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$1,200,000
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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.
Full Property Details
Full Property Details for 380 Homestead Way
General
- Price: $1,200,000
- Taxes: $9,920
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 921412
- Updated: 3/27/2026
- Added to Site: 190 day(s) ago
Interior
- Number of Rooms: 5
- Interior Features: First Floor Bedroom, First Floor Full Bath, Ceiling Fan(s), Chandelier, Chefs Kitchen, Formal Dining, Granite Counters, High Ceilings, Kitchen Island, Open Floorplan, Open Kitchen, Primary Bathroom, Recessed Lighting, Storage, Washer/Dryer Hookup
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Wood Burning
- Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Oil Water Heater
- Laundry Facilities: Yes
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: In Basement
Additional Information
- Pool: Yes
- Private Pool: Yes
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 6
- Parking Features: Driveway
Location
- County: Suffolk County
School Information
- High School District: Greenport
- Elementary School: Greenport Elementary School
- Middle School: Greenport High School
- High School: Greenport High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Forced Air, Oil
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electricity Connected, Sewer Connected, Trash Collection Public, Underground Utilities, Water Connected
Structural Information
- Architectural Style: Garden, Ranch
- Detached/Attached: Detached
- Construction: Frame, Shake Siding, Vinyl Siding
- Basement: Yes
- Basement Desc.: Full Basement, Storage Space, Unfinished
- Unfinished Attic: Yes
- Sq. Ft. Source: Public Records
- Year Built: 2017
Lot Features
- Lot Size (Acres): 0.5
- Lot Size (Sq. Ft.): 21,780
Financial Considerations
- Tax Amount: $9,920
Disclosures and Reports
- Special Conditions: None
- Property ID: 1000-040-00-02-00-012-000
Listed by Locqube New York, Inc.
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Schools
Schools serving 380 Homestead Way
School District:Greenport Union Free School District
| Name | Grades | Distance |
|---|---|---|
Greenport Elementary School 720 Front Street, Greenport, NY 11944 | PK-6 | 0.8 mi |
Greenport High School 720 Front Street, Greenport, NY 11944 | 7-12 | 0.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 380 Homestead Way
Date
Details
Price
Change
Source
10/06/2025
Listed
$1,200,000
57.89%
MLS
5/14/2021
Sold
$760,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 380 Homestead Way
Year
Property Taxes
Change
Tax Assessment
Change
2020
-100%
$5,700
10%
2021
$9,925
26%
$5,200
—
2022
$7,850
-21%
$5,200
-25%
2021
$9,925
-2%
$6,900
—
2020
$10,118
3%
$6,900
—
2018
$9,851
35%
$6,900
30%
2017
$7,280
500%
$5,300
489%
2016
$1,213
8%
$900
—
2015
$1,119
1%
$900
—
2015
$1,105
3%
$900
—
2014
$1,069
3%
$900
—
2013
$1,036
—
$900
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 380 Homestead Way
380 Homestead Way, Greenport, NY 11944 (MLS# 921412) is a Single Family property with 3 bedrooms and 2 full bathrooms. 380 Homestead Way is currently listed for $1,200,000 and was received on October 06, 2025. Want to learn more about 380 Homestead Way? Do you have questions about finding other Single Family real estate for sale in Greenport? You can browse all Greenport real estate or contact a Coldwell Banker agent to request more information.
