380 Homestead Way

Greenport, NY 11944

  • $1,200,000
  • 3 Beds
  • 2 Baths
  • 1,650 Sqft
  • 0.5 Acres
  • 2017 Built

Welcome to this beautifully appointed single-family residence ideally situated just minutes from the charming village of Greenport. Blending modern amenities with classic coastal charm, this property offers not only an exceptional retreat in one of Long Island’s most sought-after locations—but also a compelling opportunity as a fully functional or potential income-producing short-term rental. Whether you’re seeking a weekend escape, a second home that offsets its own costs, or a turnkey investment in the thriving North Fork vacation market, this home delivers versatility and value. INTERIOR FEATURES: The home showcases a thoughtfully designed open-concept layout. The gourmet kitchen features white cabinetry, granite countertops, subway tile backsplash, and premium stainless steel appliances. The spacious living area is anchored by a cozy fireplace, while hardwood floors flow throughout. Multiple bedrooms offer comfort and privacy, complemented by updated bathrooms featuring glass-enclosed showers, stone tile walls, and granite countertops—ideal for both personal use and guest accommodations. OUTDOOR LIVING: Set on over half an acre, the expansive property is designed for relaxation and entertainment. A stunning rectangular swimming pool, stone-paved deck, and extensive patio space create a resort-like atmosphere highly desirable for short-term guests and homeowners alike. Mature landscaping and privacy fencing provide a serene and secluded outdoor setting. ADDITIONAL AMENITIES: Unfinished basement offering excellent potential for recreation space or added value Dedicated laundry room Ceiling fans throughout Attached garage with paved parking INCOME & INVESTMENT POTENTIAL: Located in one of the North Fork’s most in-demand vacation destinations, this property is well-positioned for short-term rental use. With strong seasonal demand driven by wineries, beaches, and year-round tourism, buyers have the opportunity to generate income while enjoying personal use. Ideal for those looking to own a lifestyle property that can also serve as a revenue-generating asset. LOCATION & LIFESTYLE: Just a short drive from historic Greenport Village, this home offers easy access to boutique shopping, acclaimed restaurants, and waterfront activities. Enjoy proximity to award-winning wineries, pristine beaches, marinas, and a vibrant calendar of community events including the Maritime Festival and Winter Wonderland. The North Fork’s renowned farm-to-table dining, farmers markets, art galleries, and cultural venues are all within reach, along with convenient access to the Hampton Jitney and LIRR. This property offers more than just a home—it’s an opportunity to experience the best of the North Fork lifestyle while capitalizing on one of the region’s most desirable and in-demand markets. Whether for personal enjoyment, investment, or both, this is a rare offering in Greenport.

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Property Highlights
  • ELEMENTARY : Greenport Elementary School
  • MID. SCHOOL : Greenport High School
  • HIGH SCHOOL : Greenport High School
  • PRICE/SQFT : $727
  • DAYS ON MARKET : 175
  • MLS : 921412

Additional Information

ADDITIONAL INFORMATION
  • BASEMENT DESCRIPTION: Full, Storage Space, Unfinished
  • DAYS ON MARKET: 175
  • ELEMENTARY SCHOOL: Greenport Elementary School
  • ELEMENTARY SCHOOL DISTRICT: Greenport
  • HIGH SCHOOL: Greenport High School
  • LIVING AREA SQFT: 1650
  • MIDDLE SCHOOL: Greenport High School
  • ON MARKET DATE: 2025-10-06
  • PARKING: Driveway
  • PARKING SPACES: 6
  • SEWER: Public Sewer
  • STYLE: Garden, Ranch
  • TAX AMOUNT: $9,920
  • TYPE: Residential
  • UTILITIES: Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
  • YEAR BUILT: 2017
INTERIOR/EXTERIOR FEATURES
  • APPLIANCES INCLUDED: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator
  • BEDS: 3
  • CONSTRUCTION MATERIALS: Frame, Shake Siding, Vinyl Siding
  • COOLING: Central Air
  • EXTERIOR FEATURES: Pool (Private)
  • FLOORING: Hardwood
  • FULL BATHS: 2
  • HEAT: Forced Air, Oil
  • INTERIOR FEATURES: Ceiling Fan(s), Chandelier, Granite Counters, High Ceilings, Kitchen Island, Open Floorplan, Recessed Lighting, Storage
  • ROOMS: 5

Listing Courtesy of Jules Zaphire of Locqube New York, Inc. (347.657.1114).

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Location for 380 Homestead Way, Greenport, NY

Community

Greenport>

Greenport

Columbia County, New York

The last town founded in the county, Greenport was established in 1837 from a portion of the city of Hudson and at one time was a part of the town of Claverack. Home to about 2,600 residents, scenic...

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  • Julia B. Fee Sotheby's International Realty