For Sale
Open House
3D Tour3D Tour
Single family home for sale at 2280 Deep Hole Dr, Southold, NY 11952 | MLS# 943316 | Listing updated on 2026-10-07
Photo 1 of Single family home for sale at 2280 Deep Hole Dr, Southold, NY 11952 | MLS# 943316 | Listing updated on 2026-10-07
Photo 2 of Single family home for sale at 2280 Deep Hole Dr, Southold, NY 11952 | MLS# 943316 | Listing updated on 2026-10-07
Photo 3 of Single family home for sale at 2280 Deep Hole Dr, Southold, NY 11952 | MLS# 943316 | Listing updated on 2026-10-07
Photo 4 of Single family home for sale at 2280 Deep Hole Dr, Southold, NY 11952 | MLS# 943316 | Listing updated on 2026-10-07
35+
Beds Icon

Virtual Tour

Beds Icon

Street View

$2,299,000

Monthly Est:$11,443

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,400sqft

2280 Deep Hole Dr, Southold, NY 11952

$11,443/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2022

  • $-- HOA

  • 20,909 sqft lot

  • $958/sq.ft

Description

Set along one of Mattituck’s most sought-after waterfront enclaves, 2280 Deep Hole Drive offers a rare opportunity to own an exquisite waterfront residence newly built in 2022, encompassing 3,000 square feet of thoughtfully designed living space with exceptional deepwater dockage and direct access to Peconic Bay. Perfectly suited for the boating enthusiast, the property features approximately 130 feet of deepwater frontage on Deep Hole Creek and a substantial dock capable of accommodating two vessels up to 36 feet, complete with electric and water, providing protected, convenient access to the bay and beyond. The home features 9-foot ceilings on the main level, an open-concept layout filled with natural light, expansive water views, and refreshing bay breezes throughout. At the heart of the home is a custom chef’s kitchen appointed with premium, professional-grade appliances, high-end finishes, and a large center island ideal for entertaining and everyday living. The kitchen flows seamlessly into the dining and living areas, where a gas fireplace anchors the space with warmth and ambiance while framing serene water views. Sliding doors from the main living areas open to a waterside deck and balcony, creating an ideal setting for alfresco dining or relaxing in the spa-style hot tub overlooking the water. The first-floor primary suite offers a private retreat with an en-suite bath, and then there are 3+ additional spacious bedrooms, dedicated workstation areas, and 2.5 baths that provide flexibility and comfort. The full walk-out daylight basement provides expansive storage and the potential for a gym, workshop, or recreational space. Built with enhanced features for comfort and efficiency, the home includes a Navien tankless hot water system, 1,000-gallon propane tank, thermal windows, updated systems throughout, and a whole-house Generac generator for added peace of mind. Outdoors, there is room for a pool, and the waterfront setting creates an exceptional lifestyle opportunity for boating, fishing, paddleboarding, and entertaining by the water. Ideally located less than one mile from Love Lane and just minutes to local vineyards, farm stands, beaches, parks, and acclaimed North Fork dining, 2280 Deep Hole Drive is more than a home—it is a complete waterfront lifestyle defined by modern design, flexible living spaces, coveted dockage, and the unmistakable charm of Mattituck’s North Fork. Includes an option to purchase furnishings. Nearby Pool Club Membership available at Strong’s Water Club and Marina. This listing may include images that have been digitally altered or virtually staged.

  • Houzeo last checked: 30 minutes ago
  • Listing updated: October 7, 2026 at 4:43 pm
  • Listing Provided by: Susan M. Orioli (516) 287-6896 | Engel & Volkers North Fork (631) 298-7953
  • Source: OneKey MLS-NY | MLS#: 943316 OneKey MLS-NY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Suffolk County

  • City

    Southold

  • Neighborhood

    --

  • Year Built

    2022

  • HOA Fees

    -

  • Finished Area

    2,400 sqft

  • Lot Size

    20,909 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    943316

  • MLS Status

    Active

  • Days on Market

    293

  • Cumulative Days on Market

    292

Open House

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

HOA Management

James Orioli

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

Interior

  • Cooling

    Central Air

  • Heating

    Forced Air, Propane

  • Exterior Features

    Balcony, Boat Slip, Dock

  • Sewer

    Septic Tank

  • Appliances

    Dishwasher, Dryer, Oven, Refrigerator, Washer

  • Window Features

    Insulated Windows

  • Interior Features

    First Floor Bedroom, First Floor Full Bath, Built In Features, Chefs Kitchen, Double Vanity, Eat In Kitchen, Entrance Foyer, Kitchen Island, Open Floorplan, Open Kitchen, Primary Bathroom, Walk Through Kitchen

Construction

  • Year Built

    Year Built: 2022

  • Home type

    Single Family Residence

  • Property Condition

    Actual

  • Construction Materials

    Advanced Framing Technique

  • Architectural Style

    Other

Utilities & Energy

  • Water Source

    Public

  • Utilities

    Propane

  • Laundry Features

    Laundry Room

  • Parking Features

    Garage

  • Fireplace Features

    Gas, Living Room

  • Basement

    Unfinished, Walk Out Access

Other Features

  • Patio And Porch Features

    Covered, Deck

Price History

DateEventPrice

09/02/2026

Source: mls_logoOneKey MLS-NY #KEY943316

Price Decreased

$2,299,000 -8.00%

$958/sqft

07/29/2026

Source: mls_logoOneKey MLS-NY #KEY943316

Price Decreased

$2,499,000 -3.85%

$1,041/sqft

06/16/2026

Source: mls_logoOneKey MLS-NY #KEY943316

Listing Removed

$2,599,000 +13.05%

$1,083/sqft

06/16/2026

Source: mls_logoOneKey MLS-NY #KEY943316

Listed for Sale

$2,299,000 -11.54%

$958/sqft

12/19/2025

Source: mls_logoOneKey MLS-NY #KEY943316

Listed for Sale

$2,599,000

$1,083/sqft

Nearby Homes

Based on information from OneKey MLS, through Oct 09, 2026, 12:01PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group