Southold NY Real Estate & Homes for Sale

106 Properties Found

Sort Results:
1–25 of 106 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 | 5 of 5    Prev | Next
Beds:
2
Baths:
1.00
Sq.Ft.:
1,054
Status:
NEW LISTING
MLS#:
1037884
Type:
Single Family
Lot size:
0.37 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

If the perfect North Fork cottage exists, you have just found it. Timeless, elegant, and rich in character, this thoughtfully crafted home offers a rare opportunity to own a piece of Southold history. Set within Beixedon Estates, an exclusive private enclave and beautiful waterfront community discretely set between Greenport and Southold, the property enjoys an exceptional location close to everything the area has to offer. Two farm stands are near the entrance to the community, with marinas and a fish market are just around the corner. Residents also enjoy access to a pair of private sandy beaches - both steps from the cottage. Beach One feels like a hidden cove, perfect for relaxing and taking in the bay, while Beach Two provides water convenient access for launching kayaks, paddle boards, and sailboats. The charming, cedar-shingled cottage features two bedrooms plus a bonus sleeping loft and a custom kitchen with marble counters ideal for cooking big dinners with friends and family. From sun-filled summer days to cozy winter evenings beside the fireplace, this inviting home can be enjoyed in every season. The expansive lot may also offer the potential for a pool, allowing summer days to continue long after leaving the beach. Imagine warm evenings spent swimming, entertaining, and dining alfresco beneath a canopy of mature pine trees. There is a reason homes in Beixedon Estates rarely come to market. Come experience this magical North Fork retreat for yourself.

Open House:

Thursday, 8/13 5:30-7:00PM

More Open House Info >

Beds:
3
Baths:
4.00
Sq.Ft.:
2,950
Status:
NEW LISTING
MLS#:
997034
Type:
Single Family
Subdivision:
Greenfields
Lot size:
0.92 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Exit Realty Achieve 631-543-2009
View additional info

ADDITIONAL INFORMATION

Some homes are beautiful, others are truly one of a kind. 595 Greenfields Lane is both! Set on nearly an acre of meticulously landscaped property on a quiet dead end street, this exceptional custom built home is located just moments away from the historic village of Southold and the very best of the North Fork! Built by the homeowner with an uncompromising commitment to quality and craftsmanship, this 3 bedroom, 3.5 bathroom residence offers approximately 2,950 square feet of thoughtfully designed living space. Soaring cathedral ceilings, skylights, custom crown molding, solid wood doors and gleaming hardwood floors are just some of the details that distinguish this home. A stunning chef's kitchen was designed with custom cabinetry, granite counters and new stainless steel appliances, flowing naturally into spacious living and entertaining areas. The luxurious primary suite features a vaulted ceiling and spa inspired new bathroom creating a serene atmosphere to unwind at the end of the day. Adding versatility is a fully finished basement with a separate entrance and spacious living quarters ideal for extended family or those seeking additional flexibility. Outside, the property truly comes alive. Lush landscaping surrounds sitting areas, a vibrant vegetable garden, in-ground sprinklers and a charming permitted cottage. A wood-burning pizza oven creates a natural gathering place for entertaining, while multiple matching sheds, a 2-car garage and an expansive driveway accommodating up to 10 vehicles provide remarkable functionality. Every aspect of this property reflects thoughtful design and pride of ownership, from it's superior construction to it's beautifully maintained grounds. With acclaimed farm stands, wineries, beaches, restaurants and timeless character of Southold Village and the North Fork all close by, this is more than a home, it's an opportunity to embrace the lifestyle that makes this area so desirable. A rare combination of craftmanship, privacy, flexibility and location.....595 Greenfields Lane is a property that truly deserves to be experienced. Come see for yourself what makes this Southold home so special!

Open House:

Saturday, 8/15 12:00-2:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,688
Status:
NEW LISTING
MLS#:
1035706
Type:
Single Family
Subdivision:
Orient-by-the-sea
Lot size:
0.92 Acres
Year built:
1983
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
View additional info

ADDITIONAL INFORMATION

Orient By The Sea —North Fork living at Its Best- Located in the sought-after Orient By-The-Sea community, this charming two-bedroom, two-bath expanded ranch offers the ease of one-level living on a private, level, shy-acre property. With a deeded association beach and park just around the corner, this is a wonderful opportunity for both year-round and vacation living. The spacious, light-filled great room is the center of the home, with doors opening to an expansive patio with a retractable electric awning. Designed for outdoor living and entertaining, this inviting space overlooks the landscaped, park-like grounds and offers ample room for a swimming pool. The interior features two bedrooms and two full baths, including one with a generously sized walk-in shower. Additional living spaces include a welcoming dining room, comfortable living room, updated kitchen with a breakfast nook, and convenient laundry access. The home’s easy layout and abundance of natural light create a warm and inviting atmosphere throughout. The 1-car garage offers space for storage or future expansion. Enjoy all that Orient and the North Fork have to offer, with the Cross Sound Ferry, Orient State Park, and Duryea’s Restaurant just minutes away. The beautifully maintained association sound beach is a neighborhood treasure, featuring a stone path and picnic area, perfect for relaxing by the water, gathering with friends and family, and enjoying spectacular North Fork sunsets. A special opportunity to live, relax, and enjoy the North Fork lifestyle in one of Orient’s most desirable communities.

Open House:

Saturday, 8/15 11:00-12:30PM

More Open House Info >

Beds:
4
Baths:
2.00
Sq.Ft.:
2,300
Status:
NEW LISTING
MLS#:
1037377
Type:
Single Family
Subdivision:
Laurel Estates East
Lot size:
0.92 Acres
Year built:
1997
A broker reciprocity listing Courtesy: William Raveis New York LLC 631-298-0600
View additional info

ADDITIONAL INFORMATION

Discover the ease and enjoyment of North Fork living in this inviting four-bedroom, two-bath ranch, perfectly positioned on a full acre in Laurel. Designed for effortless one-floor living, the home offers a comfortable, practical layout highlighted by vaulted ceilings in the kitchen, living and dining rooms, creating an open and airy atmosphere. A wood-burning stove adds warmth, character and a cozy gathering place to the living room. Outdoors, the expansive property provides wonderful space for entertaining, gardening, recreation, or simply relaxing amid peaceful natural surroundings—with adjacent preserved land creating a beautiful and private backdrop. Whether you are seeking a welcoming year-round residence or an easy weekend escape, this property places you close to everything that makes the North Fork so special. Located within the popular Mattituck-Cutchogue School District, it is convenient to Love Lane, shopping, restaurants, farm stands and celebrated local wineries, while nearly equidistant from Breakwater and Bailie’s beaches on Long Island Sound and Veterans Memorial Park Beach on Peconic Bay. Space, privacy, convenience and possibility—all in one appealing Laurel location. Some images presented feature ai generated staging.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,327
Status:
NEW LISTING
MLS#:
1036799
Type:
Single Family
Lot size:
0.81 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

The Laurel Collection by MarrCon is an exclusive enclave of eight newly constructed luxury homes ideally located in the heart of Southold. With only 3 residences remaining, this limited offering presents a rare opportunity to enjoy exceptional new construction in one of the North Fork’s most desirable locations. 1475 Laurel Avenue showcases The Laurel Model, the largest model within the collection, offering approximately 4,375 square feet of beautifully designed living space set on .80 acres. The property is complete with a 20' x 40' heated saltwater gunite pool with an automatic cover, surrounded by an expansive Napa Stone marble patio. There is also ample room to create a pool house or outdoor kitchen. Backing to preserved land that can never be developed, the property offers lasting privacy and a peaceful, serene setting. Inside, 9ft ceilings span both the first and second floors, complemented by vaulted and coffered ceiling details and 8.5 inch white oak flooring throughout. The first floor features two bedrooms, including a luxurious primary suite with a generous walk-in closet and private access to the masonry patio, backyard, pool and gardens. The dramatic great room is anchored by a 46-inch linear gas fireplace and flows seamlessly into the beautifully appointed chef’s kitchen, featuring custom inset cabinetry, marble countertops, high-end GE Monogram appliances and a wet bar. The first floor also includes an office or flexible-use space complete with a wall of windows, built-in shelving and a wine refrigerator. Upstairs, two additional ensuite bedrooms feature beautifully finished baths with large-format tile and custom vanities. A spacious family room and oversized laundry room with custom cabinetry and a sink complete the second level, along with an additional stackable washer and dryer for added convenience. The lower level offers tremendous potential for additional living and entertaining space and can be finished to suit, with nine-foot ceilings, an egress window and walkout access already in place. Perfectly positioned to enjoy everything the North Fork has to offer, The Laurel Collection is just moments from beautiful beaches, wineries, farm stands and the charming villages of Southold and Greenport.

Open House:

Sunday, 8/16 11:00-1:00PM

More Open House Info >

Beds:
5
Baths:
6.00
Sq.Ft.:
3,240
Status:
NEW LISTING
MLS#:
1037213
Type:
Single Family
Lot size:
0.55 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its spectacular surroundings. Luxury finishes have been selected and wired for full smart home capability. Intuitively designed for both everyday living and elevated entertaining. Offering 5 bedrooms and 5 full bathrooms and one half bathroom, the layout balances both as a private retreat while still accommodating guests with ease. Featuring two primary en-suite bedrooms on both the first and second floors, three guest bedrooms and a full cabana-style bathroom in the walk-out basement for pool party guests. Salt water pool is 18x36, heated and surrounded by patio with outdoor kitchen the backyard is fully fenced in. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork.

Open House:

Saturday, 8/15 11:00-12:30PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
2,350
Status:
NEW LISTING
MLS#:
1036471
Type:
Single Family
Lot size:
0.17 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

North Fork Coastal Living by the Sound. Welcome to 155 Second Avenue, located in the charming hamlet of Peconic. The beach retreat you've been looking for, just 500 feet from both private and town beach access at Goldsmiths Inlet Beach. Custom built in 2005 by the current owner, this thoughtfully constructed beach home reflects true pride of ownership. Featuring open-concept living, dining, and kitchen areas which flow into a HUGE outdoor second story balcony, where peekaboo water views and beautiful sunsets create the perfect backdrop for relaxing or entertaining. Ready for your personal touch, the home offers a wonderful opportunity to add your own style but gives the peace of mind of an elevated and well built home. Bring your kayak paddleboard or fishing pole, spend your days on the water and your evenings exploring nearby vineyards, farm stands, restaurants, and local landmarks including nearby Horton Point Lighthouse. Well built, wonderfully located, and surrounded by everything that makes the North Fork special, 155 Second Avenue offers an easy coastal lifestyle in the heart of Peconic.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,500
Status:
NEW LISTING
MLS#:
1036267
Type:
Single Family
Lot size:
0.91 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
View additional info

ADDITIONAL INFORMATION

A rare opportunity to own a piece of history on Laurel Lake, a 33 acre kettle lake located in the hamlet of Laurel just 1 1/2 miles southwest of Mattituck. The structure was originally built as a "hunting lodge" by the Beverwyck Brewing Company of Albany, NY and placed on the lake at the 1939-1940 World's Fair in Queens to promote its beer. After the fair, the structure was relocated to its new home on Laurel Lake with 126' of lake frontage. The property was extensively restored in 2019. You have to see it to believe it! No description will ever do it justice, but certainly nothing like this exists on the North Fork of Long Island. Whether you are an avid fisherman or just inclined to sit back and enjoy the wildlife the lake attracts, a world of peace, tranquility, and beauty awaits you.

Open House:

Saturday, 8/15 1:00-3:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,100
Status:
NEW LISTING
MLS#:
1036090
Type:
Condo
Lot size:
8.71 Acres
Year built:
1983
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-477-2220
View additional info

ADDITIONAL INFORMATION

Enjoy Exceptional Water Views from this Second-Floor, 2-Bedroom, 2-Bath Condominium Featuring a Spacious Storage Loft and Private Deck Overlooking the Waterside Lawn and Bay. Cleaves Point Condominium Is Beautifully Situated on 13 Waterfront Acres at the End of Shipyard Lane in East Marion. Community Amenities Include a Private Bay Beach, Marina with Docking, Swimming Pool, Clubhouse with Gym, Tennis, Pickleball, Basketball, Community Garden, and More. Conveniently Located Near Island’s End Golf, Greenport Village, and All That the North Fork Has to Offer. Low Taxes Further Enhance This Outstanding Opportunity. Estate Sale. Sold “As Is”.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,840
Status:
Active
MLS#:
1033102
Type:
Single Family
Lot size:
0.39 Acres
Year built:
1937
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers sweeping water views, sensational sunsets, and effortless coastal living. Renovated in 2016 and completely move-in ready, the home blends sophisticated style with relaxed comfort, creating the perfect setting for both entertaining and quiet moments by the sea. Thoughtful upgrades include radiant floor heating, ducted heating and cooling with remote access, marble countertops, updated mirrors and light fixtures, keyless entry, Sonos speakers, and a beautifully appointed chef's kitchen. The primary suite includes a gorgeous bathroom, featuring a sculptural egg-shaped soaking tub perfectly positioned to capture the sunset views, separate shower and double sinks. The primary also has an office nook, and custom walk-in closet. Outdoor living is at the heart of the property. An expansive sun deck provides ample space for dining, lounging, entertaining, or morning yoga, while private stairs lead directly to the sea. A rare grandfathered lower waterfront platform creates an extraordinary setting at the water's edge for cocktails, Pilates, or simply taking in the sights and sounds of the Sound. The outdoor audio system extends the experience all the way to the property's iconic Whale Rock. Additional highlights include a detached garage offering potential for conversion into additional living space with proper permits. With dramatic water views, unforgettable sunsets, and a lifestyle centered around the Sound, this is North Fork waterfront living at its finest.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,053
Status:
Active
MLS#:
1033686
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-298-4130
View additional info

ADDITIONAL INFORMATION

A Rare North Fork Farmhouse with a Heated Barn and Endless Possibilities Tucked away on three-quarters of an acre in a quiet Mattituck neighborhood, this beautifully updated North Fork farmhouse offers the perfect blend of timeless charm, modern updates, and exceptional versatility. Surrounded by a peaceful setting, the property provides plenty of room to relax, entertain, and enjoy the North Fork lifestyle, with thoughtfully designed indoor and outdoor spaces that make you feel right at home. Designed for comfortable living and effortless entertaining, the home features four bedrooms and four full bathrooms across three finished levels. The thoughtfully renovated interior showcases hardwood floors, custom millwork, a beautifully appointed quartz kitchen with shaker cabinetry, and a wood-burning fireplace that anchors the inviting living and dining areas. All four bathrooms feature radiant heated floors, providing comfort and warmth throughout the year. A first-floor bedroom and full bath provide flexibility for guests or single-level living, while the finished lower level—with an additional bedroom, full bath, and spacious family room—offers exceptional space for recreation, a home office, or extended stays. Upstairs, the primary suite features a generous walk-in closet and beautifully appointed bath, while the second upstairs bedroom also enjoys its own walk-in closet. A standing-seam metal roof, approximately five years old, adds lasting value and peace of mind. Step outside to enjoy a freshly painted rear deck overlooking a newly fenced backyard designed for outdoor living, complete with mature landscaping, a tranquil koi pond, hot tub, dedicated fenced garden area, charming playhouse, and abundant space for a future swimming pool. A truly exceptional feature is the property's heated nearly 1,000-square-foot galvanized steel barn with convenient secondary access from Main Road. Equipped with electricity, oversized doors, soaring ceilings, a durable 12-inch concrete floor, and a wood-burning stove, this remarkable space offers endless possibilities as an artist's studio, workshop, garage, collector's showcase, or substantial storage for boats, vehicles, equipment, and hobbies. Few North Fork properties combine an updated farmhouse with a heated barn of this size and versatility. Paired with its peaceful setting just minutes from Love Lane, the grocery store, beaches, wineries, and farm stands, this is a property that offers exceptional flexibility for the way people live today.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,800
Status:
Active
MLS#:
1034331
Type:
Single Family
Lot size:
0.92 Acres
Year built:
1968
A broker reciprocity listing Courtesy: Modern Age Realty Group LLC 631-569-4513
View additional info

ADDITIONAL INFORMATION

Lovely 4 bedroom, 2bath Ranch home lg living room, dining rm and new kitchen 2years ago. Excellent investment property. Surrounded by quite farm field.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
1019799
Type:
Single Family
Lot size:
0.38 Acres
Year built:
1967
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

Welcome to North Fork living! Nestled in the desirable, private beach community of Laughing Water, this charming 3-bedroom, 2-bath Ranch sits on a 0.38-acre lot. Inside, enjoy hardwood floors throughout the living and dining areas, along with a newly updated kitchen featuring new appliances, a center island, and generous storage. A 10’ x 13’ screened-in porch provides the perfect three-season retreat overlooking the backyard. Take advantage of exclusive community amenities, including private beach access, a boat ramp, marina access (additional $900/season) , kayak storage, and a picnic area. Conveniently located just minutes from iconic North Fork farm stands, wineries, golf courses, restaurants and shopping! Don't wait! This house won't last. Call now to schedule your private showing.

Open House:

Sunday, 8/16

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,096
Status:
Active
MLS#:
1018415
Type:
Single Family
Subdivision:
Highland Estates
Lot size:
0.92 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
View additional info

ADDITIONAL INFORMATION

Welcome home to this four-bedroom two and and half bath expanded ranch style-home in the coveted Highland Estates section of Cutchogue. This corner property is set on 0.92 acres of flat landscaped property, which offers effortless indoor and outdoor living. The open concept kitchen has both Silestone and Butcher block countertops with modern floating shelves, ample cabinetry, white tiled backsplash and adequate prep space. The first floor primary suite provides a private retreat with easy access to the primary bath with tub. An inviting indoor-outdoor atrium sun-room generates the perfect space for relaxation and entertaining. There is a large family room, complete vaulted ceilings and a wood burning fireplace. Two additional upper level bedrooms and a full bathroom with walk in shower with glass surround, complete the upper level. Step outside to your own backyard oasis featuring a salt-water in-ground pool, outdoor cabana and lush landscaping, Multiple seating areas include a fire-pit, and separate grilling area. Out-door exterior lighting provide a tranquil atmosphere which allows for entertaining late into the evening, all designed to generate a peaceful setting right in the comfort of your home. A rare opportunity to own your own slice of paradise, in the sunniest place on Long Island, close to beaches, restaurants farm stands and wineries. Priced to sell, The house is being sold "as is". .

Beds:
5
Baths:
6.00
Sq.Ft.:
5,285
Status:
Active
MLS#:
1031351
Type:
Single Family
Lot size:
1.98 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
View additional info

ADDITIONAL INFORMATION

Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany front door and decking, solid wood closet systems, bespoke pantry shelving, and a handmade stone mantle and hearth. This lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with Bertazzoni and Bosch appliances, extra large island and breakfast nook, formal dining room with Butler's pantry, first floor junior primary ensuite, and library. Upstairs is a spacious primary ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar, gym, additional bedrooms or other uses. Outside enjoy multiple covered porches and your lovely pool, all surrounded by the peace and quiet of this serene and private setting. This is truly a Hampton-style masterpiece on the North Fork.

Beds:
5
Baths:
5.00
Sq.Ft.:
5,000
Status:
Active
MLS#:
1036287
Type:
Single Family
Lot size:
3.24 Acres
Year built:
1905
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-629-7675
View additional info

ADDITIONAL INFORMATION

Welcome to one of the East End's most distinguished estates. This waterfront property, built in the early 1900s, is situated on 3.24 acres and offers 170 feet on one of the North Fork’s most coveted stretches of pristine coastline, overlooking Peconic Bay, This offering represents a legacy opportunity. Upon arrival, the grandeur of the home makes a lasting impression with its sprawling lawn, magnificent trees, manicured grounds, and classic New England-style residence featuring an understated wrap-around porch and porte-cochere entry. Several years ago, the residence underwent a meticulous renovation that preserved its historic features while incorporating modern design elements and craftsmanship, enhancing the home's timeless beauty amid its coastal setting. Entering through a grand vestibule, you are welcomed by a double set of wide wooden doors with large inset glass. The spacious formal living room, complete with exposed beams, detailed oak paneling, a wood-burning fireplace, and weight-and-chain windows, provides a warm atmosphere while embracing views of the bay. The open and airy dining room features sliding doors that lead to a covered porch and provides access to a quaint library for more intimate conversations. The home's kitchen is designed for entertaining and enjoys abundant natural light. It boasts an oversized island, chef-grade appliances, custom cabinetry, beautiful countertops, and a hostess pantry, combining functionality with elegance. The casual dining area in the sunroom is surrounded by windows, allowing natural light and showcasing cascading hydrangeas, perfect for enjoying sunrises. Additionally, there is a side door leading to a blue stone patio for outdoor cooking and access to the home's waterside yard. The sunroom also includes a small alcove with floor-to-ceiling windows, providing extra seating or a quaint office space that highlights the natural beauty outdoors. The open floor plan incorporates a lounge anchored by a gas fireplace, making hosting easy with the kitchen's close proximity. The intricate staircase, both restored and timeless, leads to the home's five bedrooms, three of which face south to maximize the views. The primary ensuite captures the waterfront view and includes a spa-inspired bathroom with a soaking tub and an oversized walk-in closet. The Jr. Primary ensuite is spacious and overlooks the backyard. Two additional bedrooms, also facing the water, share a full bathroom, while the final bedroom is ensuite and overlooks the side of the property. The residence features a unique, restored two-story boathouse, providing access to the double-tiered bulkhead and beach. This space is ideal for intimate gatherings and enjoying the sound of the waves. The expansive property additionally includes a Gunite pool with a covered outdoor lounge, a powder room, and a three-car garage. Encapsulated by mature trees and hedges, the property offers exceptional privacy and serenity. Whether you are looking for a summer sanctuary or a year-round estate, this property offers a level of prestige that rarely hits the market.

Open House:

Saturday, 8/15 11:00-1:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,235
Status:
Active
MLS#:
1029495
Type:
Single Family
Subdivision:
Orient By The Sea
Lot size:
0.44 Acres
Year built:
1975
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,800
Status:
Active
MLS#:
1032350
Type:
Single Family
Subdivision:
Summit Estates
Lot size:
0.69 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Modern Age Realty Group LLC 631-569-4513
View additional info

ADDITIONAL INFORMATION

Welcome to this exceptional estate, just a short walk from a private deeded beach and dock. Designed for entertaining, this spacious property features an impressive outdoor living area complete with a covered, built-in bar and kitchen—perfect for hosting family and friends. Enjoy the quiet, peaceful surroundings while still being close to everything you need. With low taxes and move-in-ready condition, this home offers the ideal combination of comfort and convenience. Furniture is negotiable, and the property may be sold furnished.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,500
Status:
Active
MLS#:
1031524
Type:
Single Family
Lot size:
0.7 Acres
Year built:
1948
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
View additional info

ADDITIONAL INFORMATION

This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and exceptional East End retreat Stunning carpentry, high-end appliances, and designer fixtures carry throughout. The custom-built kitchen features bespoke cabinetry and hardware, flowing seamlessly into a dining area and a light-filled living room anchored by a wood-burning fireplace. Oversized windows and a vaulted ceiling define the dining room, which connects to an oversized back deck overlooking the sprawling backyard. Outside, a gunite, heated, saltwater pool complements the cedar-shingled accessory structure, which combines a pool house with its own bathroom, a garage, a covered outdoor patio with a gas fireplace, and an outdoor shower. Back inside, two additional guest bedrooms share a full bath on the second floor, while downstairs, two large recreation rooms offer further customization and flexibility. The location is just as compelling as the house itself, minutes from Goose Creek Beach, Cedar Beach, Croteaux Vineyards, and the many shops and restaurants of Southold Hamlet. This is a special property with a real point of view that you'll look forward to walking into each time you return home.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,100
Status:
Active
MLS#:
1031857
Type:
Single Family
Lot size:
0.09 Acres
Year built:
1958
A broker reciprocity listing Courtesy: Signature Premier Properties 631-765-6000
View additional info

ADDITIONAL INFORMATION

Experience waterfront living at its finest, in this exceptional cottage located directly on the Bay. This turn-key, one of a kind property, offers gorgeous water views and open concept living. The dramatic vaulted ceilings with exposed beams, create a stunning focal point, adding warmth, texture, and character throughout the living space. Step outside to your own private beach; perfect for swimming, kayaking, paddle boarding, boating, entertaining, or simply relaxing with your feet in the sand. The panoramic views create an unmatched open-bay lifestyle. Wake up each morning to the soothing sounds of the bay and breathtaking sunrises over the water, just steps from your door. This 3 bed 1.5 bath is waiting for you. Located in peaceful East Marion, this home has close proximity to the Jitney, LIRR, amazing restaurants, and the best vineyards the North Fork has to offer. Simply arrive, unwind, and enjoy the waterfront lifestyle you've been dreaming of.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
1023134
Type:
Single Family
Lot size:
0.35 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
View additional info

ADDITIONAL INFORMATION

This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

Beds:
6
Baths:
7.00
Sq.Ft.:
5,700
Status:
Active
MLS#:
964447
Type:
Single Family
Lot size:
7.49 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
View additional info

ADDITIONAL INFORMATION

Rare opportunity to own a uniquely private 7.49-acre bay front estate in Orient Village. This exceptional waterfront property features a spacious 5700 sq ft main residence with 6 bedrooms, 7 baths, three wood burning fireplaces, three bay garage, expansive front and rear covered porches and panoramic bay views. The 20 x 44 heated pool is complemented with a 860 sq ft pool house featuring open common area, kitchenette, full bath, laundry, two changing rooms, outdoor shower, & porch – creating an ideal setting for entertaining and summer living. A fully fenced clay 60 x 120 ft tennis court is expertly sited, so sun glare is never an issue. The property offers an additional free-standing two-bay garage with second floor bonus space providing flexible options for recreation, boat/bike storage or studio space. The 195 ft wide private walkout bay beach offers sweeping Harbor views of Long Beach State Park, Bug Light House and Orient Yacht Club. The property is ideally located within walking or biking distance to the Village of Orient, Orient Yacht Club, local marinas, Post Office, the Country Store, Oysterponds Historical Society and all village amenities.

Open House:

Sunday, 8/16 11:00-12:30PM

More Open House Info >

Beds:
4
Baths:
5.00
Sq.Ft.:
5,000
Status:
Active
MLS#:
1028997
Type:
Single Family
Lot size:
2.44 Acres
Year built:
2001
A broker reciprocity listing Courtesy: William Raveis New York LLC 631-298-0600
View additional info

ADDITIONAL INFORMATION

Vineyard Estate Living in the Heart of Cutchogue Set on 2.44 private acres adjacent to a North Fork vineyard and a bucolic field, 1492 Skunk Lane offers the scale and flexibility of a country estate with the comfort and ease of modern living. A gracious New England-style covered porch and classic architecture create memorable curb appeal, while the interior unfolds with a welcoming flow designed for entertaining, working from home, and relaxed everyday living. The entry foyer opens to a formal living room or dining room, and a handsome library or home office with a gas fireplace. At the center of the home, the expansive eat-in kitchen provides generous counter space, abundant cabinetry and pantry storage, and an easy connection to the spacious great room. A second, wood burning, fireplace and access to the screened porch create an inviting setting for quiet evenings or gatherings overlooking the broad, verdant lawn. The main level also includes an en-suite guest bedroom, butler’s pantry, laundry and mudroom, and direct access to the oversized three-car garage. A private staircase leads to more than 700 square feet of finished bonus space with a powder room—ideal for a studio, private office, recreation room, or your personal crafts area. Upstairs, the serene primary suite features a private bath, extensive built-ins, ample closet space, and room to create a comfortable retreat. Two additional bedrooms share a Jack-and-Jill bath, while the third-floor mezzanine provides another quiet place to work, study, read, or create, together with access to substantial walk-up attic storage. The finished lower level further expands the home’s versatility with media and fitness areas, a bathroom, utility rooms, abundant storage, and convenient garage access. Outdoors, expansive lawns, exceptional privacy, western exposure, and the adjoining vineyard create a peaceful backdrop for sunset entertaining. With ample room for a pool and additional outdoor living spaces, the property is equally suited to year-round resort-style living or a refined weekend retreat. Located minutes from Nassau Point’s Causeway Beach, Love Lane, farm stands, wineries, local shopping, and Greenport dining, 1492 Skunk Lane presents a distinctive opportunity to enjoy the beauty, space, and effortless lifestyle of the North Fork.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,522
Status:
Active
MLS#:
1027794
Type:
Single Family
Lot size:
1.02 Acres
Year built:
2016
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
View additional info

ADDITIONAL INFORMATION

This impeccably maintained residence is perfectly positioned in the heart of Mattituck, just minutes from local beaches, Love Lane, New Suffolk, and downtown Cutchogue. Set on a beautifully landscaped acre, the property offers a large in-ground pool, mature gardens, and ample room to add additional amenities such as a tennis court or accessory structure. Inside, a bright, open-concept floor plan lends itself to both everyday living and entertaining, featuring a large chefs kitchen, dining room and living room. The oversized primary suite serves as a private retreat, complete with a spacious en-suite bath and generous walk-in closets. Two additional guest bedrooms and a large home office provide flexibility for visitors, or remote work. A large laundry room, basement and detached garage provide for additional utility. Sit on your back patio overlooking the pool to take in spectacular East End sunsets. Thoughtfully maintained and ideally located, this is a home that pairs comfort, convenience, and future potential in one of the North Fork's most desirable communities.

Open House:

Sunday, 8/16 11:00-12:30PM

More Open House Info >

Beds:
3
Baths:
4.00
Sq.Ft.:
1,700
Status:
Active
MLS#:
1028434
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1920
A broker reciprocity listing Courtesy: William Raveis New York LLC 631-298-0600
View additional info

ADDITIONAL INFORMATION

Stylish Heritage Farmhouse: Dating to approximately 1910, this beautifully reimagined Queen Anne–inspired country home preserves a tangible connection to East Marion’s past. Set along the historic route once known as Kings Highway and Sunset Trail—today’s Main Road—and near Marion Lake, the residence was built when the hamlet still reflected its longstanding agricultural and maritime heritage while emerging as a sought-after North Fork summer retreat. Comprehensively renewed for contemporary living, the home pairs early-20th-century character and gracious proportions with refined interiors and exceptional outdoor potential. All major systems have been updated, offering the comfort, convenience and confidence of a modern residence within a home of enduring character. Privately situated behind stylish gates on a level, sun-filled half-acre, the property offers turnkey living in a thoughtfully landscaped setting. A welcoming wraparound porch opens to a beautifully appointed kitchen featuring stainless-steel appliances, quality finishes and sophisticated details. The open-concept living and dining areas flow naturally from the kitchen and extend to an open-air deck overlooking the expansive backyard. An existing pool permit provides an exciting opportunity to create a private outdoor retreat, while one of the property’s two substantial sheds could potentially be converted into a pool house, subject to applicable permits and approvals. The first-floor primary suite includes a beautifully finished bath with a soaking tub, while a separate powder room serves guests. Upstairs, two additional en-suite bedrooms each feature a thoughtfully designed full bath. Generous proportions continue throughout the home, with the basement providing abundant storage and a spacious laundry room. Propane heat and new central air conditioning ensure year-round comfort. The home’s flexible layout and peaceful yet convenient location also create an ideal live-work environment for remote professionals, digital nomads and those seeking a sophisticated country escape without sacrificing modern connectivity or convenience. Low East Marion taxes, two large sheds and mature landscaping further distinguish the offering. Ideally located minutes from Long Island Sound and Peconic Bay beaches, Marion Lake for kayaking and birdwatching, and the shops, restaurants and waterfront attractions of Greenport Village—with ferry connections to Shelter Island and the Hamptons—this stylish heritage farmhouse presents a rare opportunity to embrace four-season North Fork living and establish your own enduring North Fork legacy.

Refine Property Search
Page 1 | 2 | 3 | 4 | 5 of 5    Prev | Next
1–25 of 106 properties displayed
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. 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. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026, OneKey MLS, Inc. All Rights Reserved.



Southold Real Estate

Southold is located in New York. Southold, New York has a population of 23,571. Southold is less family-centric than the surrounding county with 21.26% of the households containing married families with children. The county average for households married with children is 32.94%.

The median household income in Southold, New York is $92,229. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Southold is 56.1 years.

Southold Weather

The average high temperature in July is 80.9 degrees, with an average low temperature in January of 23.6 degrees. The average rainfall is approximately 48 inches per year, with 27.3 inches of snow per year.

Southold Map

Southold Real Estate Market Conditions

  • Median sales price

    $1,580,000
    16.1%
    change since last quarter
  • # Active listings

    132
    30-day change

Southold Schools and Demographics

Education near Southold, NY

City County
High School Graduates 92.84 90.39
College Degree - 2 year 9.44 9.66
College Degree - 4 year 48.04 38.31
Graduate Degree 15.03 12.89
Expenditures per Student 30,219 30,219
Students per Teacher 12.3 12.3

Elementary Schools near Southold, NY

Grades Students P/T Ratio ZIP
Greenport Elementary School PK - 06 330 15 11944
Mattituck-Cutchogue Elementary School KG - 06 580 10.4 11935
New Suffolk School PK - 06 17 6.8 11956
Southold Elementary School KG - 06 403 11 11971

High Schools near Southold, NY

Grades Students P/T Ratio ZIP
Greenport High School 07 - 12 353 15.3 11944
Southold Junior-Senior High School 07 - 12 423 11.2 11971

Ungraded Schools near Southold, NY

Grades Students P/T Ratio ZIP
Shelter Island School PK - 12 221 6.8 11964

Demographics near Southold, NY

City County
Neighborhood Type Suburban
Population 23,571 1,522,998
Population Density 438 1,670
Median Age 56.1 41.7
People per Household 2.3 3
Median Household Income 92,229 111,660
Average Income per Capita 60,908 49,404

Real estate near Southold