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216 Broad Street, Greenport
$699,000
2 Beds ⋅ 1 Baths ⋅ 1047466 MLS
Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the "diamond in the rough" you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can't be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this in the heart of Greenport are few and far between, so don't let this one slip away.

216 Broad Street, Greenport
429 Kaplan Avenue, Greenport
$775,000
3 Beds ⋅ 2 Baths ⋅ 1037952 MLS
Charming Greenport Village Getaway Enjoy the best of the North Fork from this inviting 3-bedroom, 2-bath home, perfectly located near all that Greenport Village has to offer. Stroll to Mitchell Park, waterfront dining, restaurants, shops, and the Shelter Island Ferry, or spend the day exploring nearby vineyards and Greenport Harbor Brewing Company. A wonderful opportunity to enjoy the relaxed charm, walkability, and vibrant lifestyle of Greenport Village—close to everything, yet your own peaceful retreat.

429 Kaplan Avenue, Greenport
2820 Shipyard Lane Unit #1B2, East Marion
$779,000
2 Beds ⋅ 2 Baths ⋅ 1036090 MLS
Enjoy Exceptional Water Views from this Second-Floor, 2-Bedroom, 2-Bath Condominium Featuring a Spacious Storage Loft and Private Deck Overlooking the Waterside Lawn and Bay. Cleaves Point Condominium Is Beautifully Situated on 13 Waterfront Acres at the End of Shipyard Lane in East Marion. Community Amenities Include a Private Bay Beach, Marina with Docking, Swimming Pool, Clubhouse with Gym, Tennis, Pickleball, Basketball, Community Garden, and More. Conveniently Located Near Island’s End Golf, Greenport Village, and All That the North Fork Has to Offer. Low Taxes Further Enhance This Outstanding Opportunity. Estate Sale. Sold “As Is”.

2820 Shipyard Lane Unit #1B2, East Marion
44 (1180) Sound Road, Greenport
$799,000
2 Beds ⋅ 1 Baths ⋅ 1035656 MLS
A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the façade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures — each equipped with electricity and water, and one including a bedroom — offer flexible space for guests, a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

44 (1180) Sound Road, Greenport
308 Monsell Place, Greenport
$749,000
3 Beds ⋅ 1 Baths ⋅ 1028101 MLS
Super Cute Greenport Village home packed with charm and character. Walking distance to downtown. 3 bedrooms, 1 bath, diving area, kitchen and living area all on 1st floor with 3 bedrooms and a full bathroom above. Full walk out Basement and fenced in yard. Close to downtown Greenport, Marinas, Golf, restuarants and wineries.

308 Monsell Place, Greenport

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.