ML# :827387   Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land.Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards, marinas, golfing, boutique shopping, galleries, and more.A once in a lifetime opportunity to build your dream estate - perfect for an all inclusive equestrian facility. All with the utmost privacy in this amazing piece of paradise. Potential for 2 acre subdivision.

ML# :822706   In the last month there have been lots of updates made to this exquisite waterfront home with wrap around porches and breathtaking views. Don’t miss this opportunity to own a waterfront property on the North Fork. Perfectly situated on the protected and tranquil 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. There 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., Additional information: Appearance:ExcellentNew features include: central air, new front walkway, back yard tree removal and grass lawn installation, interior painted and new light fixtures.

ML# :3590177   Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76, 230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the ’tower’ of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!, Additional information: Appearance:immaculate, Interior Features:Lr/Dr

ML# :905803   Enjoy a beautifully updated home in the desirable Harbor Lights beach community. This home has everything you need to live an amazing North Fork life with hardwood floors throughout, an open floor plan, privacy and an amazing back deck overlooking the backyard. The first floor offers an open floor plan, a beautifully updated eat in kitchen. Enjoy the living room/dining room with a fireplace while overlooking the back patio and backyard. The second floor has 3 bedrooms and a loft. This property is part of the Harbor Lights Community where you can enjoy a private beach that overlooks the peconic bay and shelter island. If you are looking for the perfect North Fork home this is it!

ML# :3487080   A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR, , LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good

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# :922975   Stately and classic vintage farmhouse with wrap-around porch, original in-tact architectural details and hardwood floors throughout. Built in 1900 as part of the Southold Hotel on Main Road. Moved to current location in 1920. Beautifully maintained with lots of natural light, eat-in kitchen, large private back yard, walking/biking distance to Southold Village and Founders Landing Park with playground, clubhouse, & bay beach. Walk to LIRR & Jitney.

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# :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.