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$2,995,000
4 Beds ⋅ 6 Baths ⋅ 906322 MLS
Southold Stunner- New Construction This one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven, Thermador wine fridge, twin Cove dishwashers, plus Scotsman ice maker for those "bring on summer" gatherings. Quartz counters and designer finishes keep it fresh and timeless. Head downstairs: a finished lower level with a private movie theater and plenty of space. Outside, it's pure Zen mode with a 20x40 custom heated saltwater Gunite pool, extended 24x48 porcelain patio for easy entertaining, and a fire pit zone ready for end-of-day stories under the stars. If "flawless, never lived in, fully loaded by the beach" is your thing, this delivers - all the luxury, none of the pretense. Could be you! * Additional Details Include: Laundry room on first floor, additional washer/dryer on second floor, Floors 3 quarter inch Red Oak 7 inch wide hardwood flooring, Custom Wellwood European Style Cabinets, Propane forced air, Red cedar shake 5/8, No HOA, Propane fireplace, 400 Amp Electric Service, Appliances - 48 inch Sub Zero Refrigerator/Freezer, 48 inch Wolf Gas Range, 30 inch Wolf Wall Oven, 30 inch Wolf Microwave Oven, Scottsman Ice Maker, 24 inch Cobe Dishwashers, 24 inch Thermador Built in Wine Fridge, Quartz Countertops, Patio Stone and Size 24 by 48 Porcelain Patio Pavers, Pool Specs - 20 by 40 Custom Gunite Pool, Propane Pool Heater, 3 -Lennox 14 seer systems, Merit series air handlers and condensers, 5 zones total, Aprilaire 2210 merv, 16 media filters, Honeywell T6 WiFi thermostats installed on all zones, Healthy climate ERV installed in attic connected to 2nd floor system for fresh air.

80 Deer Run, Southold
$4,900,000
896328 MLS
Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres, the property includes a 4.46-acre winery parcel with development rights intact and an additional 46.36 acres of vineyard with 34.5 acres under vine. The estate features approximately 19,500 square feet across three primary buildings, including a beautifully appointed tasting room with seating for more than sixty guests, cocktail capacity exceeding one hundred, and an expansive outdoor patio overlooking the vines. The winery itself houses a temperature-controlled production facility with fermentation cellar, bottling line, and laboratory, while the barrel and storage building provides over 8,000 square feet of climate-controlled space for aging and inventory. The setting is as breathtaking as it is functional, with panoramic vineyard views, manicured lawns, and a blend of rustic charm and refined elegance that makes the property a sought-after destination for wine enthusiasts, weddings, corporate events, and private celebrations. Outdoor features include a pergola-covered patio bar, gazebo, and multiple gathering spaces designed to enhance the guest experience. The sale includes the Osprey’s Dominion brand, extensive winemaking and agricultural equipment, and existing inventory, ensuring a seamless transition for a new owner. With a loyal customer base, a wine club of hundreds of members, and a certified sustainable harvest underway, the vineyard is positioned for continued success. This is a rare chance to acquire a turnkey winery in one of New York’s most vibrant wine regions. Whether you are an experienced vintner or an investor seeking a marquee North Fork asset, Osprey’s Dominion offers unmatched prestige, proven operations, and boundless potential.

44075 Route 25, Peconic
$2,875,000
4 Beds ⋅ 5 Baths ⋅ 893733 MLS
NEW WATERFRONT CONSTRUCTION Thoughtfully crafted and beautifully finished, this 4-bedroom, 5-bath custom waterfront home offers over 2,900 sq ft of elevated living space — a seamless blend of modern luxury and timeless coastal charm. Set in a peaceful, private location, it showcases stunning panoramic water views from nearly every room and effortless indoor-outdoor flow designed to embrace the natural surroundings and relaxed beach lifestyle. HIGHLIGHTS...4 spacious en suite bedrooms....5 bathrooms...2 light-filled living areas perfect for lounging or entertaining....Custom white oak cabinetry, vanities, and detailed millwork....White oak flooring throughout..... Chef’s kitchen....Sub-Zero refrigerator and wine fridge....Wolf stove....Sleek Dekton countertops....Expansive glass doors that open the kitchen to the outdoor living space with direct water views — perfect for hosting or unwinding by the shore....Second-floor outdoor lounge terrace overlooking the water....Separate garage with finished loft....Mahogany fencing....Professionally landscaped grounds. Located just minutes from the area’s best beaches, this brand-new waterfront home offers the ultimate combination of high-end design, natural beauty, and relaxed luxury living. The photos are virtually staged.

6370 Skunk Lane, Cutchogue
$2,799,000
8 Beds ⋅ 7 Baths ⋅ 859020 MLS
2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom estate, offering the rare opportunity to personalize your dream home to suit your lifestyle and taste. Whether your envisioning a peaceful year-round residence, a high-end vacation home or a lucrative investment property, this home offers it all. Your luxury escape awaits -custom build your forever home today! Photos shown are from an identical recently built house In Southold --- Easy To Preview.

1350 Hortons Lane, Southold
$1,499,000
827387 MLS
Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards, marinas, golfing, boutique shopping, galleries, and more. A once in a lifetime opportunity to build your dream estate - perfect for an all inclusive equestrian facility. All with the utmost privacy in this amazing piece of paradise. Potential for 2 acre subdivision.

11200 N Bayview Road, 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
$1,249,000
3 Beds ⋅ 2 Baths ⋅ L3590177 MLS
Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the 'tower' of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!

2055 Boisseau Avenue, 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.