ML# :3566958 Historic Main Bayview schoolhouse converted to country residence located at 5650 N Bayview Road, Southold. Available for winter rental, September 3, 2024 - June 30, 2025 $3, 900 per mo plus utilities, etc Country residence features 5 bedrooms in historic Main Bayview Schoolhouse converted to residence - sleeps max 10 people. Pet friendly. Equidistant to Cedar Beach and Goose Creek Beach. Moments to village of Southold, North Fork wine trail, area shops and top tier restaurants. An ideal vacation destination OR winter residence. Private fenced yard. Living room features woodstove. Finished lower level offers playspace or make it a home office. Rental Permit #0336
5650 North Bayview Rd, Southold, NY, 11971
ML# :3542413 Lovely, sunlight filled ranch in ’Orient by the Sea’ community. Fully furnished, just 4 houses to gorgeous, private LI Sound beach. Eat in Kitchen, Dining & Living rooms, Ensuite primary, 2 add’l bedrooms & 2nd full bath. Front & back porches and spacious yard. Nearby Orient State Park offers miles of hiking, cycling trails, birding, wildlife viewing and a miles-long, sandy Bay beach. Scenic 10 minute drive to Greenport. Rental permit # 1100 exp. 3/25/2026.
990 Three Waters Lane, Orient, NY, 11957
ML# :3590837 Situated in a charming and serene neighborhood in Greenport and located just minutes from both Greenport Village and Southold Town Beach, this recently updated Cape offers 1, 500 sq. ft. with 4-bedrooms, 2-baths and a spacious living area that flows seamlessly into a bright and airy eat-in kitchen. A full, unfinished basement leads out to an expansive, fenced backyard, and the attached 1-car garage and driveway capable of accommodating 2 additional vehicles ensures sufficient parking for tenants. Don’t overlook the opportunity to rent this gem! Please note that the reported square footage is an approximation as the Town of Southold does not have records of the square footage for the second half story.
27 Madison Street, Greenport, NY, 11944
ML# :3586378 3 Bedrooms, 1 Bath, Living Room, Dining Room, unfinished basement. Convenient to all.
637 W Main Street, Riverhead, NY, 11901
ML# :3582754 Welcome home to this Charming, fully Furnished and Recently Renovated Cottage. No detail has been spared in making this a cozy and comfortable retreat. The home offers 2 bedrooms, a fully equipped kitchen with Stainless Steel Appliances, Vaulted Ceiling Living Room, a full bathroom and a bonus room with laundry and extra room for convenience. Step onto the deck and you’ll find yourself in a private and tranquil backyard, and with the beach just two minutes away, you’ll feel like you’re on vacation everyday.
16 Overbrook Street, Riverhead, NY, 11901
ML# :3581680 Updated Vintage Bungalow with Full Basement and Detached Garage. Hot Air Heat and Central Air Conditioning. Close to Village Center, 2 Marinas and 2 Beaches. 295 Sterling Place is also known as 505 Sterling Place. Year Round Rental at $3, 500 per Month. Pets Considered.
295 Sterling, Greenport, NY, 11944
ML# :3581131 Not available for year round rent. This is an off season rental. Charming home, originally built in approximately 1905.Main Rd, South onto South Harbor Road, Left on to Baywater Ave. Close proximity all the North Fork has to offer. Down the road. to Croteaux Vinyards and South Harbor Park for swimming, kayaking and boating. Close to the best North Fork restaurants, marinas and farm stands.
45 Baywater Avenue, Southold, NY, 11971
ML# :3580134 SPECTACULAR BAYFRONT with OPEN/FULL VIEWS OF GREAT PECONIC BAY! Enjoy a Wonderful Weekend or Work-World GETAWAY throughout the Off-Season! Great Room with southern exposure and Wonderful Bay Views from sunrise to sunset over the Great Peconic Bay. The Great Room opens to a 3-Season partially enclosed waterside porch that welcomes the warm bay breezes and an outdoor dining, star-gazing, and plenty of entertaining areas. Fully furnished with well-equipped kitchen, 3 bedrooms, 2 full baths, and laundry facilities in full basement.Live Your Best Life Here or take a Short Drive to Long Island Sound and Ocean Beaches, and Local Marinas. Nearby to Gourmet Restaurants, Wineries, Breweries, Golf, Shopping, and NF Farm Stands with Easy Access to the LIRR or NYC Jitney.
3105 Sigsbee Rd, Mattituck, NY, 11952
ML# :3553837 Beautiful North Fork home within walking distance to the beach, as well as numerous vineyards, restaurants, and local shops. Upon entering this home, you will enjoy spacious living quarters full of natural light and comfortable furnishings. The perfect mix of modern comfort, the gourmet kitchen boasts stainless steel appliances, gleaming countertops, and a large center island with a breakfast bar. When you aren’t hanging out in the living room, tuned into your favorite show in front of the heat of the fireplace, check out the equally plush bedrooms. Off the primary bedroom, you’ll have access to a walk-in shower and expansive vanity. Additional interior perks include a washer/dryer, central air conditioning, and baby gates. Surrounded by trees, enjoy spending time on the home’s back patio, barbecuing on the gas grill, and gathering around the firepit.
870 Stars Rd, East Marion, NY, 11939
ML# :3525718 Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107 RATES: MD-LD $19, 000 ; June $3500; July $7, 000’ Aug-LD $8, 000 July/Aug-LD $15, 000 - off season/Fall 2025 available.
Southold NY, 11971