380 Homestead Way, Greenport, NY 11944

$1,200,000

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… Read More 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. Read Less

Listing Courtesy of Locqube New York, Inc..

Listing Snapshot

Days Online

178

Last Updated

Apr 2, 2026

Property Type

Single Family Residence

Beds

Full Baths

Square Ft.

1,650

Year Built

2017

Property Tax

$9,920

MLS Number

921412

30 Days Snapshot Of 11944

$1.09M

-8%

(avg) sold price

-25%

homes sold

168

-8%

(avg) days on market

Snapshot

Area Map

Additional Details

Parking

Parking Total: 6, Carport Spaces: 0

Appliances & Equipment

Description: "Dishwasher", "Dryer", "Electric Range", "Microwave", "Refrigerator", "Oil Water Heater"

Basement

Description: "Full", "Storage Space", "Unfinished"

Building

Area: 1650, Architecture: "Garden", "Ranch", Construction Materials: "Frame", "Shake Siding", "Vinyl Siding", Year Built: 2017

Cooling

Details: "Central Air"

Fireplaces

Total Fireplaces: 1

Floors

Flooring: "Hardwood"

Garage

Garage Spaces: 1

Heating

Heating: "Forced Air", "Oil"

Laundry

Description: "In Basement"

Lot

Acres: 0.5

Pool

Private Pool

Utilities

Sewer: "Public Sewer", Water Source: "Public", Utilities: "Electricity Connected", "Sewer Connected", "Trash Collection Public", "Underground Utilities", "Water Connected"

Find The Perfect Home

'VIP' Listing Search

Whenever a listing hits the market that matches your criteria you will be immediately notified.

Join The List

Mortgage Calculator

Selling price

Down payment

Term (years)

Interest rate (%)

Monthly Payment

380 Homestead Way

'VIP' Listing Search

Schools In The Area

Similar Listings

Find My Dream Home

1. Neighborhoods

2. Home Type

3. Send

Buyers

Sellers

About