433 properties for sale in Southold

An exceptional new construction by one of the area’s most sought-after builders, 205 Grange Road brings together striking contemporary architecture, premium finishes, and meticulous craftsmanship. Set on nearly half an acre, this approximately 3,900sf residence offers 4 bedrooms, 3.5 bathrooms and a finished basement. A custom 5-foot-wide pivot entry door makes a distinctive first impression, opening to interiors featuring 8.5' inch premium engineered white oak flooring throughout. The sophisticated kitchen showcases modern cabinetry with quartz countertops, and Thermador appliances. The living room with gas fireplace has sliders to a large deck made from Brazilian IPE. The deck spills out to a 16’ x 32’ heated saltwater gunite pool. The 2nd floor has a stunning deck with custom wire railing. The finished basement includes an exterior walkout stair, while the garage features epoxy flooring. Additional appointments include a 2-zone Bosch heat pump system for heating and cooling, and a s

A Rare Opportunity! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long Island. The home itself offers a sun-filled living room with a fireplace and dining area, both featuring floor to ceiling windows which show off the magnificent seascape. The home also hosts an eat-in-kitchen, 3 bedrooms, 3 baths, a large basement, an oversized 2 car garage, and a large deck to enjoy the breathtaking scenery. If being on the water is for you, you've arrived. Don't miss this one time opportunity

Waterfront Living with Bay Access & Your Own Dock. Enjoy beautiful water views from this 3-bedroom, 2-bath waterfront home with bay access and a private dock. A sunny eat-in kitchen, formal dining room, and hardwood floors create an inviting setting for everyday living and entertaining. Relax in the upper-level living room or gather in the lower-level family room, with two fireplaces adding warmth and charm. The primary suite features an ensuite bath and sliding doors to a private deck—a peaceful spot to start or end your day. A large deck overlooking the water offers even more space to entertain or simply enjoy the view. Two garages, cedar closet, enclosed blueberry and vegetable gardens, oil heat, and new central air conditioning complete this waterfront retreat

This, just perfect, 3-bedroom 1.5 bath ranch sits nicely on a beautiful corner lot at just shy of 1 acre. You are welcomed home with a sweet front porch and then enter the front door to a beautiful open floor plan, including a granite and stainless-steel custom kitchen, dining room and living room. The primary bedroom has its own private door to the deck and a half bathroom. There are 2 additional bedrooms and the main bathroom is only 2 years old. Feel a cool North Fork breeze in the home with the front windows up and the rear sliding glass door slid open to the beautiful, entertaining back yard. Summers can be spent lounging on the patio around an in ground pool, BBQ’s on the deck or just reading a fabulous book in your private and peaceful surroundings. Enjoy all the North Fork of Long Island has to offer! Being within minutes of fabulous wineries, restaurants, beaches, farmstands, shopping and Cutchogue Village. You’ll find this home and its location to be perfect for year-round li

Welcome to this One-of-a-Kind 3-Bedroom, Custom Built Colonial, Beachfront Property, ideally located on the North Fork of Long Island along the Beautiful LONG ISLAND SOUND! True Meaning of LOCATION! This Spectacular Waterfront Home offers Breathtaking Panoramic Views, Direct Beach Access (Southold Beach), and the Perfect Blend of Privacy and Coastal Charm. Wake up to Stunning Sunrises and the Sound of Waves! This Beachfront Colonial Home also Features a Spacious 4th Bedroom on the 3rd Floor with Amazing Water Views! Hardwood Floors in all 3 Bedrooms! Two Full Bathrooms, inside you'll walk into the Livingroom with a Custom Granite Fireplace, A Formal Dining Room Surrounded by Water Views, And An Eat-in-Kitchen with a side door to the Wrap Around Deck Overlooking Southold Beach! High Hats Throughout, Brand New Boiler with 2 Heating Zones, 200 Amp Electric, Built on a Pile Foundation which includes a Stand-Up Crawl Space with Plenty of Storage and a Retaining Wall! Visit the Many Wineries

Set within Laurelwood Estates, a highly sought-after neighborhood, this spacious 4-bedroom, 3-bath Colonial on nearly one acre, features a comfortable, well designed layout with an attached 2 car garage, full walk-out basement, in-ground sprinklers and deeded access to the neighborhood’s private community beach. Enjoy the best of North Fork living, minutes from beautiful beaches, wineries, farm stands, shops, and restaurants

Completely renovated and ready to enjoy, this 4-bedroom, 2.5-bath Colonial in Mattituck delivers the feel of new construction without the typical new-construction tax burden, with annual taxes of just $9,560. The home has been extensively updated from top to bottom, including a new roof, new windows where needed, new doors, new central air conditioning, new wide-plank hardwood floors, new chef’s kitchen with large center island and high-end appliances, new patios, new irrigation and landscaping, new landscape lighting and more. A wood-burning fireplace anchors the main living space, while first-floor laundry adds everyday convenience. Upstairs, four generously sized bedrooms provide ample living space, including a primary suite with an en-suite bath and walk-in closet. The full basement expands the usable footprint even further, offering walk-out access (OSE) and an outfitted game room and potential gym. The additional space creates flexibility for recreation, fitness, work space, stor

Welcome to paradise. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond, plus community boating rights with access to the residents’ boat basin, the property offers exceptional privacy without sacrificing comfort or convenience. Custom built in 1993, the approximately 3,500-square-foot residence offers four bedrooms, three full baths and three levels designed for gracious year-round living. Bold proportions, soaring 20-foot ceilings, walls of glass and a sweeping staircase capture the confident glamour of grand-scale coastal architecture, while abundant natural light and extraordinary water views give the interiors a timeless quality. This is not a conventional beach h

Set on nearly two private acres in Nassau Point, this brand-new, 8,500+ square-foot residence offers three levels of thoughtfully designed living space, just minutes from the North Fork’s finest beaches, vineyards, and farm stands. Inside, 10-foot ceilings and herringbone oak floors set an elegant tone from the moment of entry, while a wall of glass frames views of the stone patio beyond. The chef’s kitchen serves as a striking centerpiece, appointed with Sub-Zero and Wolf appliances, a 9-foot island, dual dishwashers, three wine refrigerators, and a hidden walk-in pantry. The space flows seamlessly into an open dining area and expansive great room anchored by a gas fireplace and floor-to-ceiling glass doors opening to more than 1,000 square feet of patio space. Six en-suite bedrooms with radiant-heated baths include two primary suites: one on the main level for convenient single-level living and a second upstairs featuring a spa-like bath and private 400-square-foot terrace. Designed

Sound Front Sunsets. The views from this 4 bed 2 bath house are unrivaled. Breathtaking sunsets over the Long Island Sound. On a quiet cul-de-sac, this house has several different living spaces, taking advantage of the views and opening out to the gracious backyard. Ideal for entertaining or just relaxing while you watch the boats sail past or take in another dreamlike sunset

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

Pool, private beach access and the North Fork lifestyle—all in one Greenport property. Set on approximately one-third acre, this spacious Cape offers 4 bedrooms, 2 full baths and approximately 2,400 square feet of above-grade living space, surrounded by mature landscaping and exceptional outdoor amenities. The private backyard is designed for summer living and entertaining, centered around an in-ground swimming pool, expansive outdoor areas and a secluded firepit setting. Just beyond home, enjoy private community beach access (Sterling Eastern Shores) —an increasingly rare amenity and the perfect setting for swimming, relaxing by the water and unforgettable Greenport sunsets. Inside, generous living spaces include a fireplace living room, separate den, open kitchen and dining areas, large bedrooms, first-floor laundry and flexible home-office space. The layout provides room to gather as well as plenty of space to spread out. A substantial finished lower level with separate exterior ent

Check out this 5-bedroom colonial, on a quiet street! Great for year round living or summer home! Walk to the end of the cul-de-sac and see a scenery of a beautiful beach and the tranquil Hog Neck Bay. Features large sitting room, large living room, true formal dining room, spacious updated eat in kitchen and 2 updated full baths. First floor has 5th bedroom. Top floor has 4 nice size bedrooms and updated full bath. Basement is full and finished with staircase at both ends, laundry room and utility room. Propane cooking, oil heat, Central VAC, public water and split unit and much more. Photos coming soon

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage

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

Fully renovated in 2018, this spacious ranch offers more than 2,600 square feet of comfortable, flexible living space and enjoys bucolic views across surrounding vineyard and farmland beyond. Located in a private neighborhood in the heart of Cutchogue, the property spans 0.70 acres with a serene pool, outdoor patio, custom exterior fire pit, with private community beach access is just a few hundred yards away. The home's generous proportions and easy layout lend themselves equally well to everyday living and entertaining, with vaulted ceilings, charm and personality that elevate a classic ranch. Thoughtfully updated and entirely move-in ready, it offers an appealing combination of space, convenience, and quintessential North Fork surroundings. Perfectly positioned in the center of the region, the property is just minutes from Sang Lee Farms, 8 Hands Farm, Love Lane, local vineyards, and many of the area's best amenities

Private Southold Retreat on 2.18 Acres. Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries, beaches, and all attractions on the North Fork. This meticulously maintained single-level home features 4 bedrooms and 3 bathrooms, offering a versatile floor plan designed for comfortable living and entertaining. The private primary en-suite includes a beautifully updated bath with elegant tile work and soaking tub. Two additional guest bedrooms and updated hall bath provide ample accommodations, while a separate wing with its own private entrance offers endless possibilities. Ideal as a home office, guest quarters, or a secondary primary suite, this space includes a sitting room, bedroom, and fu

This Traditional 4-bedroom, 2.5-bath home sits near Orient State Park and the Cross Sound Ferry. The private, landscaped backyard has a heated pool and patio, plus a large deck with glass doors to the open-plan kitchen and family room, making it ideal for entertaining. The first floor is completed with a private living room, a dining room, laundry, and a powder room. Upstairs, the primary ensuite has a full bath with views of the backyard and pool. Three more bedrooms and a full bath complete the second floor. The finished lower level offers a large recreation space. This home is ideal year-round living or for enjoying North Fork summers

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 s

Set on a spacious, shy acre with open field views, this renovated cedar-shingled farmhouse pairs classic North Fork character with a comprehensive renovation and addition. An expansive wrap-around porch drenched in light and enveloped in beautiful mature hydrangeas gives the home an inviting presence, while the pool and surrounding grounds make the most of its peaceful Orient setting. Inside, the three-bedroom, three-bath home features an open, light-filled floor plan designed for easy living and entertaining. Multiple sets of doors open directly to the deck and porch, creating a natural connection between the interior spaces, outdoor seating areas, pool, and landscape beyond. A bonus loft and finished lower level add valuable flexibility for guests, recreation, or work-from-home space. The property offers a comfortable sense of space, privacy, and connection to its surroundings in one of Orient’s most desirable pastoral locations

Perfectly positioned on a bluff overlooking the Long Island Sound, this Nantucket-style cedar-shingled home captures sweeping water views and spectacular sunsets from nearly every vantage point. Multiple waterside decks and balconies make the most of the setting, while a heated pool, outdoor kitchen, and stairs to a private beach create an exceptional environment for summer living and entertaining. Inside, beautifully appointed living spaces include en-suite bedrooms on both the first and second floors, offering flexibility for owners and guests alike. A separate waterside office with balcony round out the second floor. A finished lower level with a private theater provides additional space for recreation. Less than a mile from the heart of Greenport Village, this exceptional waterfront property combines coastal beauty, privacy, and proximity to one of the North Fork’s most desirable destinations

790 Vanston Road is a meticulously maintained, spacious 1.5 story modified Cape set on a beautifully landscaped 0.65-acre lot in prestigious Nassau Point. This 3-bedroom, 3-bath home features a desirable first-floor primary suite, an open kitchen flowing seamlessly into the family room with a striking fireplace, creating the perfect setting for effortless entertaining. Separate living room, formal dining room, and bonus rooms galore provide flexibility for a home office, gym, or hobbies. Enjoy year-round living from the covered porch with radiant heat, host gatherings on the expansive patio, and take advantage of the generous yard, which offers plenty of room for a pool. Additional highlights include a 2-car garage, a partial house propane generator, and a full basement offering storage and future possibilities. New high-efficiency Reverse Osmosis (RO) water purification system and softener. Blending timeless coastal charm, thoughtful design, and an unparalleled setting, this is a rare

Cutchogue Showstopper. Perched atop a 55-foot bluff overlooking the Long Island Sound, this extraordinary Barnes Coy designed waterfront home offers rare architectural pedigree and an unrepeatable setting. Designed by Barnes Coy Architects, the award-winning firm known for some of the East End’s most distinctive modern residences, this 4,200 SF jewel box estate is set within a private neighborhood with its own park and private stairs to the beach. Filled with natural light and premium finishes, the home features polished limestone floors with radiant heat, two primary ensuite bedrooms with ample closet space, smart home technology controlling lights, blinds, temperature, and front gate; solar panels for energy efficiency, and a full-house generator. The lower level with full bath offers flexible space for a media room, gym, office, or guest overflow. An attached two-car garage is also included. Outside, a heated saltwater gunite pool, hot tub, 1000 sf rooftop deck, firepit, and back la

Waterfront Property Southold, NY! MINT, Turnkey Contemporary w 3 bedrooms, 2 full bathrooms, on 3/4 Canal-front acres w 91ft on Cory Creek

Once operated as a bed and breakfast, this distinctive property sits on 11.31 private acres, including 9.31 acres of open space and 2-acres of buildable space in one of Southold's most prestigious enclaves. Offering exceptional versatility and income potential, the property features a serving kitchen, dining room, library, five fireplaces, tile flooring throughout, and a four-car garage with a basement featuring 10-foot ceilings. An irrigation system and two-stall barn add to the appeal. A rare combination of privacy, space, and opportunity, ideal for horses, gardens, a potential income-producing venture, or future development

Known as The Old King Farmhouse and Owl Hollow, this historic 1.05± acre compound is one of Peconic’s most distinctive properties, pairing a beautifully preserved c. 1860 Italianate Victorian residence with a remarkably purpose-built artist’s studio in the heart of the North Fork. Rich in history and thoughtfully stewarded over time, the approximately 3,260-square-foot residence offers four bedrooms and two-and-a-half baths while preserving many of its original architectural details, including period fireplaces, wide-plank wood floors, oversized windows, and graciously proportioned rooms filled with natural light. The interiors strike a rare balance between historic character and understated elegance, allowing the home’s craftsmanship and surrounding landscape to take center stage. Across the grounds, Owl Hollow serves as an extraordinary extension of the property. The approximately 1,200-square-foot studio is defined by soaring timber trusses, dramatic north-facing windows, a wood-bur

Set on a private. 98-acre lot at the end of a cul-de-sac, this spacious 4-bedroom, 3.5-bath traditional home, built in 2003, offers approximately 2,900 sq. Ft. of comfortable living space. The inviting interior features hardwood floors, an eat-in kitchen with Sub-Zero refrigerator, Wolf range, soapstone countertops, kitchen island and pantry, formal dining room, living room with wood-burning fireplace, mudroom, home office, and first-floor bedroom with nearby half bath. Upstairs, enjoy a family room with fireplace, luxurious primary en suite with Jacuzzi tub and separate shower, two guest bedrooms and additional guest bath. Outside, a fenced rear yard features a heated in-ground pool and bluestone paver patio—perfect for entertaining and summer enjoyment. Additional amenities include a one-car attached garage, whole-house water filtration system, home security system, and deeded beach rights. A wonderful opportunity to enjoy the Orient lifestyle in a beautiful private setting

A mid-century modern gem on three-quarters of an acre, exceptionally private and beautifully secluded. The main floor is designed for effortless single-level living. From the foyer, step into a great room with an open living, dining, and kitchen space. A wall of windows and skylights fills the room with natural light. A wood-burning fireplace and built-in bookshelves anchor the living area. The kitchen features a farmhouse sink and soapstone counters, and glass doors open to the deck, adding even more light and making outdoor dining a natural part of daily life. Oak floors run throughout. The primary suite includes its own full bath, and two additional bedrooms share a second full bath. From the deck off the kitchen, a staircase descends to a heated saltwater gunite pool and a two-story barn with electricity, offering storage or workspace. The ground floor holds a two-car garage, laundry room, storage space, and glass doors that open to the pool. Established landscaping, with many spec

Nestled in the highly sought-after Yennecott neighborhood of Southold, this ranch offers the perfect blend of comfort, privacy, and North Fork living. Featuring 3 bedrooms and 2.5 baths, the home is surrounded by spacious front and rear yards with mature landscaping, a welcoming deck, and a cozy fire pit area ideal for outdoor entertaining and relaxation. The expansive backyard offers potential for a pool. Conveniently located near Southold Village, local shops, restaurants, vineyards, farm stands, and beautiful North Fork beaches. Enjoy the best of North Fork living in this desirable Southold location

Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious. 39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional and inviting layout featuring a comfortable living area, three nicely sized bedrooms, a full bathroom, dining room and an eat-in kitchen. The full basement provides an abundance of additional space for storage, utilities, a workshop, or the potential for future finishing. A detached garage adds even more storage and convenience. Outside, the generous. 39-acre property offers plenty of room to relax, entertain, garden, or create your ideal outdoor retreat. Conveniently located near Southold's charming village, local shops and restaurants, beaches, wineries, farm stands, and all that the North Fo