ML# :3555058   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!!, Additional information: Appearance:Mint, Separate Hotwater Heater:N

ML# :3509055   Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150., Additional information: Interior Features:Lr/Dr

ML# :832312   Head inside this custom-built, one-owner home nestled in a serene mid-block location, just moments from Southold’s finest beaches including Kenney’s and McCabe’s Beach and a few blocks from Little Fish restaurant. This move-in-ready post-modern home boasts an open-to-above entry with gleaming hardwood floors, well-appointed rooms, and a professionally designed kitchen featuring high-end stainless steel appliances, including a built-in wine fridge, a professional-grade Thermador gas range and a Thermador dishwasher. The open-concept layout is perfect for entertaining, with a spacious family room complete with a gas fireplace, seamlessly connecting to the kitchen. Make memories on the large custom built maintenance-free Trex deck, ideal for outdoor gatherings or for simply enjoying amazing sunsets in the serenity of your private backyard with room for an IG pool with site inspection on file with town. Designed for year-round comfort, this home features a two-zone gas heating and two-zone central air systems with oversized Andersen windows that flood the space with natural light. The upper level includes a luxurious primary suite with two walk-in closets and a spa-like bath, along with three additional bedrooms and the convenience of a second-floor laundry room. Additional highlights include an oversized two-car garage and a full basement with 9-foot ceilings, offering ample storage and potential for finishing. Built to green-certified standards with engineered framing for lasting quality, this Southold gem is the perfect blend of comfort, convenience, and luxury.

ML# :804563   The Perfect Beach Bungalow Getaway! An Idyllic Location, With Kenney’s Beach Practically At Your Doorstep, This Charming Bungalow Offers Ample Space For Everyone With Five Bedrooms And Two Bathrooms. Relax And Unwind On The Outside Decks Enjoying Morning Coffee, Fresh Sea Breezes And Evening Sunsets Or Warm-up Indoors by the Fireplace. With Its Wonderful Location, Numerous Amenities And Proximity To Local Attractions, This Beach Bungalow Offers Everything You Need For A Memorable Escape. Prepare For A Rejuvenating Retreat At Kenney’s Beach!

ML# :827612   Welcome to this beautifully maintained 3-bedroom, 2-bath ranch set on a pristine half-acre. Enjoy the best of indoor and outdoor living with a spacious living room w/FP, bright den and primary BR ensuite. Step outside to your own private oasis - an expansive 16’x32’ inground pool surrounded by manicured landscaping and plenty of room for entertaining. Private cul de sac and association with its own boat ramp and common area at end of street. Easy access to boating and kayaking and just minutes from town, beaches, vineyards, and farmstands. This home offers the perfect blend of serenity and convenience. Move-in ready and perfect for year round living or a weekend retreat.

ML# :820321   Amazing opportunity to own a charming 1830s home with a detached accessory apartment built in 2016. Renovated in 2003, this home sits on an acre of land surrounded by unbuildable land, offering privacy and a peaceful setting. With great bones and timeless appeal, the main house features a well-designed floor plan, a cozy living room with a wood-burning fireplace, and plenty of character throughout. Located in a fantastic spot close to the beach, this property combines historic charm with modern convenience. A separate 1 bedroom cottage adds flexibility—perfect for guests or extended family. A rare find in an unbeatable location! Room for pool!

ML# :887530   Tucked away in the heart of Southold, this adorable 3-bedroom, 2.5-bath ranch offers a rare combination of privacy, small-town charm, spacious living, and tranquil outdoor amenities — including access to dockage (with application from town), with direct bay access and ideally located a few steps from all the conveniences of downtown Southold shopping, dining and the Hampton Jitney.Set on a generous and beautifully landscaped lot, the home welcomes you with a breezy open-concept layout where the living room with fireplace flows seamlessly into the dining area. Large windows invite natural light and peaceful backyard throughout the main living space.Step outside onto a back deck, perfect for entertaining, dining al fresco, or simply enjoying the sights and sounds of nature as well as a beautiful pond view. The expansive backyard offers ample room for gardening, recreation, or even a pool.With three comfortable bedrooms, including a primary suite, hardwood floors, and an easy single-level layout, this home is ideal for year-round living or a weekend getaway.Located in the vibrant village center of Southold — close to beaches, vineyards, farm stands, and local favorites — this property is a rare find that blends convenience, serenity, and North Fork lifestyle at its finest.

ML# :840724   ***NEW IMPROVED PRICE**Ideal for the Self-Employed Buyer or Multigenerational family: Flexibility, and Income Potential in Southold’s Wine Country.This beautifully renovated farmhouse blends timeless charm with modern comfort—perfectly suited for self-employed professionals. With 5 spacious bedrooms and 3 elegantly updated bathrooms across 2 floors, this home offers flexibility.A comprehensive gut renovation done less than five years ago, gives buyers the opportunity to unpack and enjoy!For those looking to generate additional income or accommodate multigenerational living, the layout provides an ideal opportunity—pending proper permits—to create a separate 2-bedroom, 1-bath rental unit. This option adds a layer of flexibility and long-term value for self-employed buyers who may benefit from rental income or guest accommodations. A full basement offers generous storage and the potential for a home gym, studio, or workshop.The detached 1.5-car garage and two driveways offer parking for up to 8 vehicles! The spacious yard provides plenty of room for a pool or outdoor entertaining.Located just minutes from pristine beaches and only a mile from Southold’s quaint downtown with shops, dining, and a vibrant local scene, the home is also close to farm stands, award-winning wineries, breweries, and boating—making it the ideal base for a fulfilling and inspired lifestyle.

ML# :862942   Lovely light-filled 3-bedroom 3 bath inland end-unit in The Cove – a small hidden gem of a waterfront community nestled in the heart of the North Fork. There are boat slips for your boat with easy access to the beautiful Peconic Bay, boat racks for your paddleboard/kayak, a gunite in-ground pool, and combination tennis/pickleball court – both of which were just resurfaced this year! The airy open concept living room and dining room share a wood burning fireplace and there is a balcony off the living room. The kitchen has granite counters and sliding glass doors to the deck and the backyard. Also on the first floor is a spacious primary bedroom suite with sliders to the deck and a large ensuite bathroom. The 2nd level has two more generous bedrooms, a library/media room, and full bath. There is storage galore in the finished basement with a separate laundry area, and a one-car garage. The entire community is presently in the process of being re-shingled with handsome grey Hardi-shingles and white trim. Beaches, wineries, farms, breweries, golf, & hamlet shopping, dining, and transportation just moments away! A perfect, maintenance-free Retreat!

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.