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470 Windy Point Lane, Southold
$1,350,000
3 Beds ⋅ 2 Baths ⋅ 1062583 MLS
Waterfront Property Southold, NY! MINT, Turnkey Contemporary w 3 bedrooms, 2 full bathrooms, on 3/4 Canal-front acres w 91ft on Cory Creek.

470 Windy Point Lane, Southold
1635 Ships Drive, Southold
$869,000
3 Beds ⋅ 2 Baths ⋅ 1065134 MLS
Discover comfortable one-level living in the heart of the North Fork. Located at 1635 Ships Drive in the desirable town of Southold, NY, this ranch-style home offers an efficient and functional floor plan. The main level features 3 bedrooms and 2 bathrooms, providing a well-proportioned layout. The property is designed for outdoor enjoyment, highlighted by a private in-ground swimming pool. This home also boasts a full, unfinished basement complete with an egress window and door. Situated a short distance from the pristine shores of Goose Creek Beach, this property offers convenient access to coastal recreation and the natural beauty that Southold is known for. This is a rare opportunity to own a versatile home in a prime Southold location. Contact today to schedule your private tour and see the potential of this well-situated property.

1635 Ships Drive, Southold
205 Grange Road, Southold
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 1063190 MLS
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

205 Grange Road, Southold
650 Grove Drive, Southold
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 1044427 MLS
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.

650 Grove Drive, Southold
275 Main Bayview Road, Southold
$849,000
3 Beds ⋅ 2 Baths ⋅ 1059141 MLS
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!

275 Main Bayview Road, Southold
2380 Laurel Avenue, Southold
$850,000
3 Beds ⋅ 3 Baths ⋅ 1060305 MLS
Nestled in the highly sought-after Yennecott neighborhood of Southold, this ranch offers the perfect blend of comfort, privacy, and North Fork living. Featuring 3 bedrooms and 2.5 baths, the home is surrounded by spacious front and rear yards with mature landscaping, a welcoming deck, and a cozy fire pit area ideal for outdoor entertaining and relaxation. The expansive backyard offers potential for a pool. Conveniently located near Southold Village, local shops, restaurants, vineyards, farm stands, and beautiful North Fork beaches. Enjoy the best of North Fork living in this desirable Southold location.

2380 Laurel Avenue, Southold
430 Grove Road, Southold
$699,000
3 Beds ⋅ 1 Baths ⋅ 1060683 MLS
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.

430 Grove Road, Southold
2220 Akerly Pond Lane, Southold
$999,000
5 Beds ⋅ 2 Baths ⋅ 1054880 MLS
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.

2220 Akerly Pond Lane, Southold
2025 Little Peconic Bay Lane, Southold
$1,695,000
3 Beds ⋅ 2 Baths ⋅ 1061179 MLS
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.

2025 Little Peconic Bay Lane, Southold
965 Smith Road, Peconic
$675,000
1059204 MLS
A rare opportunity to own one of the last remaining vacant parcels in the highly desirable Indian Neck Park Association. This .32-acre lot offers the chance to create your own vision in a sought-after beach community, just a few houses down from the private association bay beach. Set within an established neighborhood surrounded by beautiful homes, this property provides a unique opportunity to build a new home tailored to your lifestyle and take advantage of the relaxed North Fork setting. Not in a flood zone, and a flat level lot. Enjoy private beach rights to the pristine white sandy Peconic Bay, all while being part of a well-established community. Opportunities to purchase vacant land in this neighborhood are exceptionally limited—this may be your chance to secure one of the last available lots and create something of your own!

965 Smith Road, Peconic
1455 Cedar Point Drive E, Southold
$2,150,000
3 Beds ⋅ 2 Baths ⋅ 1058940 MLS
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.

1455 Cedar Point Drive E, Southold
Main Bayview Main Bayview, Southold
$999,000
4 Beds ⋅ 4 Baths ⋅ 1059170 MLS
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.

Main Bayview Main Bayview, Southold
1045 Fanning Road, New Suffolk
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 1056663 MLS
Just a few hundred feet from Shagwong Marina and less than half a mile from New Suffolk Beach and Legends and Minnow restaurants, this renovated and expanded ranch offers turnkey living in the heart of New Suffolk. A 2021 addition added a large garage and second-floor living room with a full bath, providing valuable additional space and flexibility. Comfortable and easy to maintain as it stands, the property also offers room for a pool and future expansion. An appealing opportunity to enjoy one of the North Fork’s most desirable hamlets, with the waterfront, beach, dining, and boating all close at hand.

1045 Fanning Road, New Suffolk
29400 County Road 48, Peconic
$795,000
3 Beds ⋅ 2 Baths ⋅ 1053365 MLS
Just add a farm stand to this prime high-visibility Peconic location! Set on 1.22 acres, this classic three-bedroom, one-and-a-half-bath home has the space and character that makes country living so appealing. Gorgeous vineyard views, great flexibility with a 3 bay garage perfect for a workshop, greenhouse, or storing vehicles. Owned solar panels also add to the ease of this property. A true North Fork original farmhouse with plenty of room to create memories and enjoy the North Fork country life. Could be you!

29400 County Road 48, Peconic
9680 N Bayview Road, Southold
$2,999,000
4 Beds ⋅ 6 Baths ⋅ 1052436 MLS
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.

9680 N Bayview Road, Southold
1430 Bay Haven Lane, Southold
$2,548,000
4 Beds ⋅ 4 Baths ⋅ 1054890 MLS
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.

1430 Bay Haven Lane, Southold
3525 Paradise Point Road, Southold
$4,299,000
4 Beds ⋅ 3 Baths ⋅ 1053616 MLS
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.

3525 Paradise Point Road, Southold
61341 Route 25, Southold
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 1050202 MLS
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.

61341 Route 25, Southold
3995 Wells Avenue, Southold
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 1051232 MLS
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.

3995 Wells Avenue, Southold
705 Wildberry Lane, Southold
$824,000
1050238 MLS
A rare opportunity to create a custom North Fork residence in desirable Wildberry Fields. This .61-acre level, wooded parcel is situated on a private 9-lot country road and backed by picturesque vineyards, offering beautiful vineyard views and a peaceful, private setting. Protective covenants help preserve the character and value of the community, requiring residences of more than 3,000 sq. ft. with natural exterior materials. Underground utilities are already in place. Located within the desirable Southold Park District, offering residents access to Founders Landing, Emerson Park and other Park District amenities, with opportunities for beach access, swimming, kayaking and seasonal boat and kayak slip lotteries. Just minutes from farm stands, acclaimed restaurants, wineries and Greenport Village. An exceptional opportunity for a luxury builder or buyer looking to create a custom North Fork home. Building options are available through North Fork Building Company, if desired. Bring your vision to life in one of Southold’s most beautiful settings.

705 Wildberry Lane, Southold
1200 Indian Neck Lane, Peconic
$2,950,000
5 Beds ⋅ 5 Baths ⋅ 1048014 MLS
Known as The Old King Farmhouse and Owl Hollow, this historic 1.05± acre compound is one of Peconic’s most distinctive properties, pairing a beautifully preserved c.1860 Italianate Victorian residence with a remarkably purpose-built artist’s studio in the heart of the North Fork. Rich in history and thoughtfully stewarded over time, the approximately 3,260-square-foot residence offers four bedrooms and two-and-a-half baths while preserving many of its original architectural details, including period fireplaces, wide-plank wood floors, oversized windows, and graciously proportioned rooms filled with natural light. The interiors strike a rare balance between historic character and understated elegance, allowing the home’s craftsmanship and surrounding landscape to take center stage. Across the grounds, Owl Hollow serves as an extraordinary extension of the property. The approximately 1,200-square-foot studio is defined by soaring timber trusses, dramatic north-facing windows, a wood-burning fireplace, and its own Certificate of Occupancy, offering exceptional flexibility as an artist’s studio, creative workspace, guest retreat, entertaining pavilion, or wellness space. Set among mature specimen trees, clipped hedges, perennial gardens, and a fenced vegetable garden, the grounds unfold as a series of outdoor rooms centered around a heated 18’ x 36’ saltwater pool. A rare pre-existing, non-conforming wattle-and-daub stable offers additional storage or future possibilities, while separate driveways, updated utilities, new septic systems, rental permits, and separate Certificates of Occupancy further enhance the property’s versatility. Both the residence and studio have an established history as luxury rentals. Located in the bucolic hamlet of Peconic, moments from renowned vineyards, farm stands, beaches, and marinas, The Old King Farmhouse and Owl Hollow represent an increasingly rare opportunity to own a historic North Fork compound where architecture, landscape, and creative living exist in perfect harmony.

1200 Indian Neck Lane, Peconic
9305 Soundview Avenue, Southold
$2,950,000
4 Beds ⋅ 4 Baths ⋅ 963793 MLS
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.

9305 Soundview Avenue, Southold
2560 Hyatt Road, Southold
$629,000
1041384 MLS
Ideally Located Vacant Land. A Rare Opportunity to Create Your Own North Fork Retreat or Year-Round Home on Desirable Hyatt Road, a Quiet Setting Just Off Soundview Avenue in Southold. This Ideally Located Vacant Parcel is Just a Short Distance from Memorable McCabe’s Town Beach. The Lot is Reported to Include Coveted Deeded Rights to a Private Long Island Sound Beach. Enjoy the Tranquility of a Peaceful North Fork Setting While Remaining Just a Short Drive from the Vibrant Centers of Southold and Greenport, with Their Celebrated Restaurants, Shops, Wineries, Marinas, and Coastal Attractions. An Exceptional Opportunity to Build Your Dream Getaway or Year-Round Home and Embrace the Best of the North Fork Lifestyle—Beautiful Beaches, Picturesque Surroundings, and Relaxed Coastal Living. No Survey Available. See Photo for Approximate Lot Dimensions. Sellers Will Not Consider Offers with Contingencies. Road is a Private Road. Do Not Visit or Walk the Property Unattended. Buyer is Advised to Independently Verify the Accuracy of All Information

2560 Hyatt Road, Southold
2600 Boisseau Avenue, Southold
$549,999
3 Beds ⋅ 1 Baths ⋅ 1043112 MLS
Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional and inviting layout featuring a comfortable living area, three nicely sized bedrooms, a full bathroom, dining room and an eat-in kitchen. The full basement provides an abundance of additional space for storage, utilities, a workshop, or the potential for future finishing. A detached garage adds even more storage and convenience. Outside, the generous .39-acre property offers plenty of room to relax, entertain, garden, or create your ideal outdoor retreat. Conveniently located near Southold's charming village, local shops and restaurants, beaches, wineries, farm stands, and all that the North Fork has to offer. Whether you're looking for a year-round residence or a weekend getaway, 2600 Boisseau Avenue offers a fantastic opportunity to make Southold home! With taxes less than $5k, what more can you ask for?

2600 Boisseau Avenue, Southold
390 Wildberry Lane, Southold
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 1039113 MLS
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.

390 Wildberry Lane, Southold
225 Lakeside Drive S, Southold
$2,200,000
3 Beds ⋅ 3 Baths ⋅ 1038709 MLS
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.

225 Lakeside Drive S, Southold
1025 Seawood Drive, Southold
$1,277,000
4 Beds ⋅ 4 Baths ⋅ 1032396 MLS
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.

1025 Seawood Drive, Southold
49295 Route 25, Southold
$699,000
1035534 MLS
High-Visibility Commercial Land in Southold. Rare opportunity to acquire a highly visible vacant parcel along main road in Southold Town. Zoned "General Business", the property offers a wide range of potential uses and flexibility for an owner-user, investor, or contractor. Permitted uses include retail and wholesale businesses, convenience store, contractor-related uses, storage, and residential with accessory dwelling, among other possibilities subject to applicable Town approvals. With strong road exposure and versatile zoning, this property presents an excellent opportunity to establish a business, create a mixed-use concept, or hold for future investment in one of the North Fork’s most desirable communities. Bring your vision and explore the possibilities.

49295 Route 25, Southold
1135 Wildberry Lane, Southold
$2,795,000
5 Beds ⋅ 6 Baths ⋅ 1037213 MLS
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.

1135 Wildberry Lane, Southold
36595 County Rd 48, Peconic
$799,000
4 Beds ⋅ 3 Baths ⋅ 1034331 MLS
Discover an exceptional North Fork opportunity in the heart of Peconic. Set on approximately .92 acre and surrounded by picturesque farm fields, this spacious four-bedroom ranch offers privacy, comfort and the relaxed lifestyle that makes the North Fork so desirable. The home features an updated kitchen, generous living and dining areas, central air conditioning and a flexible single-level floor plan. The expansive property provides plenty of outdoor space for entertaining, gardening and enjoying the peaceful pastoral setting. Ideally located near Southold and convenient to North Fork beaches, vineyards, farm stands, restaurants and all the area has to offer. Whether enjoyed as a year-round residence, weekend retreat or investment opportunity, this property offers tremendous potential at an attractive price point. A wonderful opportunity to own in Peconic for under $800,000.

36595 County Rd 48, Peconic

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

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