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MLS ID KEY943316Last updated Oct 10, 2026

Single Family

2280 Deep Hole Drive

Active · Southold · Suffolk County, NY 11952

Bedrooms
3 Beds
Bathrooms
3 Baths
Year built
2022
Est. monthly taxes
$1,465.65
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About this home

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.

Listing snapshot

Days on site
59 days
Listed on MLS
Dec 19, 2025
Full baths
2
Half baths
1
Annual property tax (MLS)
$17,587.82
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Engel & Volkers North Fork
MLS ID
KEY943316
Last updated
Oct 10, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
2022
Garage
Yes
Garage spaces
2
Parking
Garage
Water source
Public
Sewer
Septic Tank
Utilities
Propane

Interior features

Basement
Unfinished, Walk-Out Access
Heating
Forced Air, Propane
Cooling
Central Air
Interior
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
Appliances
Dishwasher, Dryer, Oven, Refrigerator, Washer
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Other
Construction materials
Advanced Framing Technique
Exterior
Balcony, Boat Slip, Dock
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. Price changed to $2,299,000
  3. First seen on this site
  4. MLS status changed

Location

Southold · Suffolk County, NY 11952Show interactive map
2280 Deep Hole Drive

Southold · Suffolk County, NY 11952

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Estimate monthly payment

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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.