Southold NY Real Estate & Homes for Sale

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Beds:
4
Baths:
5.00
Sq.Ft.:
5,200
Status:
NEW LISTING
MLS#:
1071908
Type:
Single Family
Lot size:
3.25 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

Paradise Point Bayfront With Dock, 200' Of Sandy Beach, 4 Beds/5 Baths, 3.25 Acres. Majestic bayfront residence set on 3.25 private acres in one of Southold's most sought-after locations awaits! Enjoy the North Fork's waterfront lifestyle with private dock, 200 feet of waterfront and views of Shelter Island and beyond. Home features four bedrooms, five baths, a first-floor primary suite, entry foyer, formal dining room, family room, living room and two wood-burning fireplaces. Includes 2 additional detached garages, 2 horse stalls and a storage shed. Garage capacity for up to 6 cars plus multiple parking spots. Spacious property can accommodate a much larger home with pool. This is truly a rare opportunity to own an exceptional waterfront property with privacy, scale, and breathtaking surroundings.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,600
Status:
NEW LISTING
MLS#:
1070418
Type:
Single Family
Lot size:
0.45 Acres
Year built:
1967
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

The perfect ranch home with in-ground pool, one mile to the beach! Two full bedrooms and versatile bonus space to enjoy a peaceful North Fork lifestyle. In addition to the main living areas, a legally converted garage provides a spacious 14' x 20' bonus room with sliders that open to the pool, has a legal half bath ideal for a home office, media room, guest overflow, or additional entertaining space. Step outside to your own private backyard retreat, featuring a 16' x 32' heated swimming pool perfect for summer gatherings and relaxing afternoons. With town-owned land bordering the rear of the property, the backyard is a peaceful, natural backdrop with added quiet and privacy. There is a full walk out basement ready to be finished with laundry and a washer-dryer hook up on first floor if needed. Located approx. one mile from Southold Village and Hampton Jitney stop and one mile to beloved Goose Creek Beach and minutes to Southold's charming village, local wineries, farm stands, and waterfront destinations, this property offers an inviting opportunity to enjoy the best of North Fork living. Whether you're looking for a year-round residence or a weekend escape, 600 Gardiners Lane is ready to welcome you home! Some photos have been virtually staged.

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:
Active
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
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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
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ADDITIONAL INFORMATION

Bay Haven — 1430 Bay Haven Lane, Southold A modern interpretation of classic coastal Shingle Style, this newly built custom residence offers refined North Fork living within the desirable Bay Haven beach community, just three houses from its private community beach. Thoughtfully designed for both year round enjoyment and effortless summer entertaining, the home features approximately 3,035 square feet of living space with four bedrooms and four full bathrooms, complemented by approximately 3,340 additional square feet of garage, pool house, storage/art, and under-house utility and storage space. Inside, soaring 10 foot first floor ceilings, 9-foot second floor ceilings, natural hardwood floors, abundant sunlight, and exceptional custom millwork create an atmosphere of understated coastal elegance. Built ins, handcrafted details, and site built closets reflect the attention to quality throughout. Two generously appointed primary suites, one on each level, provide exceptional flexibility for owners and guests. Both feature walk in closets, ensuite bathrooms with radiant heated floors, and electric fireplaces. The first-floor suite includes a private office, while the second floor suite enjoys seasonal bay views. The centerpiece of the home is a locally handcrafted kitchen featuring custom cabinetry extending to the 10 foot ceiling, a 48 inch professional style gas range beneath a distinctive arched hood, dual dishwashers, a smart combination wall oven, farmhouse sink, pot filler, dual zone wine refrigeration, and extensive custom storage. Designed for both everyday living and entertaining, the kitchen brings together craftsmanship, functionality, and timeless design. Indoor and outdoor spaces connect seamlessly through a beautifully appointed three season room featuring custom cabinetry, a television hookup, and an electric fireplace. Beyond, landscaped grounds surround a 16' × 36' heated in ground pool, creating a private setting for summer gatherings and relaxation. A convenient poolside mudroom provides direct access to a full bathroom, shower, and changing area. The separate pool house enhances the entertaining experience with a wine bar, dual-zone wine refrigeration, and glass doors opening directly toward the pool. Additional spaces offer remarkable versatility, including a detached garage, approximately 770 square feet of second floor storage ideally suited for an art or creative space, and approximately 1,800 square feet of under-house storage and utility space. Equally impressive is the home's infrastructure: a high-efficiency five zone heat pump heating and cooling system, three independently controlled radiant heated bathroom zones, comprehensive spray foam insulation, a hybrid heat pump water heater, three stage whole house water filtration, controlled under-house dehumidification, energy-efficient pool heating, smart pool controls and lighting, Ring security, an I/A septic system, and 300 amp electrical service. Bay Haven offers a distinctive combination of privacy, quality construction, and relaxed coastal living. With the private community beach just three houses away, the waters of the Peconic Bay become a natural extension of everyday life. Seasonal second floor bay views, thoughtfully designed indoor and outdoor entertaining spaces, and convenient access to Southold's shops, restaurants, wineries, and local attractions complete an exceptional North Fork retreat designed to be enjoyed in every season.

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
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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.:
5,400
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

Turnkey new construction completed in October 2026, this bespoke residence in Southold’s coveted Wildberry Fields masterfully pairs timeless coastal architecture with serene North Fork country living. Spanning over 5,400 square feet across three finished levels, the home offers 4 bedrooms, 4.5 baths, and a generous bonus room/office above the attached 3-car garage. Clad in natural Alaskan cedar siding with Andersen 400 Series windows, the exterior invites effortless outdoor living with a sweeping wraparound front porch, a natural gas heated 18' x 36' saltwater pool, and an outdoor shower. Inside, wide-plank natural white oak floors unify sun-drenched living spaces anchored by a gas fireplace and a chef’s kitchen appointed with luxury appliances and quartz countertops. Dual first and second-floor primary suites, custom glass shower enclosures throughout, and expansive walk-in closets in every bedroom ensure refined comfort. The full finished lower level elevates everyday wellness and entertaining with 9.5-foot ceilings, a private outside entrance, a full bath, a built-in wine fridge, and oversized double glass doors opening into a private gym and custom cedar sauna. Engineered for modern convenience, the residence integrates a hardwired Ring security camera system, 5-zone Sonos audio, hardwired eero mesh Wi-Fi, Lutron smart lighting, and Wi-Fi-controlled pool and irrigation systems. Complete with exclusive Southold Park District rights granting access to private beaches, kayak launches, and Founders Landing, this exceptional property sits just minutes from Long Island Sound beaches, Sound View Dunes, acclaimed vineyards, farm stands, and Southold 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
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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
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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.

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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

    66
    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