2280 Deep Hole Dr

Mattituck, NY 11952

$2,599,000
Price
3
Beds
3,000 Sq. Ft.
$866 / Sq. Ft.
3,000
Sq. Ft.
$866
per Sq. Ft.
Open: 1/31 11:00AM - 12:30PM
Open: 1/31 11:00AM - 12:30PM
Rare opportunity to own a premier waterfront property with deep-water dockage
Protected deep-water dock designed for effortless docking and secure mooring
A true boater’s estate offering privacy, views, and easy bay access
Relaxed waterfront living with seamless indoor-outdoor flow
Aerial view showcasing the home’s prime waterfront location with expansive water frontage and deep-water dockage
Endless water views from nearly every angle, creating a true coastal retreat
Front-row seat to breathtaking views and tranquil waterfront scenery
Delightful views capturing open water access and the property’s commanding waterfront presence
Spa-style hot tub with front row views of the water and dock
Aerial view of home and Deep Hole Creek
Chef's kitchen thoughtfully positioned to enjoy water views while cooking and entertaining
Bright, open kitchen with generous counter space and hi end finishes
Well appointed kitchen flowing effortlessly into dining and living areas
Easy access to waterside deck perfect for alfresco dining
Casual yet refined dining area with direct sight lines to the water
Open and inviting living spaces designed to capture water views and coastal breezes
Elegant waterfront living room with fireplace
Comfortable gathering space ideal for entertaining after a day on the water
Inviting family room with abundant natural light, water views and balcony access
Light filled bedroom with peaceful ambience
Wake up to calming waterfront vistas
Tastefully finished bathroom with timeless details
Guest bedroom designed with privacy and natural light
Well designed bathroom offering comfort and functionality
Classic interior details complementing the home's waterfront setting
Multi purpose music room easily adapted to your lifestyle
Versatile room ideal for home office or den
Plenty of windows creating a warm and inviting atmosphere as soon as you enter the front door
Waterfront living at its finest
New exquisite stone walkway
Beautiful front entrance
Private waterfront oasis with ample outdoor living space
Waterfront elegance blended with comfort and functionality
Boater’s dream with substantial dockage accommodating multiple watercraft
Steps from home to dock, offering seamless waterfront living
Peaceful waterside retreat with easy access to boating, fishing, and kayaking
Aerial view of stellar waterfront home and dock
Deepwater dock for multiple boats
Quick boat ride to Peconic Bay and beyond
Maintained deep water channel for easy access in and out
Nearby Sandy Peconic Bay Beach

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...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. A unique music room offers creative space for the artistically inclined and can easily be converted into 2 bedrooms if desired. 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.
  1. Listed by Susan M. Orioli • Engel & Volkers North Fork
    P: (631)-298-7953 C: (631)-298-7953 susan.orioli@evrealestate.com

Property Details for 2280 Deep Hole Drive

City/Township
Southold
View
Water
Architectural Style
Other
Garage Spaces
2.00
Waterfront
Yes
Section Area
New Suffolk Avenue

Open Houses

Saturday, Jan 31st

11:00 AM - 12:30 PM

Public

LISTING UPDATED: 01/30/2026 10:43 AM

Property Details for 2280 Deep Hole Drive

StatusActive
MLS #943316
Days on Market42
Taxes$17,588 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built2022
Lot Size0.48 AC / 20,909 SF
CountySuffolk County

Location

Listing Courtesy of Engel & Volkers North Fork, Susan M. Orioli
Add your commute

Building Information for 2280 Deep Hole Drive

Stories-Year Built2022Building Size-Lot Size0.48 AC / 20,909 SF

Payment Calculator

$14,133 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,667

Property Taxes

$1,466

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 2280 Deep Hole Drive

Summary
Location and General Information
  • Senior Community YN: No
  • Directions: Main Road to New Suffolk Ave to Deep Hole Drive
  • Year Built Effective: 2022
  • Property Attached: No
  • Structure Type: false
  • Property Condition: Actual
  • Frontage Length: 130
  • State Or Province: NY
  • Water Access YN: Yes
School Information
  • School District: Mattituck-Cutchogue
  • Elementary School District: Mattituck-Cutchogue
  • Elementary School: Mattituck-Cutchogue Elementary Sch
  • Middle Or Junior School District: Mattituck-Cutchogue
  • Middle Or Junior School: Mattituck Junior-Senior High School
  • High School District: Mattituck-Cutchogue
  • High School: Mattituck Junior-Senior High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 1000-123-00-04-00-006-000
  • Tax Assessed Value: $10,800.00
  • Additional Fees: No
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Balcony, Boat Slip, Built-in Features, Chefs Kitchen, Covered, Deck, Dock, Double Vanity, Eat in Kitchen, Entrance Foyer, First Floor Full Bath, Gas, Insulated Windows, Kitchen Island, Laundry Room, Living Room, Open Floorplan, Open Kitchen, Other, Primary Bathroom, Public, Walk Through Kitchen, Water Access, Water View, Waterfront
  • 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
  • Appliances: Dishwasher, Dryer, Oven, Refrigerator, Washer
  • Number Of Kitchens: 1.0
  • Total Rooms: 6
  • Basement: Unfinished, Walk-Out Access
  • Attic Description: Full,Pull Stairs
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Gas, Living Room
  • Location Amenities: Other/See Remarks, Walk Out Basement, Balcony, Dock/Mooring, 1st Fl Master Bedroom, Chef's Kitchen, Dual Sinks, Eat in Kitchen, Entry Foyer, Foyer, Island Kitchen, Open Kitchen, Walk Through Kitchen, Deck, Water View, Water Access
  • Laundry Features: Laundry Room
  • Spa: Yes
  • Window Features: Insulated Windows
  • Living Area: 3,000.00
  • Basement: Yes
Exterior Features
  • Exterior Features: Balcony, Boat Slip, Dock
  • Exterior Property Features: Balcony, Boat Slip, Dock, Covered, Deck, Garage, Insulated Windows
  • Elevation Certificate: No
  • Patio And Porch Features: Covered,Deck
  • Construction Materials: Advanced Framing Technique
  • Waterfront Features: Water Access, Waterfront
  • Horse: No
  • Pool Private: No
Lot Information
  • Additional Parcel: No
  • Building Area Units: Square Feet
Parking
  • Parking Features: Garage
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Forced Air, Propane
  • Heat Fuel Type: Forced Air, Propane
  • Number Of Heating Zones: 2
  • Sewer: Septic Tank
  • Water Source: Public
  • Utilities: Propane
Green Features
  • Green Features: Insulated Windows, Dishwasher, Dryer, Oven, Refrigerator, Washer, Forced Air, Propane, Balcony, Boat Slip, Dock
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 2280 Deep Hole Drive

DateEvent & SourcePriceAppreciation
Apr 11, 2019

Sold (Public Record)

Public Record #645402276

$375,000

+31.9% / yr

Mar 14, 2006

Sold (Public Record)

Public Record #197336243

$10,000—
DateEvent & SourcePrice
04/11/2019

Sold (Public Record)

Public Record #645402276

$375,000

+31.9% / yr

03/14/2006

Sold (Public Record)

Public Record #197336243

$10,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 2280 Deep Hole Drive

Taxable ValueLand$1,800Additions$9,000Total$10,800
Home Facts
Beds0Lot Size20,909 SqFtStyleSingle Family ResidenceZoningR-40CountySUFFOLKAPN1000-123.00-04.00-006.000

Schools near 2280 Deep Hole Drive

This home is within Mattituck-Cutchogue Union Free School District.
Rating
School
Type
Grades
Distance
Mattituck Cutchogue Elementary School
Public - K to 6
Mattituck Junior Senior High School
Public - 7 to 12
Rating
School
Distance
Mattituck Cutchogue Elementary School
PublicK to 6

Mattituck Junior Senior High School
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 2280 Deep Hole Drive, Mattituck, NY 11952

2280 Deep Hole Drive is a single family home for sale in Mattituck, NY 11952. This property was listed for sale on December 19, 2025 by Engel & Volkers North Fork, it's currently listed at $2,599,000. It has been on the market for a total of 42 days and was last sold on April 11, 2019. This listing's school district is Mattituck-Cutchogue Union Free School District. Nearby schools include Mattituck Cutchogue Elementary School and Mattituck Junior Senior High School. 2280 Deep Hole Drive is a 3-bed, 3-bath, 3,000 sqft single family home built in 2022.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Engel & Volkers North Fork, Susan M. Orioli

Based on information submitted to the MLS GRID as of 01/30/2026 10:43 AM. 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. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and 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. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.