Bedrooms: 4, Bathrooms: 3, Half baths: 1, Lot size: 1.8 acres (0.73 ha) , MLS#: 3563000

Southold, Paradise Point Bayfront. Private peninsula in Paradise Point Community. Water on 3 sides with sweeping, open views across Southold Bay to Shelter Island and beyond. This unique waterfront setting includes 994 feet of shoreline and a deep-water dock in a protected boat basin. Approach this 5,100 sq. ft. home from the circular drive. Beautiful plantings frame the entry. Step into the grand entry foyer of this 2 story, 4 bedroom, 3.5 bath Nantucket style residence, with views through the foyer and house onto the open bay. A dramatic and exquisite first impression. High ceilings, huge gracious rooms. An open first floor design, living room with wood burning fireplace. Expansive windows, glass doors and transoms allow flow to the large outside wrap around waterside porch. Incredible light, and extraordinary sunset views. Oak floors throughout. First floor sitting room with gas fireplace and an office/den alcove. Huge chef's kitchen, with stainless appliances and granite counters, overlooking the bay and pool. Space for casual dining in kitchen, and a formal dining room overlooking the boat basin. Laundry room, one bayside en-suite primary bedroom, and an additional half bath complete the first floor. Second floor primary en-suite bedroom and sitting room with magnificent views over the pool and open bay. 2 additional large bedrooms with water views and additional full bath. The open second floor landing boasts sweeping water views. Elevator accessed by 3 floors, generator, spacious walkout basement waiting for your imagination with endless possibilities. Waterside heated pool and 2 car garage. 1.8 acres. Specimen plantings. Beautiful shoreline landscaping. If you are looking for an exceptional home and property, this is it....

Bedrooms: 5, Bathrooms: 5, Half baths: 4, Lot size: 1.9 acres (0.77 ha) , MLS#: 3544128

Luxurious Coastal Retreat in Southold's Prestigious Deer Run Nestled on a private, nearly 2-acre lot within the exclusive Deer Run community, this remarkable 5-bedroom, 9-bathroom cedar shake home epitomizes coastal luxury and refined living. Spanning an impressive 6,000 square feet and surrounded by 37 acres of preserved land, this home is a haven of grandeur and comfort. Its thoughtful design features transom windows, coffered ceilings, paneled walls, and crown moldings. An open floor plan includes a gourmet kitchen with Carrera marble island, top-of-the-line appliances, and white cabinets with glass accents. The living room is anchored by a fieldstone fireplace with a driftwood mantle. French doors lead to a radiant-heated screened porch with its own wood-burning fireplace, ideal for seamless indoor-outdoor entertaining. The main floor master suite offers expansive walk-in closets and a marble bathroom. Upstairs, find four en-suite bedrooms, a bunk room, and a den. The lower level boasts a theater and a glass-enclosed gym. This property efficiently combines high-performance blow-in insulation with a dual water system, utilizing well water for a comprehensive 16-zone irrigation and municipal water for safe, in-home use. Outdoors, enjoy a 20x40 heated saltwater gunite pool with a waterfall jacuzzi, surrounded by a 1,500 square foot bluestone patio, an outdoor fire pit, and a pergola. This property also features a lush lawn, a basketball/pickleball court, and proximity to Peconic Bay, beaches, and local wineries. Experience unparalleled luxury in this exquisite Southold home....

Bedrooms: 4, Bathrooms: 5, Half baths: 1, Lot size: 0.7 acres (0.28 ha) , MLS#: 3555160

Welcome to your bespoke farmhouse retreat nestled in the serene beauty of the North Fork of Long Island. This custom-crafted home offers an unparalleled blend of luxury, comfort, and tranquility, enveloped by a meticulously designed landscape that creates a secluded oasis. Approaching the property, you're greeted by a custom landscape package featuring Belgian block pathways, crushed pea gravel, and towering 20-ft established trees and shrubs, evoking a sense of timeless elegance and privacy. Exterior lighting gracefully illuminates the walkways and architectural details, while wall wash cove lighting on the masonry-covered porch casts a gentle glow over the pool area, inviting you to unwind in its serene ambiance. Step into the enclosed backyard to discover a sanctuary of relaxation and entertainment, complete with elegant blue stone paths, a spacious entertaining patio, and an in-pool lounge deck with dual umbrella stands. A mesmerizing masonry water feature adds a touch of sophistication, while the in-pool beverage bench ensures refreshments are always close at hand. The rear of the house has been thoughtfully designed with architectural elements that tell a captivating story from every angle, creating a visual masterpiece that complements the surrounding landscape. Approach the double entry wood doors to find an oversized masonry sitting porch, perfect for indulging in weekend morning coffee conversations or simply soaking in the tranquil surroundings. Inside, the home boasts luxurious amenities at every turn. Off the foyer, a large den with custom cabinetry provides a peaceful retreat, while the two-story living room serves as the heart of the home, anchored by a granite fireplace and bathed in natural light. The professional kitchen is a chef's dream, featuring a Kohler pre-rinse faucet, a 45 inch workstation sink with sound deadening technology, and custom lighting that highlights the island and cabinet details. The open floor plan seamlessly flows into the dining space, offering stunning views of the yard, pool, and covered porch. A mudroom with slate plank floors and shoe lockers in the custom designed cabinetry leads to the laundry room, complete with a deep stainless steel sink, slide out laundry baskets for each of the four bedrooms and a pet washing station. The main floor suite boasts an elegant walk-in closet and a luxury bath fitted with a Toto washlet toilet, a freestanding soaking tub, and a roll-in shower. Upstairs, each bedroom offers ceiling details and attached bathrooms, while the custom open staircase leads to a finished basement featuring a movie theater, a home office space, and a beverage center. The walk-out basement opens to a covered cocktail patio and bluestone path leading to the pool deck. Located in a waterfront community with direct access to Goose Creek sandy beach, this home offers the ultimate retreat for those seeking luxury and tranquility on the North Fork. Don't miss your chance to experience the epitome of North Fork living....

Bedrooms: 5, Bathrooms: 4, Half baths: 1, Lot size: 13.08 acres (5.29 ha) , MLS#: 3471355

Down a graceful country road, on the North Fork of Long Island your dream home awaits. Sprawling over 13 acres with 354 feet of waterfront on Arshamomaque Pond leading out to the Peconic Bay. There is a 20 x 40 gunite pool, a barn with horse stalls should you choose or for use as an art barn! Plenty of room for tennis. Inside this magical home is an exceptional chef's kitchen with a Wolf range, butler's pantry and plenty of entertaining space - including a generous fireplace and a 3 season porch. There are two wings - one which has 3 ensuite bedrooms, including the primary suite. The other has a full kitchen, two bedrooms and 1 bathroom. This home also features a wine cellar and walkout basement. A property of this caliber does not come to the market often on the North Fork of Long Island. Let's make your dreams come true - this could be you!!...

Bedrooms: 5, Bathrooms: 4, Half baths: 1, Lot size: 0.85 acres (0.34 ha) , MLS#: 3538082

Beautiful custom home located in the hamlet of Southold captures amazing views of the LI Sound. Architectural details include an open floor plan, floating staircase, private roof-top, mahogany decks with horizontal cable railings, and all custom European windows and doors. An expansive luxury kitchen, a chic water-view lounge, and a first-floor ensuite bedroom provide a sophisticated North Fork retreat. The exterior is board and baton mixed with cedar. The pool is 20 x 40 with room for a pool house or cabana. The full basement provides an additional 1500 sq ft that can be finished. Southold Town Beach is less than 0.5 miles, approximately 10 min walk. Close to all that the East End has to offer. Professional photos will be coming soon....

Bedrooms: 3, Bathrooms: 4, Lot size: 0.6 acres (0.24 ha) , MLS#: 3527638

Builders own Romantic,Beauty with the look of a Landmark.Vintage home. Park like setting, Magnificent Sunsets from your 100 foot porch facing Goose Creek and Goose Bay. WaterViews of the Bay and Creek.Walk to the beach.across the street.Master on Main level with Ensuite Separate Entrance from porch to Heated pool. Soaring Cathedral ceilings in Living Room.Stairways to upper level flanking your oversize Black Granite Fireplace with White Mantle...Second floor balconies. inground heated Pool with manicured Gardens. Privet hedges and sweeping lawn . Basement walk out to the Fenced heated Pool.Garage oversized for your sportscar. Nature abounds..All types of Natural beauty and Wildlife. Stargazing in a panaramic view of the nightscape. Just a Wonderful Classic home. Year round or vacation.Too many other amenities to list.Mooring allowed on Goose Bay.....

Bedrooms: 3, Bathrooms: 3, Lot size: 1.5 acres (0.61 ha) , MLS#: 3556367

This quintessential vintage farmhouse is the epitome of old-world charm meets modern sophistication! Sited on 1.5 acres of park-like property and lovingly renovated with thoughtful additions including a heated saltwater gunite pool, electric pool cover, pool house with an outdoor fireplace, outdoor kitchen with a Gaucho grill and sink, a separate office studio, 3 bedrooms and 3 bathrooms. Plenty of room for expansion and incredible lush landscape designed with each season in mind and tons of privacy. Southold Park District beach rights, A quarter mile to Horton's Lighthouse beach, 1 mile to McCabe's beach and a short stroll to downtown Southold! This is your sunshine on a cloudy day!...