MD-LD $50,000; June $15,000; July $20,000; August-LD $20,000 Rustic luxury on the North Fork! Located within a waterfront enclave in Mattituck and close to all creature comforts, this renovated barn will not disappoint. 5 bedrooms, 3.5 bathrooms, heated pool, large EIK and den, views of Mattituck Inlet and access for kayaking, swimming and paddleboarding.

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.

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.

GREENPORT WATERFRONT CONDO . Enjoy your life in this well- appointed Bayfront 2 bedroom, 2 bath condo with stunning views of Shelter Island and Greenport Harbor. Amenities include a waterfront pool, tennis & pickle ball court, 200 Ft of private sandy bay beach, and your own boat slip in the private marina.

CHIC RETREAT! A glamorous getaway! You won't know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon.

This Completely Renovated One-Of-A-Kind Historic Religious Structure was built in 1879. Stylish And Close To Everything In Greenport. Soaring Cathedral Ceilings, Mesmerizing European Stained Glass Windows, Brand New Kitchen And Full Bath. Located In The Heart Of The Much Coveted Greenport Village.

Welcome to this spectacular waterfront home overlooking the Long Island Sound. This spacious 5000 sqft retreat features an open floor plan with four large bedrooms, 4.5 baths, and a versatile bonus room. Revel in breathtaking sunsets from nearly every room or the expansive back deck and patio. Amenities include a home gym, outdoor shower, multiple fireplaces, and beach access.

2026 Rates: July $34,500; August 1-LD $44,500: New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio.

Beautifully Renovated in 2023. 3 Bedrooms/2 Bathroom. One Floor Living with Deck and Nice Yard. Fully Furnished. Off Season - November 2025 to May 2026 $3,000. Year Round $4,200. Rental Permit #0946.

Welcome to 455 West Shore Road, Southold, NY. This charming 4-bedroom, 2. 5-bathroom rental property offers 1,600 square feet of comfortable living space. Nestled in a serene location, the home provides exclusive beach rights, perfect for summer enjoyment. The spacious layout includes a well-appointed kitchen, inviting living areas, and ample storage.

Luxurious Modern Home with Heated Inground Pool in Private Community with Memorable Bay Beach 3 Blocks Away. Short Distance to Golf and Greenport Village. Off Season (November 2025 to May 2026) - $10,000 per month (single to multiple months considered); Year-Round - $10,500 per month; Summer 2026 - June $20,000; July $35,000. Permit # 0634.

2025 Rates: Memorial Day-Labor Day $87,500, June $22,500, July $32,500, July-August $67,000 and August-Labor Day $35,000. Looking for a resort like retreat just outside of bustling Greenport Village? Look no further! This 6 bedroom, 4.5 bathroom stunner offers everything you could ask for and more.