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$3,675,000
5 Beds ⋅ 6 Baths ⋅ 1031351 MLS
Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will consider owner financing. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany front door and decking, solid wood closet systems, bespoke pantry shelving, and a handmade stone mantle and hearth. This lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with Bertazzoni and Bosch appliances, extra large island and breakfast nook, formal dining room with Butler's pantry, first floor junior primary ensuite, and library. Upstairs is a spacious primary ensuite with two walk in closets, 3 more bedrooms, 2 full baths, a laundry room, and a bonus family room. The walk out basement is ready for you to finish as you wish, with room for home theatre, wine cellar, gym, additional bedrooms or other uses. Outside enjoy multiple covered porches and your lovely pool, all surrounded by the peace and quiet of this serene and private setting. This is truly a Hampton-style masterpiece on the North Fork.

150 Deer Run, Southold
$1,475,000
4 Beds ⋅ 4 Baths ⋅ 1024798 MLS
Coveted Maple Lane setting in the heart of Southold Village with easy access to all Southold Village amenities and LIRR ~ This recently transformed shingled Craftsman Style residence offers 4 bedrooms, 3.5 baths, timeless architectural character, exceptional private outdoor living, and a truly special North Fork lifestyle. Beautifully landscaped with specimen plantings, the property is designed for relaxed year-round or seasonal enjoyment. Outdoor amenities include a new heated 16 x 32 inground saltwater pool, hot tub, outdoor shower, and gracious covered porches at both the front and rear of the home. Classic Craftsman details enhance the curb appeal, including Arts & Crafts-style columns on river rock bases, double-dipped cedar shingles, a custom garage door, and a signature Craftsman front door. Inside, the main level offers an inviting open layout with wood floors throughout. The spacious living room features a wood-burning fireplace, while the eat-in kitchen, dining room, and window-filled den provide warm, functional spaces for everyday living and entertaining. Both the kitchen and den open directly to the rear covered porches, creating an easy flow for indoor-outdoor living. The first floor also includes two bedrooms, one full bath, one half bath, and a mudroom/laundry room. Distinctive interior details include oak trim around the windows and doors, as well as a beautiful staircase with a one-of-a-kind custom newel post. Upstairs, the primary suite serves as a private retreat with a generous sitting and office area, two-sided gas fireplace, sauna, and a fabulous tiled bath with spacious walk-in shower. A newly added junior primary suite, completed in 2026, adds comfort, privacy, and flexibility for guests or extended stays. Just a few doors from the edge of charming Southold Village, the Southold Historical Society and close to Founders Landing Bay Beach and Park, this exceptional home offers easy access to the marina, restaurants, shops, wineries and NYC transportation. This is a rare Southold Village offering with remarkable character, amenities, and the superior North Fork location you have been looking for.

425 Maple Lane, Southold
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 1016785 MLS
Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three bath Center Hall Colonial combines timeless design, thoughtful updates, and an exceptional location near Southold's most sought-after waterfront destinations. A welcoming portico leads into a home with wood floors throughout. The living room features a wood burning fireplace, while the formal dining room overlooks the rear yard through a bay window. A butler's passthrough connects to the kitchen, complete with stone countertops, a massive center island, stainless steel appliances, and a stainless-steel range hood. The first floor includes a full bath and adjacent family room that could easily become a first-floor primary suite or private guest space. Upstairs, the primary suite offers a private bath and second floor laundry. Three additional bedrooms share a hall bath. Additional features include an attached two car garage with mudroom access, a full basement with outside entrance, and recently updated roof, heating system, and central air. Life on Bayview Peninsula is all about the water. Pine Neck Boat Ramp, Goose Creek Beach, and Cedar Beach are all nearby. Enjoy award winning wineries, farm stands, and restaurants throughout the North Fork, with the Orient Point Ferry just a short drive away for easy access to New England. Whether you are looking for a year-round residence or a North Fork getaway, 1075 Ships Drive offers an outstanding opportunity to enjoy coastal living in one of Southold's most desirable neighborhoods.

1075 Ships Drive, Southold
$985,000
5 Beds ⋅ 2 Baths ⋅ 1017107 MLS
Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

230 Booth Road, Southold
$2,899,000
4 Beds ⋅ 3 Baths ⋅ 1005049 MLS
Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed living space, plus a finished 1,166-square-foot lower level. Sun-drenched interiors showcase wide-plank wire-brushed white oak flooring, custom millwork and cabinetry, Restoration Hardware lighting, recessed lighting, and Sonos sound throughout both the home and outdoor entertaining spaces. Every room in the home captures stunning water views, creating a seamless connection to the surrounding waterfront setting. The spectacular gourmet kitchen is designed for both everyday living and entertaining, featuring a Sub-Zero refrigerator, Wolf gas cooktop and double ovens, quartz and Caesarstone countertops, oversized center island, Bosch and Fisher & Paykel dishwashers, and a stunning butler’s pantry accented with Cle Tile backsplash. The living room is equally impressive with a custom wood-burning fireplace, built-in cabinetry, and an elegant wet bar complete with Sub-Zero beverage refrigerator, wine refrigerator, ice machine, and designer finishes throughout. The fully finished lower level offers exceptional additional living space with a kitchenette, double egress windows, and Fujitsu mini-split system—ideal for guests, recreation, or extended entertaining. Upstairs, four spacious water-view bedrooms include a luxurious primary suite featuring cathedral planked ceilings, a handmade vintage wood mantel, private deck access, walk-in closet, and spa-inspired bath. Elegant lime-washed walls add warmth and character to every bathroom. Outdoor living is nothing short of extraordinary with expansive first and second floor decking, a rooftop deck with panoramic water views, premium IPE Brazilian hardwood decking, covered outdoor entertaining area with built-in heaters and ceiling fans, outdoor shower, wired railings, cedar shake siding, Andersen 400 Series windows and doors, and beautifully landscaped grounds surrounded by mature privacy hedges. A true boater’s paradise, the property accommodates a large boat and offers direct access to Peconic Bay, Shinnecock Bay, and nearby sandbars for boating, kayaking, paddleboarding, clamming, and enjoying the ultimate North Fork waterfront lifestyle.

405 Williamsburgh Drive, Southold
$1,799,000
992553 MLS
Calling all builders and investors! Beautiful 8.65 acres of cleared, leveled land in Southold Town. This parcel is zoned R-80, (2 Acre zoning) and has 250' of frontage on Sound Avenue (North Road) and access from adjacent Leon Road. Sellers will not consider offers "subject to" any permits or approvals.

420 Leon Road, Southold
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 973460 MLS
Build your dream home on this exceptional waterfront lot offering unobstructed, forever views and breathtaking sunsets over the pristine waters of the sound. With plans already in place, you can break ground on your custom home without delay. Nestled in one of the most sought-after locations on the North Fork, this property offers the perfect blend of privacy and convenience—just minutes from local vineyards, farm stands, dining, beaches, and marinas. Set in a serene and scenic location, this property offers direct access to miles of beach for peaceful walks along the shore, and is just moments from the tranquil Goldsmith Inlet, perfect for kayaking, paddleboarding, or simply enjoying nature at its finest. Whether you’re looking for a peaceful weekend retreat or a full-time coastal haven, this rare opportunity delivers it all. A one-of-a-kind acre-and-a-half property situated on a 40-foot-high bluff above the Long Island Sound, with clear views of the Connecticut shoreline and gorgeous northwest sunsets! Hidden off North Road (County Road 48) in Peconic, access is via a mile-long private road. This is the final piece of a six-lot subdivision. Delivering a powerful feeling of privacy, in a totally natural setting! Truly a MUST SEE for the individual searching for solitude, privacy, and relaxation! Full Building Permits Approved. Price listed is for vacant lot only including permits to build, which can be modified. Come see this extraordinary location and design your dream home!

4760 Blue Horizon Bluffs, Peconic
$1,550,000
4 Beds ⋅ 4 Baths ⋅ 953464 MLS
The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the community. New Construction Package – $1,400,000 In partnership with respected local builder, this option delivers a thoughtfully designed 2,215 sq ft home that blends timeless details with coastal luxury. Plans include 4 bedrooms, 3 full baths with 9 foot ceilings throughout, creating an airy and elegant space. The first floor of the home features an open-concept kitchen, living, and dining perfect for hosting and easy flow of day-to-day living. Walk up the front porch and enter the front door to a spacious living room accompanied by a warm fireplace for those cooler nights. As you continue you’ll pass through the dining area with floor-to-ceiling doors that look out over the backyard. Enter the brand-new chef’s kitchen featuring a large kitchen island, stainless steel appliances, and beautiful walk-in pantry! The main floor also features a full bath and bedroom, perfect for guests or single-floor living. Upstairs, you’ll find 3 additional bedrooms — 2 that share the full bath in the hall, and a primary bedroom with walk-in-closet and en suite bathroom. Laundry is a breeze with a washer-dryer on the second floor! Outdoors, appreciate the intentional details designed with North Fork living in mind. The detached garage features a beautifully integrated pool cabana, accessed by a man door. Designed to suit outdoor entertaining and living, the cabana comes equipped with an island bar top, sink, half bath, and space for a grill — the perfect spot to entertain or wind down after a day at the beach with family or guests. At 500 Summer Lane, you’re less than 1.5 miles from some of Southold’s best gems like Croteaux Vineyard, Goose Creek Beach, Sophie’s Restaurant, and local farm/flower stands. A little further you’ll find the charming Southold Town, Cedar Beach, endless vineyards, Greenport Harbor Brewery, and so much more. The North Fork is Calling Your Name!

500 Summer Lane, Southold
$6,850,000
5 Beds ⋅ 5 Baths ⋅ 946886 MLS
Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum structural integrity, energy efficiency and elevated finishes throughout. The sleek open-concept design encompasses approximately 4,500 square feet of living space. The light-filled residence showcases curated architectural features, ranging from floor-to-ceiling glass, floating staircases, bluestone and covered patio, water-view balcony, and a walk-out lower terrace. The Modern custom kitchen is adorned with ceiling-high cabinetry, Thermador appliances, marble countertops and porcelain inlay backsplash. The adjoining great room is anchored by a stunning gas fireplace surrounded by textured porcelain and this main level also includes an office, dining room and junior en-suite offering private access to the water and soon to be built saline heated pool. An upper level primary en-suite includes a private balcony and three additional spacious bedrooms, luxury baths, laundry and unfinished bonus space. The lower level offers 2,000 square feet for new owners to reimagine and personalize. The offering is complete with Founders Landing Beach, wineries, farm to table dining and a vibrant North Fork atmosphere.

1750 Hobart Road, Southold
$2,399,000
3 Beds ⋅ 2 Baths ⋅ 943087 MLS
Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporary home offers open water views, beautiful sunrises and sunsets, and a seamless indoor–outdoor flow. The light-filled main level features a newly built modern kitchen that opens directly to the outdoor entertaining area, along with a waterside first-floor primary suite. Large windows invite the views in, creating a relaxed, airy atmosphere throughout the home. Outside, the property lives like a private shoreline retreat. Enjoy the new heated saltwater pool with automatic cover, an enclosed outdoor shower, and generous patio space perfect for lounging or hosting. The private dock provides more than just waterfront enjoyment—there’s direct boating access to Southold Bay and Peconic Bay, with easy routes to Greenport, Shelter Island, and even Sag Harbor for dining, marinas, and day trips. A turnkey waterfront residence that blends comfort, modern updates, spectacular views and the best of coastal living!!!

470 Goose Creek Lane, Southold
$799,000
817145 MLS
Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life; You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom Conventional Septic System, (I/A NOT REQD.) Making It Ready For Your Grand Vision. Whether You're Looking To Build A Sprawling Family Estate, A Charming Vineyard Retreat, Or Anything In Between, The Possibilities Are Endless. Truly "Shovel Ready" Embrace The Tranquility Of Country Living With All The Benefits Of Being Near The Heart Of The North Fork’s Sought-After Attractions. Don’t Miss This Rare Opportunity To Create Your Own Slice Of Paradise!

1350 Hortons Lane, Southold

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.