Southold NY Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,680
Status:
NEW LISTING
MLS#:
1069295
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1974
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

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 specimen trees and shrubs, surrounds the property and enhances its privacy.

Beds:
4
Baths:
5.00
Sq.Ft.:
2,500
Status:
NEW LISTING
MLS#:
1069597
Type:
Single Family
Lot size:
0.44 Acres
Year built:
2016
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
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ADDITIONAL INFORMATION

Modern waterfront living on the Sound, this sophisticated custom residence offers 100 feet of private water frontage on a property extending over 267 feet deep, complete with direct access to a sandy beach and spectacular sunset views. Built by Seifert Builders, the home showcases exceptional craftsmanship and premium materials imported from Germany, including a low-maintenance fiber cement exterior with cedar trim. Walls of glass frame panoramic water views, while expansive sliding glass doors open completely to the outdoor decking, creating a seamless connection between indoor and outdoor living. A rare heated, saltwater gunite pool and rooftop deck provide exceptional spaces for relaxation and entertaining. Inside, the home features four ensuite bedrooms, a dedicated office, and a powder room, along with a chef’s kitchen equipped with Sub-Zero, Viking, and Bosch appliances and a wine cooler. Additional highlights include motorized window shades throughout, propane heating, a whole-house Kohler generator, an installed security system, and a Sonos sound system. Thoughtfully designed to maximize its extraordinary waterfront setting, this residence offers a rare combination of modern architecture, luxury amenities, and direct beach access.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,154
Status:
Active
MLS#:
1066280
Type:
Single Family
Lot size:
0.21 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
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ADDITIONAL INFORMATION

A home defined by a natural, organic aesthetic, meticulously restored with an appreciation for simplicity, texture, and timeless materials. The result is a residence that feels both refined and deeply connected to its surroundings, with mature landscaping offering privacy and a quiet retreat. Well-proportioned rooms and incredible natural light create an airy sense of space, while carefully preserved exposed beams, wide-plank pine floors, and beadboard detailing lend warmth and architectural character. The kitchen centers on a generous custom-made island, an AGA range, and a farmhouse sink, while the dining room is anchored by a sunny bay window and decorative plaster medallion. A cozy home office sits alongside a large living room at the west end of the first floor. Upstairs, a vaulted top-floor bedroom offers a private escape, complemented by two additional bedrooms. A full basement offers additional flexibility. Just a few blocks from the heart of Greenport Village and 5th Street Beach, the home balances understated beauty with everyday functionality in a setting that feels both private and connected to village life.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,925
Status:
Active
MLS#:
1066839
Type:
Single Family
Lot size:
1.37 Acres
Year built:
1976
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-288-6244
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ADDITIONAL INFORMATION

Distinctive Design. Natural Privacy. Your North Fork Retreat. Tucked into a cul-de-sac on 1.37 acres, 600 Highwood Road in Southold is a thoughtfully customized two-bedroom, two-bath A-frame where striking architecture meets relaxed North Fork living. Roman clay, white oak flooring, and exposed wood beams bring warmth and texture to the double-height great room, while custom built-ins add character and functionality throughout. Designed for effortless entertaining, the home offers inviting spaces to gather in every season. A soft, monochromatic palette continues into the kitchen, featuring a quartz-topped island, plaster hood, stainless steel appliances, and a farmhouse sink. Above, a versatile loft offers additional space for entertaining or unwinding, complemented by a cozy reading nook. Outdoors, mahogany decking creates an inviting setting for dining and entertaining amid the natural surroundings. A rooftop terrace offers a bird’s-eye view of the property, a special place to unwind above the treetops and watch the sunset. Surrounded by nature and close to the water, the property offers a peaceful setting for summer escapes and year-round living. A two-car garage and dedicated laundry room add everyday convenience, while the expansive grounds offer room to explore an addition or pool, subject to necessary approvals. Beautifully detailed and full of possibility, your North Fork retreat awaits.

Beds:
5
Baths:
2.00
Sq.Ft.:
2,300
Status:
Active
MLS#:
1065984
Type:
Single Family
Lot size:
0.13 Acres
Year built:
1956
A broker reciprocity listing Courtesy: John Savoretti Realty 516-327-6400
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
1062583
Type:
Single Family
Lot size:
0.74 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Keller Williams Rty Gold Coast 516-482-0200
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ADDITIONAL INFORMATION

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

Beds:
4
Baths:
4.00
Sq.Ft.:
3,900
Status:
Active
MLS#:
1063190
Type:
Single Family
Lot size:
0.41 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

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 septic system designed for 6 bedrooms. A distinctive new construction offering that brings together modern architecture, quality materials, and effortless indoor-outdoor living. Located close to Southold town, bay and sound beaches and all the North Fork has to offer. . Additional Professional Photos Coming Soon

Beds:
4
Baths:
2.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
1044427
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-477-2220
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ADDITIONAL INFORMATION

Welcome to 650 Grove Dr, a delightful 4-bedroom, 2-bathroom home nestled in the heart of the popular Reydon Shores community. This cherished, well-established residence offers a slight water view from the comfort of your living room and two upstairs bedrooms. The main level features a cozy bedroom, a full bathroom equipped with a washer and dryer, and an inviting eat-in kitchen and a dining room perfect for hosting memorable meals. Ascend to the upper level to find three more spacious bedrooms and another full bathroom. Step outside to experience the charm of the private beach community, complete with a marina and a beach just around the corner. This home, filled with endless memories of great summers, is an opportunity to create your own cherished moments. Experience the best of what the North Fork has to offer in this welcoming community where the sea meets the sky. Let the tranquility of 650 Grove Dr become your everyday reality.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,270
Status:
Active
MLS#:
1059141
Type:
Single Family
Lot size:
0.33 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-477-2220
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ADDITIONAL INFORMATION

Welcome to 275 Main Bayview in Southold, a warm and inviting home close to all the North Fork has to offer. This delightful Cape-style home boasts 3 spacious bedrooms, including a unique loft bedroom upstairs, and 2 bathrooms. Step inside and be greeted by a welcoming living room, complete with a cozy fireplace to warm those chilly nights. The expansive kitchen offers ample room for culinary adventures and leads conveniently into a dedicated laundry/mud room. Step outside to a serene back patio, perfect for dining or a morning cup of coffee. The backyard is a private haven, with an open view, surrounded by impressive rock walls at both the entrance and rear. This outdoor space is a testament to the beauty of nature, offering a peaceful retreat. The home's central location is a true highlight. You're just a stone's throw away from a variety of shops, wineries, restaurants, and beaches. As part of the Southold Town park district, you'll enjoy access to the picturesque Founders and South Harbor beaches. This property is more than just a home; it's a lifestyle. It offers the perfect blend of private tranquility and vibrant community life. Whether you're a foodie, a beach lover, or someone who appreciates a cozy night by the fire, this home has something for everyone. Come and experience the charm of 275 Main Bayview Rd, where every day feels like a vacation. This could be the home you've been waiting for. So why wait? Make the move today!

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
1060683
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-629-7719
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ADDITIONAL INFORMATION

Welcome to 430 Grove Road, Southold — Where the North Fork Lifestyle Becomes Your Everyday Life! Imagine starting your mornings with coffee on your beautiful, window-filled enclosed porch, spending your afternoons exploring local vineyards, breweries, and beaches, and ending your evenings enjoying the peaceful charm of the North Fork. This inviting 3-bedroom ranch offers the perfect opportunity to embrace a lifestyle that feels like a vacation every day. Tucked away in a wonderful Southold setting, this home features a bright, enclosed porch surrounded by windows, a detached garage, and an outdoor shower — perfect for rinsing off after a day on the water or at the beach. Just down the street, enjoy convenient water access where you can launch your paddleboard, kayak, or canoe and explore the beauty of the surrounding waterways. Whether you're looking for a year-round residence, a weekend escape, or your very own North Fork retreat, this property offers so much more than a place to call home. brand new furnance and oil tank in 2020 and hot water heater 2024. You're not just purchasing a house — you're purchasing the North Fork lifestyle! From award-winning vineyards and local farm stands to waterfront dining, beautiful beaches, and endless outdoor adventures, everything that makes the North Fork so special is waiting for you at 430 Grove Road.

Beds:
5
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
1054880
Type:
Single Family
Lot size:
1.92 Acres
Year built:
1800
A broker reciprocity listing Courtesy: Century 21 Albertson Realty 631-765-3800
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ADDITIONAL INFORMATION

Steeped in history dating back to the early 1800s, this five-bedroom, two-bathroom home once served as the main farmhouse of an expansive agricultural tract. Set on two sprawling acres, the property features a large gambrel barn, sweeping lawns, and a white picket fence that complements its classic farmhouse charm. Surrounded by preserved farmland, this pastoral setting is conveniently located in the heart of Southold Hamlet.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,376
Status:
Active
MLS#:
1061179
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1977
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
1059170
Type:
Single Family
Lot size:
0.34 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Corcoran SRG Residential 516-774-2446
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ADDITIONAL INFORMATION

Welcome to 5045 Main Bayview Road, an inviting three-bedroom retreat nestled within Southold’s prestigious Goose Neck community, where privacy, coastal charm, and the relaxed elegance of North Fork living come together. Designed for effortless indoor-outdoor living, the home’s standout feature is its resort-style backyard, a private oasis complete with a beautiful swimming pool, expansive deck, and built-in barbecue. Whether spending leisurely afternoons poolside, dining outdoors, or entertaining family and friends, this exceptional outdoor setting is perfectly suited for enjoying the best of summer on the North Fork. The primary bedroom opens to a private deck overlooking the backyard, offering a peaceful place to begin or end the day while taking in the serene surroundings. A sunroom featuring a hot tub provides an additional space to relax and unwind throughout the seasons. Located within the coveted Goose Neck community, residents enjoy the added luxury of private beach access, creating the quintessential North Fork lifestyle just moments from home. Southold’s celebrated vineyards, farm stands, beaches, restaurants, shops, and charming village destinations are all within easy reach. Perfect as a year-round residence, sophisticated weekend escape, or summer retreat, 5045 Main Bayview Road presents a special opportunity to enjoy privacy, recreation, and coastal living in one of Southold’s most desirable settings.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,250
Status:
Active
MLS#:
1058940
Type:
Single Family
Lot size:
0.47 Acres
Year built:
1972
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
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ADDITIONAL INFORMATION

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

Beds:
4
Baths:
6.00
Sq.Ft.:
7,000
Status:
Active
MLS#:
1052436
Type:
Single Family
Lot size:
11.31 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
6,374
Status:
Active
MLS#:
1054890
Type:
Single Family
Lot size:
0.4 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
View additional info

ADDITIONAL INFORMATION

Bay Haven — 1430 Bay Haven Lane, Southold Classic coastal architecture meets contemporary North Fork living in this newly built custom residence set within the Bay Haven beach community, just three houses from the private community beach. Designed for effortless North Fork living, the home offers 3,035 square feet of living space, with four bedrooms and four full baths, complemented by approximately 3,340 additional square feet of garage, pool house, storage/art, and under-house utility and storage space. Inside, 10 foot first-floor ceilings, 9 foot second floor ceilings, natural hardwood floors, abundant natural light, custom millwork, built-ins, and site-built closets create a refined yet relaxed interior. Two primary suites, one on each floor, offer flexibility for year-round living and guests. Each features a walk-in closet, ensuite bath, and electric fireplace, while radiant-heated floors enhance the primary bath spaces. The first floor suite also includes a private office, while the second-floor suite enjoys seasonal bay views. At the heart of the home is a locally handcrafted kitchen with cabinetry extending to the 10 foot ceiling, a 48-inch professional style gas range beneath a custom arched hood, dual dishwashers, smart combination wall oven, farmhouse sink, pot filler, dual-zone wine refrigeration, and extensive custom storage. Indoor and outdoor living flow naturally through the three-season room, complete with custom cabinetry, TV hook up and fireplace, to the landscaped grounds and a heated pool. A poolside mudroom provides direct access to a full bath, shower, and changing area. The pool house adds another layer of entertaining space with a wine bar, dual zone wine refrigeration, and glass doors opening directly to the pool. The property extends well beyond the main residence with a detached garage and approximately 770 square foot second floor storage, ideally suited for an Art Space, plus approximately 1,800 square feet of under-house storage and utility space. Behind the design is a substantial infrastructure package: a high-efficiency five zone heat pump heating and cooling system, 3 zones of radiant heat, comprehensive spray foam insulation, a hybrid heat-pump water heater, three stage whole house filtration, controlled under-house dehumidification, energy efficient heat pump pool heating, smart pool control and lighting systems, Ring security, an I/A septic system, and 300-amp electrical service. Bay Haven combines privacy, craftsmanship and modern comforts with immediate access to the Bay. Cedar Beach is just 1.5 miles away, with the shops and restaurants of Southold nearby. Seasonal second floor bay views and year round glimpses of the water complete a home equally suited to summer escapes and year-round North Fork living.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,500
Status:
Active
MLS#:
1053616
Type:
Single Family
Subdivision:
Paradise Point
Lot size:
2.38 Acres
Year built:
1995
A broker reciprocity listing Courtesy: William Raveis New York LLC 631-298-0600
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ADDITIONAL INFORMATION

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 house; it is a substantial bayfront residence designed to make an impression. The dramatic double-height great room is anchored by a rare natural coral-stone fireplace and opens to more than 1,500 square feet of exterior decking—an exceptional setting for entertaining, dining outdoors or simply watching the light move across the bay. A formal waterside dining room complements the spacious eat-in kitchen, which provides generous counter space and an inviting place for everyday gatherings. The main level also includes pantry and laundry areas, together with a flexible 4th bedroom or den and adjacent full bath—ideal for guests, a private home office or convenient first-floor living. Ascend the sweeping staircase to the waterfront primary suite, a private retreat featuring magnificent bay views, its own waterside terrace, a luxurious full bath and walk-in closet. Two additional bedrooms and another full bath complete the upper level. The finished lower level expands the home’s recreational possibilities with a game or media area, direct access to a waterside terrace and an attached multicar garage. Outside, the expansive, level grounds provide ample room for entertaining, recreation and quiet enjoyment amid beautiful natural surroundings. A private boardwalk leads directly to the sandy beach, where days can be spent swimming, fishing, kayaking, paddleboarding or launching a morning adventure on the bay. Although wonderfully private, the estate is only minutes from Southold Village and the restaurants, vineyards, farm stands, shops, beaches and boating destinations that define North Fork living. Additional amenities include public water, a supplemental well, oil-fired forced-air heat and central air conditioning. Rare acreage, substantial private beach frontage, community boating access and a dramatic waterfront residence come together in one extraordinary Southold offering. Paradise Found.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
1050202
Type:
Single Family
Lot size:
2.18 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
View additional info

ADDITIONAL INFORMATION

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 full bath with a handicap-accessible shower. The spacious, light-filled kitchen is designed for both everyday living and entertaining. Featuring an abundance of cabinetry, expansive counter space, and an efficient layout, the kitchen offers plenty of room for meal preparation and storage. The open design flows into the dining area and living room, creating an inviting atmosphere for casual gatherings or larger celebrations. The dining area offers sliding doors leading to a large deck overlooking the scenic grounds, the perfect setting for outdoor dining, relaxing, or entertaining. The full basement with outside entrance offers endless possibilities for expansion of the living space if desired. Every detail of this residence reflects exceptional care and pride of ownership. Beautifully maintained, the home presents with the feel and quality of new construction. A rare opportunity to own a pristine country retreat with room for a pool, where privacy, natural beauty, and convenience come together in perfect harmony.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,300
Status:
Active
MLS#:
1051232
Type:
Single Family
Lot size:
0.52 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Hedgestone Commercial Rlty LLC 855-733-3188
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ADDITIONAL INFORMATION

Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes from Southold Village, beaches, vineyards and celebrated local restaurants. Property is being sold as-is.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,241
Status:
Active
MLS#:
963793
Type:
Single Family
Lot size:
1.68 Acres
Year built:
1972
A broker reciprocity listing Courtesy: Thomas J McCarthy Real Estate 631-765-5815
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ADDITIONAL INFORMATION

Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location. Held in the same family for more than 50 years, the over 4000-square-foot home is set on two private acres overlooking the natural beauty of Great Pond. Expansive light-filled rooms, walls of glass and bold architectural lines create a residence that feels as compelling today as it was when first conceived. Mature landscaping, an inground pool, abundant wildlife and magnificent sunsets all contribute to the architectural composition. These features enhance the sense of retreat and home, while two beautiful Long Island Sound beaches—Kenney’s and McCabe’s—are just moments away. A true North Fork treasure, equal parts architectural time capsule and North Fork, grab this opportunity before it's gone.

Beds:
4
Baths:
5.00
Sq.Ft.:
5,100
Status:
Active
MLS#:
1039113
Type:
Single Family
Lot size:
0.67 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Migrate Realty LLC 631-699-5011
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ADDITIONAL INFORMATION

Ready to Move In -- New Construction Luxury Southold Home completed October 2026. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with peaceful North Fork country living. Features 5,100+ SF of living space on 3 levels with 4 Bedrooms and 4.5 Bathrooms plus a bonus room/office over your attached 3 car garage. This stunning home has everything including a Giant front wrap-around-porch, heated saltwater 18x36 pool, outdoor shower and both first and second level primary bedrooms with ensuite baths. Every bedroom has large walk-in-closets. All high-end finishes were used throughout including Natural Alaskan Cedar Siding, Anderson 400 Series Windows, Luxury Appliances and Quartz Countertops, Wide Plank Natural White Oak Floors, Gas Fireplace, Custom Glass Shower Doors throughout, and more. Full Finished Basement with 9.5’ ceilings, Outside entrance to the lower level, full lower level bathroom, built in wine fridge, and luxury oversized double glass doors leading to your Gym and Custom Cedar Sauna. Equipped with the latest smart home technology including Hard Wired Ring Camera System, 5 Zone Sonos Sound System, Hard Wired EERO wifi access points, Lutron Smart Lighting, Wifi Pool Equipment, Wifi Sprinkler control, and more. Enjoy exclusive Southold Park District rights—offering access to private beaches, kayak launches, and Founders Landing—while being just minutes from stunning Long Island Sound beaches, scenic Sound View Dunes, world-class vineyards, farm stands, and charming village dining.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
1038709
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1974
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
View additional info

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
4.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
1032396
Type:
Single Family
Lot size:
0.33 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 516-307-9406
View additional info

ADDITIONAL INFORMATION

Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully! Experience the relaxed sophistication of North Fork living in this beautifully, maintained, move-in-ready 4 bedroom, 3.5 bath Colonial in the heart of Southold. Filled with natural light and designed for modern living this home features 9' ceilings, hardwood floors and an easy-flowing layout designed for both everyday living and entertaining. The spacious open areas connect seamlessly to the gourmet eat in kitchen, featuring marble countertops, stainless steel appliances and abundant cabinetry, while a cozy fireplace adds warmth and character. A standout feature is the expansive lower/ground level with 10' ceilings and sliding glass doors opening directly to the backyard--offering outstanding potential for additional living space, perfect for great room, media room, gym, office and entertainment area. Outside enjoy the expansive deck and private, serene backyard ideal setting for morning coffee, summer gatherings, or quiet evenings at home. Perfectly positioned near Southold's beaches, wineries, farm stands, marinas, waterfront parks, boutique shops and top North Fork dining. This move-in-ready home delivers the space, privacy and effortless coastal living that makes the North Fork so special.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,750
Status:
Active
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

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 finished basement with cabana-style bathroom. The basement features a walk-out entry leading to the pool and outdoor kitchen area, for pool party guests. Salt water pool is 16x36, heated and surrounded by patio with outdoor kitchen the backyard is fully fenced in and irrigated. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork.

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 for boaters and beach lovers! It's all about the lifestyle. Nestled in the desirable, private beach community of Laughing Water, this charming 3-bedroom, 2-bath Ranch sits on a 0.38-acre lot. Enjoy the private community atmosphere, including a private beach, a boat ramp, two marina in your "backyard" (additional $900/season) & kayak storage. Hardwood floors throughout the living room, dining area and bedrooms. Updated kitchen featuring newer appliances, a center island, and ample cabinets and storage. A 10’ x 13’ screened-in porch provides the perfect three-season retreat overlooking the backyard. Conveniently located just minutes from iconic North Fork farm stands, wineries, golf courses, restaurants and shopping!

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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

    $1,119,000
    16.1%
    change since last quarter
  • # Active listings

    67
    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