105 Waterview Dr

Southold, NY 11971

$3,850,000
Price
4
Beds
4,103 Sq. Ft.
$938 / Sq. Ft.
4,103
Sq. Ft.
$938
per Sq. Ft.
Listed By Compass
Listed By Compass
an aerial view of a house with a yard and lake view
an aerial view of a house with a yard and lake view
a front view of a house with yard
a view of an entryway with wooden floor and front door
a living room with furniture and a fireplace
a living room with furniture a fireplace and a flat screen tv
a living room with furniture fireplace and a flat screen tv
a view of a dining room with furniture window and outside view
a kitchen with a white cabinets stove and sink
a kitchen with a stove a refrigerator and a view of living room
a view of a dining room with furniture window and wooden floor
a bedroom with furniture and a window
a bedroom with a bed and a window
a bedroom with a large bed and a window
a kitchen with a sink a stove and a mirror
a view of an entryway with wooden floor
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a living room with furniture and a window
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a bedroom with a large bed and a potted plant
a bathroom with a sink vanity and a mirror
a bathroom with a bathtub and a window
a bedroom with a bed and a table
a bedroom with a bed and a table
a bedroom with a bed and a window
a bathroom with a sink and a mirror
a utility room with dryer and washer
a view of a house with pool and sitting area
a view of a patio with a table and chairs
a view of balcony with wooden floor
a view of a balcony with lake view and wooden floor
a bathroom with a sink and mirror
a view of yard with wooden floor and fence
a view of a large white house with a yard covered with snow in front of house
a view of a dry yard with trees in the background
a backyard of a house with barbeque oven and outdoor seating
a view of a lake with a mountain in the background
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Description

Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 4-bedroom, 3-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room.
Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential. The versatile 700+ bonus area has rough plumbing, while the enormous attic, featuring 8.5+ ft ceilings,...Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 4-bedroom, 3-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room.

Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential. The versatile 700+ bonus area has rough plumbing, while the enormous attic, featuring 8.5+ ft ceilings, offers the possibility of a third-floor buildout. The walk-out basement, with 9+ ft ceilings, two egresses, and plumbing in place, adds even more room for customization.

Resort-style amenities continue across the grounds: a 16' x 32' heated saltwater gunite pool with electric cover is set into a 2,100 SF deck, a high-end 6-person hot tub and an outdoor shower. A wide path leads to a fire pit area and the private dock, which previously accommodated a 23' Grady-White and provides direct access to the bay.

Inside, a chef’s kitchen, wood-burning fireplace, and generous ceiling heights enhance the home’s warm yet refined ambience. Radiant heat warms the eat-in kitchen, all bathrooms, and additional spaces throughout. Recent upgrades include the new pool and hot tub, a newly constructed circular driveway, freshly painted Hardie board siding, all-new interior paint, updated lighting, and modern hardware.

A truly exceptional offering of space, serenity, and waterfront luxury—ideal as a full-time residence or a memorable seasonal escape.

Property Details for 105 Waterview Drive

City/Township
Southold
View
Water
Architectural Style
Colonial
Garage Spaces
3.00
Waterfront
Yes
Section Area
Main Bayview
LISTING UPDATED: 12/13/2025 12:39 PM

Property Details for 105 Waterview Drive

StatusActive
MLS #928708
Days on Market46
Taxes$17,588 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built2006
Lot Size6.50 AC / 283,140 SF
CountySuffolk County

Location

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Building Information for 105 Waterview Drive

Stories-Year Built2006Building Size-Lot Size6.50 AC / 283,140 SF

Payment Calculator

$20,490 per month

30 year fixed, 6.28% Interest

Principal and Interest

$19,024

Property Taxes

$1,466

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 105 Waterview Drive

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • Levels: Three Or More
  • Property Condition: Updated/Remodeled
  • Frontage Length: 490
  • State Or Province: NY
  • Water Access YN: Yes
School Information
  • School District: Southold
  • Elementary School District: Southold
  • Elementary School: Southold Elementary School
  • Middle Or Junior School District: Southold
  • Middle Or Junior School: Southold Junior-Senior High School
  • High School District: Southold
  • High School: Southold Junior-Senior High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: First
  • Room Type: Living Room
  • RoomDescription 1: 24 X 16.5 with 9 foot ceiling including wood burning fireplace, recessed lighting, expansive windows with water views
Room 2 Information
  • Room Level: First
  • Room Type: Dining Room
  • Room Description: 16 x 13 with custom wainscot paneling, crown moldings, two large windows, crystal chandelier and sconces, 9 foot ceilings
Room 3 Information
  • Room Level: First
  • Room Type: Den
  • Room Description: 14 x 13 cathedral ceilings with three sides of window with open water view
Room 4 Information
  • Room Level: First
  • Room Type: Kitchen
  • Room Description: 21 x 25 eat in chef's kitchen with slate radiant floor, walk in pantry, wood cabinets, slider leading to expansive deck/pool, open water view
Room 5 Information
  • Room Level: First
  • Room Type: Office
  • Room Description: 14 x 15 study/office with 9 foot ceiling over looking pool with water views
Room 6 Information
  • Room Level: First
  • Room Type: Bathroom 1
  • Room Description: 9 x 5 with tub shower combo, slate tile, large window and new vanity
Room 7 Information
  • Room Type: Bedroom 1
  • Room Description: 15 x 12.5 9 foot ceiling, crown molding, three large windows
Room 8 Information
  • Room Level: Second
  • Room Type: Primary Bedroom
  • Room Description: 16.5 x 16.5 double walk in closets, en suite sitting room with balcony with panoramic water views, en suite bath with sauna
Room 9 Information
  • Room Level: Second
  • Room Type: Primary Bathroom
  • Room Description: 13 x 10 large walking shower with heat lighting, radiant heat floors, soaking tub with water views, sauna, marble vanity and floors
Room 10 Information
  • Room Level: Second
  • Room Type: Sauna
  • Room Description: 4 x 7 Scandinavian spa like sauna with two tier bench
Room 11 Information
  • Room Level: Second
  • Room Type: Bedroom 2
  • Room Description: 14 x 14 with double closets, large windows and 8 foot ceiling
Room 12 Information
  • Room Level: Second
  • Room Type: Bedroom 3
  • Room Description: 13 x 12with double closets, large windows and 8 foot ceiling with niche for deck
Room 13 Information
  • Room Level: Second
  • Room Type: Bathroom 2
  • Room Description: 11 x 5 bright windowed bathroom with tub shower combo and radiant heat floor
Room 14 Information
  • Room Level: Second
  • Room Type: Laundry
  • Room Description: 12 x 9 high capacity washer and dryer, separate large linen closet and laundry sink
Room 15 Information
  • Room Level: First
  • Room Type: Auxiliary Room
  • Room Description: Additional windowed pantry with built in shelving and closet
Room 16 Information
  • Room Level: Lower
  • Room Type: Basement
  • Room Description: Walkout windowed with egress and rough plumbing in place
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 1000-078-00-07-00-009-000
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Bath, Bayfront, Built-in Features, Cathedral/Vaulted/High Ceiling, Ceiling Fan(s), Central Vacuum, Chandelier, Chefs Kitchen, Colonial, Crown Molding, Eat in Kitchen, Entrance Foyer, First Floor Full Bath, Formal Dining, Granite Counters, Hardwood Floors As Seen, High Ceilings, His and Hers Closets, Laundry Room, Living Room, Marble Counters, Masonry, Outdoor Pool, Pantry, Pool Cover, Primary Bathroom, Public, Recessed Lighting, Salt Water, Sauna, Soaking Tub, Stone Counters, Storage, Tile, Walk In Closet, Washer/Dryer Hookup, Water View, Waterfront, Wood Burning
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Central Vacuum, Chandelier, Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, His and Hers Closets, Marble Counters, Pantry, Primary Bathroom, Recessed Lighting, Sauna, Soaking Tub, Stone Counters, Storage, Walk-In Closet(s), Washer/Dryer Hookup
  • Appliances: Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Freezer, Microwave, Oven, Refrigerator, Washer
  • Number Of Kitchens: 1.0
  • Total Rooms: 10
  • Basement: Full, Unfinished, Walk-Out Access
  • Attic Description: Full,Pull Stairs,Unfinished
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Fireplace Features: Living Room, Masonry, Wood Burning
  • Location Amenities: Walk Out Basement, Hardwood Floors As Seen, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Chef's Kitchen, Eat in Kitchen, Entry Foyer, Foyer, Formal Dining Room, Granit Countertops, High Ceilings, Marble Countertops, Pantry, Soacking Tub, Storage, Walk In Closet, WD Hookup, Pool Outdoor, Water View
  • Laundry Features: Laundry Room
  • Spa Features: Bath
  • Spa: Yes
  • Flooring: Hardwood, Tile
  • Living Area: 4,103.00
  • Foundation Details: Concrete Perimeter
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Outdoor Pool, Pool Cover, Salt Water, Driveway, Garage, Garage Door Opener, Off Street, Private
  • Elevation Certificate: No
  • Construction Materials: Advanced Framing Technique, Batts Insulation, Frame, HardiPlank Type
  • Waterfront Features: Bayfront, Waterfront
  • Pool Private: Yes
  • Pool Features: Outdoor Pool,Pool Cover,Salt Water
  • Pool Details: Outdoor Pool,Pool Cover,Salt Water
Lot Information
  • Additional Parcel: Yes
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Garage, Garage Door Opener, Off Street, Private
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Forced Air, Oil, Radiant, Radiant Floor
  • Heat Fuel Type: Forced Air, Oil, Radiant, Radiant Floor
  • Sewer: Septic Tank
  • Water Source: Public
  • Utilities: Electricity Connected, Water Connected
Green Features
  • Green Features: Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Freezer, Microwave, Oven, Refrigerator, Washer, Forced Air, Oil, Radiant, Radiant Floor, Outdoor Pool, Pool Cover, Salt Water
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 105 Waterview Drive

DateEvent & SourcePriceAppreciation
Dec 31, 2020

Sold (Public Record)

Public Record #692679083

$2,149,000—
DateEvent & SourcePrice
12/31/2020

Sold (Public Record)

Public Record #692679083

$2,149,000

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

Public Records for 105 Waterview Drive

Taxable ValueLand$3,900Additions$7,700Total$11,600
Home Facts
Beds0Lot Size239,580 SqFtStyleSingle Family ResidenceZoningR-40CountySUFFOLKAPN1000-078.00-07.00-009.000

Schools near 105 Waterview Drive

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

Southold 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 105 Waterview Drive, Southold, NY 11971

105 Waterview Drive is a single family home for sale in Southold, NY 11971. This property was listed for sale on October 30, 2025 by Compass, it's currently listed at $3,850,000. It has been on the market for a total of 46 days and was last sold on December 31, 2020. This listing's school district is Southold Union Free School District. Nearby schools include Southold Elementary School and Southold Junior Senior High School. 105 Waterview Drive is a 4-bed, 3-bath, 4,103 sqft single family home built in 2006.

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 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.

Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/15/2025 07:26 PM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.