ML# :916546   Nestled on .49 acre corner lot, this 2-bedroom, 1-bath home offers a thoughtful blend of comfort, charm, and modern updates. The heart of the home is the large kitchen, beautifully redone in 2018 with granite countertops, stainless steel appliances, a pantry, coffee bar, wine fridge, and a peninsula with seating that makes entertaining effortless. An open dining area flows naturally into the living room, where a wood-burning stove creates a warm and welcoming atmosphere. A spacious den provides endless possibilities, currently set up as a sunlit lounge—but you may envision a home office, playroom, gym, or future guest room conversion. Additional conveniences include first-floor laundry, propane gas cooking, oak wood floors throughout, and a full unfinished basement for storage or expansion.This home has been meticulously maintained and upgraded, offering peace of mind with a brand-new HVAC system (2024), roof, siding, windows, and Trex deck (2020). A detached 2-car garage and full-house generator add to its appeal. Low taxes! Ideally located near both Southold Village and historic Greenport, the property offers the best of both worlds. Wineries, local farms, and farm-to-table dining are just moments away, while boating enthusiasts will appreciate nearby marinas. Serene beaches like Town Beach and Goose Beach are close by. Rental permit in place. Furniture potentially included with sale, if desired. Whether you’re seeking a year-round residence, a North Fork retreat, or investment opportunity — this move-in ready gem invites you to settle in and start enjoying the North Fork lifestyle right away!

ML# :856377   Residential/Hamlet Business OpportunityBeautifully restored and updated Colonial Path House located in the heart of wine country. The front facade of the house has been restored to clapboard siding and cedar shake. The original rooms on the first floor include a parlor with wood burning fireplace, an adjacent dining room, farm kitchen and full bath/laundry room. Antique wide plank floors throughout. The second floor has 2 bedrooms, large storage closet, and full bath with an antique soaker tub. A new addition in 2007 compliments the old part of the house while modernizing the space with an ensuite bedroom, living room, a year-round sunroom, and working fireplace with a hand carved mantle from a Victorian Mansion. 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. A successful and popular bed and breakfast was operated in this new addition. An accessory cottage is perfect for your studio or office. Access to Founders Landing Beach.

ML# :817145   Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot, Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life, You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom Conventional Septic System, (I/A NOT REQD.) Making It Ready For Your Grand Vision. Whether You’re Looking To Build A Sprawling Family Estate, A Charming Vineyard Retreat, Or Anything In Between, The Possibilities Are Endless. Truly Shovel Ready Embrace The Tranquility Of Country Living With All The Benefits Of Being Near The Heart Of The North Fork’s Sought-After Attractions. Don’t Miss This Rare Opportunity To Create Your Own Slice Of Paradise!

ML# :860794   Summer Cottage in Southold – Just steps from the Long Islands Sound. Experience quintessential North Fork living in this completely renovated charmer featuring 3-bedrooms, and 1-bathroom perfectly positioned just steps from the beach and minutes drive away from other local beaches. Offering unrivaled access to stunning sunsets and the coastal lifestyle, the cottage features warm wood-beamed ceilings, hardwood floors, and a bright, open living area that flows effortlessly into the kitchen and dining nook — ideal for relaxed summer living and entertaining. While modest in size, this home’s true value lies in its unbeatable location and lifestyle appeal — a prime investment for those seeking a serene seasonal retreat or an exclusive North Fork address.

ML# :889540   Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this property - medical property, nursery school, place or worship and many more!

ML# :848766   Discover this beautifully maintained 2-bedroom, 1-bathroom cottage nestled on a tranquil road just moments from the beach. Perfectly blending modern comforts with coastal charm, this home offers a serene retreat for beach lovers and those seeking a peaceful lifestyle. Enjoy the convenience of being close to the beach, allowing for easy access to sun, sand, and sea. Relax in your own secluded outdoor space, ideal for gardening, entertaining, or unwinding in solitude.This cottage has been meticulously maintained, ensuring a move-in-ready experience for its new owners. Situated in the back of the property is a carriage house. This extra space allows for an opportunity for guests to stay and enjoy on their own timeframe. If offers a murphy bed, full bath and kitchen. Or if you need more space, it’s perfectly situated to be used as a studio, office, or hideawayWhether you’re seeking a year-round residence or a seasonal getaway, this cottage provides the perfect setting to enjoy coastal living at its finest.

ML# :919707   Discover a beautifully renovated unit featuring ceramic tile throughout and two modern marble full bathrooms, including a primary ensuite with walk-in custom closets. Enjoy a spacious open living room with a cozy fireplace and sliders leading to a patio, seamlessly connected to the dining area and large eat-in kitchen. Convenient main floor washer and dryer. The property boasts a very large, clean, and dry full-size basement. Nestled in a 55+ community with lush greenery, an in-ground pool, and a clubhouse perfect for socializing. Ideally located just a short distance from town, train, shopping, the library, and the beach.

ML# :917302   Southold - Jonathan Jennings House circa 1761- Moved to its current location in 1761, this clapboard home has historical and architectural significance. The original wood frame house was built with interlocking joists and carelessly dressed ceiling beams. The house has a baker’s brick oven with an ash pit, two fireplaces, and a brick foundation. Reportedly the first owner, Jonathan Jennings, served as a soldier in the Revolutionary War, was captured by the British, and died on a prison ship in New York Harbor. Located at the intersection of Main Bayview Road and Baywater Road, the property was also known as Halfway House because of its position on the Bayview Peninsula. Subsequent ownership included Southold blacksmith Doc Billy Glover at the turn of the 20th century. Currently, the two-story house consists of a dining room with a brick floor, kitchen, office, parlor room with fireplace, living room with fireplace, three bedrooms and two bathrooms. The level treed property is .63 of an acre. In addition to the house, there are two outbuildings: a two-car garage and a storage building. The storage building has a partially finished second level. Opportunity to own and restore a property with a rich history that is ready for its next chapter. Please call for additional information or to schedule a viewing. Access to Southold Park District beaches. Enjoy the North Fork experience: restaurants, golf, beaches, shopping, farm stands, wineries, breweries, boating. It’s all right here.

ML# :912228   Rare opportunity to build your dream home on this approved parcel, complete with permits and BOH approval for a stunning 4-bedroom, 3.5-bath residence. Plans include a single-car garage and a spacious 9’ basement with outside entrance and egress windows, offering a total of 3, 100 square feet including the lower level. The property also offers the option to join the Goose Creek Association, where you can enjoy private docking rights, a sandy beach, and dedicated space for your kayaks and paddle boards. Whether you’re looking for a full-time residence or a seasonal retreat, this property is perfectly positioned to deliver a lifestyle of comfort, recreation, and coastal charm.

ML# :874383   Turn-key 7-acre vineyard that you’ve been dreaming of in Southold! Perfectly situated near the village and shops. The vines are in their prime and have been meticulously maintained. Planted in 2006 is 2.2 Acres of Chardonnay and 2.5 Acres of Merlot and 1/2 acre Muscat Ottonel was planted in 2019. Producing approximately 2-3 tons per acre of grapes annually. Fully deer fenced, irrigated by well water, bird netting and connected to electric. This right-sized vineyard may be just what you need to create your first vintage or add an additional fruit source to your existing farm operation. This farm has all development rights sold and is for agricultural use only.