vibes in Greenport Village.

Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 1,000 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 1,300 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and an additional 300 square feet of living area, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly installed crushed-stone driveway with Belgian block edging, a large rear lawn, full irrigation, and a charming front porch. A substantial 600-square-foot, two-car garage and additional storage shed further enhance the property's functionality. Whether you're an investor seeking a ready-made income-producing property or an end user looking to offset carrying costs with rental income, 430 First Street presents a compelling opportunity in the heart of Greenport Village. Located just two blocks from Greenport's vibrant business district, the property offers convenient access to public transportation, shops, restaurants, grocery stores, local farm stands, parks, and beaches—all while providing the space, condition, and versatility that make this a truly special offering.

Set along the quiet shoreline of Pipers Cove Bay in Shelter Island Heights, this west-facing waterfront retreat is tucked at the end of a private drive and has been thoughtfully reimagined by Heiberg Cummings, whose signature approach to layered design transforms the home into something both sophisticated and deeply connected to its surroundings. Every room on both levels is oriented toward the water, creating a constant dialogue between the interiors and the landscape beyond. Natural textures, a restrained palette, and carefully considered details allow the landscape to remain the focal point. The house unfolds around the view with a central wood-burning fireplace anchoring the open living room, kitchen and dining space. Glass doors open onto a series of waterfront decks, blurring the line between indoors and out and offering a front-row seat to the island's spectacular western sunsets. The primary suite occupies the main level, complete with an en-suite bath and private waterfront terrace. Downstairs, two bedrooms and a full bath are complemented by a generous waterfront den and library, creating an inviting second living space with uninterrupted views across the cove. On the opposite side of the den, a shaded terrace offers another quiet place to read, relax, or escape the afternoon sun. Outside, the property reveals itself one destination at a time. Multiple outdoor living spaces, perfect for hosting summer dinners on the terrace overlooking the water, or sunset cocktails in the private beach garden with two fire pits and a lantern lit dining area. Fully equipped beach bar , integrated outdoor sound system disappears into the landscape. Mooring rights for a vessel up to 40 feet make it easy to explore the surrounding waters before returning home for sunset. Private, thoughtfully designed, and deeply connected to the water, this is a home that captures the quieter side of the East End, where mornings begin on the beach, afternoons are spent on the water, and each day ends with the sun setting over Pipers Cove Bay. Residents also enjoy access to the Shelter Island Heights community tennis courts, while the Ferry, Marie Eiffel Market, Leon 1909, and the Heights' shops and waterfront are all just a short distance away, placing some of the island's favorite destinations within close proximity.

Dating back to the original 1871 layout of the Shelter Island Grove and Camp Meeting Association, Spring Garden Avenue is celebrated for its organic, rolling streetscapes and preserved 19th-century architecture. 5 Spring Garden Avenue is an authentic 1880 Victorian residence that embodies the classic style of the era, from its steeply pitched rooflines to its expansive exterior woodwork. The interior layout is expansive and true to its vintage, characterized by distinctive octagonal rooms on both the first and second floors. With five bedrooms, a sprawling third-floor attic loft, and a substantial footprint of covered decks and porches, the home offers a generous canvas within a historic setting. A significant structural update was completed in 2008, replacing the older foundation with a new poured concrete basement and structural footings, alongside the installation of a new roof. Featuring full access to the Shelter Island Heights Association tennis courts and beach club, this property represents an authentic piece of island history.

What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the landscape each season.Inside, the home has an easy, open flow with wood floors, a spacious hallway leading to the bedrooms, and a living room and kitchen that connect naturally for everyday living and entertaining. Just off the garage, the laundry room and mudroom create a practical drop zone for shoes, bags, beach gear and everything else that helps keep the main living spaces organized.The fenced backyard has its own personality, with an outdoor fire pit, established vegetable gardens, a huge fig tree and an additional garden shed for tools, bikes and outdoor storage. It is the kind of yard that already feels lived in, cared for and ready to enjoy.Location adds another layer to the lifestyle. Iconic 67 Steps Beach is within walking distance at the end of Sound Rd for minutes away for those incredible sunsets over Long Island Sound, while Greenport's coffee shops, restaurants and village destinations are close enough that grabbing your morning coffee does not always have to involve getting in the car.It is a home that combines comfortable everyday living with gardens, outdoor spaces and one of the things that makes Greenport so special: the ability to enjoy the beach, the village and the North Fork lifestyle right outside your door,

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

Rare opportunity to own a charming early-1900s Victorian farmhouse in the historic Heights. Set on a quiet road, this inviting home features an extra-large yard perfect for entertaining and a welcoming wraparound porch ideal for relaxing summer evenings. Inside, the home boasts a spacious living room with a wood-burning fireplace, a gracious parlor, formal dining room, and a first-floor bedroom with a full bath. Upstairs are two additional bedrooms and another full bath. A full basement provides ample storage and utility space. Just a stone’s throw from downtown shopping, restaurants, and all that the Heights has to offer, this is a rare find in one of Shelter Island’s most sought-after neighborhoods.

A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the façade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures — each equipped with electricity and water, and one including a bedroom — offer flexible space for guests, a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

Set in the wonderful North Fork beach community of Summit Estates, this spacious 3 bedroom, 2-bath cedar shake expanded ranch is ideal with its single-story living design and large yard ~ perfect for a pool and poolhouse. The Community beach, park, and dock are down an elegant private lane to a community parking lot and a magical paved trail. So handy to easily transport your beach and boat equipment from car to beach and boat! Close to Island’s End Golf Course, wineries, and the transportation hub and shopping/dining in the historic seaport Village of Greenport. A lovely North Fork retreat!

Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home.

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .44-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery.

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is known for their spectacular sunsets. This .58-acre vacant lot backs up to historic Westmoreland Farms creating a beautiful backyard views.

Rare opportunity to own .62 Acres of waterfront buildable land along West Neck creek, offering a beautiful setting with water views and direct access to the shoreline. Nestled within the peaceful Silver Beach community, this private and tranquil property is surrounded by nature and offers an exceptional opportunity to create a waterfront retreat. Across the water, protected preserved land ensures that the natural setting and peaceful views will remain undisturbed, adding to the property's sense of privacy and tranquility. Buyers should conduct their own due diligence regarding zoning, permits, wetlands, building potential, waterfront regulations, and all other applicable requirements.

Step behind the hedges. Founders Landing, Southold. Private park-like .63 acre. Custom Arts & Crafts influenced home. Bay beaches, marina, restaurants, shopping & transportation all just a stone's throw away. Exquisitely landscaped. Gracious front porch. Large foyer with a one-of-a-kind staircase with crafted newel posts. Vaulted ceilings, large windows w/ transoms and an openness that invites nature inside. Imposing brick wood-burning fireplace. Custom kitchen, dining room w/ tray ceiling. French doors lead to sunroom w/ west, south & north exposures. 1st fl master suite.. Beautiful fenced backyard w/ brick patio & specimen plantings. Plenty of room for the pool of your dreams. Whole house generator. Meticulously maintained and move-in ready. Adjacent .64 acre property also available. Call for details. Your family compound might just be in sight.

Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum structural integrity, energy efficiency and elevated finishes throughout. The sleek open-concept design encompasses approximately 4,500 square feet of living space. The light-filled residence showcases curated architectural features, ranging from floor-to-ceiling glass, floating staircases, bluestone and covered patio, water-view balcony, and a walk-out lower terrace. The Modern custom kitchen is adorned with ceiling-high cabinetry, Thermador appliances, marble countertops and porcelain inlay backsplash. The adjoining great room is anchored by a stunning gas fireplace surrounded by textured porcelain and this main level also includes an office, dining room and junior en-suite offering private access to the water and saline heated pool. An upper level primary en-suite includes a private balcony and three additional spacious bedrooms, luxury baths, laundry and unfinished bonus space. The lower level offers 2,000 square feet for new owners to reimagine and personalize. The offering is complete with Founders Landing Beach, wineries, farm to table dining and a vibrant North Fork atmosphere.

Coveted Maple Lane setting in the heart of Southold Village with easy access to all Southold Village amenities and LIRR ~ This recently transformed shingled Craftsman Style residence offers 4 bedrooms, 3.5 baths, timeless architectural character, exceptional private outdoor living, and a truly special North Fork lifestyle. Beautifully landscaped with specimen plantings, the property is designed for relaxed year-round or seasonal enjoyment. Outdoor amenities include a new heated 16 x 32 inground saltwater pool, hot tub, outdoor shower, and gracious covered porches at both the front and rear of the home. Classic Craftsman details enhance the curb appeal, including Arts & Crafts-style columns on river rock bases, double-dipped cedar shingles, a custom garage door, and a signature Craftsman front door. Inside, the main level offers an inviting open layout with wood floors throughout. The spacious living room features a wood-burning fireplace, while the eat-in kitchen, dining room, and window-filled den provide warm, functional spaces for everyday living and entertaining. Both the kitchen and den open directly to the rear covered porches, creating an easy flow for indoor-outdoor living. The first floor also includes two bedrooms, one full bath, one half bath, and a mudroom/laundry room. Distinctive interior details include oak trim around the windows and doors, as well as a beautiful staircase with a one-of-a-kind custom newel post. Upstairs, the primary suite serves as a private retreat with a generous sitting and office area, two-sided gas fireplace, sauna, and a fabulous tiled bath with spacious walk-in shower. A newly added junior primary suite, completed in 2026, adds comfort, privacy, and flexibility for guests or extended stays. Just a few doors from the edge of charming Southold Village, the Southold Historical Society and close to Founders Landing Bay Beach and Park, this exceptional home offers easy access to the marina, restaurants, shops, wineries and NYC transportation. This is a rare Southold Village offering with remarkable character, amenities, and the superior North Fork location you have been looking for.

Extraordinary North Fork Bayfront Estate on a Private Peninsula on Paradise Point, Southold- Welcome to one of Southold's most exceptional waterfront offerings, a spectacular bayfront estate set on a private 1.6-acre peninsula within the coveted Paradise Point community. Surrounded by water on three sides and boasting an extraordinary 335 feet of Bayfront shoreline and private dock in a protected boat basin, this remarkable property captures sweeping panoramic views across Southold Bay to Shelter Island and beyond. Approached by a circular drive framed by mature specimen plantings and meticulously landscaped grounds, the residence immediately impresses with its timeless Nantucket-inspired architecture and commanding waterfront presence. Encompassing approximately 5,100 square feet, the home offers 4 bedrooms and 3.5 baths thoughtfully designed to maximize light, space, and breathtaking water vistas from nearly every room. A grand two-story foyer welcomes you with a dramatic sightline through the home to the open bay beyond. Soaring ceilings, expansive living spaces, and walls of windows create an atmosphere of elegance and tranquility. The open-concept main level features a gracious living room with a wood-burning fireplace, a waterfront sitting room with a gas fireplace, and an office alcove. The expansive chef's kitchen is designed for both entertaining and daily living, featuring stainless steel appliances, granite countertops, and captivating views of the bay and heated waterside pool. Casual dining overlooks the water, while the formal dining room enjoys picturesque views of the protected boat basin. The first floor also includes a bayside en-suite primary bedroom, laundry room, and powder room. Upstairs, the luxurious primary suite and private sitting room offer unrivaled views over the boat basin and open bay. Two additional oversized guest bedrooms, each with water views, share a full bath, while the open landing provides yet another spectacular vantage point. Additional amenities include an elevator to all three level, whole house generator, spacious walkout basement ready for customization, 2-car garage and a heated waterfront pool. Rarely does a property combine such privacy, waterfront frontage, boating access, and panoramic views in one extraordinary setting. This is a once-in-a-generation opportunity to own a signature North Fork estate with dock and waterside pool. A truly exceptional waterfront retreat unlike any other.