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MLS ID KEY1033174Last updated Sep 18, 2026

Single Family

26905 Main Road

Pending · Southold · Suffolk County, NY 11935

Bedrooms
4 Beds
Bathrooms
2 Baths
Year built
1770
Est. monthly taxes
$682.21
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About this home

26905 Main Rd aka 115 Highland Rd. A rare opportunity to own a remarkable piece of history, this beautifully preserved residence seamlessly blends Colonial origins with timeless Georgian elegance. Originally built circa 1770, the home has evolved through generations of thoughtful additions and renovations while retaining its extraordinary architectural character. The gracious center hall floor plan welcomes you with a historic staircase and spacious rooms filled with period charm. A stunning 14 x 25 country kitchen, added around 1820, features soaring cathedral ceilings, a loft overlooking the space, ample room for everyday dining, and direct access to a private terrace—perfect for entertaining or enjoying peaceful mornings outdoors. Historic details abound throughout the home, including exposed hand-hewn oak beams in the formal dining room, exceptionally wide-plank wood floors measuring up to 18 inches on the second level, elegant period moldings, and beautiful marble fireplaces. A major Georgian-style renovation completed between 1850 and 1860 introduced the stately entrance portico, the full two-story roofline, and the impressive 40-inch-wide staircase, enhancing both the home’s beauty and functionality. Offering four bedrooms and two full bathrooms—one on each level—the home combines historic craftsmanship with comfortable everyday living. Complementing the residence is a carriage barn-style garage, built in 2003, featuring space for three vehicles, a spacious second-floor loft ideal for a studio, workshop, storage, or future possibilities, plus an attached tool shed. Situated on a generously sized parcel with .93 acres, the property is framed by mature trees that provide privacy while the expansive lawn offers endless opportunities for gardening, recreation, entertaining, or future enhancements. Rich in history, craftsmanship, and character, this one-of-a-kind property offers the rare chance to own a home where over 250 years of architectural heritage meet the comforts of modern living.

Listing snapshot

Days on site
59 days
Listed on MLS
Jul 31, 2026
Full baths
2
Half baths
0
Annual property tax (MLS)
$8,186.46
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Engel & Volkers North Fork
MLS ID
KEY1033174
Last updated
Sep 18, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1770
Garage
Yes
Garage spaces
3
Total parking
3
Parking
Driveway, Garage, Off Street
Water source
Public
Sewer
Public Sewer
Utilities
Electricity Connected, Sewer Connected, Trash Collection Private

Interior features

Basement
Bilco Door(s), Crawl Space, Unfinished
Heating
Hot Water, Oil
Cooling
None
Interior
Beamed Ceilings, Eat-in Kitchen, Formal Dining, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Walk Through Kitchen, Washer/Dryer Hookup
Appliances
Gas Range, Refrigerator, Washer
Fireplace
Yes
Fireplaces
4

Exterior features

Architectural style
Colonial, Farmhouse, Saltbox
Construction materials
Shingle Siding, Wood Siding
Private pool
No

Schools (MLS)

Elementary school
Mattituck-Cutchogue Elementary Sch
Elementary school district
Mattituck-Cutchogue
Middle school
Mattituck Junior-Senior High School
Middle school district
Mattituck-Cutchogue
High school
Mattituck Junior-Senior High School
High school district
Mattituck-Cutchogue

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. First seen on this site
  3. MLS status changed

Location

Southold · Suffolk County, NY 11935Show interactive map
26905 Main Road

Southold · Suffolk County, NY 11935

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
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Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.