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103 Middle Pond Road, Southampton
$2,095,000
4 Beds ⋅ 3 Baths ⋅ 949783 MLS
Set on a picturesque acre in Southampton, this four-bedroom, three-bath residence offers a rare combination of water views, an in-ground pool, and an all-weather tennis court. Designed for effortless Hamptons living, the home features generous light-filled interiors with seamless indoor-outdoor flow ideal for entertaining and relaxation. The thoughtfully laid-out floor plan includes comfortable living and dining spaces, a spacious kitchen, and multiple bedrooms to accommodate guests with ease. Outdoor amenities are highlighted by expansive grounds, mature landscaping, a sun-drenched pool area, and a private tennis court—creating a true resort-like setting. With tranquil water views from the upper level and close proximity to Southampton Village, ocean beaches, and local amenities, this property presents an exceptional opportunity to enjoy the Hamptons lifestyle in a coveted location. This property is an offering to be reimagined and offers endless potential to create your Hampton’s home

103 Middle Pond Road, Southampton

91 Fresh Pond Road, Northport
$2,000,000
6 Beds ⋅ 3 Baths ⋅ 1030897 MLS
A rare offering on the Long Island Sound in Northport: waterfront, private, and open to a horizon that goes on for miles. Every room looks out at the water. Every day starts with salt air and bare feet. Walk out your back door and onto the beach. Fresh Pond sits just across the road for kayaking and quiet paddles. Inside, your eyes go straight through the house to the water. Two-story living room, soaring ceilings, wood-burning fireplace, and walls of glass that never let you forget where you are. The dining room and kitchen carry the view forward, with a breakfast bar, Wolf six-burner range, and Sub-Zero refrigeration, built for long dinners that end on the sand. Six bedrooms, three full baths, two staircases. The first-floor primary suite opens to a sun-filled solarium and a spa-inspired bath with deep soaking tub and separate glass shower, plus an oversized walk-in closet. A second bedroom, full bath, and laundry complete the main level. Four bedrooms upstairs, a walk-in cedar closet, and a shared balcony made for sunsets. Roughly .50 acres, bulkheaded. Andersen windows, cementitious cedar shake siding, wood and tile floors, oil heat, natural gas to house for cooking,central air, 200-amp electric, two-car garage. Deeded rights to the private community beach association (fee) open onto miles of beach. Minutes to Indian Hills Country Club golf and the charming waterfront village of Northport. Easy access to parkways. Northport schools. Bring your vision: refresh and upgrade what's here, or build the beach house you've been imagining. Addresses like this one rarely come available.

91 Fresh Pond Road, Northport

4 Bayview Avenue, Shelter Island Heights
$1,999,999
6 Beds ⋅ 6 Baths ⋅ 1045616 MLS
Welcome to 4 Bayview Avenue, a remarkable residence nestled in the historic heart of Shelter Island Heights. This expansive property, designed with the art of entertaining in mind, offers a generous six bedrooms and five and a half bathrooms, providing an abundance of space for comfortable living. Upon entering, you'll be welcomed by an array of inviting sitting areas spread throughout the main house, each offering a unique setting for relaxation or socializing. The fully finished lower level, complete with direct access to the pool and backyard, adds a layer of versatility to the living space. This home is equipped with a variety of desirable features such as central air, a cozy fireplace, and a dedicated office space, ensuring your every comfort and convenience is met. The private guest quarters serve as a separate haven for visitors, enhancing the overall accommodation. The outdoor space is a haven of peace and privacy, with beautifully landscaped grounds and mature trees. The newly installed expansive mahogany decks, adorning both the main house and guest house, offer the perfect backdrop for outdoor gatherings and soaking in the surrounding natural beauty. The property also invites you to partake in community amenities such as a beach club and tennis, allowing you to fully embrace the joys of coastal living. A two-car garage with radiant heat flooring adds to the property's convenience, while the heated gunite pool and outdoor shower offer additional luxuries. With a vast area of approximately 6,098 square feet, this home is designed to cater to a variety of lifestyle needs. This exceptional property in Shelter Island Heights is waiting for you to make it your own. Don't miss this opportunity. Schedule a private viewing.

4 Bayview Avenue, Shelter Island Heights

589 Caledonia Road, Dix Hills
$1,999,999
5 Beds ⋅ 5 Baths ⋅ 1034343 MLS
Behind the gates of this prestigious Caledonia enclave in Dix Hills lies a residence of rare distinction. Inspired by the timeless elegance of a French Chateau, this custom-crafted home is gracefully set on over an acre of exquisitely landscaped grounds, offering an extraordinary sense of privacy, tranquility, and refinement. Located within the acclaimed Half Hollow Hills School District, this exceptional property embodies the very best of luxury living. Spanning approximately 5,000 square feet, the residence presents five generously appointed bedrooms and four-and-a-half impeccably designed baths. Every detail has been thoughtfully curated, from rich hardwood floors and bespoke millwork to imported marble and artisan tile, creating interiors that are both timeless and effortlessly sophisticated. Designed with equal emphasis on gracious entertaining and everyday comfort, the home unfolds through elegant formal spaces anchored by impressive overs-sized fireplace & walls of glass, while the gourmet chef's kitchen serves as the heart of the residence with exceptional craftsmanship and custom appointments. The primary suite is a private sanctuary, offering a spa-inspired bath and an atmosphere of quiet luxury, while spacious guest accommodations provide exceptional comfort for family and visitors alike. A collection of thoughtfully integrated lifestyle amenities transforms the lower level into a destination of its own, featuring a private theater, fitness studio with full bath, gaming and entertaining lounge, wine tasting room with cellar, workshop, and abundant storage & spaces designed to elevate daily living while accommodating every occasion. Outdoors, the house reveals a true resort setting. Mature specimen trees and professionally designed gardens frame a recently renovated saltwater swimming pool surrounded by custom bluestone & brick patios, maintaince free decking, creating an idyllic backdrop for entertaining or peaceful retreat. The expansive grounds offer the rare opportunity to substantially expand the residence while preserving its existing footprint, presenting remarkable flexibility for future vision. A gated courtyard drive welcomes guests with a sense of arrival befitting the home's architectural presence. Combining timeless European influence with exceptional craftsmanship, resort-inspired amenities, and one of Dix Hills' most coveted locations, this is a residence of enduring beauty created for those who appreciate privacy, elegance, and uncompromising quality of life.

589 Caledonia Road, Dix Hills

2245 Little Peconic Bay Lane, Southold
$1,999,999
3 Beds ⋅ 3 Baths ⋅ 1022803 MLS
Rarely does a Southold waterfront property offer such a compelling combination of privacy, direct bay access, and expansive water views. Set on a protected inlet with a permitted dock and kayak launch, this three-bedroom, three-bath home is designed around its extraordinary setting. Sun-filled rooms open to a supersized waterfront deck, with a chef's kitchen with soapstone counters, a welcoming living room with fireplace, and water views throughout. The first-floor primary suite is a quiet retreat, and a rooftop observation deck captures sweeping vistas across Little Peconic Bay. The permitted lower level adds two bedrooms, a bath, a den, a second fireplace, and a wine cellar, with sliding doors opening to the water. The next owner also inherits a head start. The sellers have applied for a pool permit, so approvals are already in motion, and they have applied for a Grant toward a new IA septic system that transfers with the property. Approximately 3,900 square feet of finished living space on a half-acre, plus a one-car garage and shed, in a truly special Southold waterfront setting.

2245 Little Peconic Bay Lane, Southold

121 S Jamesport Avenue, South Jamesport
$1,999,999
6 Beds ⋅ 6 Baths ⋅ 932455 MLS
Step into the timeless grandeur of Wisteria Court, one of South Jamesport's most admired historic estates. Wisteria Court stands proudly as an iconic 1913 Queen Anne Colonial set on a .75-acre double corner property in the heart of South Jamesport, just two blocks from the beautiful Great Peconic Bay. This grand residence offers rare legal two-family status and expansive living space, surrounded by lush, mature landscaping and an extraordinary wraparound porch with over 950 square feet of covered outdoor living. Built off a storied local love story, the home carries both historic charm and remarkable scale, with approximately 4,500 square feet of legal living area, including additional space of a full basement and expansive walk up attic, nearly doubling the square footage, all with low taxes. Inside, the home features period details, tall ceilings, and multiple formal and informal gathering rooms filled with natural light. Dual dining areas include a gracious formal dining room ideal for hosting and an additional dining space off the galley kitchen suited for everyday meals. The upper levels offer an array of spacious guest bedrooms with warm wood floors, original trims, and the inviting character of early-century design. Guest bathrooms have been tastefully updated with classic finishes while honoring the home’s vintage aesthetic. Significant recent upgrades elevate the home’s functionality and longevity, including new electric service with dual meters and an upgrade to 350 amps, a new alarm system with perimeter video cameras, and extensive renovations to the rear apartment including new floors, ceilings, paint, and furnishings. Additional updates include a new oil tank, new living room floors and paint, a new HVAC system, all new major appliances—stoves, dishwashers, washing machines, dryers, refrigerators, and microwaves—as well as a new home theater television and sound system (some lights to be excluded from sale). Exterior enhancements include new front walkway pavers, new lawn installation, a new gravel driveway, and new Belgian block driveway borders. There is a pickle ball court on premise. All of these improvements have been completed since May 2024. The property also includes a new septic tank installed in 2019 and a new water heater added in 2020. Designed for effortless entertaining, the property provides dining for 22, sleeping for 14+ guests, and parking for up to 15 cars. Estate-like grounds, established hedgerows, and a substantial street presence create a private and elegant setting. Just steps from sandy bay beaches, Wisteria Court remains one of South Jamesport’s most distinguished legacy homes—a rare opportunity to own a treasured piece of North Fork history. With low taxes of $13,138!

121 S Jamesport Avenue, South Jamesport

3 Wincoma Drive, Huntington Bay
$1,999,999
6 Beds ⋅ 6 Baths ⋅ 842578 MLS
Set Within The Sought-After Wincoma Association, This Exceptional 100 Year Old Expansive Home Offers Just Shy 5000 Square Feet Of Living Space. Timeless Architectural Details And Old World Charm. This Property Is Situated On Level .64 Acre With Mature Plantings, Brick Patio, Walkways And Rocking Chair Front Porch With Peeks Of Waterview. Elegant Formal Living Room With Wood Burning Fireplace, Formal Dining Room With Large Windows Providing Abundant Sunlight. Inviting Sky-Lit Kitchen With High End Appliances, Tiled Floor And Cozy Fireplace. Library/Family Room With Beautiful Parquet Flooring, Vaulted Ceiling, Custom Built-In Shelving And Cabinetry With French Doors Leading To A Brick Patio. Billiards/Game Room Also Featuring Custom Parquet Floors, Wet Bar and French Doors to Patio. Kingsize Primary Bedroom With A Gas Fireplace And Juliet Balcony And Waterview. The Main House Offers Four Additional Bedrooms And Four Full Baths Plus A Powder Room. The Multi-Level Layout Offers Flexibility Across Three Levels Providing Ample Space For a Variety Of Uses Including Guest Accommodations, Work-From-Home Or A Multi-Generational Home. Large Detached Two Car Garage With A Finished Studio And Full Bath Adds Exceptional Versatility And Potential For A Wide Range Of Uses. Enjoy Access To Wincoma Association Amenities, Including Private Beach, Dock, Mooring Rights, And Playground, Offering A Unique Coastal Setting.

3 Wincoma Drive, Huntington Bay

2 Penny Lane, Nissequogue
$1,999,000
5 Beds ⋅ 3 Baths ⋅ 1038110 MLS
Waterfront on the Long Island Sound, this rare offering features 75 feet of direct frontage and is set on a beautifully landscaped acre at the end of a quiet cul-de-sac within a private beach community. An entertainer’s dream, the property features a stunning bluestone patio overlooking the water, complete with a gazebo and generous seating areas—all positioned to take in expansive views of the Sound and spectacular sunsets. The perfect setting for hosting summer BBQs or simply relaxing and unwinding in your own waterfront oasis. Private steps lead directly to the beach and water below, creating an exceptional setting for outdoor dining, entertaining or simply enjoying the waterfront. The traditional 5-bedroom, 3-full-bath Center Hall Colonial features spacious formal rooms, wood floors and an impressive formal entry hall with soaring ceilings and a custom bridal staircase. The eat-in kitchen features white cabinetry, granite countertops, a center island with seating and a large dinette area, and opens directly to the beautiful great room with soaring ceilings, a wood-burning fireplace and large windows that bring the beauty of the surrounding landscape indoors. Glass sliders open to a large entertainment deck, extending the living space outdoors. A first-floor bedroom, equally well suited as a home office, and conveniently located laundry add flexibility to the main level. The second-floor primary suite offers a private retreat with beautiful views of the Long Island Sound, an electric fireplace and two walk-in closets. The spacious ensuite bath features double sinks and a Jacuzzi tub positioned beneath a wall of windows, creating a peaceful place to relax while taking in the water views. Three additional generously sized bedrooms, a spacious main full bath with double sinks, and a private outdoor deck complete the second floor. A full basement offers substantial additional space and storage with the potential to be finished in the future, while the 3-car garage with a car lift provides added versatility. Professionally landscaped grounds are enhanced by landscape lighting, a hot tub, generous driveway parking and multiple outdoor spaces for dining, gathering and relaxing by the water. With the Long Island Sound just beyond the backyard, private beach access and gorgeous sunsets unfolding across the horizon, the setting offers the feeling of being on vacation year-round, all from the privacy of your own home.

2 Penny Lane, Nissequogue

39 Sloop Walk, Ocean Beach
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 000078 MLS
WELCOME TO THE SOUGHT-AFTER SUMMER CLUB ON FIRE ISLAND! This impeccable 2,160 sq. ft. sprawling ranch delivers the perfect coastal escape, beginning with a welcoming foyer that flows into an airy open-concept layout where the living room, dining area, and kitchen seamlessly connect. Triple glass doors lead to the exterior, creating effortless indoor-outdoor living. The home also features a gas fireplace with a beautiful mantle surrounded by custom built-in bookshelves, vaulted ceilings, high-hat lighting, and ceiling fans throughout. The spacious primary bedroom offers an ensuite bath, while three additional generously sized bedrooms and two more full bathrooms provide plenty of room for family and guests. A dedicated laundry room adds convenience. Step outside to expansive wraparound decks designed for entertaining, complete with an outdoor kitchen, hot tub, and outdoor shower—all located just three houses from the ocean. Situated on a RARE DOUBLE LOT with lush landscaping, the property offers the potential to add a pool, creating an even more private retreat. Two sheds provide additional storage. As a homeowner in the exclusive Summer Club community, you’ll enjoy access to the clubhouse amenities including a gym, tennis, ping pong, shuffleboard, billiards, darts, and boat moorings. A setting built for entertaining, relaxing, and creating unforgettable Fire Island memories—all in true move-in condition. Outdoors, an expansive decks wrap the home - all designed for gatherings, complete with an outdoor kitchen, hot tub, and shower—just steps from the ocean (three houses to be exact). Set on a rare double lot with lush landscaping, the property offers room to add a pool if desired, creating an even more private retreat. Two sheds also. As a Summer Club homeowner, you’ll also enjoy access to the community’s clubhouse featuring a gym, tennis, ping pong, shuffleboard, billiards, darts, and boat moorings. A setting built for entertaining, relaxing, and making unforgettable Fire Island memories—all in move-in condition.

39 Sloop Walk, Ocean Beach

680 Private Road Unit #17, Southold
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 1017642 MLS
Charming, private, and uniquely connected to the water, this cedar-shingled three-bedroom cottage offers a compelling combination of immediate enjoyment and future potential. Set on nearly an acre, the property includes a 50' wide section that extends to the bay, where a beachside double deck and stairs provide direct access to your private stretch of sandy beach. Inside, the living room is anchored by a beautiful fireplace and opens to a brick patio, creating an easy flow between indoor and outdoor living. Wrapped in glass, the sunroom addition serves as a cozy retreat, immersing you in the property's natural surroundings. Multiple en-suite bedrooms round out the offering. Whether enjoyed as a quintessential North Fork getaway or expanded to create a larger coastal residence, the setting is exceptional. True private bayfront at a price point that rarely exists.

680 Private Road Unit #17, Southold

11 N Quarter Road, Westhampton
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 996772 MLS
Beautifully renovated and move-in ready, this Westhampton contemporary offers 4 bedrooms, 4 full baths, a finished lower level, heated saltwater pool and hot tub, pool house, and attached two-car garage on nearly an acre just minutes from Westhampton Beach Village and ocean beaches. Spanning 2,350 SF, the home blends clean contemporary design with bright, open living spaces and effortless indoor-outdoor flow ideal for both entertaining and everyday living, with expansive outdoor areas creating a true private retreat. A first-floor primary suite adds convenience and flexibility, while the finished lower level offers versatile space for a gym, media room, office, or recreation. Turnkey and thoughtfully executed, this is a compelling Westhampton offering with style, substance, and exceptional proximity to the Village, dining, shopping, and beaches.

11 N Quarter Road, Westhampton

36 Charla Drive, Southampton
$1,995,000
6 Beds ⋅ 6 Baths ⋅ 990217 MLS
Discover an exceptional offering in the Hamptons-this beautifully updated six-bedroom, six-bathroom residence presents the perfect balance of refined Hamptons living and outstanding investment potential. Renovated in 2021, the home features a thoughtfully designed open floor plan ideal for both everyday living and entertaining. The light-filled living area flows seamlessly into a well-appointed eat-in kitchen and spacious dining area, all opening to an expansive deck that enhances the indoor-outdoor lifestyle. The first floor offers a versatile layout, including a junior primary suite with a full bath, and two additional guest bedrooms served by a well-appointed hall bath-providing comfort and flexibility for and guests alike. The second level is highlighted by a generous primary suite featuring a stylish private bath and a peaceful retreat feel. Two additional guest bedrooms-one en-suite and another with a separate hall bath-ensure ample privacy for visitors. A dedicated second-floor office offers an ideal work-from-home environment. The finished lower level expands the living space even further, complete with a kitchenette, den, and full bath-perfect for extended guests or recreation. Outdoor amenities are equally impressive, featuring a heated pool and hot tub, built-in outdoor kitchen, outdoor shower, and a private basketball court. Designed for relaxation and entertaining, the property delivers the ultimate Hamptons lifestyle. Ideally located in Shinnecock Hills, the home is just minutes from ocean beaches, renowned restaurants, and local shops. Whether enjoyed as a primary residence, seasonal retreat, or income-producing rental, this property offers year-round appeal and strong investment potential.

36 Charla Drive, Southampton

980 Manhanset Avenue, Greenport
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 915982 MLS
This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up! Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom adds convenience and flexibility. High ceilings and expansive windows frame the water views, filling the space with natural light. The custom chef’s kitchen features top-of-the-line appliances and flows easily into both formal and informal dining areas. The large living room includes a gas fireplace, game area, and a striking marine-lacquered wet bar complete with fridge/freezer adjacent to both pool and living areas. An additional den with water views offers a quiet retreat or extra space for guests. Outdoors, cedar fencing encloses a private backyard with a heated saltwater pool, areas for al fresco dining, and space to relax. Upstairs features two guest bedrooms sharing a well-appointed designer bath, tub shower combo. The primary suite has stunning water views, cathedral-ceiling, a separate sitting room/office, spacious dressing room, and a spa-like bath with soaking tub, large shower, and separate water closet with bidet. Stone steps lead through beach grass to a private dock—perfect for boating, kayaking, or paddle boarding. Located a few blocks outside Greenport village, yet tucked away from the crowds, and near one of the North Fork’s best bay beaches, this home offers the ideal balance of serenity and convenience. Also available furnished.

980 Manhanset Avenue, Greenport

131 Bayview Avenue, Northport
$1,950,000
3 Beds ⋅ 4 Baths ⋅ 1010075 MLS
A rare opportunity to own an 1890 Victorian house on Long Island’s North Shore. Historic Bayview Avenue is the setting for this property featuring sweeping year-round views, beautiful terraced gardens, and a private waterfront dock, all just moments from the center of Northport Village. Take in the colorful boating activity and spectacular sunsets as you relax and entertain guests. Join your neighbors with a stroll to the Farmers Market and summer concerts at the bandshell. The renowned John W. Engeman theater, plentiful restaurants and boutiques all beckon nearby. This historic waterfront home features 3 bedrooms and 3.5 baths with inviting living spaces that include a welcoming front porch, a sunroom with spectacular harbor views, an open living room and dining room with a fireplace, and a well-appointed kitchen with custom cabinetry and classic finishes.The home office provides a perfect work-from-home space, while the recreation room and additional storage offer flexibility for a variety of uses. Upstairs bedrooms capture beautiful harbor views, including a serene primary bedroom with sweeping water vistas. Outside, beautifully manicured grounds create a gardener’s dream leading to your water-level dock on Northport Harbor, offering the perfect setting for boating, kayaking, or simply enjoying the peaceful waterfront surroundings.

131 Bayview Avenue, Northport

56 Sage Hollow Court, Dix Hills
$1,920,000
5 Beds ⋅ 4 Baths ⋅ 1030819 MLS
Welcome to this exceptional Center Hall Colonial, where timeless sophistication meets modern luxury. Nestled on more than one acre of beautifully maintained, level property in a private cul-de-sac setting, this impressive residence offers over-the-top comfort, space, and amenities designed for today's discerning buyer. Boasting 5 spacious bedrooms, 3.5 bathrooms, and a full basement, the home features an expansive floor plan with soaring 10-foot ceilings, a dramatic cathedral-style entry, and elegant hardwood floors throughout much of the main level. Formal living and dining rooms showcase crown moldings and refined architectural details, while a versatile first-floor office/library and spacious first floor bedroom and full bathroom provide the flexibility today's lifestyle demands. The heart of the home is the oversized gourmet eat-in kitchen, complete with a center island, custom off-white cabinetry, striking black granite countertops and backsplash, and premium stainless-steel appliances, including a Sub-Zero refrigerator, double Thermador ovens, Thermador gas cooktop, Bosch dishwasher, and Bosch microwave. The adjoining family room is larger than standard Whitney models and features a cozy wood-burning fireplace, creating the perfect gathering space. The home has a three car garage and a second front service entrance. Sliders from the Kitchen bring you to an expansive Cambridge paving stone patio with outdoor kitchen that features BBQ, sink 2 burners and a refrigerator. The Fully Fenced Flat property has IGS and offers versatility for endless outdoor entertaining options with a sport court and putting green. The shed has both water and electric hookups. The Chandelier operates on a key lift. The lifetime architectural roof is 14 years young, the Dual hot water heaters are under 2 years old, there is three zone gas heat with Rheem professional grade HVAC systems and 3 zone CAC. The home has 300 Amp electric, Alarm system, central vac, Andersen windows, custom window treatments and Newer front door, driveway and front walk way. The second floor primary bedroom is every homeowners dream space. This wonderful space has a tray ceiling in the oversized primary, a separate sitting room with a gas fireplace. His and Her walk in closets and a spa like bathroom with a walk in shower, jacuzzi tub and double vanity with granite counters and vaulted ceiling. There are three additional large bedrooms all with ample closets and a full bathroom with double vanity and a combination tub/ shower. This home offers everything a discerning buyer is looking for. HHH SD feeding to Signal Hill ES, West Hollow Middle School and HHH HS East. Too much to list- come see for yourself and be wowed!

56 Sage Hollow Court, Dix Hills

2 Fiddlers Green Drive, Lloyd Harbor
$1,900,000
5 Beds ⋅ 3 Baths ⋅ 1009173 MLS
Welcome to this spectacular Mid-Century Modern residence designed by renowned architect Roy S. Johnson, perfectly positioned atop a hill with breathtaking water views of Lloyd Harbor and the surrounding community. Showcasing Johnson's signature architectural elements—including dramatic triangular rooflines, soaring vaulted ceilings, expansive walls of glass, and seamless indoor-outdoor living—this extraordinary home masterfully blends modern design with its natural surroundings. From the moment you arrive, you'll be captivated by the serene setting and striking architecture. A charming front pathway leads to a welcoming porch where you can relax and take in the peaceful surroundings before stepping inside. The home is flooded with natural light, highlighting the beautiful hardwood floors, oversized rooms, and thoughtfully designed open floor plan. The spacious living room features panoramic water views, a stunning floor-to-ceiling brick fireplace, and sliding doors leading to a deck overlooking Lloyd Harbor. Adjacent to the living room, the family room is enhanced by new skylights and offers direct access to both the side deck and rear patio, further embracing the home's connection to nature. The eat-in kitchen features a second floor-to-ceiling brick fireplace and a dining area designed for both everyday living and entertaining. The main level also includes a second primary en-suite bedroom, two additional generously sized bedrooms. The private primary suite occupies the upper level, offering a tranquil retreat with its own en-suite bath and spectacular water views. A distinctive loft area overlooks the living spaces below and waterview which provides an inspiring vantage point to enjoy the surrounding landscape. The finished lower level with walk out access offers exceptional flexibility, featuring a private apartment with a newly renovated full bathroom, abundant storage space, a wet bar, and an expansive recreation room with sliding doors leading to the backyard. This versatile space is ideal for hosting gatherings, entertaining guests, or accommodating extended family. Located within the highly sought-after Fiddlers Green Beach Association, residents enjoy access to a private community dock with mooring rights, as well as deeded access to a Long Island Sound beach where community events and gatherings are held throughout the year. In addition, residents have access to the Village of Lloyd Harbor Beach, offering summer camp programs, tennis, pickleball, swimming, and additional mooring rights. A rare architectural treasure in one of Long Island's most desirable waterfront communities, this one-of-a-kind home offers an unparalleled combination of design, comfort, privacy, and natural beauty. Additional Information: prestigious Cold Spring Harbor Schools! Condition Mint! 4 Cars Garage. $1800/year association dues – Fiddlers Green Beach Association

2 Fiddlers Green Drive, Lloyd Harbor

28 Club Lane, Remsenburg
$1,900,000
6 Beds ⋅ 7 Baths ⋅ L3568865 MLS
Rare opportunity in Remsenburg! This six-bedroom, six-bathroom home offers approximately 4,400 square feet of luxurious living space on a generous 1.25-acre property. Upon entering, you'll be impressed by the grand design of the house, featuring a spacious Primary suite complete with a cozy fireplace and a private deck. The second floor offers stunning water views, adding to the serene atmosphere. Situated on a secluded and private flag lot, It includes a private tennis court and basketball court for active enjoyment. In addition to these amenities, the home boasts an excellent rental history, making it a compelling investment opportunity. Conveniently located just minutes from the Westhampton Yacht Squadron, you'll have easy access to waterfront activities and beach rights. Additionally, you're only a short 10-minute drive to Westhampton Beach shops and Restaurants., Additional information: ExterioFeatures:Tennis,Interior Features:Guest Quarters,Separate Hotwater Heater:1

28 Club Lane, Remsenburg

5 Jacquelyn Court, Dix Hills
$1,899,988
5 Beds ⋅ 5 Baths ⋅ 1033127 MLS
Welcome to 5 Jacquelyn Court, a beautifully expanded ranch set on 1.23 private acres at the end of a cul-de-sac in Dix Hills. Offering approximately 4,200 square feet of thoughtfully designed living space, this exceptional home features 5 bedrooms including two primary en-suite bedrooms, 4.5 bathrooms, and a floor plan designed for both comfortable everyday living and effortless entertaining. Expanded and extensively updated between 2010 and 2012, the residence blends timeless design with modern comfort. Brazilian cherry hardwood floors enhance the main living areas, complemented by beautifully proportioned living spaces and quality craftsmanship throughout. The main-level primary suite features oak hardwood flooring, a walk-in closet, and a door leading directly to the Trex deck and backyard. Occupying the entire second floor, the private primary suite offers a walk-in closet and a spa-inspired bath with a Jacuzzi soaking tub, steam shower, bidet, Toto toilet, and luxury finishes. At the heart of the home, the eat-in kitchen features a Sub-Zero refrigerator, DCS gas range, Thermador hood, Bosch dishwasher, abundant cabinetry, and generous workspace. Designed for entertaining, the formal dining room showcases a wood-burning fireplace, custom wet bar with wine cooler, and sliding glass doors that seamlessly connect to the Trex deck and outdoor living areas. Two additional first-floor bedrooms provide flexibility for guests, extended family, or a home office. The fully finished basement adds exceptional living space with a climate-controlled wine cellar, sauna, cedar closet, abundant storage, and direct access to the attached two-car garage. Additional amenities include central vacuum, a chandelier lift, six-zone oil baseboard heating, three-zone central air conditioning, and a 14-zone in-ground sprinkler system. Beautifully landscaped grounds feature a heated saltwater in-ground pool, paver patios, a covered patio, expansive Trex deck, mature gardens, and a cabana for additional storage. The circular driveway enhances the home's curb appeal while providing access to the attached two-car garage. Beautifully maintained and thoughtfully updated, this exceptional home combines a flexible floor plan, quality finishes, and outstanding indoor and outdoor living on a private 1.23-acre cul-de-sac property. Conveniently located near shopping, dining, parks, and major roadways, this is a home you won't want to miss.

5 Jacquelyn Court, Dix Hills

170 Landing Lane, Baiting Hollow
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 1037542 MLS
Tucked away on one of the area’s most desirable and peaceful streets sits a stunning modern home designed by award-winning NYC architect, Mark DuBois. Surrounded by privacy in an idyllic setting and nestled among beautiful homes, it offers a rare sense of seclusion in a location that few even know exists. Built in 2019, this practically new and meticulously maintained 2-level home offers a rare combination of sophisticated design, exceptional craftsmanship, and an unbeatable location just 100 feet from deeded, private HOA beach access. Offering ~1,800 sf on the main level and a ~700 sf primary suite above, the home is designed to maximize views and natural light with top of the line Andersen E-Series windows throughout, especially from the spectacular 33-foot rear wall of glass that connects the interior and outdoor living spaces. A dedicated gas line for an outdoor BBQ makes al fresco dining effortless and 80 feet of Brazilian hardwood decking creates great setting for entertaining. Enjoy beautiful winter water views, particularly from the upstairs primary suite with adjoining terrace. The open-concept living and dining areas are anchored by a dramatic double-sided fireplace and soaring ceilings, and the spacious chef’s kitchen features premium highend appliances, quartz counters, an impressive 10-foot waterfall-edge island, and sleek contemporary finishes. Throughout the home, luxurious Porcelanosa tile, fixtures, and bath finishes from Spain create a refined, spa-like atmosphere. Downstairs, the finished lower level adds ~1,100 sf of flexibility for recreation, work, guests or additional gathering space and boasts 9-foot ceilings as well as direct, ground level access to the backyard resort-style oasis. There, an 18’ x 40’ heated saltwater pool is surrounded by Techo-bloc pavers providing a variety of areas for lounging and entertainment. An outdoor shower completes the space. Designed for modern living, this smart home with advanced technology is completely wired for audio, visual, alarm, and security camera systems. A 12-zone Wi-Fi-enabled in-ground sprinkler system keeps the beautifully landscaped grounds thriving. The thoughtfully designed pollinator gardens provide year-round beauty and support local wildlife. Privacy is exceptional, with the property backing wooded land and adjoining a wooded side yard, creating a peaceful, secluded setting. Combining timeless modern architecture, premium materials, cutting-edge technology, and a coveted beachside location, this extraordinary home offers a truly one-of-a-kind lifestyle.

170 Landing Lane, Baiting Hollow

34 Locust Lane, Huntington Bay
$1,895,000
4 Beds ⋅ 3 Baths ⋅ 1045218 MLS
Introducing a rare opportunity to own a beautifully reimagined 1906 carriage house in Huntington Bay, where timeless character meets sophisticated modern living just moments from the water. Set on approximately one acre of professionally landscaped, park-like grounds, this distinctive residence has been thoughtfully renovated while preserving the architectural details and warmth that make it truly one of a kind. Inside, sun-filled living spaces, rich hardwood floors, a marble chef’s kitchen, updated baths and two possible primary suites create an effortless blend of elegance and comfort. Expansive windows and French doors invite the outdoors in, opening to an impressive wraparound deck designed for al fresco dining, entertaining and enjoying the beauty of the surrounding landscape. With winter water views, a nearby path to the waterfront, and a setting that feels both private and connected to the bay, this is coastal living with a sense of history and soul. More than a home, 34 Locust Lane is a beautifully restored piece of Huntington Bay’s past—refined for the way we live today. Total taxes including Incorporate Village are $20,312.

34 Locust Lane, Huntington Bay

14 Dupont Court, Dix Hills
$1,860,000
5 Beds ⋅ 4 Baths ⋅ 1034999 MLS
Light, bright and impeccably maintained, this inviting center hall colonial offers timeless style, exceptional flow and beautifully designed living spaces throughout. Rich wood floors, elegant moldings and sun-filled rooms create a warm and sophisticated atmosphere from the moment you enter. Spacious kitchen and great room, seamlessly connected and designed for both everyday living and entertaining with direct access to the level backyard. Banquet sized dining room with convenient butler's pantry. A private guest suite/office located just off the kitchen provides flexibility for today's lifestyle.Upstairs 4 generously sized bedrooms include a luxurious primary suite with soaring ceilings-a true retreat. An open loft area offers the perfect spot for reading, relaxing or a quiet work space. Large basement offers endless options. Set on beautifully maintained flat property, this immaculate residence blends timeless elegance with comfortable living. Welcome home!

14 Dupont Court, Dix Hills

29 E Bayview Avenue, Ocean Bay Park
$1,850,000
3 Beds ⋅ 2 Baths ⋅ 998635 MLS
*** PRICE IMPROVEMENT **** WELCOME TO 29 EAST BAYVIEW AVE, THE ONLY BAYFRONT HOME FOR SALE! This impeccably maintained beach home is ideally situated in Ocean Bay Park, Fire Island. The first floor features a vestibule with floor-to-ceiling cabinets, a spacious living room with a custom-built couch and open shelving, skylights, knotty pine vaulted ceiling with cross beams, dining area, and cozy sitting area adjacent to the dining room. The updated kitchen offers stainless steel appliances, including a new refrigerator, ample cabinet and counter space, and an island. A newly renovated bathroom with a walk-in shower completes this level. Upstairs, three generous bedrooms with hardwood floors and ceiling fans await, along with another full bathroom featuring a walk-in shower and plenty of closet space. The shed houses the washer/dryer and hot water heater. Recent updates include a new back roof. Step through the sliding glass doors onto the expansive deck, perfect for entertaining while enjoying stunning bay views, your private beach, and a brand-new bulkhead. This home is an entertainer’s dream with an outdoor shower and approximately 50 feet of waterfront decking. Bring your boat and get ready for endless fun and relaxation!

29 E Bayview Avenue, Ocean Bay Park

1 Weeping Cherry Lane, Commack
$1,849,000
4 Beds ⋅ 3 Baths ⋅ 1037229 MLS
Welcome Home! This is the one you have been waiting for! This meticulous 4 bedroom, 2.5 bath modern colonial was built like a fortress. You would be proud to call this home your own. Renovated in the past 2 years this beautiful brick colonial is professionally landscaped and maintained featuring specimen trees and plantings throughout the property. You are greeted by a two story entry with soaring ceilings that include the entire living room. The gorgeous chandelier shines through the window. The living room easily flows into the big, bright family room. This house has so much natural light. The family room features floor to ceiling windows, an electric fireplace and custom book shelves. The kitchen in this house is truly the heart of home. The large island with the quartzite counter, plays host for most gatherings! The custom cabinets are beautiful and go all the way to the ceilings for extra storage. The stove is gas! There are 2 pantries and a separate beverage/coffee center stategically located in between the family room, the kitchen and the dining room for easy access. There is a separate laundry room. The bridal staircase is where all of the pictures will be taken. It leads to your double door primary bedroom with high ceilings, 2 walk-in-closets and an elegant ensuite bathroom with marble flooring and shower, a double vanity and claw tub for soaking. There are 3 more nice sized bedrooms and a full bath that is up to the minute. The basement is unfinished and it is huge, with 12 foot ceilings and 2 staircases. Enter the yard from the French door in the kitchen or the sliders from the family room. The new Trex deck is fenced with gates so there is protection from the pool. There is also a fabulous awning and a gas barbecue. The pool was refurbished last year and is Salt Water, Heated with a Waterfall. Picture perfect. The backyard has grown specimen trees making the yard completely private. Roof 4 months old, Cesspool 2000, 200 Amp, CAC 2 Zones, Boiler 2000, Sprinkler front and back - brand new in the backyard.

1 Weeping Cherry Lane, Commack

333 Concord Court, Dix Hills
$1,849,000
5 Beds ⋅ 4 Baths ⋅ 1031517 MLS
Welcome to this exceptional brand new home at 333 Concord Court in Dix Hills. Set on a private 1 acre property, this custom-built 5-bedroom, 3.5-bathroom residence offers approximately 3,915 square feet of thoughtfully designed living space, combining timeless craftsmanship with modern luxury. The open floor plan is highlighted by a 2 story entry foyer, extensive custom millwork, and designer finishes throughout. The gourmet kitchen flows seamlessly into the spacious dining and living areas, creating the perfect setting for everyday living and effortless entertaining. A beautiful gas fireplace surrounded by custom built-in cabinetry and a 65” TV anchors the rec room, adding warmth and character year-round. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bathroom and an oversized walk-in closet. Four additional bedrooms provide exceptional flexibility for guests, or a home office, while the home’s beautifully appointed bathrooms showcase premium finishes and meticulous attention to detail. The finished basement offers valuable additional living space, ideal for a recreation room, home gym, media room, or home office. An attached garage provides convenience and ample storage. The exterior is equally impressive, featuring premium Maibec cedar siding that delivers timeless curb appeal and lasting durability. The expansive property is professionally landscaped, sodded and serviced by an underground sprinkler system. There is a very large rear deck, as well as a large and private rear yard for entertaining, recreation, or the future addition of a pool and outdoor living areas. Located in the highly desirable Dix Hills community, this exceptional new construction home offers the perfect blend of luxury, privacy, and modern living in one of Long Island’s most sought-after neighborhoods. Estimated 2026/2027 real estate taxes (12/1/26 – 11/30/27) - $10,500. Estimated 2027/2028 real estate taxes (12/1/27 – 11/30/28) - $26,000 (this estimate is based on the most current tax rate available, and does not include the Basic Star Program)

333 Concord Court, Dix Hills

426 Wolf Hill Road, Dix Hills
$1,849,000
5 Beds ⋅ 4 Baths ⋅ 1018644 MLS
Welcome to this beautifully renovated and thoughtfully updated 5-bedroom, 3.5-bath Colonial nestled in the heart of sought-after Dix Hills. From the moment you arrive, you’ll appreciate the timeless curb appeal and exceptional pride of ownership that defines this special home. Inside, a spacious and inviting layout offers the perfect blend of elegance and modern comfort. The beautifully updated interiors feature generous living spaces designed for today’s lifestyle, including sun-filled rooms, stylish finishes, and thoughtful upgrades throughout. The home provides the ideal setting for both everyday living and effortless entertaining. Step outside and discover your own private resort-style retreat. The meticulously landscaped backyard is a true showpiece, featuring stunning specimen plantings, lush privacy, sparkling pool and a Tiki Bar, creating the ultimate outdoor oasis. Whether hosting summer gatherings, relaxing poolside, or enjoying quiet evenings surrounded by nature, this backyard offers a vacation-like experience right at home. Perfectly situated in Dix Hills, this exceptional property combines modern updates, spacious living, and an extraordinary outdoor environment — a rare opportunity to own a home where comfort, style, and resort living come together.

426 Wolf Hill Road, Dix Hills

2100 Glenn Road, Southold
$1,849,000
4 Beds ⋅ 4 Baths ⋅ 1008927 MLS
This turnkey opportunity in Southold, bordering beautiful Goose Creek, offers a private dock and is perfect for those seeking a North Fork beach house with a boater's lifestyle. Situated on more than two-thirds of an acre, this contemporary home features modern lines, abundant natural light, and a stunning yard ideal for outdoor entertaining. Upon arrival, you are welcomed by a spacious driveway leading to an inviting entrance and foyer. The open floor plan, vaulted ceilings, and coastal color palette create a warm atmosphere, enhanced by sunlight flooding in through the windows that showcase the mature, landscaped backyard. The living room, anchored by a wood-burning fireplace, provides a generous seating area, while the formal dining area is elegantly situated in the center. The expansive chef's kitchen is equipped with high-end appliances and custom cabinetry, offering ample storage space, sleek lines, side island seating, and a cozy hostess nook. On the main floor, there is also a guest bedroom and a well-appointed full bathroom. Upstairs, the primary bedroom is located on one side, while a catwalk leads to two additional bedrooms and a full, spa-inspired bathroom. The lower level features a finished recreation space complete with a lounge, bar, and pool table. A bathroom, extra closets, and a bonus room complete this level. Outdoors, the two-tier entertaining area includes a spacious deck and a lower-level patio immersed in a well-landscaped yard with specimen plantings. The property also has an approval for a waterside pool, permit in hand. The dock is in excellent condition and has electric and water, providing direct access to Peconic Bay. This wonderful location is perfect for paddling, kayaking, and boating, and is close to everything the beautiful East End has to offer, including wineries, farm stands, the Southold town village, dining options, and the picturesque Goose Creek beach—just a short paddle away.

2100 Glenn Road, Southold

1020 Ruch Lane, Southold
$1,835,000
3 Beds ⋅ 3 Baths ⋅ 960778 MLS
Welcome to Sunset Cottage! Perfectly situated on one of Southold’s most desirable streets, this beautifully renovated waterfront beach house with deeded beach rights and offering the ultimate North Fork lifestyle. Enjoy spectacular sunsets from the new mahogany waterside deck overlooking Hashamomuck Pond which is ideal for kayaking, paddle boarding, fishing, and crabbing. The spacious living room features a wood-burning fireplace and flows into a light-filled great room. Offering 3 bedrooms and 2.5 baths, including a primary ensuite with direct deck access. Thoughtfully designed with handicap accessibility, an irrigation system, generator, and outdoor shower. Set on a rare double lot of approximately 0.40 acres and located less than half a mile to Southold Town Beach and under 10 minutes to Greenport Village. Not in a flood zone. Excellent rental history!

1020 Ruch Lane, Southold

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.