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 potential 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.
Single-familyProperty Type
1976Year Built
1.37 acresLot Size
$451Price/Sq.Ft.
2 car garageParking
Listing by Alexis Meadows• Douglas Elliman Real Estate
Contact: 631-288-6244
Bought with Lauren Spiegel• Douglas Elliman Real Estate
Est. $1,795 per month, based on comparable rentals
Sale and tax history for 600 Highwood Rd
Sale History
Tax History
Date
Event
Price
OneKey® MLS as Distributed by MLS Grid #983742
Jul 13, 2026
Sold
$882,000
$451/sq ft
May 8, 2026
Pending
—
Mar 20, 2026
Listed
$999,999
$512/sq ft
OneKey® MLS as Distributed by MLS Grid #L3172240
Jul 27, 2020
Sold
$550,000
$281/sq ft
Apr 27, 2020
Price Changed
$579,000
$296/sq ft
Feb 1, 2020
Price Changed
$599,000
$307/sq ft
Oct 11, 2019
Listed
$799,000
$409/sq ft
Wonderful A-Frame style home with large dramatic windows on a beautiful, well treed half acre lot! Soaring 2 story cathedral ceiling Living Room with sliders to deck, builder's own house with beautifully finished open rafter ceilings, 2 bedrooms, huge 3rd bedroom 2nd story loft with storage. Great lower level with full bath, laundry room and 2-car garage built-in. Convenient access to Southold bay beaches., Additional information: Appearance:Pristine,Business Located At:,Rental Income:,Separate Hotwater Heater:Y
Year
Property tax
Land + Additions
Assessment*
2025
$8,339
$1,100 + $4,400
$5,500
2024
$8,339 (+4.6%)
$1,100 + $4,400
$5,500
2023
$7,975 (−2.2%)
$1,100 + $4,400
$5,500
2022
$8,155
$1,100 + $4,400
$5,500
2021
$8,155 (+8.1%)
$1,100 + $4,400
$5,500
2020
$7,542 (+25.4%)
$1,100 + $4,400
$5,500
2019
$6,015 (+3.2%)
$1,100 + $4,400
$5,500
2018
$5,827 (+2.8%)
$1,100 + $4,400
$5,500
2017
$5,667 (−13.4%)
$1,100 + $4,400
$5,500
2016
$6,540 (+5.4%)
$1,100 + $5,200
$6,300
2015
$6,206 (+11.6%)
$1,100 + $5,200
$6,300
2014
$5,559 (+2.2%)
$1,100 + $5,200
$6,300
2013
$5,438 (+3.1%)
$1,100 + $5,200
$6,300
2012
$5,274 (−7.0%)
$1,100 + $5,200
$6,300
2011
$5,670 (+2.5%)
$1,100 + $5,200
$6,300
2010
$5,531 (+13.1%)
$1,100 + $5,200
$6,300
2009
$4,889
$1,100 + $5,200
$6,300
Public record
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
1.37 Acres
Year renovated
—
Sq. Ft.
—
Year built
—
Style
Single Family Residential
County
Suffolk County
APN
1000078000900046001
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 31, 2026.
Property details
Parking
Parking Information
Carport YN: No
Parking Features: Attached
Garage Information
Garage Spaces: 2
Has Garage
Interior
Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Oil
Interior Features
Interior Features: First Floor Bedroom,First Floor Full Bath,Eat-in Kitchen,Entrance Foyer,High Ceilings
Appliances: Other
Levels: Tri-Level
Room Information
Basement YN: Yes
Attic: See Remarks
Rooms Total: 8
Basement: Full, Unfinished, Walk-Out Access
Bathroom Information
Bathrooms Full: 1
Exterior
Exterior Features
Construction Materials: Frame
Waterfront YN: No
Lot Information
Additional Parcels YN: No
Property Information
Living Area Source: Plans
Living Area (Sq. Ft.): 1954.00
Property Sub Type: Single Family Residence
Financial
Tax Information
Tax Year: 2025
Tax Source: Municipality
Tax Annual Amount: $8,339
Financial Information
Buyer Financing: Conventional
Utilities
Utility Information
Electric Company: PSEG
Sewer: Septic Tank
Utilities: Water Connected
Location
School Information
Elementary School: Southold Elementary School
Elementary School District: Southold
Middle Or Junior School: Southold Junior-Senior High School
Middle Or Junior School District: Southold
High School: Southold Junior-Senior High School
High School District: Southold
Location Information
Directions: Main Bayview to Cedar. L on Cedar to N Bayview Ext R onto HIghwood
County Or Parish: Suffolk County
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 1.37 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Suffolk County
APN: 1000078000900046001
Home facts updated by county records on Aug 31, 2026
Around this home
Schools
Southold Elementary School
Public K-6 • Assigned • 1.4mi
6/10
Southold Junior Senior High School
Public 7-12 • Assigned • 1.4mi
6/10
Provided by GreatSchools
Historical weather
Southold, NY • 11971
Average low and high temperatures (°F)
35
26
37
26
50
36
59
44
68
53
79
63
83
69
79
63
74
60
65
52
54
43
42
31
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
69/ 100
Moderate sunlight
Sunscore
There appears to be some shading by surrounding buildings, terrain, and vegetation.
7.6 hrs
3.7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$975,000 – $1.18M
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