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MLS ID KEY1033686Last updated Oct 4, 2026

Single Family

365 Rachels Road

Active · Southold · Suffolk County, NY 11952

Bedrooms
4 Beds
Bathrooms
4 Baths
Year built
1990
Est. monthly taxes
$656.92
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About this home

A Rare North Fork Farmhouse with a Heated Barn and Endless Possibilities Tucked away on three-quarters of an acre in a quiet Mattituck neighborhood, this beautifully updated North Fork farmhouse offers the perfect blend of timeless charm, modern updates, and exceptional versatility. Surrounded by a peaceful setting, the property provides plenty of room to relax, entertain, and enjoy the North Fork lifestyle, with thoughtfully designed indoor and outdoor spaces that make you feel right at home. Designed for comfortable living and effortless entertaining, the home features four bedrooms and four full bathrooms across three finished levels. The thoughtfully renovated interior showcases hardwood floors, custom millwork, a beautifully appointed quartz kitchen with shaker cabinetry, and a wood-burning fireplace that anchors the inviting living and dining areas. All four bathrooms feature radiant heated floors, providing comfort and warmth throughout the year. A first-floor bedroom and full bath provide flexibility for guests or single-level living, while the finished lower level—with an additional bedroom, full bath, and spacious family room—offers exceptional space for recreation, a home office, or extended stays. Upstairs, the primary suite features a generous walk-in closet and beautifully appointed bath, while the second upstairs bedroom also enjoys its own walk-in closet. A standing-seam metal roof, approximately five years old, adds lasting value and peace of mind. Step outside to enjoy a freshly painted rear deck overlooking a newly fenced backyard designed for outdoor living, complete with mature landscaping, a tranquil koi pond, hot tub, dedicated fenced garden area, charming playhouse, and abundant space for a future swimming pool. A truly exceptional feature is the property's heated nearly 1,000-square-foot galvanized steel barn with convenient secondary access from Main Road. Equipped with electricity, oversized doors, soaring ceilings, a durable 12-inch concrete floor, and a wood-burning stove, this remarkable space offers endless possibilities as an artist's studio, workshop, garage, collector's showcase, or substantial storage for boats, vehicles, equipment, and hobbies. Few North Fork properties combine an updated farmhouse with a heated barn of this size and versatility. Paired with its peaceful setting just minutes from Love Lane, the grocery store, beaches, wineries, and farm stands, this is a property that offers exceptional flexibility for the way people live today.

Listing snapshot

Days on site
59 days
Listed on MLS
Aug 8, 2026
Full baths
4
Half baths
0
Annual property tax (MLS)
$7,883
Tax year
2025
Area source (MLS)
CubiCasa
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY1033686
Last updated
Oct 4, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1990
Garage
No
Total parking
4
Parking
Driveway, Storage
Water source
Well
Sewer
Septic Tank
Utilities
Cable Connected, Electricity Connected

Interior features

Basement
Finished, Full
Heating
Hot Water, Oil, Radiant Floor
Cooling
Ductless
Interior
First Floor Bedroom, First Floor Full Bath, Ceiling Fan(s), Chefs Kitchen, High Speed Internet, His and Hers Closets, Natural Woodwork, Primary Bathroom, Quartz/Quartzite Counters, Recessed Lighting, Storage, Walk Through Kitchen, Walk-In Closet(s), Washer/Dryer Hookup
Appliances
Convection Oven, Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater
Flooring
Hardwood
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Farmhouse
Construction materials
Frame, Shingle Siding
Exterior
Other
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 11952Show interactive map
365 Rachels Road

Southold · Suffolk County, NY 11952

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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

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