luxury houses with terrace for sale Greenport, United States

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.

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.

This 2024 constructed 5,800-square-foot modern waterfront residence, built by Fountainhead Construction Inc., offers 250 feet of sandy beach and extraordinary panoramic water views. 180 degrees of sweeping water views from Crab Creek to North Haven Point and across Great Peconic Bay, with 250 feet of sandy beach along the shoreline. Walls of glass in the kitchen, dining area, living room, and select bedrooms frame the remarkable water views and glowing sunsets, creating a seamless connection between indoors and out. Step onto the waterfront patio or terrace to experience the setting even more fully. The sleek five-bedroom home includes six full baths and two half baths, with sophisticated finishes and amenities throughout, including 10-foot doors, a kitchen with custom Italian cabinetry and natural stone countertops, a fireplace, media room, and heated waterside pool. Set on 2.12 secluded acres, this exceptional property offers a rare opportunity for refined waterfront living

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.

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.

Shelter Island Ranch style home with 3 bedrooms and 2 bathrooms. Situated close to town and easy access to all beaches and either ferry this adorable home is currently configured as a 2 bedroom (large oversize primary bedroom with sliders to deck, guest bedroom, 2 newly renovated bathrooms, kitchen with new appliances, open living and dining area has stone surround fireplace and sliders to deck area. The lower level has finished space, laundry area, and doors to steps to access pool area. Large attic space and a separate garage with second level storage space.

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.

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.

Architecturally distinctive and deeply connected to its coastal setting, 126 South Midway Road is a private compound that captures the spirit of Shelter Island's artistic legacy. A private sanctuary comprising a four-bedroom main residence, a dedicated large art studio, and an independent two-bedroom casita, the property is thoughtfully arranged to maximize natural light, privacy, and sweeping water views. The architecture recalls relaxed modernism of iconic beach houses, an approach rooted in simplicity, creativity, and a fluid relationship with the landscape. Clean lines, a sleek pool and an intuitive indoor-outdoor flow create spaces that feel both intentional and effortlessly livable, ideal for a design-minded coastal lifestyle. The separate studio enhances the compound's creative sensibility, offering a quiet, light-filled environment for work or reflection, while the two-bedroom casita provides comfortable, private accommodations for guests or extended stays. Together, the structures form a cohesive yet flexible retreat, equally suited to intimate living and hosting. Comprised of 3,400 sq. feet living space across 3 levels in the main house plus additional storage, an expansive art studio of 1,400 sq. ft and 2-bedroom Casita living 1,140 sq feet with multiple decks and outdoor entertaining spaces this incredible compound is moments from Wades Beach. The property offers a rare combination of architectural character and proximity to one of Shelter Island's most celebrated shorelines. Longtime Shelter Island residents David Rankin OAM and Lily Brett OAM, both internationally recognized for their contributions to the visual arts and literature, have stewarded the home with a deep appreciation for creativity and place. (OAM denotes the Order of Australia Medal, a national honor recognizing distinguished contribution.) A compelling offering for those drawn to thoughtful design, privacy, and coastal modernism, 126 South Midway Road is a singular Shelter Island retreat.

Beautifully updated & fully renovated in 2020, Arts & Crafts style home in the heart of Orient Village, one block from Orient Harbor, walking distance to post office, country store & all village amenities. Open concept dining/living room with large wood burning fireplace. Updated gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher, & wine cooler. Enclosed front porch sunroom. Second floor master bedroom with large balcony overlooking the garden with ensuite bath – 2 sinks, free-standing tub & walk-in shower. Two additional bedrooms and full bath with tub and front-loading washer/dryer. Fenced yard, outdoor shower, backyard deck & lower patio for outdoor dining & entertaining. Professionally landscaped with mature trees and flower beds. Detached 1-car garage.

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a "to be built" opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor-outdoor lifestyle experience. The living room, dining area, and gourmet chef's kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range. Designed for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six person barrel sauna and cold plunge. Beautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor-outdoor lifestyle experience. The living room, dining area, and gourmet chef's kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range. Designed for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six person barrel sauna and cold plunge. Beautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature.nnSpanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise-to-sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level.nnThe upper level reveals the homes most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor outdoor lifestyle experience. The living room, dining area, and gourmet chefs kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range.nnDesigned for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six-person barrel sauna and cold plunge.nnBeautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Newly built cedar-shake estate on approximately 2.37 acres overlooking Fresh Pond and Sag Harbor Bay. in coveted North Haven. Offering 8,030± SF of living space, this traditional-style residence blends classic Hamptons architecture with modern scale, just minutes from Sag Harbor Village, marinas, beaches, and dining. The home features 7 bedrooms, 7 full and 2 half bathrooms, with wide-plank white oak floors, tray ceilings, and a wood-burning fireplace anchoring the main living spaces. Walls of sliding glass doors create seamless indoor-outdoor flow and enhance natural light throughout. An eat-in chef's kitchen with premium appliances serves as the heart of the home, complemented by a first-floor office/den. Multiple living and dining areas provide flexibility for everyday living and entertaining. Upstairs includes a beverage center, spacious bedroom suites, and two rear balconies with pond and bay outlooks. The layout is designed for comfort, scale, and easy living. Outdoor amenities include a 20' x 50' heated pool with bluestone patio, covered dining and lounge areas, and a fireplace-centered outdoor living room for year-round enjoyment. A rare highlight is the opportunity to add a 2,500± SF guest house, offering exceptional flexibility for future expansion. A refined North Haven offering with water views, privacy, and timeless design close to Sag Harbor Village.

Minutes from the bustle and charm of Sag Harbor Village, set on an exceedingly private and gated acre-plus flag lot with mature hedges, this immaculate 7 bedroom, 6500 square foot traditional checks all the boxes of a quintessential Hamptons summer home with a heated, gunite pool and spa, exceptional outdoor spaces, lined with hydrangeas, built-in BBQ grill kitchen, and an expansive finished lower level. Through the automated gate, a tree-lined approach leads to the handsome, white, shingled traditional with an attached 2-car garage. Adorned with shiplap, the bright, full height foyer creates a dramatic first impression. With lovely indoor and outdoor flow, the open concept floor plan offers a gourmet eat-in kitchen with an adjacent living room with fireplace and sitting area, with two sets of French door leading to the covered porch overlooking the pool area and rear grounds. A formal dining room with passthrough wet bar and wine storage serves the kitchen. A guest bedroom suite, pool full bath, foyer powder bath, expansive mud room, laundry room, and two-car garage completes the main level. Upstairs has a generous primary suite with luxurious bath including a freestanding tub and floating dual vanity. Three spacious en suite guest bedrooms supplement. The finished lower level features a gym, recreation area, and two bedrooms. Unique opportunity to own a turnkey home of excellent quality on a private acre-plus flag lot with a heated, gunite pool and spa and outdoor spaces fit for summer in the Hamptons.

Located in the sought-after Orient by the Sea community, this charming ranch is just .3 miles from the Association Sound Beach. The .437-acre property includes a spacious fenced backyard with mature specimen trees and three sheds. Interior highlights include an exposed-beam living room ceiling, solid hardwood doors and cabinets, oak and tile floors, a wood-burning stove, and an updated kitchen. Enjoy one floor living in this well-built home.

Two houses positioned just one block from Main Streets' American Hotel and the famous Sag Harbor Superyacht docks. 25 Rector Street offers an exceptionally rare and legal multi-family configuration. Comprising two character-rich structures-The Whaler's Cottage and The Artist's Retreat-the property benefits from a highly coveted, pre-existing non-conforming status, making it an incredibly unique find in the heart of Sag Harbor Village. Steeped in heritage, the one and a half bedroom Whaler's Cottage anchors the eastern portion of the property and dates back to the mid-1800s as a whaling industry supply building. Directly adjacent on the western side sits the one bedroom Artist's Retreat, which was beautifully renovated in 2016 and features an enchanting studio-turned-bedroom. A massive 1500 sq ft brick patio flows from the kitchen's French doors, and offers a spacious finished area for outdoor dining and relaxation. The property has a rich artistic legacy, which is only matched by its incredible future potential. Because the property is not on the list of the Village's inventory of historically significant structures, it allows more freedom to make the house your own. For those seeking multi-generational living, an irreplaceable location, and unrepeatable history- this is a once-in-a-generation opportunity.

Location is everything. Privately set on 2.1 secluded acres, this stylish and charming farmhouse style home is approached by a long winding drive that reveals a striking 1,000-square-foot post-and-beam barn before opening to sweeping views of the property's picturesque grounds. Thoughtfully maintained and rich in character, the home offers a traditional floor plan complemented by hardwood flooring throughout and a substantial wood-burning fireplace that anchors the main living space. The kitchen has been tastefully updated with a gas range and generous peninsula seating, flowing seamlessly into a dining area overlooking the manicured landscape and seasonal water views beyond. Upstairs, four well-proportioned bedrooms include three guest bedrooms served by a full hall bath, while the sun-filled primary suite offers a private retreat overlooking the property, also offering those peek-a-boo winter water-views. A rare opportunity to enjoy privacy, acreage, and timeless North Fork charm in an exceptional setting w/ ample room an in-ground pool or equestrian activities. This is the country house on the North Fork you've searching for!

Welcome to your dream home, built by the legendary Farrell Building Company. Completed in 2023, this stunning new construction is situated on a tranquil and completely private 2.35-acre lot, boasting sweeping views of the 11th hole of Noyac Golf Course. Just moments away from Sag Harbor Village, this 8,500 square foot, 8-bedroom, 9-bathroom property offers water access through the Noyac Hills Estate Association, making it the perfect retreat for modern living. Step inside and be immediately greeted by the open floor plan, tri-tone kitchen, sweeping views of your backyard that are framed out by the golf course. The spacious living room, dining area, family room, laundry room, and first-floor primary bedroom provide all the comfort and convenience you could ask for. Upstairs, you'll find a secondary laundry area, 4 guest bedrooms with en suite bathrooms, and a luxurious primary bedroom featuring an en suite bathroom, roomy walk-in closet, and sliding doors to your private balcony offering breathtaking views. But the amenities don't stop there. This property also features a media room, bonus room, great room, and a gym, ensuring that you'll always have plenty of space to relax and entertain. Outside, the frame construction and wood siding give the property a timeless appeal. An attached 3-car garage, sunken tennis court, and heated gunite pool with a separate spa provide a private haven for relaxation and entertainment. Don't miss out on the opportunity to own this masterpiece of a home, built by one of the most renowned builders in the industry. With its luxurious amenities and prime location, this property truly has it all.