- Overview
- Description
- Property Details
- Location
- HOA Management
- Facts & Features
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$2,299,000
Monthly Est:$11,443
3 Beds
- 3 Baths
2 full baths + 1 half bath
2,400sqft
2280 Deep Hole Dr, Southold, NY 11952
$2,299,000
$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

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
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

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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
| Date | Event | Price |
|---|---|---|
09/02/2026 Source: | Price Decreased | $2,299,000 -8.00% $958/sqft |
07/29/2026 Source: | Price Decreased | $2,499,000 -3.85% $1,041/sqft |
06/16/2026 Source: | Listing Removed | $2,599,000 +13.05% $1,083/sqft |
06/16/2026 Source: | Listed for Sale | $2,299,000 -11.54% $958/sqft |
12/19/2025 Source: | Listed for Sale | $2,599,000 $1,083/sqft |
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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.
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