Southold NY Real Estate & Homes for Sale

Southold-Reydon Shores-Inviting 3/4 acre landscaped property with specimen plantings is the backdrop for this spacious well-maintained ranch in the sought after waterfront community of Reydon Shores. Easy access to the Association Bay Beach and protected Marina. Plenty of room for family and guests to gather in the large living room with a wood burning fireplace and doors to the outside rear deck. Formal dining room, eat-in kitchen open to living room, and an additional sitting room. Two generous ensuite primary bedrooms. Additional guest bedroom and hall bathroom. Hardwood floors. The heated inground swimming pool catches the sun throughout the day and is surrounded by a paver patio. YOU can have a lot of fun here! A move-in ready North Fork home just waiting for you to enjoy.

Introducing 3715 Main Bayview Road in Southold, NY. This modern home offers 3 bedrooms, 2.5 bathrooms, and a spacious lot spanning 39582 square feet. Inside, the open concept living creates a welcoming ambiance for entertainment. The Chefs kitchen has modern appliances with ample counter space and storage. The main floor Master ensuite is its own private sanctuary. Outside, enjoy the tranquil back yard and direct creek front access for kayaking or paddle boarding to near by Goose Creek Beach. Schedule a showing today and experience the allure of 3715 Main Bayview Road for yourself.

**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 it's own wbfp, 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 salt water gunite pool with a waterfall jacuzzi, surrounded by a 1500' bluestone patio, an outdoor fire pit, and pergola. This property also features a lush lawn, basketball/pickleball court, and proximity to Peconic Bay, beaches, and local wineries. Experience unparalleled luxury in this exquisite Southold home.

Your Going to Flip Over This Location! Nestled In The Goose Bay Estate With Beautiful Views of Goose Bay. This Adorable Cottage Is Just Waiting for You To Make It Your Own Dream Come True. Imagine Spending Time on The Front Deck Overlooking the Bay as The Sun Sets. Don't Miss Out On This Once in A Lifetime Opportunity!

This charming Farmhouse offers a quintessential North Fork living experience. With hardwood flooring and period details throughout, it exudes warmth and authenticity while the tasteful renovations foster modern comfort and livability. The spacious half-acre has a large, fenced rear yard with a pool and patio, perfect for outdoor entertaining. Ideally situated at the edge of Southold Hamlet commercial district, next to the iconic North Fork Table and Inn and delightful Deep Roots Farm. This home perfectly encapsulates North Fork living with beaches, farmstands, wineries, and Greenport Village all minutes away.

This charming ranch-style home offers a picturesque setting at the end of Ruch Lane, boasting water views of Hashamomuck Pond. Situated on a generous half-acre lot, the property presents an ideal canvas for single-story living or potential renovation and expansion opportunities. Approved Southold Town building permit in place for a stunning five-bedroom, 4.5-bath residence complete with a pool and detached garage. Plans are available for review at showings. Scaled-back expansion utilizing the oversized two-car garage and full basement offers another avenue for customization, providing flexibility to tailor the property to suit specific needs and preferences. Just minutes from Southold Hamlet and Greenport village and a quarter mile deeded sound beach access.

Southold--Reydon Shores--Beautiful, charming, farmhouse invites you in. 3-bedroom, 2.5 bath home in sought after community of Reydon Shores with easy access to the Association Bay beach and Marina. First floor large primary en-suite bedroom, chef's kitchen with top shelf stainless appliances including a Thermador cooktop and double oven. Radiant heat in Primary Bath and Kitchen. Closets beyond belief and hardwood floors throughout. Light, bright, and spacious with good flow. The kitchen opens to a great room and dining area Additional living space with a cozy wood burning fireplace. Upstairs-- two oversized guest bedrooms with hall bath and loft area. Immaculately updated and maintained, move-in ready. Doors open to the outdoor space including a large patio, trex deck, 2-car detached garage, and barn offering endless opportunities--workshop, studio, garden work area--let your imagination lead you. Level, landscaped shy half acre property. A perfect North Fork home waiting for you.

Exquisite waterfront home with wrap around porches and breathtaking views. Perfectly situated on the protected water way of Arshomomaque, where you can enjoy fishing, crabbing, clamming, boating, or just relax and listen to the birds. The first floor has a dining room, living room with a stone fireplace, den, laundry room, water side all-season room and a beautifully renovated eat in kitchen. The second floor has a master ensuite, 3 nice size bedrooms and an office. Their is plenty of room for storage in the detached garage or in the full size clean basement. Centrally located between Southold and Greenport villages, this home is also with-in the Southold Park District offering Founders and South Harbor Beach access.

Come and explore the charm of cul de sac living on the serene North Fork! This expansive colonial home offers approximately 3200 square feet of living space nestled on nearly an acre of land. Step inside to discover a wealth of features designed to enhance your lifestyle. Recently updated bathrooms are adorned with radiant heated floors, providing a touch of luxury and comfort. With ample bedrooms, there's plenty of room for everyone to spread out and unwind. Additionally, an extra living space awaits, perfect for a home office or artist studio, allowing you to pursue your passions right from the comfort of home. The proximity to the Long Island Sound means you're just moments away from enjoying the beach life. Alternatively, if you prefer to stay closer to home, the in-ground pool offers a refreshing oasis right in your backyard, providing the best of both worlds. Don't miss out on the opportunity to make this exceptional property your own. Schedule a tour today and experience the beauty and tranquility of North Fork living for yourself!

Absolutely flawless! Recently renovated throughout, this house showcases exquisite hardwood flooring, a stone fireplace, vaulted ceilings, newly appointed stone bathrooms, and a chef's kitchen with island open to the outdoor area. Outdoor entertaining is a dream with an oversized bluestone patio featuring a summer kitchen equipped with a gas grill, a cozy fire pit, and a deluxe hot tub nestled within a charming wooden platform. The meticulously landscaped gardens with an array of specimen trees, lush plants, and an abundance of vibrant flowers complete this offering. Conveniently located with convenient access to Southold Village, local vineyards, and farm stands this home offers

Wonderful opportunity to live in prime Southold Town Village location, less than half a mile from the center of town. Clean and pristine, this adorable cape has potential for expansion on the upper and lower levels. Corner lot with detached 1.5 garage. Full basement with high ceilings and bilco doors to the outside and back workshop. Entry way opens to living and dining areas with separate sunroom. There is an eat in kitchen and 2 large bedrooms and full bath on the first floor. There are stairs that lead up to two other rooms which could be converted to additional bedrooms. Other features include central air conditioning, natural gas, and public water. Beautiful and quiet neighborhood.

Meticulously restored and maintained 19th C Italianate style residence, beautifully set on elevated 1.25-acre lot. Built around 1850 by Silas Horton and occupied by his descendants until the 1960's. original wrap around porch, 17.5' floor to ceiling windows, ornate Cupula, marble fireplace mantles, original wide floorboards, in-tact period moldings, trims, banisters, and doors. Large, updated kitchen and baths, wood burning fireplace, large walk-up attic. Rarely does a house of this vintage and quality become available.

This property is a treasure trove of possibilities, boasting 2.7 acres of land, a spacious 3280 square foot home, and a substantial 2600 square foot barn. The main residence features an accessory apartment with a functioning bed and breakfast license. The barn presents further income potential, with five stalls or the space can be converted into an accessory living area. This property can also be an extraordinary family compound, featuring ample living spaces perfect for creating cherished memories. A heated saltwater pool, complete with electric cover, beckons relaxation and fun-filled moments, while solar panels underscore the commitment to sustainable living. Outdoor amenities abound, including an outdoor shower, a cozy fire pit for gathering under the stars, and vast expanses of land to explore and enjoy.Garden enthusiasts will be delighted by the fully irrigated vegetable gardens and flourishing orchard, adding to the property's allure and self-sufficiency. Offering far more than the ordinary, this property is available at an unbeatable price, presenting a rare opportunity in today's market.

Whoo Hoo! Surrender to Serenity in this Private Community Known as Goose Neck Estates! The Ideal Location for Your Vacation! Better Yet, Make it Your Year Round Dream Spot! Either Way, this Most Inviting and Beautiful Home Awaits Your Arrival! Once a Quaint Cottage, Then Transformed, Expanded Upon and Renovated in 2010 by Long Time Local Builder John Bertani. This Home Boasts a Spectacular and Airy Open Floor Plan with Two Bedrooms and Bath on the First Floor. Make your way Upstairs and Enjoy a Full Floor Primary Suite with Spacious Sitting Area with Partial Water Views of Goose Creek, Two Walk in Closets and Bathroom Complete with Soaking Tub and Large Shower. Situated Only Two houses from Private Goose Neck Estates Beach with a Second Entrance for Boaters just Across the Street! Docking Rights upon availability. Make it Yours Before Summer!

BEACH MEET BARN "Two Worlds Collide" in this breathtaking modern barn, nestled on 1.9 pastoral acres just a stone's throw from Duney, ocean-like Kenneys Beach, Sunsets and renowned Seaside Restaurant. This stunning residence features approximately 4700 sq ft of living space, a 4-car garage, separate service entrance, butler's station, a substantial light-filled kitchen, pantry room, and a great room with soaring ceilings, remote-controlled double-sided fireplace, Smart lighting controls at 8 locations for interior and exterior lighting, Sonos AV system - 8 speakers - 4 interior 4 exterior. The first floor includes a powder room, laundry room and a primary bedroom ensuite wing, complete with a naturally lit sitting area/office that opens directly onto a porch clad in "Blue Ice" and a 20'x40' "Black Onyx" pool with "Blue Ice" coping. The upper level offers a sizable loft that overlooks the great room, plus three additional bedrooms: one ensuite and two with separate wash areas leading to a shared bathing and privy room. There's also a powder room and a secondary laundry area. Completing this extraordinary home is an approximately 1000 sq ft artist studio/craft or game room. This stunning Estate is a must-have for the selective purchaser seeking "THE BEST of BOTH WORLDS"!

Welcome to your dream beach home nestled in a serene beach community on the North Fork! This newly constructed residence offers the perfect blend of modern comfort and coastal charm, presenting an ideal sanctuary for those seeking the quintessential beach lifestyle. Upon entering, you'll be greeted by an inviting open floor plan, seamlessly connecting the living, dining, and kitchen areas, creating a spacious and airy ambiance perfect for both relaxing and entertaining. The main floor boasts a convenient mudroom/laundry area, providing easy access for one-level living convenience. With four bedrooms, with three of the bedrooms featuring its own attached bathroom, including one on the main floor, this home offers unparalleled comfort and privacy for all occupants. Whether hosting guests or enjoying personal retreats, everyone will appreciate the luxury and convenience of ensuite facilities. Step outside onto the covered porch, where summer dining awaits amidst the gentle sea breezes and tranquil views of the preserved land beyond the backyard. The fenced backyard, featuring a sparkling pool for refreshing dips on hot days and outdoor seating surrounding a cozy fire pit, ideal for gathering under the stars on summerl evenings. The sandy beach community adds to the allure, offering a park area complete with picnic tables, panoramic views of the water, and access to a sandy beach where summer breezes beckon for leisurely strolls along the shoreline. This property presents a rare opportunity to experience the best of North Fork beach living. Whether you're seeking a seasonal retreat or year-round residence, this home promises a lifestyle of comfort, convenience, and coastal charm. Don't miss your chance to make memories and create your own slice of paradise in this idyllic seaside haven.

Ready This Season in June! Welcome to the Tranquil and Highly Sought-After Community of Beixedon Estates-a Private Neighborhood Consisting of 75 Acres of Waterfront Property and Overlooking Serene Pastoral Farmland. This Hidden Gem Location Offers Two Points of Deeded Water Access!! Ideally Situated One Mile from Charming Southold Village and in Close Proximity to Greenport's Eclectic Shops, Nightlife and Vibrant Food Scene! New Construction Deliverable 100% Turn-Key Ready for This Season w/Heated 16x32 Saltwater Pool and Convenient Pool House w/Bathroom. Expertly Crafted Floor Plan Features Over 3,100 Sq. Ft. Over Three Levels, First and Second Floor Bedroom Suites, and Bursting With Luxury Finishes And Amenities Included - Custom Double Cabinetry Stacked To The Ceiling, Imported Italian Tile, Premium Appliances, 2 Inch Mitered Kitchen Island Countertop, 4 In. Wide-Plank White Oak Flooring Throughout, Massive 10 Ft. Ceilings on Semi-Finished Lower Level w/Egress and Outside Entrance, Plush Sod, Sprinklers and more! Pics are of model home. FInishing touches available to be customized for a very limited time!

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.

Welcome to 630 Calves Neck Road! This new construction North Fork diamond boasts 4,400 square feet of luxury with 4 en-suite bedrooms, 5.5 baths and a huge bonus room with skylights. Set on .75 acres and offering seamless architectural details, the meticulous craftsmanship is evident in a gorgeous EIK with center island, high end finishes including Wolf and Sub-zero appliances, marble and porcelain baths, radiant heat, and double washer/dryers. One sun-filled room flows into the next for the ultimate in comfort, convenience and modern day living. Each detail has been thoughtfully designed from the vaulted ceilings, built-ins, cabled railings and pantry, to a fully fenced heated salt water in-ground pool, first floor primary bedroom, gas fireplace, and gleaming hardwood floors. Close to marinas, beaches, boating, golf, shopping and world class restaurants, farms and vineyards. Don't miss out on the opportunity to make it all yours!

Welcome to Founders Village - an exclusive 55+ community offering the epitome of comfort and convenience! This immaculate home 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 your own beautifully maintained two-bedroom, two-bath condo. With a full 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!

Looking for a new updated house on the water but don't want to do the work? Come look at this newly renovated farmhouse-style residence harmoniously combines rustic charm with modern elegance, all while boasting a prime waterfront location complete with a private bulkhead , Deepwater dock and 15 feet of sandy beach off the Peconic bay. You can enjoy the serene waterfront lifestyle with a deep water dock to go fishing or just launching the paddle board. This farmhouse-style home on the North Fork represents a perfect blend of pastoral charm and modern living, offering a unique opportunity to enjoy a peaceful, waterfront lifestyle in one of the most coveted locations on the island. With its natural materials, thoughtful design, and unparalleled setting, it's a true haven for those seeking a north fork life style. HOUSE STILL UNDER RENOVATION

This 5 bedroom, 4 full bathroom home offers a truly luxurious living experience. The open concept design seamlessly connects the kitchen to the dining and living areas, creating a warm and inviting space for gatherings. Step outside and you'll discover a true oasis. The inground pool invites you to cool off during hot summer days. The beautiful stone hardscape finishes add a touch of elegance and sophistication to the outdoor space, creating a serene atmosphere for outdoor entertaining. Set on a generous .92 acre lot, you'll have plenty of space to enjoy outdoor activities, whether it's gardening, playing sports, or simply taking a leisurely stroll. The well-manicured grounds provide a picturesque backdrop for the home. One of the unique features of this property is the accessory apartment with a separate entrance and a fully equipped kitchen. This additional living space offers flexibility and versatility, allowing for multigenerational living or a private guest suite. Close to beaches, wineries, town and restaurants!

Just 2 blocks from historic Hortons Point Lighthouse & LI Sound, this exquisite 3800sf Nantucket style home, a 1900s farmhouse redesign, is set back 180' from road. Mahogany front porch surrounds double entrance w/views of beautiful, perennial garden & hydrangeas. Entering, you'll find a spacious foyer, living room, & private office. French doors lead to gorgeous stone patio, huge exotic wood deck, fire pit. Expansive first floor main suite w/huge walk-in closet & newly remodeled large en suite bath w/Carrera marble, soaking tub & shower. Second floor offers 3 generous bedrooms w/plenty of closet space, full bath, & sitting area w/balcony overlooking living room. The home features HW floors & custom woodwork throughout. Spacious farmhouse kitchen w/huge center island provides views of meticulously landscaped backyard. Formal dining room just off kitchen for entertaining. Expansive private yard, w/room for pool and distant farm views, is a secluded sanctuary.

Must see charming waterfront cottage. Newly renovated and with direct access to Arshamamoque Pond. Features 2 bedrooms & 1 completely new bathroom, painted wood floors and wood burning fireplace, 2-3 Car Parking Space & Electric Outlet Nearby. Amazing views from the open kitchen, living room and sunroom. Relax and enjoy beautiful sunrises, cool breezes and alfresco dining on the deck and at the fire pit. Move in ready.

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