Southold NY Real Estate & Homes for Sale

Quintessential North Fork Farmhouse circa 1909, renovated for the comfort and convenience of today's discriminating buyers. This home is loaded with charming, period details. It has 10-foot ceilings on 1st floor 9-foot ceilings on 2nd floor. On the first floor you have an enclosed front porch for receiving guests, living room, formal dining room, home office, laundry room, half bath and the front parlor, which could be a 4th bedroom. Also on the first floor is the beautifully renovated kitchen with a new center Island with marble top, granite countertops with custom backsplash, wine refrigerator, stainless appliances and a copper sink and faucet. The kitchen also features toe kick heaters for economical heating. There are mini splits throughout the first floor for economical air conditioning. There is central air on the second floor where you will find 3 bedrooms and a full bath with both a shower and a whirlpool tub. There are pull down stairs to a full, stand up attic with blown in insulation. There is a full, unfinished basement, set up as a den, with a room for yoga/ martial arts. The exterior of the home has been lovingly transformed. There is a new driveway with a cobblestone apron and edging, a new bluestone walkway, composite decking, PVC fence, and lantern lights. You will enjoy entertaining on the patio with pavers, or sitting quietly surrounded by new landscaping and privacy trees. The landscaping can be easily maintained with the new irrigation system. Automotive enthusiasts will plotz when they see the separate 4 car garage with double pane windows. There is electric in the garage if you want to convert part of it to a workshop. This beautiful home is located within the Southold Park District providing access to the town's best beaches, including nearby Goose Creek Bay Beach. There is a town boat launch .5 miles away. You are minutes away from the shops in Southold, and 5 miles to the nightlife of Greenport.

BOATING, BEACHES and BEAUTY - Come Discover this Sublime Waterview 4-bedroom, 4.5-bath Contemporary Farmhouse: and approximately 3200sq' of Conditioned Living space, plus covered porches, upper-level deck, 2 car garage, full basement and Inground pool on over a 1/2 ac of land. This home boasts ample well-appointed kitchen and Great room with double sided indoor/outdoor Fireplace, to take the chill out of those cool autumn nights, large dining room/library, 1st floor primary ensuite, 4" white oak flooring throughout, mahogany clad upper and lower level decks, 18'x36' Black Onyx pool all situated on the picturesque bayside of Southold and within the desirable Southold Park District which offers access to Founder Landing Beach, complete with playground, and South Harbor Park Beach. Enjoy water views of West Creek and boat basin where you can dock your boat or jet ski, at a prepaid dock slip for the 2024 season-renewable and capable of accommodating a boat of up to 24 feet, just a mere stone's throw from your doorstep or launch your kayak at the end of Glenn Road. Just around the corner you'll find a celebrated Christmas Tree farm including a farmstand, along with a restaurant/sports pub just minutes away. This location is close to vineyards/wineries, brewery, beaches, charming Southold Town, restaurants, and close proximity to beautiful Goose Creek's sandy bay beach with a playground, and yacht club, among many other attractions!

Experience Serene Living in This Newly Renovated 2-Bedroom, 2-Bath Condo in the Highly Sought-after Founder's Village, a Premier 55+ Community. Enjoy Upgrades Throughout, Modern Bathrooms, a Sleek Stainless Steel Appliance Package, and Convenient first-floor Laundry. Relax on Your Own Private Patio or Take Advantage of the Community Pool and Elegant Clubhouse. With Easy access to Local Shops, Dining, Public Transportation and Cultural Activities, This Home Offers the Perfect Blend of Privacy, Comfort, and Convenience In a Prime Location.

Beautifully restored and updated Colonial Path House with Landmark distinction. The front facade of the house has been restored to clapboard siding and cedar shake. The original rooms on the first floor include a cozy parlor with wood burning fireplace, an adjacent dining room, farm kitchen and full bath/laundry room. All with antique wide plank floors. The second floor has 2 bedrooms and large storage closet, as well as a full bath with an antique soaker tub. A new addition in 2006 doubled the living area. The design of the addition compliments the old part of the house while modernizing the space with an ensuite bedroom, living room, a year-round sunroom, wide plank hardwood floors and working fireplace with a hand carved mantle from a Victorian mansion in the Hudson Valley. The kitchen has been updated with built in cabinets, a farm sink, a Bosch dishwasher and Viking stove. A bluestone patio is directly off the Primary bedroom. From 2020 to 2023 a successful and popular bed and breakfast was operated in this new addition. An accessory cottage is perfect for your studio or office. House in the heart of wine country. Top Southold Restaurants: John Fraser's North Fork Table and Chef Panyard's Southold Social.

Welcome to this stunning, fully renovated home, where classic charm meets modern luxury. Nestled in a serene neighborhood, this exceptional property offers an inviting open floor plan, highlighted by elegant finishes and thoughtful updates throughout. The main level features a spacious living room with a cozy fireplace, seamlessly flowing into a brand new beautiful kitchen equipped with top-of-the-line stainless steel appliances, sleek countertops, and custom cabinetry. Adjacent to the kitchen, the dining area is perfect for both everyday meals and entertaining guests. The main level also includes a luxurious bedroom and a spa-like en-suite bathroom, as well as an additional family room and half bathroom. Upstairs, you'll find three generously sized bedrooms with ample closet space, as well as a beautiful brand new full bathroom. Outside, the expansive backyard provides a private oasis with a patio area, perfect for outdoor gatherings and summer barbecues. Additional Highlights include New siding, New roof, New doors, New floors, New electrical and plumbing systems, New kitchen, New bathrooms, New Anderson windows and a Two Car Garage. Don't miss the opportunity to make this beautifully renovated home yours!

Welcome to Founders Village - 55+ community offering the epitome of comfort and convenience! This unit boasts a prime location, just minutes away from town and all its amenities. Relax and unwind in the community pool, or enjoy the tranquility of this two-bedroom, two-bath condo. With a partial finished basement offering endless possibilities, and situated in a sought-after neighborhood, this property is the epitome of desirable senior living. Don't miss out on this opportunity to embrace the best of what Founders Village has to offer!

Discover your dream home in this turn key and meticulously maintained waterfront property situated on 1.25 sprawling acres. This home has been recently expanded and completely renovated throughout, all while preserving the unique charm of its original 1930's design. As you enter, you'll be greeted by bright, airy spaces that highlight the home's exquisite design and attention to detail. Large windows provide picturesque views of the surrounding gardens and waterfront. The spacious living areas are perfect for gatherings, while the well-appointed kitchen features custom cabinetry and enhanced amenities that any home chef would appreciate. The sunroom, newly built in 2021, provides an escape to a cozy atmosphere that can be enjoyed year round. With an abundance of closets throughout this home, there is plenty of storage space available. The primary ensuite is a luxurious retreat that seamlessly combines comfort and elegance with the brand new primary bathroom as a standout feature newly completed in 2023. A private balcony off the primary invites you to unwind and soak in breathtaking views. Step outside to enjoy the lush gardens and expansive grounds, where you can relax amidst the vibrant flora or host summer barbecues on the spacious deck with an outdoor wood burning stone fireplace. The property also includes a private dock with bay access, allowing you to indulge in boating, fishing, or simply soaking in the stunning waterfront. In addition to its idyllic outdoor spaces, this home offers a garage that provides ample storage and additional recreational uses, making it ideal for those with hobbies or outdoor equipment. And there is plenty of room for a pool. The surrounding area also offers opportunities for golfing, cycling and exploring quaint shops and local eateries. Experience the ultimate in waterfront living in this Southold gem, where comfort and charm meet the beauty of nature!

Introducing 465 Tarpon Drive, a stunning property in the coveted Southold Shores Bayfront beach community on the North Fork. This contemporary and expanded cape is situated on a private, secluded road, surrounded by marinas, beaches, farms, and wineries. With an airy open floor plan, this home boasts a light-filled living space and a primary floor owner's suite. The living room features soaring cathedral ceilings and a charming wood burning fireplace, while the bright and airy den offers vaulted ceilings and large windows to take in stunning woodlands behind the house and the winter water views of Brick Cove. The spacious eat-in kitchen is awaiting your personal touch. With 2-3 bedrooms and 2.5 baths, this home offers substantial decking providing an ideal setting for entertaining. Other features include basement laundry, utilities, and storage, as well as an attached 1++ car garage. Nestled on a peaceful lane in the Southold Shores bayfront beach community, this property offers a private yard, association beach access and is conveniently located between Southold Village and Greenport. Don't miss this opportunity to enjoy the best of seaside living in the North Fork!

Charming, Sleek, and Sexy waterfront cape-style home with exceptional water views located on Jockey Creek! This private retreat boasts 3 bedrooms, and 2 baths and is situated on .66 acres with a dock, and room for a pool. Enjoy an updated kitchen and beautiful baths, a bright and open floor plan, a living room with wood-burning stove, and sliders to the waterfront deck. Other features include wood floors throughout, central air conditioning, and the home was recently converted to natural gas. There is also a full basement with walkout doors which can be transformed into an incredible living space. Outside the property is fully fenced and there is an outdoor shower. This quintessential North Fork waterfront retreat won't last long!

Classic expanded Saltbox with open concept floor plan and high-beamed ceilings finished in a timeless Nantucket style! Completely renovated in 2020-2021, this move-in ready home boasts 3 bedrooms, including a primary with en-suite bath, large second-level loft with clerestory windows that is convertible to a fourth bedroom. The living room has a beautiful wood-burning fireplace and sliders to an antique-style real brick 17x40 outdoor dining, and lounging patio with an integrated firepit! This spectacular pond-front property has unobstructed Southern views across the Bay to the South Shore from the second level. Located in one of the most prestigious areas of Southold in a quiet, private association community with Creek access and a private community beach. The quintessential North Fork Beach house!!

This Founders Village two-bedroom end unit is full of sun light with fantastic southern exposure.

SOUTHOLD WATERFRON - Step back in time and connect with nature at the historic Allen Tobey Carriage House. Constructed in 1910, this charming residence was relocated to the verdant expanse of Jockey Estates in the 1950s, becoming a part of the "Red Road" community. Today, the house is nestled within private, mature grounds, featuring 300-year-old trees. The expansive lawn rolls down to a creek, offering kayak and canoe access. The residence boasts a formal living room with a fireplace, a library, a spacious sunroom, a kitchen, a light-filled dining room, a first-floor master suite, a powder room, and a large recreation room with an endless pool, hot tub and shower. Pool room can be converted into playroom, additional bedroom(s), or artist's studio. Bad weather? Generator included in sale. Additionally, the property includes a sizeable two-car garage with an attached screened porch and a shed. A boat launch is conveniently located at the end of the street, and there's a community beach in close proximity. Come, let yourself relax and simply drink in the natural beauty all around.

Best of Both Worlds - Enjoy The Seclusion Of This 2 Acre Parcel, Yet Close To Town, Shopping, Beaches & Vineyards. Photos Shown Are From Identical House Recently Completed In Southold. Easy To Preview!

Discover tranquility and convenience in this inviting 3-bedroom, move-in ready home nestled on a shy acre in a private, quiet neighborhood. Located just moments from the village and pristine beaches, this property offers the perfect blend of privacy and accessibility. Step inside to find a meticulously maintained interior boasting ample natural light and a cozy atmosphere. The spacious living areas are ideal for relaxation and entertaining. Outside, enjoy the expansive yard surrounded by lush greenery, providing a peaceful retreat for outdoor gatherings or quiet moments. Plenty of room for a pool. With plenty of room to personalize and make your own, this home offers endless possibilities. Don't miss the opportunity to make this tranquil retreat yours. Schedule your private tour today and envision the lifestyle awaiting you in this sought-after community.

This bright and airy 3-bedroom, 2-bathroom home on Southold's charming Hyatt Road offers a perfect blend of open and closed living spaces. With numerous windows and skylights, the home seamlessly integrates with the surrounding mature landscaping. Each bedroom boasts vaulted ceilings and picturesque views of the park-like setting, the primary has a large ensuite bath. Conveniently located just 0.3 miles from McCabes Beach and a short drive to both downtown Southold and Greenport, this property provides both tranquility and easy access to local amenities. Full basement and attached 1 car garage.

Gagen's Landing Retreat awaits your arrival, ready to be your summer home or year-round retreat with the perfect blend of relaxation and adventure. With ample space for a pool and potential for expansion, this 3-bedroom home offers all the amenities of a beach community. A short stroll takes you to the water, perfect for escaping with your paddle board or kayak, leading out to Goose Creek Beach where you can relax in the sand or just enjoy and watch the boats go by. Craving a taste of local life? The welcoming town center is just around the corner, teeming with shops, restaurants, and friendly faces. This North Fork home offers the best of both worlds: tranquility near the water and the convenience of in-town amenities close by. Come escape away to this community and start living your lifestyle today!

This Beautiful two-bedroom end unit 55+ Co-op is located in the center of Southold Town. Easy access to shopping and transportation. This co-op offers ground floor living with the extra privacy as an end unit. There is an eat in kitchen, large living / dining room, full bathroom, oak hardwood flooring, washer & dryer, and a rear patio. Common charges include heat, water, ground care, management and more. The community is located with-in the Founders Beach and Park district.

Discover elegant and tranquil living in this meticulously maintained 2-bedroom, 2-bathroom condo primely located on the exterior loop of Founders Village, an exclusive 55+ community in Southold within Long Island's North Fork Region. This residence offers a perfect blend of comfort and convenience, starting with a spacious living room featuring a cozy fireplace and a sliding door leading to a serene brick patio, ideal for morning coffee or evening relaxation with complete privacy. The well-appointed kitchen is smartly designed with an adjacent dining area for seamless entertaining. Retreat to the primary en-suite bedroom, complete with a tiled bath and ample closet space, ensuring privacy and comfort. An additional guest bedroom and guest bath provide flexibility for visitors. Residents of Founders Village enjoy a community pool, clubhouse, and proximity to Founders Landing Beach and Greenport, enhancing the appeal of this community's prime location. With Southold Village nearby, residents have easy access to shops, restaurants, the library, and transportation options. Don't miss this exceptional opportunity for refined coastal living in a vibrant community that offers both relaxation and convenience.

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.

Property with vast potential in Prime location, close to Southold beaches, vineyards and short drive to town. Manufactured Home from the early 70's in disrepair, separate one car garage and shed.

Welcome To 1745 N Parish Dr - A Coastal Gem On One Of Southold's Most Desirable Streets! With Its BayFront Location, You'll Enjoy Panoramic Water Views Of Peconic Bay, Shelter Island And Beyond! Just Steps Away Is Goose Creek Beach And Southold Yacht Club Adding To A Vibrant Fun Community Atmosphere. This Wonderful Family Home Filled With Natural Light Boasts 4 Bedrooms and Is The Perfect Blend Of Comfort And Luxury. A Generously Sized Waterfront Deck Provides An Ideal Setting For Sunrise Viewing, Alfresco Dining, Or Simply Soaking Up The Sun. Plus, With Your Own Private Beach, Every Day Feels Like A Vacation. This Home Is More Than Just A Place To Live - It's A Lifestyle. Whether You're A Water Sports Enthusiast Or Someone Who Appreciates The Tranquility Of A Waterside Retreat With Amazing Views, This Property Has Something For Everyone. So, Are You Ready To Take The Plunge?

Designer Modern Farmhouse set on over 3.35 acres, renovated 2023, Open Concept LR/DR/KIT, Gorgeous EIK with quartz countertops, SS Appl., new siding, new windows, new doors, new flooring throughout, beautiful new baths, new boiler, new well pump and tank, spectacular new 20x40 in ground pool with Cambridge paver patio, front porch with farm views. Stroll down to McCabe beach or quick drive for incredible sunsets. Access to Town beaches, boat ramps and parks with town permit. Farm animals permitted.

Experience Summer Camp Bliss at 2480 & 2335 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, 2480 & 2335 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.

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 sun room. 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.

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.