$6,500 per month
400 Town Creek Ln, Southold, NY 11971
400 Town Creek Ln, Southold, NY 11971Explore North Fork
$6,000 per month
540 2nd St, Greenport, NY 11944
Be a part of the action in Grernport Village. Lovely 2 bedroom 1.5 bath house, with a 3rd pass through bedroom. Central air. Gas stove. Renovated in 2023. All modern appliances and bathrooms. Combining the charm of an antique home with modern comfort. Quiet location, yet close to all that Greenport offers. [[Rental Registration # R25-046]]
$2,700 per month
1215 Main St Unit 1A, Greenport, NY 11944
Pristine first floor Greenport apartment featuring kitchen, dining area, laundry, living room (ceiling fan), bedroom (ceiling fan), full bath. utilities included. Year lease $2,700/mo. Permit# 1063
Janet Markarian Daniel Gale Sothebys Intl Rlty
$2,500 per month
53995 New York 25 Unit 1, Southold, NY 11971
Brand New Tastefully Renovated Furnished Apartment conveniently located in the heart of Southold. The apartment is Available to rent for Year Round or flexible time-frame(s). Public transportation is in near proximity, along with everything else the North Fork has to offer.
Joseph Divello Century 21 Albertson Realty
$5,000 per month
145 Founders Path, Southold, NY 11971
Beautiful Charming Cottage Located in the Coveted Community of Founders. Close to a gorgeous sandy beach, grocery shopping, coffee shop, restaurants, jitney stop, and all things North Fork. Three bedrooms, one bath, LR, kitchen, outdoor deck, fire pit, outdoor shower. Available Sept. $5000, Oct & Nov $4000, Dec through March $2,800, April $3,500. May $5,000, June $6,000 and August $10,000.
Diane Mollica Compass Greater NY LLC
$3,000 per month
314 North St, Greenport, NY 11944
Location, location, location. Located in the Village of Greenport this quaint year-round rental is just a short distance into the Village with all the shops, restaurants, public transportation and parks. This home has a large property, 2 bedrooms, 1 bathroom, a lovely kitchen and a family room. For your convenience there is a washer and dryer. Application is required. Tenant to pay all
Barbara Poliwoda Douglas Elliman Real Estate
$3,400 per month
2555 Youngs Ave Unit 11E, Southold, NY 11971
Year Round Rental Opportunity in Founders Village 55 and over Community in the heart of Southold Village. Beautiful end-unit overlooking open space., one of the best locations in the entire condo community. Primary en-suite, bath with tub/shower. Guest bedroom with hall bath and walk-in shower. Living room with fireplace leading to a brick patio. Washer & dryer on main living level, full
Nancy Cervelli Daniel Gale Sothebys Intl Rlty
$14,000 per month
21 Stirling Cove Unit E, Greenport, NY 11944
Welcome to your ultimate retreat in the charming village of Greenport, NY. This luxurious condo offers both relaxation and adventure, with stunning bay views and private beach access. The open layout features elegant hardwood floors and central air conditioning, seamlessly blending indoor and outdoor living with a private space for entertaining or unwinding. During the bright summer, enjoy your
Jennifer Benton Compass Greater NY LLC
$10,000 per month
4630 Blue Horizon Bluffs, Peconic, NY 11958
It's all about the view! Perched on a bluff overlooking the Long Island Sound this home is a retreat and nature lovers paradise. Summer rental available for August or September, two week minimum or reserve for the 2026 season. Easy beach access with your own private staircase, you'll enjoy morning walks looking for beach glass and driftwood then spend the evenings watching breathtaking sunsets.
Melissa Principi Douglas Elliman Real Estate
$4,800 per month
1155 Tasker Ln, Greenport, NY 11944
one of a most desirable spot at Greenport - Super Spacious !. This charming home offers generous rooms, ample storage, and a detached 2-car garage with a full-size loft—perfect for a studio or extra storage. Located in the heart of Greenport, a quaint, short distance to seaside village filled with shops, galleries, quiet rustic storefronts, and picturesque harbor scenes. Enjoy true beach
Chrisand Castella Douglas Elliman Real Estate
$11,200 per month
750 Kerwin Blvd, Greenport, NY 11944
Greenport-Immaculate and spacious home. A welcoming front porch leads to the sunny Living room and dining room. A fully equipped gourmet kitchen with Thermador appliances with sliding doors to back deck, family room with vaulted ceilings also has access to large back deck, there is another den/office, a full bathroom with shower and laundry all on the first floor. The second floor there are two
Amy Kirincic The Agency Northshore NY
$3,000 per month
55 Snug Harbor Rd, Greenport, NY 11944
Experience the charm of coastal living at 55 Snug Harbor Road, Greenport, NY. This inviting off-season rental spans a 13,068-square-foot lot and features 3 bedrooms and 2 bathrooms, providing a perfect escape. The property is part of the Cleaves Point community, offering privileged access to a serene private beach. The home is elegantly appointed with an eat-in kitchen and a formal dining room,
Jennifer Benton Compass Greater NY LLC
$3,250 per month
213 E Front St Unit A, Greenport, NY 11944
Newly renovated 3 bedroom apartment in the heart of downtown Greenport. All the conveniences of living in the village, tucked away on a quiet street, just yards away from the main commercial district. The first level features a large kitchen that opens up to a living room filled with natural light and a updated half bath. The 2nd level features 3 bedrooms and a large updated full bath. Enjoy
Shane Hafer Compass Greater NY LLC
$3,400 per month
2555 Youngs Ave Unit 4D, Southold, NY 11971
Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful
Susan Orioli Engel & Volkers North Fork
$3,500 per month
538 Main Rd Unit upper, Greenport, NY 11944
This charming 2-bedroom, 1-bathroom apartment offers generous living space on 2nd floor apartment. Unwind by the fireplace , or bask in the natural sunlight that fills the sun/media room. The kitchen's stylish granite countertops and a gas stovetop are complemented by essential appliances like a dishwasher, microwave and the in-unit washer/dryer for modern convenience.
Isaac Israel Richmond Realty Corp
$15,000 per month
1854 N Bayview Rd, Southold, NY 11971
Last Minute deal on Summer rental. Amazing location with private beach, amazing waterviews and a private dock! Home is fully furnished and has 2 bedrooms, 2 full bathrooms and a 1/2 bathroom. Bring your boat or kayaks!
Isaac Israel Richmond Realty Corp
$3,900 per month
4225 Stars Rd, East Marion, NY 11939
East Marion Rental! This immaculate high ranch home has a deeded private beach located less than 400 ft. away. It features an updated eat-in kitchen, separate dining room, three spacious bedrooms, three full baths and two living rooms - one on the main level and the other located on the lower walk-out level. The expansive rear yard is ideal for entertaining and enjoying summer bbq's and those
Connie Liappas Compass Greater NY LLC
$5,000 per month
215 Leon Rd, Southold, NY 11971
Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plus an additional bedroom and full bath. The well-equipped kitchen opens to the dining and living rooms, where a cozy fireplace adds charm and warmth. Sliding glass doors lead to a deck overlooking a large backyard, perfect for
Jeanmarie Bay William Raveis New York LLC
$26,000 per month
365 Chablis Path, Southold, NY 11971
Space, Luxury, and Privacy Await in This Stunning Contemporary Home! Experience the perfect blend of elegance and comfort in this beautiful home, offering an expansive backyard ideal for dining, lounging, and entertaining. Enjoy endless hours of relaxation in the inground pool, or gather with loved ones in the spacious yard. A charming gazebo provides a welcome retreat from the sun, weather, or
Diane Arpaia Signature Premier Properties
$12,000 per month
64230 County Road 48, Greenport, NY 11944
Enjoy summer fun on the North Fork in this MINT farmhouse on beautiful sprawling property! There's plenty of room for family and friends in this spacious home with 4 large bedrooms, 3 full baths, aneat-in-kitchen perfect for gatherings, impressive primary ensuite, den/home office and laundry room. Additionally, the basement is fully finished with a large and fun recreation room, full bathroom
Donald Bracken Thomas J McCarthy Real Estate
$9,000 per month
525 S Harbor Rd, Southold, NY 11971
NORTH FORK FALL RENTAL! Enjoy this Privately Situated Home in the Heart of Southold Yet Close to All that the North Fork Has to Offer- Visit the Farms, Vineyards and Shopping. Open Concept Liv Rm, Din Rm, Updated Kit, Renovated 4 Bed/5.5 Bath Home With Family and Guests in Mind. Windowed Doors Lead Out to a Fabulous Resort Style Yard. Enjoy The North Fork At This Unforgettable Poolside Paradise.
Teresa Rogers Douglas Elliman Real Estate
$5,600 per month
3175 Kenneys Rd, Southold, NY 11971
Lakefront vacation property with a fantastic view, central air and hot tub. This space is open and updated with 3 bedrooms, and bonus room. Walk to Kenney's Beach with all beach gear included. This Neighborhood is close to restaurants, wineries, farm stands and music.
Jason Romaniello Blue Shark Realty Group Inc
$40,000 per month
1160 Goose Creek Ln, Southold, NY 11971
Step back in time-without sacrificing comfort-in this beautifully preserved 5-bedroom, 3-bath home brimming with charm and nestled along the tranquil banks of Goose Creek. Surrounded by water on two sides and set on a private road, this unique property offers a rare blend of historic character and modern amenities. From the moment you arrive, you'll be captivated by the timeless architecture,
Sheri Winter Parker Corcoran
$3,800 per month
315 Lake Dr, Southold, NY 11971
Rental Permit # 0966 Fantastic home set directly on Great Pond and a block (975 feet) from Kenney's Beach with restaurant Little Fish just around the corner. This bright 3 bedroom and 2 full bathroom, with a 3 season room all window porch home has an expansive rear deck overlooking the fresh water pond. Watch osprey dive bomb for fresh water bass while geese, ducks and egrets meander across the
Alexander Aquino Douglas Elliman Real Estate
$10,000 per month
3650 Bay Shore Rd, Greenport, NY 11944
Your Fabulous Beach House Vacation! 2 Week Rentals or Monthly! Spacious summer house in the coveted Peconic Bay Estates private beach community on the Bay. A darling hidden path brings you to the sweetest surprise little wooden bridge to cross over to arrive on the sandy beach. Fun! No shirt, no shoes, lazy day, Yes! Very quiet water front cove, lots of area biking, kayaking, taking beach
Kate Carpluk William Raveis New York LLC
$12,000 per month
39595 Main Rd, Orient, NY 11957
Spacious Traditional Home with 4 bedrooms, 2.5 baths near Orient State Park and Cross Sound Ferry.The private landscaped backyard features a pool with patio and lounge chairs and a large deck with glass doors to the kitchen. The first floor has a private living room space and a kitchen/family room open plan for entertainment. The second floor has a master ensuite with full bath overlooking the
Janet Markarian Daniel Gale Sothebys Intl Rlty
$7,375 per month
2700 Sound Dr, Greenport, NY 11944
2025 Rates: September 1-30 $29,500; October $25,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4
William Walters Daniel Gale Sothebys Intl Rlty
$15,000 per month
63615 North Rd, Greenport, NY 11944
Rental Permit # 1304 Chalet-Style Retreat with Private Soundfront Beach – Summer Rental in Greenport, NYNestled on 2.52 secluded acres along the North Fork’s coveted Soundfront, this architectural chalet-style home offers the ultimate summer escape. Featuring 3 oversized bedrooms and 4 full bathrooms, this expansive and warm retreat blends rustic charm with modern luxury.Soaring
Marco Maida Compass Greater NY LLC
$35,000 per month
Unlisted Address
Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood
Janet Markarian Daniel Gale Sothebys Intl Rlty
$4,850 per month
775 Hickory Rd, Southold, NY 11971
Delightful North Fork Year-Round Rental located at 775 Hickory Road, Southold. Completely furnished, high end appliances, radiant heat, updated electric, and more. The large eat in kitchen is open to the dining & living area with a fireplace and sliding doors that lead you out to the expansive patios, where you will relax and enjoy the sea breeze. There is a master suite with full bath, guest
Jeanmarie Bay William Raveis New York LLC
$3,800 per month
22950 Main Rd, Orient, NY 11957
Orient Village Area - Bright, Spacious And Updated Unfurnished Year Round 3 Bedroom/2 Bath Ranch Rental With Family Room, Brand New Kitchen, Central Air Conditioning, Heated In Ground Saltwater Pool And Nice Yard. Located Close To Village Lane, Oysterpond's School, Young's Road Public Long Island Sound Beach And New York City Transportation. Permit #0132.
Paul Loeb Douglas Elliman Real Estate
$12,000 per month
425 Lake Dr, Southold, NY 11971
Welcome to Paradise!! 425 Lake Drive is a magical lake-front beach home located in Southold on the North Fork. Adventure abounds on beautiful fresh-water Great Pond. Explore the lake on two kayaks, two canoes, take a swim, or just relax in the hammock and then enjoy the refreshing outdoor shower. This 3-bedroom, 1-bathroom home comes fully equipped and comfortably furnished. Dine al fresco on the
Robert Wilner Douglas Elliman Real Estate
$2,000 per month
475 Youngs Ave Unit c, Southold, NY 11971
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
Nicholas Planamento William Raveis New York LLC
$7,500 per month
580 Stars Rd, East Marion, NY 11939
YEAR ROUND RENTAL! Step into stylish comfort with this beautifully designed modern farmhouse, offered fully furnished and move-in ready. This stunning 4-bedroom, 3.5-bath home combines rustic charm with contemporary elegance, perfect for comfortable family living or entertaining in style.Inside, you’ll find rich hardwood floors throughout and an open-concept living space that flows seamlessly
William Walters Daniel Gale Sothebys Intl Rlty
$49,000 per month
57305 Route 48, Greenport, NY 11944
Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full
Zepur Diktas Compass Greater NY LLC
$3,500 per month
6710 Soundview Ave, Southold, NY 11971
Enjoy Southold this Summer at a Sleek Scandinavian Style Farm Ranch. Available for Bi-Weekly Rental Only. The Rate is Weekly at a Bi-Weekly Minimum. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout.
Rene Giacobbe Douglas Elliman Real Estate
$10,000 per month
425 Old Shipyard Ln, Southold, NY 11971
Southold-Enjoy the North Fork in this adorable cottage. Located in Founder's Landing Southold beach community. Three bedrooms, living room, kitchen with dining area and sunroom overlooking yard and pool. This charming home has everything you need for a great summer getaway. Close to community beach and Park. Close to town, restaurants, shopping, The giving room yoga and juice bar, Southold fish
Amy Kirincic The Agency Northshore NY
$22,000 per month
45 Budds Pond Rd, Southold, NY 11971
Available for two week rentals! Escape to your dream Southold summer in this spacious 5-bedroom, 2-bathroom home boasting an in-ground heated pool and convenient dock space. Bathed in natural light and surrounded by lush gardens, this home offers ample space for entertaining and ensuring guests feel right at home. Spend sunny afternoons basking by the pool under the awning or take a leisurely
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$10,000 per month
495 N Parish Dr, Southold, NY 11971
Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just
Nicholas Planamento William Raveis New York LLC
$15,000 per month
580 Gin Ln, Southold, NY 11971
Wonderful opportunity to spend time in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the community's private bay beach. There is more than ample space to host in this brightly renovated cape with room for everyone. The main level is comprised of a lounge area with fireplace and dry bar, an open kitchen and a large
Scott Bortzner Compass Greater NY LLC
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