Southold NY Real Estate & Homes for Sale

REYDON HEIGHTS GEM! Expertly finished space for premier living, entertaining and enjoyment - inside and outside! In the summer, enjoy all the fun and activities outdoors in a private, enclosed backyard complete with an oversized, freeform, in-ground pool, hot tub, outdoor kitchen and plenty of chaise lounges and comfy chairs to enjoy the lazy days of summer! Inside the home's modern open flair is interspersed with traditional touches for maximum entertainment, enjoyment and relaxation. Wonderful, open space allows you to move throughout the main level from the living and dining area to the large eat-in kitchen, the den with it's inviting fireplace and built-in, sit-down bar, to a large light and bright sunroom. Everything connects to the private outdoor space, including a full bath, for maximum accessibility. Upstairs there's a large master suite with a soaking tub and shower and a built-in closet to die for! Two good-sized additional bedrooms and a full bath complete the second level. The home is complemented by a lower level with two-car garage and private outdoor parking. Hurry and you may be able to catch some of this summer in your new home! NEW TO THE MARKET.

Let your North Forth dreams come true in this eco-friendly paradise! Kayak in Great Pond off your own back yard, or enjoy beautiful Kenney's Beach right around the corner. Every room in this serene gem has been lovingly turned into a sanctuary of peace and expansiveness. Open plan living and dining are ready for your 'beach-life'. Upstairs boasts two large airy bedrooms and a spa-like bath. The downstairs studio is functional in so many ways. Bamboo floors give a warm glow to each room, while the views will take you to a place far away from the bustle of the world. Abundant native plantings have been nurtured and thrive with water from rainwater cisterns, while solar panels feed most of your electricity needs. Come unwind in a very special beach community. An Oasis for the true environmentalist.

Here it is, a wonderful opportunity to own a water view cottage in Goose Bay Estates. Hardwood floors enhance the charm of this home, with attention drawn to the wonderful outdoor spaces. A large screened porch extends the living space, while the terraced patio includes a Tiki bar and grilling nook for your entertaining pleasure. The bonus features of an outdoor shower, shed, and enhanced heated garage add to the appeal of this coastal cutie.

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!

Discover this Beautifully Renovated Bay Haven Ranch where your deeded bay beach is mere steps away. This Open Floor Plan house boasts a Large Open Great Room, 4 bedrooms, Office & 3 baths, all nestled on a spacious shy half acre lot. Immerse yourself in the North Fork dream lifestyle, with Farm to Table Restaurants, Beaches, Boating, Vineyards, Biking, and Golf right at your fingertips. Make this home your gateway to endless adventures and relaxation.

Welcome to your NOFO waterfront oasis, perfect for kayaking, paddle boarding, sailing, jetskiing, power boating, fishing, etc.! This immaculate 3-bedroom, 2.5-bath Ranch home is perfectly situated on 1 acre surrounded by lush mature landscaping, and features 280 feet of waterfrontage on Long Creek & Hashamomuck Preserve. The open floor plan is accentuated by skylights that bathe the space in natural light and a cozy gas fireplace perfect for relaxing evenings. The modern kitchen boasts white cabinetry, stainless steel appliances, a large pantry, and plenty of counter space for all your culinary endeavors. The primary suite offers a tranquil retreat with an en-suite bath, while two additional bedrooms provide ample space for guests. Step outside to an expansive deck with a retractable awning and outdoor speakers that overlooks the serene water-ideal for entertaining or simply soaking in the views. The large basement with high ceilings presents endless opportunities for customization, whether you envision a home gym, media room, or additional living space. Located on the border of Southold & Greenport, close to many sandy beaches, fresh fish markets, local farm stands, plenty of wineries and Greenport Village shops & restaurants. Not in a flood zone. Schedule your private tour today and experience single level waterfront living!

Beautifully landscaped acre, walk to Kenneys Beach and Little Fish Restaurant, Plenty of room for pool. Over 3,300 sq ft. Large spacious rooms .Situated on a private road shared by only four homes.

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.

Welcome Home to this sunny 3-bedroom, 2.5-bath Equestrian home built in 2001set on a sprawling 1.94-acre lot with 2-stall horse barn! Full basement with 8ft ceilings & OSE to yard, 2-car attached garage & fenced horse pasture. Formal Living Room with Vaulted ceilings, Formal dining room, large EIK with sliders to rear deck & patio. Large Primary bedroom suite with bathroom, large WIC and views of the yard. 2 Additional Spacious bedrooms & full bath complete the second floor. Oak hardwood flooring throughout house. New CAC system & newer heating coil in burner. Barn is a well-constructed 24 x 24 Pole Barn with electric & water on cement slab with footings w/ Hardie board & T-111 siding. Accessory shed for hay & horse supplies included. Room for Pool!! Act fast! This property will not last!!

Incredibly charming North Fork farmhouse offering an idyllic retreat with beautiful open protected field views and luxurious amenities. Nestled amidst serene surroundings and extensive, mature landscaping, this stylishly updated three-bedroom home is bathed in natural light and character, featuring both interior and exterior fireplaces that enhance its chic but cozy ambiance. The living spaces are thoughtfully designed, providing a perfect blend of modern comfort and classic farmhouse charm. Outdoors, the resort-like pool area has an attractive pool house, patio, and gas fire pit. The surrounding views of neighboring vineyards and fields create a picturesque backdrop for relaxation and entertainment. Less than a mile to beaches, farmstands and southold hamlet shops and restaurants.

Stunning waterfront modern with sweeping views of the Peconic Bay from every room. The 130' of bay frontage is complimented by your 70' dock, waterside gunite pool and five ensuite bedrooms overlooking the water. With soaring ceilings, a chef's kitchen, wood burning fireplace, and a dedicated teak balcony for each second-floor bedroom, the property blends the luxury vacation experience with the comforts of home.

Experience Summer Camp Bliss at 2335 & 2480 Minnehaha Blvd, Southold Step into a world of endless summer fun at this quintessential summer camp property, perfectly sited on two lots with expansive bayfront views featuring picturesque sandbars and a pristine beachy landscape. This Nantucket-style cedar shake home, with its charming Dutch doors and expansive decks, invites you to soak in the refreshing sea breeze and panoramic vistas of the creek, bay, and the impressive yacht docked right at your doorstep. The open floor plan seamlessly connects the gourmet kitchen to a cozy living room equipped with a built-in wet bar, where you can enjoy your favorite drinks while gazing through the picture window at the serene waters. Originally designed as a main floor master suite, the home's addition now serves as a state-of-the-art golf simulator room, adding a playful twist to luxury living. Embrace your love for the water with riparian rights and a private dredging permit valid for ten years, ensuring your dock remains in prime condition for your 66' yacht. A waterside storage shed keeps all your water toys, from paddleboards to kayaks, within easy reach, making spontaneous adventures a breeze. The current black lab resident epitomizes the joy of this property, eagerly chasing after paddleboards and kayaks, and even racing across a nearby island to lead the way back into the water. It's a true testament to the playful spirit that defines this unique home. For those moments when you seek tranquility, multiple decks, patios, and a private man-made beach on Corey Creek offer serene spots to unwind. Alternatively, the natural beach of the Laughing Waters homeowners association on Hogs Neck Bay provides an idyllic setting for relaxation, where the sounds of the residents laughing epitomize the joyous community spirit. This property is not just a home; it's a lifestyle, where every day feels like summer camp. Perfect for those who cherish waterfront living, active recreation, and the simple joys of nature, 2335 & 2480 Minnehaha Blvd is a dream come true for both humans and their furry friends. Don't miss the chance to make this enchanting retreat your own and create memories that will last a lifetime.

Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you're greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1,400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney's Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether you are meandering east towards Horton's Point Lighthouse or west towards Goldsmith's Inlet, the journey is as captivating as the destination. The nearby 60-acre nature trail just down the beach invites leisurely exploration, enhancing the natural allure of the area. Perfect for those who cherish peace, privacy, and the unique beauty of coastal living, this home offers promising unforgettable sunsets and a tranquil lifestyle nestled in a coveted private beach community.

Nestled in Founders Village, Southolds premier 55+ active community, this 2 Bedroom 2 Bathroom condo is perfectly suited for North Fork living. It's location allows for a quick stroll to local shopping and transportation. Owners enjoy a beautifully maintained landscape and have access to a clubhouse and private pool. The large living room boasts high ceilings and a fireplace complete with a custom mantle. The primary bedroom includes nice closet space and an en-suite bathroom complete with a tub. It also features a barn style door that can be closed creating privacy for both the owners and their guests. The guest bedroom currently is used as a reading room and comes with built in shelving and a relaxing aubergine color. Enjoy the outdoors on the back patio. Create a raised vegetable garden and a lounge chair area or set it up for the ultimate grill and chill! The full size basement offers great storage and is large enough create a hobby room or workshop. Come check this out! $430 monthly common charges

Charming 6-room building, located in the heart of the Hamlet Business District of Southold Town, is currently being used as Surveyors Office, and has the potential to be converted to a residential dwelling with the addition of a kitchen The property is conveniently located near municipal parking, LIRR & Jitney transportation. Just a stone's throw to fine shops, renowned restaurants and so much more. The property consists of two lots and room for possible expansion. Come see the potential for your next venture!

Welcome to your dream colonial home nestled in the charming Southold North Fork area! This exquisite residence boasts four spacious bedrooms and three luxurious baths, offering ample space and comfort for you and your loved ones. Enter into the heart of the home, where the open-concept kitchen awaits. A vision in white, with sleek Cortez countertops that provide both style and functionality. This kitchen is a chef's paradise, perfect for entertaining guests or enjoying meals together. Renovated in 2018, this home effortlessly blends classic colonial charm with modern elegance. Gorgeous hardwood floors add warmth and character throughout, while solar panels ensure energy efficiency and cost savings. Situated on a generous half-acre property, this home offers a serene retreat from the hustle and bustle of everyday life. Tucked away between two cul-de-sacs, enjoy privacy and tranquility in this idyllic setting. Conveniently located near beaches, vineyards, and shops, you'll have endless opportunities to explore and indulge in the best that the North Fork has to offer. Whether you're lounging on the sand, sipping wine at a local vineyard, or browsing quaint boutiques, you'll love calling this colonial oasis home. Don't miss your chance to make this slice of paradise yours!

Welcome to 700 Bayview Ave, in Southold. This charming retreat is across the street from Hashamomuck Marine Waterway, inlet to Peconic Bay. Featuring a bright and airy layout with tons of potential and charm. 3 bedrooms, 2 bathrooms. Newer hardwood floors on 2nd floor. Full finished tiled basement. Large yard with newer PVC fence and shed. Side and front trex steps recently installed. Centrally located to both Southold Village and Greenport Village.

Just in time for summer! Completely renovated expanded ranch offering more than 3200 sq feet for family and friends. The open floor plan exudes natural light, a beautiful chef's kitchen with a spacious quartz island, and plenty of dining and lounge space. The primary ensuite bedroom, situated on the main floor, is adorned with a luxury spa bathroom, a walk-in closet, and a bonus space for an office or nursery. The lower level has a junior primary ensuite, two additional bedrooms, another full bath, a large family room or entertaining space, and walkout access to the backyard. The two-car-attached garage leads to the mud room, laundry room, and a half bath. Renovation details include crafted doors, wood flooring, Anderson 400 series windows/doors, spa bathrooms, and a gourmet kitchen. Hardy Board siding, Azek, and maintenance-free decking complete the offering. Room for a pool. Close to all that the beautiful East End has to offer. Wineries, beaches, restaurants, farm stands, and Southold's quaint town are all within minutes of this property. Moments from Goose Creek Beach!

Embrace North Fork living at its finest in Goose Neck Estates, where you can store your kayaks at the private beach and keep your boat in the marina! Nestled within this charming neighborhood, a cozy 2-bedroom ranch awaits your personal touch. The bonus breezeway, complete with a wood stove, offers a welcome retreat for relaxation. Outside, a private deck and patio create a peaceful haven, perfect for both quiet moments and hosting barbecues with loved ones. The spacious side yard, fully irrigated, invites endless possibilities for outdoor recreation or gardening pursuits. Don't miss this opportunity to create your ideal full or part time home!

Imagine spending spring and summer days soaking up the sun on the private HOA bay beach, just down the road from your recently renovated 4-bedroom Cape at Paradise Shores. Then, when the weather cools, cozy up by the wood-burning fireplace for relaxing nights. The open floor plan on the first floor creates a perfect flow for entertaining. Two bedrooms and a full bath on the first level offer convenience, while two additional bedrooms and a full bath upstairs provide privacy. Sliding doors open onto the back yard deck, perfect for grilling or enjoying al fresco meals under the warm sun. Many upgrades in 2024 including new kitchen and appliances, 2 new full baths, carpeting, interior and exterior painting, water filtration system and much more!

Find serenity at Great Pond!. The best of two waterscapes - Lake and Sound. The house has 100 feet of lakefront and is one block from Kenney's Beach on the Sound. This light filled ranch is the perfect place to relax and renew. It features a living/dining space with a picture perfect view of the pond. Location is the key! The Basics - Kitchen, LR/DR w/Fireplace, three bedrooms and a bath, plus wrap-around deck and outdoor shower. The Intangibles - Relaxing in a hammock by the pond and living a dream come true!

Introducing one of the North Fork's most iconic properties, seamlessly blending historical grandeur with contemporary living. Originally constructed circa 1915, this Georgian estate served as additional living quarters for the family of the former 40-acre waterfront Cosden estate. Today, this exceptional residence offers over 6000 square feet of luxurious living space featuring six bedrooms, all ensuite and is situated on a serene acre of land positioned across from a scenic preserve. An entertainer's dream, the house welcomes guests with a magical courtyard entrance, setting the stage for epic gatherings with family and friends. Inside, soaring ceilings and abundant windows infuse the home with natural light, creating a bright and inviting atmosphere. A large great room features trayed ceilings, herringbone floors and a huge wood-burning fireplace, adding warmth and character to the space. The recently renovated chef's kitchen is anchored by an oversized center-island with an enormous custom skylight above. A formal dining room with vaulted ceilings awaits holidays and dinner parties. A large playroom serves as a flex media room. The south-wing of the residence features the original stables with a secluded and private office just beyond. Additionally, a large temperature-controlled wine cellar in the basement caters to connoisseurs and collectors alike. Step outside to the park-like backyard, where a heated gunite pool awaits amidst mature specimen trees and ornamental plantings, offering a private retreat. An outdoor shower is designed to take in the beautiful gardens. A timeless East End investment in the heart of the North Fork.

This expanded farmhouse has one of the most desirable North Fork Locations in between the Southold town shops and the Founders beach & park. As you enter the home you will admire the original wide plank hardwood floors throughout. The first-floor entry begins with a large living room complete with coal burning stove, a first-floor bedroom, full bathroom, dining room, kitchen and a den that overlooks the lush gardens of the backyard. From the den you can step out on the balcony deck and will see a water view of Town Creek. On the second floor there are an additional 3 bedrooms and a full bathroom. There is plenty of storage offered with this property in the large barn or in the two-car garage with full loft area above. This home offers everything you need to live the perfectly relaxing life on the North Fork.

Welcome to serene living at its best! Nestled in a well-sought-after neighborhood, this charming ranch offers 1800 Sq Ft of living space, perfect for experiencing the North Fork lifestyle and entertaining guests. This residence borders Goose Creek with over 100 ft of waterfront, a private dock, and access to the Peconic Bay. An ideal location for boating enthusiasts or those who enjoy the tranquility of nature and waterfront views. Close to all that the beautiful East End has to offer. Wineries, beaches, restaurants, farm stands, and Southold's quaint town are all within minutes of this property.

Meticulously maintained condo in desirable Founders Village 55+ Community. Features include spacious living room with fireplace and slider to brick patio, dining area, eat-in-kitchen, Primary en-suite bedroom with tiled bath, additional guest bedroom, guest bath, first level laundry, and full basement. Enjoy the community pool and club house, convenient location to Founders Landing Bay beach and park and a short walk to Southold Village, shops, restaurants, library and transportation. An opportunity that will not last.