Skip to main content

MLS ID KEY1038110Last updated Sep 18, 2026

Single Family

2 Penny Lane

Pending · Smithtown · Suffolk County, NY 11780

Bedrooms
5 Beds
Bathrooms
3 Baths
Year built
1997
Est. monthly taxes
$2,982.33
Property gallery0 / 36
Loading photo…Photo unavailable

About this home

Waterfront on the Long Island Sound, this rare offering features 75 feet of direct frontage and is set on a beautifully landscaped acre at the end of a quiet cul-de-sac within a private beach community. An entertainer’s dream, the property features a stunning bluestone patio overlooking the water, complete with a gazebo and generous seating areas—all positioned to take in expansive views of the Sound and spectacular sunsets. The perfect setting for hosting summer BBQs or simply relaxing and unwinding in your own waterfront oasis. Private steps lead directly to the beach and water below, creating an exceptional setting for outdoor dining, entertaining or simply enjoying the waterfront. The traditional 5-bedroom, 3-full-bath Center Hall Colonial features spacious formal rooms, wood floors and an impressive formal entry hall with soaring ceilings and a custom bridal staircase. The eat-in kitchen features white cabinetry, granite countertops, a center island with seating and a large dinette area, and opens directly to the beautiful great room with soaring ceilings, a wood-burning fireplace and large windows that bring the beauty of the surrounding landscape indoors. Glass sliders open to a large entertainment deck, extending the living space outdoors. A first-floor bedroom, equally well suited as a home office, and conveniently located laundry add flexibility to the main level. The second-floor primary suite offers a private retreat with beautiful views of the Long Island Sound, an electric fireplace and two walk-in closets. The spacious ensuite bath features double sinks and a Jacuzzi tub positioned beneath a wall of windows, creating a peaceful place to relax while taking in the water views. Three additional generously sized bedrooms, a spacious main full bath with double sinks, and a private outdoor deck complete the second floor. A full basement offers substantial additional space and storage with the potential to be finished in the future, while the 3-car garage with a car lift provides added versatility. Professionally landscaped grounds are enhanced by landscape lighting, a hot tub, generous driveway parking and multiple outdoor spaces for dining, gathering and relaxing by the water. With the Long Island Sound just beyond the backyard, private beach access and gorgeous sunsets unfolding across the horizon, the setting offers the feeling of being on vacation year-round, all from the privacy of your own home.

Listing snapshot

Days on site
40 days
Listed on MLS
Aug 16, 2026
Full baths
3
Half baths
0
Annual property tax (MLS)
$35,788
Tax year
2026
Association / maintenance fees (MLS)
$500 / Annually
Fees include (MLS)
Snow Removal
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY1038110
Last updated
Sep 18, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1997
Garage
Yes
Garage spaces
3
Parking
Driveway, Garage
Water source
Public
Sewer
Septic Tank
Utilities
Cable Connected, Electricity Connected, Underground Utilities, Water Connected

Interior features

Basement
Full, Storage Space, Unfinished
Heating
Baseboard, Hot Water, Oil
Cooling
Central Air
Interior
First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Crown Molding, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, High Speed Internet, His and Hers Closets, Kitchen Island, Pantry, Primary Bathroom, Recessed Lighting, Storage, Walk-In Closet(s), Washer/Dryer Hookup
Appliances
Convection Oven, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Washer, Oil Water Heater
Flooring
Carpet, Hardwood, Tile
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Colonial
Construction materials
Frame, Vinyl Siding
Exterior
Lighting, Mailbox, Rain Gutters
Private pool
No

Schools (MLS)

Elementary school
St James Elementary School
Elementary school district
Smithtown
Middle school
Nesaquake Middle School
Middle school district
Smithtown
High school
Smithtown High School-East
High school district
Smithtown

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. First seen on this site
  2. Listing updated from MLS
  3. MLS status changed

Location

Smithtown · Suffolk County, NY 11780Show interactive map
2 Penny Lane

Smithtown · Suffolk County, NY 11780

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.