Southold, NY Real Estate & Homes for Sale | Andrew Stype Realty, Inc.

Southold, NY 11952

$4,950,000

3 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3460.00:#

Single Family For Sale ML# 3484887

This Bay front estate is absolutely spectacular! Over 1.5 acres, 132 feet of sugar sand beach and endless, incredible views. An eat-in-kitchen that overlooks your pool, pool house and private beach with Viking appliances and full wine fridge, living room with a gas fireplace, den/flexible space and a laundry room. 3 BR, 3.5BA including a primary suite with a bayside balcony, fireplace, spa-like bathroom with radiant heated floors, double water closets, gym and walk-in closet. Outside you have a pool house with living space and half bath, 20 x 40 heated waterside pool, driving range & putting green, outdoor shower, beach and Bay access from your backyard, and a whole house generator. Steps from Strong’s Marina and near all the North Fork has to offer... This is a must see!

Presented By: Corcoran 631-765-1300

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

Orient, North Fork - Nantucket inspired waterfront estate with 130’ private beach. Featuring over 5, 000 sf of upscale living space, this home takes advantage of the hilltop setting & encompasses sweeping views over the LI Sound. Luxury is apparent: spacious covered porch entry leads to foyer, LR w/clerestory windows overlooking the water & vaulted ceilings, large dining room, immaculate kitchen w/breakfast area overlooks the lush landscape of this coastal retreat. Open plan family room w/gas fireplace leads to waterside terrace, primary floor owner’s suite w/fireplace, sunroom/sitting room & a home office w/private en suite bath (or 5th bedroom). Upstairs is found a large sitting room, billiard/family room, sewing/craft room, junior owner’s suite w/full bath, plus an additional 2 bedrooms w/’Jack & Jill’ bath. Immaculate and well-maintained, this ’estate’ also features a wine cellar, full house generator, outdoor shower & other quality details not to be missed. Room for a waterside pool. No flood insurance needed. North Fork living at its BEST!

36

Southold, NY 11957

$4,250,000

5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 5200.00:#

Single Family For Sale ML# 3559218

Orient, North Fork - Nantucket inspired waterfront estate with 130’ private beach. Featuring over 5, 000 sf of upscale living space, this home takes advantage of the hilltop setting & encompasses sweeping views over the LI Sound. Luxury is apparent: spacious covered porch entry leads to foyer, LR w/clerestory windows overlooking the water & vaulted ceilings, large dining room, immaculate kitchen w/breakfast area overlooks the lush landscape of this coastal retreat. Open plan family room w/gas fireplace leads to waterside terrace, primary floor owner’s suite w/fireplace, sunroom/sitting room & a home office w/private en suite bath (or 5th bedroom). Upstairs is found a large sitting room, billiard/family room, sewing/craft room, junior owner’s suite w/full bath, plus an additional 2 bedrooms w/’Jack & Jill’ bath. Immaculate and well-maintained, this ’estate’ also features a wine cellar, full house generator, outdoor shower & other quality details not to be missed. Room for a waterside pool. No flood insurance needed. North Fork living at its BEST!

Presented By: Town And Country Real Estate 631-298-0600

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

37

Southold, NY 11944

$3,799,999

4 Bedrooms 5 Full Baths 2 Half Baths Sq. Ft. 5220.00:#

Single Family For Sale NEW ML# 3590145

Stunning Resort-Style Home with Modern Smart Features on the North Fork Discover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by tranquil Islands End public golf course, the popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. This neighborhood beach/park offers paddleboard and kayak stations along the marina, this home is perfect for embracing the North Fork’s outdoor lifestyle. As a state-of-the-art smart home, the apps provide remote access for lighting, heating, and air conditioning, music indoors and outdoors, and televisions strategically placed on the second floor, in the main living areas, and in a private TV room in the basement. The expansive floor plan offers not one, but two luxurious owner’s suites, one on the main level and another on the second floor, complemented by two additional bedrooms with private bathrooms. With a sleek, modern aesthetic, the home is thoughtfully designed for indoor-outdoor living. Outside, an elegant pool with a waterfall and evening lighting package becomes the centerpiece of the outdoor experience, complete with an option for an outdoor kitchen. Stunning dining area, and a lounge with a fireplace-perfect for entertaining or relaxing in style. This property brings the quality of its design and build to the forefront across all three levels, offering a flawless blend of comfort, functionality, and contemporary elegance. Indulge in this rare opportunity to own a slice of resort-like paradise on the North Fork.

Presented By: Century 21 Albertson Realty 631-765-3800

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

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.

37

Southold, NY 11971

$3,799,999

4 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 6366.00:#

Single Family For Sale ML# 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.

Presented By: Century 21 Albertson Realty 631-765-3800

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

This property truly is a fantastic opportunity to have boutique winery or create a private estate that produces its own wine label. With its established vineyards, ample living spaces, and multiple structures, it offers a unique chance to step into the world of winemaking with a solid foundation. Whether you’re dreaming of producing your own wines or creating a serene estate surrounded by vineyards, this property is well-equipped to fulfill those ambitions. The North Fork, known for its fertile soil and favorable climate for vineyards. Nearly 13 acres of land, Large Barn - Potential for winery operations, storage, or event space, 5-Bedroom - Farmhouse Could serve as a primary residence, guest house, or rental, 4-Bedroom - House Additional living space, rental property, or guest accommodations, Multiple Outbuildings - Could be used for tasting room, equipment storage, workshops, or additional event space. Vineyard Details: Varietals Planted, Merlot-2 acres, Cabernet Franc- 2 acres, Pinot Noir-1 acre, Pinot Grin-1 acre, Sauvignon Blanc- 2 acres, Chardonnay-1 acre, Moscato- 1 acre, Irrigation, Drip irrigation system in place, ensuring efficient water use and healthy vines, Vine spacing: 4 feet, Row spacing: 8 feet. This setup is ideal for someone looking to enter the wine industry. The combination of established vineyards, residential and operational buildings, make it a unique opportunity.

31

Southold, NY 11948

$3,795,000

5 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2380.00:#

Single Family For Sale ML# 3575441

This property truly is a fantastic opportunity to have boutique winery or create a private estate that produces its own wine label. With its established vineyards, ample living spaces, and multiple structures, it offers a unique chance to step into the world of winemaking with a solid foundation. Whether you’re dreaming of producing your own wines or creating a serene estate surrounded by vineyards, this property is well-equipped to fulfill those ambitions. The North Fork, known for its fertile soil and favorable climate for vineyards. Nearly 13 acres of land, Large Barn - Potential for winery operations, storage, or event space, 5-Bedroom - Farmhouse Could serve as a primary residence, guest house, or rental, 4-Bedroom - House Additional living space, rental property, or guest accommodations, Multiple Outbuildings - Could be used for tasting room, equipment storage, workshops, or additional event space. Vineyard Details: Varietals Planted, Merlot-2 acres, Cabernet Franc- 2 acres, Pinot Noir-1 acre, Pinot Grin-1 acre, Sauvignon Blanc- 2 acres, Chardonnay-1 acre, Moscato- 1 acre, Irrigation, Drip irrigation system in place, ensuring efficient water use and healthy vines, Vine spacing: 4 feet, Row spacing: 8 feet. This setup is ideal for someone looking to enter the wine industry. The combination of established vineyards, residential and operational buildings, make it a unique opportunity.

Presented By: Corcoran 631-765-1300

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

Located on a bucolic road, in the heart of wine country. This homestead has 2 acres of vines and incredible vineyard views, a large agricultural barn and is surrounded by development rights sold land. A true chef’s kitchen, 4 spacious bedrooms, 4 bathrooms, 2 half baths, 2 laundry rooms, large living room, and a gorgeous sunroom leading out to a spectacular 40’x25’ heated gunite pool with a slate patio and built-in BBQ, full basement with a wine cellar, and to top it all off, an incredible 8 car garage with an apartment that has a fireplace. You will never want to leave!

30

Southold, NY 11935

$3,750,000

4 Bedrooms 4 Full Baths 2 Half Baths Sq. Ft. 5465.00:#

Single Family For Sale ML# 3539723

Located on a bucolic road, in the heart of wine country. This homestead has 2 acres of vines and incredible vineyard views, a large agricultural barn and is surrounded by development rights sold land. A true chef’s kitchen, 4 spacious bedrooms, 4 bathrooms, 2 half baths, 2 laundry rooms, large living room, and a gorgeous sunroom leading out to a spectacular 40’x25’ heated gunite pool with a slate patio and built-in BBQ, full basement with a wine cellar, and to top it all off, an incredible 8 car garage with an apartment that has a fireplace. You will never want to leave!

Presented By: Corcoran 631-765-1300

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

34

Southold, NY 12534

$3,700,000

4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 4505.00:#

Single Family For Sale ML# H6332031

Introducing The Mayor’s House. Built in 1836 by Oliver Wiswall, this stately Greek Revival home sits perched upon a hillside just outside of Hudson, NY in the coveted Mt Merino neighborhood with legendary views up the Hudson River. Pulling into the tree lined driveway and turning to the West, it’s easy to see why this area inspired a generation of artists known as the Hudson River School of Painters, the first native school of painting in the United States. The solid brick home retains the grand feeling of its original prominence with dentil moldings, Doric & Ionic order columns and three stories of living space plus a full basement. The main floor boast high ceilings, beautiful restored moldings, 2 front sitting rooms with fireplaces and a large dining room. A striking 1980’s addition is connected to the rear of the house with a 20+ foot vaulted ceiling and features a modern kitchen, pantry area with laundry, casual dining, sitting area, and access to a stone patio to enjoy the jaw dropping views. Upstairs find a primary ensuite, additional bed and ensuite bath. A third floor provides two additional bedrooms, a third full bath and den. Wood floors, big windows, tons of natural light and views throughout. A recent renovation includes all new heating and cooling, new roof, new septic tank, new kitchen and baths, new landscaping and driveway, new fixtures and finishes. The property is just under 40 acres of open lawn surrounding the home and woods in the back. Located under 2 miles to Warren Street in Hudson, convenient to the Rip Van Winkle Bridge, Amtrak Train, Olana and many of the Hudson Valley’s most popular destinations.

Presented By: Rouse + Co Real Estate LLC 845-750-0196

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

37

Southold, NY 11971

$3,600,000

5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4240.00:#

Single Family For Sale ML# 3582528

Down a graceful country road, on the North Fork of Long Island your dream retreat awaits. Spanning 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 is an exceptional chef’s kitchen with a Wolf range, butler’s pantry and plenty of space to entertain guests, or snuggle up by the stone fireplace and your 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 market often in Southold. Make your dreams come true - let this be you!

Presented By: Corcoran 631-765-1300

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

37

Southold, NY 11971

$3,456,000

4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2800.00:#

Single Family For Sale ML# 3559554

Experience summer camp bliss at 2480 & 2335 Minnehaha Blvd, Southold. This quintessential Nantucket-style cedar shake home offers expansive bayfront views, picturesque sandbars, and a pristine beachy landscape. Featuring charming Dutch doors, expansive decks, and an open floor plan, the gourmet kitchen flows into a cozy living room with a built-in wet bar, ideal for enjoying the serene waterfront vistas. A state-of-the-art golf simulator adds a playful touch, while riparian rights and a private dock accommodate a 66’ yacht. With multiple decks, a man-made beach on Corey Creek, and access to the Laughing Waters HOA beach, this property is a true waterfront retreat. Perfect for nature lovers and their pets, it’s a lifestyle where every day feels like summer camp.

Presented By: Daniel Gale Sothebys Intl Rlty 631-734-5439

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

Escape to paradise at this stunning waterfront home nestled on 8.9 acres of land along West Creek, providing access to the beautiful Peconic Bay. This remarkable property offers deeded beach rights just steps away and is situated in a serene setting that is simply irresistible. With seven generously-sized bedrooms, each featuring its own private ensuite bathroom, there is plenty of space for relaxation and privacy. The culinary kitchen is a chef’s dream, boasting a spacious layout that is perfect for entertaining. In addition, the property features a 32-foot indoor pool, complete with an exhilarating water park slide and a soothing hot tub, ensuring year-round entertainment. Whether you’re taking a break from remote work or winding down after a long day, the porch with fireplace is the perfect spot to gather with friends and family, while enjoying the breathtaking views. Speaking of views, nearly every room in this home offers captivating waterviews, allowing you to fully immerse yourself in the natural splendor that surrounds you. Outdoor activities abound, with opportunities for golfing and tennis at the nearby country club, as well as swimming, fishing, and kayaking right from your own backyard. This property also presents an excellent opportunity for a bed and breakfast, with its spacious layout creating an inviting retreat for guests. Immerse yourself in the tranquility and natural beauty of this incredible waterfront home, and experience a lifestyle that seamlessly combines luxury, comfort, and the wonders of nature. This home also features an expansive great room, multiple fireplaces, a theatre room, a gym and has potential for an inground pool and pickleball court. Truly a gem of the North Fork!

31

Southold, NY 11935

$3,399,000

7 Bedrooms 6 Full Baths 4 Half Baths

Single Family For Sale ML# 3549432

Escape to paradise at this stunning waterfront home nestled on 8.9 acres of land along West Creek, providing access to the beautiful Peconic Bay. This remarkable property offers deeded beach rights just steps away and is situated in a serene setting that is simply irresistible. With seven generously-sized bedrooms, each featuring its own private ensuite bathroom, there is plenty of space for relaxation and privacy. The culinary kitchen is a chef’s dream, boasting a spacious layout that is perfect for entertaining. In addition, the property features a 32-foot indoor pool, complete with an exhilarating water park slide and a soothing hot tub, ensuring year-round entertainment. Whether you’re taking a break from remote work or winding down after a long day, the porch with fireplace is the perfect spot to gather with friends and family, while enjoying the breathtaking views. Speaking of views, nearly every room in this home offers captivating waterviews, allowing you to fully immerse yourself in the natural splendor that surrounds you. Outdoor activities abound, with opportunities for golfing and tennis at the nearby country club, as well as swimming, fishing, and kayaking right from your own backyard. This property also presents an excellent opportunity for a bed and breakfast, with its spacious layout creating an inviting retreat for guests. Immerse yourself in the tranquility and natural beauty of this incredible waterfront home, and experience a lifestyle that seamlessly combines luxury, comfort, and the wonders of nature. This home also features an expansive great room, multiple fireplaces, a theatre room, a gym and has potential for an inground pool and pickleball court. Truly a gem of the North Fork!

Presented By: Engel & Volkers North Fork 631-298-7953

Call Today: (631)298-8760, (631)298-8760, or Email: Andrew Stype Realty Inc

Southold Homes for Sale

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