- Overview
- Description
- Property Details
- Location
- Facts & Features
- Getting Around
- Nearby Homes





Street View
$1,150,000
Monthly Est:$5,724
4 Beds
- 4 Baths
4 full baths
2,053sqft
365 Rachels Rd, Southold, NY 11952
$1,150,000
$5,724/moEst:
Get Pre-Approved
Single Family Residence
Built in 1990
$-- HOA
32,670 sqft lot
$560/sq.ft
Description
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.
- Houzeo last checked: 1 hour ago
- Listing updated: October 4, 2026 at 6:09 pm
- Listing Provided by: Jon L. Tomlinson (646) 528-5121 , Natalie Hough | Daniel Gale Sothebys Intl Rlty (631) 298-4130
- Source: OneKey MLS-NY as distributed by MLS GRID | MLS#: 1033686

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1990
HOA Fees
-
Finished Area
2,053 sqft
Lot Size
32,670 sqft lot
Basement Area
- sqft
MLS Name
OneKey MLS
MLS Number
1033686
MLS Status
Active
Days on Market
93
Cumulative Days on Market
57

Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 4
Interior
Exterior Features
Other
Cooling
Ductless
Heating
Hot Water, Oil, Radiant Floor
Flooring
Hardwood
Appliances
Convection Oven, Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater
Window Features
Double Pane Windows, Energy Star Qualified Windows, Insulated Windows
Sewer
Septic Tank
Interior Features
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
Construction
Year Built
Year Built: 1990
Home type
Single Family Residence
Architectural Style
Farmhouse
Property Condition
Actual
Construction Materials
Frame, Shingle Siding
Utilities & Energy
Utilities
Cable Connected, Electricity Connected
Water Source
Well
Laundry Features
Gas Dryer Hookup, In Basement, Washer Hookup
Fireplace Features
Wood Burning
Basement
Finished, Full
Parking Features
Driveway, Storage
Other Features
Patio And Porch Features
Deck
Lot Features
Back Yard, Cul De Sac, Front Yard, Garden, Landscaped, Level, Near Public Transit, Near School, Near Shops, Sprinklers In Front, Sprinklers In Rear
Price History
| Date | Event | Price |
|---|---|---|
08/06/2026 Source: | Listed for Sale | $1,150,000 $560/sqft |
08/03/2026 Source: | Coming Soon | $1,150,000 +39.39% $560/sqft |
06/15/2025 Source: | Price Decreased | $825,000 -5.71% $402/sqft |
04/27/2023 Source: | Sold | $875,000 $426/sqft |
Nearby Homes
Find Homes by Property Features in Southold, NY
Based on information from OneKey MLS® through Nov 05, 2026, 12:46PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 OneKey MLS. All rights reserved.
Advertising Broker: Derek Greene | The Greene Realty Group










