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Property Description
Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.
Full Property Details
Full Property Details for 600 Highwood Rd
General
- Price: $999,999
- Taxes: $8,339
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 983742
- Updated: 4/18/2026
- Added to Site: 4 day(s) ago
Interior
- Number of Rooms: 8
- Interior Features: First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen, Entrance Foyer, High Ceilings
- Appliances: Other
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Parking
- Garage: Yes
- Garage Spaces: 2
- Parking Features: Attached
Location
- County: Suffolk County
- Cross Streets: N Bayview Ext
- Driving Directions: Main Bayview to Cedar. L on Cedar to N Bayview Ext R onto HIghwood
School Information
- High School District: Southold
- Elementary School: Southold Elementary School
- Middle School: Southold Junior-Senior High School
- High School: Southold Junior-Senior High School
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Forced Air, Oil
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Water Connected
Structural Information
- Architectural Style: A-Frame
- Detached/Attached: Detached
- Construction: Frame
- Basement: Yes
- Basement Desc.: Full Basement, Unfinished, Walk-Out Access
- Sq. Ft. Source: Plans
- Year Built: 1976
Lot Features
- Lot Size (Acres): 1.37
- Lot Size (Sq. Ft.): 59,677
- Road Maintenance: Public Maintained Road
Financial Considerations
- Tax Amount: $8,339
Disclosures and Reports
- Special Conditions: None
- Property ID: 1000-078-00-09-00-046-001
Listed by Douglas Elliman Real Estate
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Schools
Schools serving 600 Highwood Rd
School District:Southold Union Free School District
| Name | Grades | Distance |
|---|---|---|
Southold Elementary School 420 Oaklawn Avenue, Southold, NY 11971 | K-6 | 1.5 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 600 Highwood Rd
Date
Details
Price
Change
Source
4/15/2026
Listed
$999,999
81.82%
MLS
7/27/2020
Sold
$550,000
—
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.
Estimate the Cost
Estimate the Cost for 600 Highwood Rd
600 Highwood Road, Southold, NY 11971 (MLS# 983742) is a Single Family property with 3 bedrooms and 2 full bathrooms. 600 Highwood Road is currently listed for $999,999 and was received on April 15, 2026. Want to learn more about 600 Highwood Road? Do you have questions about finding other Single Family real estate for sale in Southold? You can browse all Southold real estate or contact a Coldwell Banker agent to request more information.
