For Sale
Single family home for sale at 365 Rachels Rd, Southold, NY 11952 | MLS# 1033686 | Listing updated on 2026-10-04
Photo 1 of Single family home for sale at 365 Rachels Rd, Southold, NY 11952 | MLS# 1033686 | Listing updated on 2026-10-04
Photo 2 of Single family home for sale at 365 Rachels Rd, Southold, NY 11952 | MLS# 1033686 | Listing updated on 2026-10-04
Photo 3 of Single family home for sale at 365 Rachels Rd, Southold, NY 11952 | MLS# 1033686 | Listing updated on 2026-10-04
Photo 4 of Single family home for sale at 365 Rachels Rd, Southold, NY 11952 | MLS# 1033686 | Listing updated on 2026-10-04
22+
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Street View

$1,150,000

Monthly Est:$5,724

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon2,053sqft

365 Rachels Rd, Southold, NY 11952

$5,724/moEst:

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  • 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 inter
ior 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 OneKey MLS-NY as distributed by MLS GRID

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Suffolk County

  • City

    Southold

  • 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

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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

DateEventPrice

08/06/2026

Source: mls_logoOneKey MLS-NY #KEY1033686

Listed for Sale

$1,150,000

$560/sqft

08/03/2026

Source: mls_logoOneKey MLS-NY #KEY1033686

Coming Soon

$1,150,000 +39.39%

$560/sqft

06/15/2025

Source: mls_logoOneKey MLS-NY as distributed by MLS GRID #KEYL3425560

Price Decreased

$825,000 -5.71%

$402/sqft

04/27/2023

Source: mls_logoOneKey MLS-NY #KEYL3425560

Sold

$875,000

$426/sqft

Nearby Homes

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

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