Gracious Waterfront Colonial South of Montauk! Step into timeless elegance at this stately 12-room Colonial nestled on a rare 75’ wide waterfront lot with bulkhead and bay access. Boasting over 5,400 sq. ft. of living space, this 5-bedroom, 4-bath residence combines classic charm with spacious modern living. Highlights include formal living and dining rooms, a sun-drenched family room, sunroom, and a grand primary suite with dual walk-in closets. The third floor offers two additional bedrooms, a sitting room, and bath—perfect for guests or extended family. Enjoy summer nights by the water, host gatherings around the fire pit or gas grill, and take in serene views from the lush 16,553 sq. ft. lot. Located just south of Montauk Highway, this home is close to South Shore University Hospital, shopping, and Bay Shore’s vibrant village amenities. A rare opportunity to own a historic gem with modern updates in one of Bay Shore’s most desirable waterfront enclaves. House also offers 2 car detached garage with full standing room attic.
Pending
Price cut: $99K (6/18)
$999,999
44 S Montgomery Avenue, Bay Shore, NY 11706
5beds
5,486sqft
Single Family Residence, Residential
Built in 1900
0.38 Acres Lot
$-- Zestimate®
$182/sqft
$-- HOA
What's special
- 108 days
- on Zillow |
- 313 |
- 6 |
Zillow last checked: 7 hours ago
Listing updated: August 12, 2025 at 07:26am
Listing by:
Eric G Ramsay Jr Assoc LLC 631-665-1500,
Tammy J. Ramsay 516-319-8605,
Scarlett Leone 631-741-5588,
Eric G Ramsay Jr Assoc LLC
Source: OneKey® MLS,MLS#: 856820

Travel times
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Other
- Description: Primary Br w/2 WIC's, Laundry Room, Office, Bath, Sunroom, 2 Brs, Full Bath
- Level: Second
Other
- Description: 2Brs, Sitting Room, Bath
- Level: Third
Other
- Description: EIK, FDR, Bath, FLR, Family Room, Sunroom
- Level: First
Heating
- Has Heating (Unspecified Type)
Cooling
- Central Air
Appliances
- Included: Gas Oven
Features
- Beamed Ceilings
- Basement: Partial
- Attic: Full,Partial
- Number of fireplaces: 1
Interior area
- Total structure area: 7,054
- Total interior livable area: 5,486 sqft
Property
Parking
- Total spaces: 3
- Parking features: Garage
- Garage spaces: 3
Features
- Exterior features: Fire Pit, Gas Grill
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Bulkhead
- Frontage length: 75
Lot
- Size: 0.38 Acres
Details
- Parcel number: 0500394000100095000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence, Residential
Materials
- Clapboard
Condition
- Year built: 1900
Utilities & green energy
- Sewer: Other
- Water: Public
- Utilities for property: Cable Available, Cable Connected, Electricity Connected, Natural Gas Available, Natural Gas Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: Bay Shore
Financial & listing details
- Price per square foot: $182/sqft
- Tax assessed value: $82,800
- Annual tax amount: $26,956
- Date on market: 5/12/2025
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
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