Property Description

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.

Features
Heating System:
Oil, Forced Air
Cooling System:
Central Air
Basement:
Full, Unfinished, Storage Space
Appliances:
Dishwasher, Refrigerator, Microwave, Dryer, Oil Water Heater, Electric Range
Fireplace Features:
Wood Burning
Fireplaces Total:
1
Flooring:
Hardwood
Garage Spaces:
1
Interior Features:
Granite Counters, Open Kitchen, Open Floorplan, High Ceilings, Storage, Chefs Kitchen, Kitchen Island, Washer/dryer Hookup, Formal Dining, First Floor Bedroom, Primary Bathroom, Ceiling Fan(s), Chandelier, First Floor Full Bath, Recessed Lighting
Laundry Features:
In Basement
Parking Features:
Driveway
Sewer:
Public Sewer
Utilities:
Underground Utilities, Trash Collection Public, Water Connected, Electricity Connected, Sewer Connected
Address Map
City:
Southold
State:
NY
Street:
Homestead
Street Number:
380
Street Suffix:
Way
Postal Code:
11944
Floor Number:
0
Longitude:
W73° 37' 27.8''
Latitude:
N41° 6' 42.4''
PostalCity:
Greenport
Additional Information
Architectural Style:
Ranch, Garden
Construction Materials:
Frame, Vinyl Siding, Shake Siding
Elementary School:
Greenport Elementary School
High School:
Greenport High School
Agent MlsId:
25225
MiddleOrJunior School:
Greenport High School
PhotosCount:
39
Special Listing Conditions:
No
Tax Annual Amount:
$9,920
Water Source:
Public
Office MlsId:
LOCQUB

Residential - MLS# 921412

380 Homestead Way, Southold, NY

3 Bedrooms
2 Bathrooms
1,650 Sqft
$1,149,900
Listing ID #921412
Basic Details
Property Type :
Residential Sale
Property SubType :
Single Family Residence
Listing Type :
For Rent
Listing ID :
921412
Price :
$1,149,900
Rooms :
5
Bedrooms :
3
Bathrooms :
2
Bathrooms Total :
2
Square Footage :
1,650 Sqft
Lot Area :
0.50 Acre
Year Built :
2017
Status :
Active
Listing Agent :
Jules Zaphire
Listing Office :
Locqube New York, Inc.
Agent info
Coldwell Banker American Homes
284 West Park Ave
Contact Agent
Walkscore