Charming Oregon Road1800’s Farmhouse with Sweeping Bucolic Views and year round stunning sunsets. Experience country living at its finest in this beautifully maintained farmhouse overlooking scenic agricultural farmland. This inviting home features 3 bedrooms and 2 full baths, blending historic charm with peaceful rural surroundings. Enjoy breathtaking views, open skies, and the tranquility of farm country while being within easy reach of local amenities. Full basement, 1 car garage, storage shed.
Discover this stunningly renovated 4-bedroom, 3-bath home, offering an expansive open floor plan, a cozy den, and a versatile bonus room. Designed for both comfort and style, the chef’s kitchen includes a massive eat-in-quartz island and boasts top-of-the-line Fisher & Paykel appliances, including a double-drawer dishwasher, induction cooktop, and convection oven.
Perfect for entertaining and everyday living, this home features multiple dining areas (indoors, outdoors, and in a charming screened porch). Utilize easy work-from-home options with several dedicated spaces, while the heated 18′ x 36′ pool and lush, inviting lawn just shy of a full acre provide the ultimate setting for summer relaxation.
Nestled on a quiet residential street, this exceptional home is just a short distance from beautiful beaches, vibrant downtown shops, and many restaurants and wineries. A perfect blend of modern convenience and coastal charm—this is a home you won’t want to miss!
WINTER 2026/2027 – October 2026 – $12,000.. November 2026 to March 2027 -$8,000 per month (for single or multiple months). SPRING 2027 – April and May 2027 – $12,000 per month. SUMMER 2027 -Memorial Day to Labor Day $90,000; June $20,000; July $30,000; August to Labor Day $40,000. Permit #1281.
Completely renovated and ready to enjoy, this 4-bedroom, 2.5-bath Colonial in Mattituck delivers the feel of new construction without the typical new-construction tax burden, with annual taxes of just $9,560. The home has been extensively updated from top to bottom, including a new roof, new windows where needed, new doors, new central air conditioning, new wide-plank hardwood floors, new chef’s kitchen with large center island and high-end appliances, new patios, new irrigation and landscaping, new landscape lighting and more. A wood-burning fireplace anchors the main living space, while first-floor laundry adds everyday convenience. Upstairs, four generously sized bedrooms provide ample living space, including a primary suite with an en-suite bath and walk-in closet. The full basement expands the usable footprint even further, offering walk-out access (OSE) and an outfitted game room and potential gym. The additional space creates flexibility for recreation, fitness, work space, storage or a combination of uses. Outside is where the property truly separates itself. Set on an extremely private and flat .91-acre parcel, the yard offers a rare amount of usable lawn, privacy and open farm views backdropped by sunsets. A brand-new heated saltwater pool serves as the centerpiece, complemented by new sod, and newly completed front and rear patios. The property also includes a two-car garage. The location places you close to everything that makes the North Fork such a sought-after destination, with Harbes Family Farm just moments away, local vineyards and farm stands around the corner, and the famous Love Lane less than five minutes from the property. With nearly every major improvement already completed, low taxes, substantial indoor and outdoor living space and a setting that is difficult to replicate, this is a turnkey Mattituck property that offers the opportunity to move in and immediately begin enjoying the home and its surroundings.
Charming 2-bedroom, 1-bath home in desirable Cutchogue, featuring an attached 2-car garage and room for a pool. A wonderful opportunity to make it your own, with potential to expand, upgrade, and design to suit your vision. Close to restaurants, beaches, and North Fork vineyards.
MIAMI MODERNISM MEETS THE NORTH FORK. Set on a spacious and private .60-acre hilltop parcel in coveted Nassau Point, this fully updated four-bedroom modernist ranch offers an unexpected departure from the ordinary. Its traditional exterior gives little indication of the sleek, light-filled interiors within—an independently conceived home with the confident glamour of Miami and the relaxed ease of Cutchogue.
Individual design matters. Rather than repeating a familiar, cookie-cutter floor plan, this residence has an architectural identity all its own, expressed through gleaming white marble floors, clean lines, generously proportioned rooms and a seamless connection between indoor and outdoor living. The result feels distinctive, sophisticated and refreshingly personal.
At the heart of the home is a spectacular chef’s kitchen designed for serious cooking and effortless entertaining. It opens to a private garden courtyard, creating an intimate setting for morning coffee, outdoor dining or summer evenings with friends, and an ideal location for a future pool. A comfortable den with fireplace leads to more than 600 square feet of decking, while the bright formal living and dining rooms provide gracious spaces for larger gatherings.
Nearly 2,000 square feet of living space includes four bedrooms offering exceptional flexibility for overnight guests, working from home, fitness or creative pursuits. The expansive primary suite is a private retreat with a dedicated office area, large walk-in closet and sparkling marble bath. A guest bath and separate laundry room complete the main level, while the finished lower level provides valuable additional space for recreation, media or hobbies. An oversized two-car garage offers generous parking and storage.
Just up the road from sublime Fisherman’s Beach, the property enjoys access to Nassau Point’s rights-of-way beaches and nearby Causeway Beach on the Peconic Bay. Spend the day swimming, kayaking, paddleboarding or boating, then return home for cocktails on the deck or dinner in the garden courtyard. Causeway Beach also offers a designated swimming area, summer lifeguards, picnic facilities, playground equipment, a basketball court and restrooms.
This sought-after Cutchogue location places vineyards, farm stands, celebrated restaurants, local shops and the villages of the North Fork within easy reach. Private but never isolated, stylish without being conventional, this is a rare opportunity to experience the Nassau Point lifestyle in a home with a point of view all its own.
Welcome home to an unparalleled North Fork retreat located on over 2 acres, nestled at the end of a winding stone driveway. This striking new construction farmhouse perfectly blends sophisticated craftsmanship with the casual elegance of coastal country living. Spanning approximately 3,000 square feet, the open layout features four spacious bedrooms and 4.5 beautifully appointed bathrooms. Designed for ultimate flexibility, the home boasts two luxurious primary suites—one conveniently located on the first floor and a second on the upper level. The full basement with direct outside access, offers an ideal canvas for a custom home gym, media room, or a private wine cellar. The home’s impressive exterior design seamlessly gives way to an outdoor entertainment oasis. Hidden behind a lush border of mature trees, the sprawling, professionally landscaped grounds feature a heated saltwater pool and a dedicated chiminea area for cozy evening gatherings. You can spend your days relaxing under the deep, welcoming covered front porch, hosting dinners on the rear porches, or taking in elevated views from the private balcony. Situated in the heart of Mattituck, this exceptional property balances absolute privacy with effortless access to all the North Fork has to offer.
Welcome to 1355 Watersedge Way, a delightful Bayfront home offering breathtaking water and sunset views in Southold. Nestled next to a nature preserve with 300 feet of private beach, this home provides both serenity and direct water access.
Inside, the spacious living room features a a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze. The eat-in kitchen, two bedrooms, and one full bath complete the main level.
The lower level offers even more space to relax and entertain, with a family room, wet bar, third bedroom, full bath, and washer/dryer, plus easy access to the outdoor shower and beautiful backyard.
Whether you’re looking for a peaceful retreat or a waterfront getaway, this home is a rare find. Don’t miss the opportunity to experience the best of Bayfront living!
2026 Rates: August $14,500, Sept $8,000, October $7,000. WINTER RATES $4,500 per month November through April. RP# 0929
Two week minimum rental. Available in July and August, $4,500 / week. August 16 through Labor Day, $5,500/week. 3% discount for rentals longer than 3 weeks.
Perfectly situated in one of the North Fork’s most desirable beach communities, this welcoming 4-bedroom, 2-bath, 2-story beach bungalow is just a 3 minute stroll to the sandy shoreline of Kenney’s Beach, 7 minutes to the Great Pond, a 10 minutes to McCabe’s beach and a 2 minutes over to Little Fish restaurant.
Oozing vintage beach-house charm, this gem makes for the perfect seaside getaway with family or friends where you can park your car and leave the city behind.
What makes the house special is being surrounded by sandy outdoor space, the comfortable gathering spaces for family and friends, anchored by two levels of patio, an outside fire pit on the sand, and an indoor wood-burning fireplace for cooler evenings. It feels like your own private beach oasis and a private after-hours evening at the beach.
The spacious main-level deck is ideal for al fresco dining after a day at the beach, and a private second-floor deck off one of the bedrooms where you can enjoy evening sunsets, and views toward Long Island Sound.
Fire up the new grill after a day by the water, unwind with a good book on the deck, or grab the provided beach chairs and umbrella and stroll to Kenney’s Beach for swimming, beachcombing, or simply watching the sunset.
Beyond the neighborhood, discover the very best of the North Fork, from award-winning wineries and farm stands to waterfront restaurants, galleries, boutiques, and charming village centers.
Other nearby favorites are Horton Point Lighthouse, a beach stroll that connects the coast from Horton’s Lane (one of the most picturesque inlets) to MacCabe’s and Kenny’s Beach (40 minute walk), easy hiking and walking trails at Goldsmith Inlet Park, and Little Ram Oysters farm stand. Close proximity to Greenport, East Marion and Southold.
Whether you’re planning a family vacation or a getaway with friends, this inviting Southold retreat offers the perfect combination of beach bungalow charm, comfort, convenience, walkability and the effortless coastal lifestyle that makes the North Fork such a special destination.
A quintessential North Fork retreat in Beixedon Estates in an extraordinary waterfront setting. Tucked beside the winding Hippodome Creek and surrounded by lush coastal landscape, this charming month-to-month rental offers privacy, tranquility, and beautiful water views just moments from the Bay. The property’s peaceful natural surroundings create the perfect backdrop for relaxed morning coffee outdoors, cozying up to the fireplace indoors, days spent exploring the North Fork, and evenings enjoying the coastal breeze. A truly special escape where the beauty of the North Fork is right outside your door. Ask about available months. Southold Town Rental Permit #1510
Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the “diamond in the rough” you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can’t be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this in the heart of Greenport are few and far between, so don’t let this one slip away.
Available Seasonally June 20K, August 16th-Labor Day15K
TIMELESS TRANQUALITY ON GARDINERS BAY – An inviting seasonal beachfront retreat on Gardiners Bay, thoughtfully designed as a peaceful escape from the demands of everyday living. Begin your mornings with beautiful sunrises over the water and settle into the quiet rhythm of bayfront living throughout the day. The home offers an open airy layout with three full sized water-facing bedrooms, updated fully equipped kitchen and baths and comfortable modern amenities throughout. A generous enclosed porch provides a versatile space for dining, working remotely or simply slowing down. Outdoors, a charming portico invites alfresco meals with a gas grill while an outdoor shower completes the experience– an effortless calming setting for refined yet relaxed bayfront living. Fully furnished and equipped with necessary linens and towels. Close to fine dining, golf and a versatile selection of wineries for additional enjoyment and entertainment.
Southold, North Fork: Discover the epitome of easy living at Unit C “Baldwin T. Payne” in Southold, North Fork. This condo-like residence, part of the North Fork Resident’s Inn, offers a one-of-a-kind opportunity to embrace a modern lifestyle in a historic setting. The unit boasts a spacious layout with direct garden access, abundant natural light, and contemporary furnishings. With upscale appliances (including gas range, refrigerator/freezer with ice maker, dishwasher, on-site laundry, and more), wide plank floors, and elegant marble touches, every detail has been carefully considered. The property is conveniently located near public transportation, quality shopping, parks, and beaches, making it an ideal choice for anyone seeking a convenient and comfortable living space. With flexible rates throughout the year (MD-LD $19k; June $5.5k; July $7k, Aug-LD $8k, Bal of Sept $5.5k; October $4.5k; November through April $3k per month; year-round $3.5k per month; weekly $2k -2 week min.) and the possibility of bringing pets with landlord approval, this property is a standout option for those looking to vacation or settle into the North Fork lifestyle. Broker/Owner. Rental Permit #0171
2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!
Broadwaters Cove Bliss: The Ultimate Peconic Bay Summer Retreat
Welcome to your quintessential seasonal getaway on Broadwaters Cove, where classic, laid-back “summer camp” nostalgia meets modern comfort. This cozy waterfront haven features direct, seamless access to the spectacular Peconic Bay and boasts inviting, practical updates, including a fully refreshed kitchen and clean, updated bathrooms. Designed for simple, easy living, the property offers stunning water views from comfortable outdoor seating areas and features a massive, flat, open green lawn that is absolutely perfect for lively afternoon tournaments of croquet, frisbee, or your favorite lawn games under the sun.
Bring your boat and tie up right at your private dock for a summer of effortless adventure. Broadwaters Cove and the surrounding Peconic Bay waters are legendary among anglers, allowing you to spend your quiet mornings casting a line straight from the dock for local favorites like fluke, porgy, and striped bass. Because your boat is securely moored right at the property, you can skip the marina lines entirely and head out whenever the mood strikes to explore the scenic bay, cruise over to Shelter Island, or seek out the best deep-water fishing hot spots.
When you aren’t out on the boat, the property serves as your personal launching pad for waterfront fun with handy outdoor gear fully included. You can explore the calm, protected waters of the cove at your own pace using the house kayak and stand-up paddleboard. For days when you want to feel the sand between your toes, the scenic Nassau Point Causeway beach is just a half-mile down the road. We’ve even provided four beach chairs and an umbrella to make your seaside excursions completely effortless. Unwind, unplug, and reel in a relaxing, authentic North Fork summer at this welcoming waterfront escape.
Fully rented Sept. 1, 2026 to June 30, 2027. Ask about Summer 2027
Bayfront historic artist’s home in Peconic. Built in 1911, this home was the residence of 2 prominent artists. Gorgeous views of the Peconic Bay with private stairs down to the beach. Peconic bay beach is long and sandy. Several outdoor tables and benches to take in the water views. A large lawn perfect for games. The interiors are decorated with antiques and contemporary furniture. A screened in dining porch with bay views. Evening dinners with the moon over the bay. Large kitchen with a separate pantry. Stairs off the kitchen to a private room that may be used as an office and has a single bed. The 16′ X 33′ open living/dining room and 4 of the 5 bedrooms have mini split AC. Most of the time the bay breezes and big trees keep the home cool. High speed wifi. Side patio has outdoor shower and changing room and gas grill.
This is a place to spend a few weeks and experience the old North Fork at it’s best!
2026 is booked. Available summer 2027.
