ML# :3456053 Remodeled to perfection! This beautiful home features an open floor plan with wood flooring throughout, a cozy living room with bay windows and a fireplace, 3 bedrooms including 1st floor primary bedroom ensuite, screened in porch, large backyard with 16x32 heated, salt water IG pool and a fire pit, perfect for family gatherings! Don’t miss out on this beauty! Surrounded by North Fork award winning vineyards, marinas, renowned restaurants, farm stands, beaches and great shopping. Permit #24-0264
44 Legend Lane, Riverhead, NY, 11947
ML# :3567118 Welcome to your ideal summer getaway! This charming 4-bedroom, 2.5-bathroom home offers 2400 sq ft of living space on a sprawling 41818 sq ft lot. Prepare to dive into relaxation as this home features a saltwater pool and deck for al fresco dining, with plenty of open space for indoor entertaining. This summer rental is the perfect haven for your seasonal escape!
1300 Parkview Lane, Southold, NY, 11957
ML# :3556906 Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000.
6430 Hortons Lane, Southold, NY, 11971
ML# :3513356 Mattituck, North Fork: Sunshine and solace await you in this immaculate and recently renovated vacation home with a brand NEW, heated, saltwater pool (16x34 gunite)! Large open and bright rooms with lots of natural light allow you to relax in comfort and enjoy your time off. Home accommodates a maximum of 6 guests and features first floor bedroom with luxurious bath, open concept dining room/kitchen with terrace access, large living room for rainy day enjoyment. Upstairs are 2 more bedrooms and full bath. Large, level and private lot conveniently located by area vineyards, popular Love Lane and both LI Sound and Bay beaches. Immaculate and awaiting your stay. Flexible dates; pets on individual basis; no smoking. Southold Town Rental Permit #1022.
Southold NY, 11952
ML# :3371622 Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet’s Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day. Available April: $12, 000, May: $17, 500, June: $22, 500, July: $35, 000. August: $40, 000. Two week minimum. Permit# 0501.
935 Southern Cross Rd, Southold, NY, 11935
ML# :3526989 Greenport village 5 bedrooms, 2 baths with sweeping Water Views, adjacent to 6th St bay beach & park. Architect-designed & decorated interiors, chef’s kitchen, 2nd floor sundeck and large yard with garden & outdoor dining area. Huge water-facing sun porch with wall of windows looking out on the bay. Short distance to farmers markets, wineries, shopping, LIRR & Jitney. RP# 22-298
130 6th Street, Southold, NY, 11944
ML# :3524519 Village Lane summer house - full season rental - historic charm seamlessly blended with modern amenities. Water views. Hardwood floors, lots of light, unique architectural interest with sophisticated decor for the discerning traveler. Rent reflects MD-LD.
1800 Village Lane, Southold, NY, 11957
ML# :3505394 Spectacular updated Cape with a heated pool at 25 Moose Trail, Cutchogue. Enjoy the chefs’ kitchen & many spacious living and entertaining areas, including dining room, game room with pool table & arcade games, bedroom, & a full bath on the first floor, all tastefully furnished. Outside you have an expansive deck off the kitchen that takes you to the heated pool surrounded by a paver patio & professionally landscaped yard. This home also has beach rights to a beautiful sandy bay beach and park. Many wonderful vineyards, restaurants, and farm stands are close by. This is the perfect home for entertaining & family gatherings! RP# 0422 , AVAILABLE 2025 Memorial Day thru LD $59, 000, June $12, 000, July $22, 000, August $25, 000.
25 Moose Trail, Southold, NY, 11935
ML# :3467464 Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play.
3675 Wells Avenue, Southold, NY, 11971
ML# :3555837 Escape the hustle and bustle of everyday and spend a month in Orient’s most coveted beachfront estate enclaves. You will be captivated by the breathtaking 180-degree water views and grand sunsets that greet you at every turn in this beautifully designed and expertly built home by the sea. With 4800 square feet of living space, this beachfront retreat offers an abundance of room for relaxation and family entertainment. Begin your day in the private gym and sauna, offering a sanctuary for health and well-being. Channel your inner chef in the state-of-the-art kitchen. Entertain with ease in the grand greet room, boasting a wood-burning fireplace and floor to ceiling windows overlooking the gorgeous beach. Just outside is expansive decking and a beautifully furnished large screened Mahogany porch for relaxing with friends and dining al-fresco overlooking the beachfront. Inside you will find four spacious bedrooms and additional guest suite with big water views; each featuring full baths ensuite for added convenience and privacy. After a day of seaside adventures, unwind in the movie room or den, where relaxation meets entertainment in unparalleled luxury. There is a well appointed office for those times you will need a professional atmosphere, but with the same captivating beach views. This home offers a peaceful retreat and an idyllic setting for memorable gatherings in Orient for those who love that one of a kind beachfront experience. Whether hosting family gatherings or entertaining guests, this haven provides the perfect setting for unforgettable moments by the sea. Close Jitney and Ferry, several farm stands, Orient’s historic district, Yacht club, Golf course, Village lane shops, Duryea’s, private fish charters, world class vineyards and Zagat rated restaurants. 5 minutes to Greenport with ferry service to the Hamptons. Only available August 1st - August 14th, 2025 $20, 000. Rental Permit# 1135
905 Stephensons Rd, Southold, NY, 11957