2025 Rates: June $8K, July $12K, A1-LD $13K, September $8K, October $7K Charming Nassau Point Cape Cod. Enjoy sprawling private grounds with community beach access as you enjoy the summer months in this ideal 3 bedroom 2 bathroom escape. The main level features and open dining/, kitchen leading to wood deck, main floor bedroom, full bathroom and living room.

Charming Laurel Country Estates, comfortable three bedroom ranch, private bay beach for neighborhood residents. Central air conditioning. Rear yard with deck off kitchen for outdoor entertaining. Convenient to Mattituck Shopping Center, and recreational activities. Act now to reserve your desired dates for the 2025 Summer Season. Available: July and August through Labor Day.

August 1-16 $40,000; August 17-31 $40,000; August $80,000 PRIVACY AND LUXURY COLLIDE! Down a private driveway with breathtaking views of the sea, privacy and luxury collide! This impressive beach estate rests on 12.3 acres and 460' of waterfront beach tucked away in a protected cove on the Long Island Sound.

Welcome to your very own pied-a-terre cottage nestled on the world renowned grounds of Harbor Knoll guesthouse. Bask in this waterfront, private and secluded oasis of calm, while still being within arms reach of everything Greenport Village has to offer.

An outdoor oasis is one element of this extraordinary property. This one of a kind 5 bedroom, 3.5 bath residence is the perfect home to make special memories this season. The perfect rental with one of the most extraordinary pool and garden areas on the North Fork.

Available for summer 2025! Modern farmhouse with 4 bedrooms, all with ensuite baths. Get away from it all in this hotel-like Orient home. Open concept kitchen, dining, living with beautiful light filled bedrooms. Enormous blue stone patio leads to in-ground pool and beautifully landscaped yard beyond. Minutes from the private association beach, Orient State Park and Duryeas Restaurant & Bar.

Pristine and newly renovated craftsman home in Nassau Farms. Easy access to Nassau Point Beach. Bright and sunny great room with open floor plan; kitchen featuring granite counter tops, custom cabinetry, and high end appliances. Private backyard with bluestone patio, built-in outdoor sound system, stone fireplace, and outdoor cooking. Ideal vacation home on the North Fork.

ENDLESS POSSIBILITIES IN GREENPORT VILLAGE Now Available as a Rental pop-up! This iconic location is a prime commercial opportunity in the heart of Greenport Village. Now Available as a short term rental pop-up High traffic, high visibility, 3,900 square feet, 2 attached garages, 3 rear parking spots. Perfect for a gallery, retail, showroom, professional offices.

Just a ferry ride from Sag Harbor and the Hampton's, take in expansive waterfront views of the bay and Greenport harbor from the second floor balcony in this renovated open concept waterfront condo located in the private Stirling Cove condominium association.

Beautiful office suite is now available for rent on Main Road in the Village of Southold. Tired of working from home or are you looking to expand your professional business? Second floor "Unit A" office suite includes three private office areas, private kitchenette and private bathroom. Rent of $2,000 per month includes water and electric. Tenant responsible for street gas and cable/internet.

Enjoy the Sounds of Silence at this Hill Top Chalet Overlooking the North Fork's Mattituck Inlet. This 4 Bedroom and 2 Full Bath Home is Grand, Open, and Inviting. Great for Entertaining or a Private Escape Away from It All. Located Off the Beaten Path Though Just Around the Corner from Everything We Love on the North Fork.

2025 Rates: Last two weeks of June: $10,000.00, September 2-30 $15,000.00, October $12,500.00, Off season $6,000.00/month: Stunning New Construction in Southold's Hog Neck community. Enjoy open living w/ high vaulted ceilings in this sprawling modern farm house.