2 Deepwells Lane, Saint James — Home Profile
Saint James doesn’t get nearly enough credit. Tucked into the incorporated village of Head of the Harbor, away from the noise and the over-built corridors, it holds a particular kind of quiet that’s genuinely hard to find this close to the city. 2 Deepwells Lane sits squarely in that world — a brick colonial built in 2002 on 1.70 private acres, nearly 4,800 square feet of living space, a 3-car garage, and an in-ground pool, in one of the North Shore’s most cohesive private enclaves.
This profile pulls together everything that matters beyond what a standard listing tells you: verified MLS data, school district context, neighborhood history, and the financial picture you actually need to make a decision.
Property Details
The Basics
- StyleColonial
- ConstructionBrick
- Bedrooms5
- Full Baths3
- Half Baths2
- Total Rooms10
- Living Area (GLA)4,788 sq ft
- Building Area Total5,954 sq ft
- Lot Size1.70 acres (74,052 sq ft)
- Year Built2002
- StoriesTwo
- Garage3-Car Attached
- ParkingDriveway, Private, Garage Door Opener
- BasementYes — Finished, Full
- AtticFull, Unfinished, Walkup
- FlooringHardwood, Tile, Combination
- Fireplaces2 — Bedroom & Family Room
Systems & Utilities
- CoolingCentral Air
- HeatNatural Gas
- WaterPublic
- SewerOther (see remarks)
- PoolYes — In-Ground
- HOANone
- WaterfrontNo
Key Interior Features
- 1st FloorBedroom + full bath, formal dining room, living room, family room w/ fireplace, kitchen, foyer, lavatory
- KitchenGranite & quartz counters, center island, eat-in area, gas range, convection oven, open to family room
- Primary SuiteSecond floor — walk-in closets, private bath, soaking tub
- Upper Level3 additional bedrooms + 2 baths (incl. primary)
- BasementFull finished + lavatory — see listing remarks
- HighlightsCathedral ceilings, crown molding, high ceilings, natural woodwork, his & hers closets, recessed lighting, chandelier, breakfast bar
- AppliancesGas range/oven, convection oven, dishwasher, microwave, refrigerator, SS appliances, washer/dryer hookup
Tax & Financial Data
Sourced from OneKey MLS and Suffolk County municipal records. All figures should be independently verified with the Town of Smithtown Receiver of Taxes.
Tax ID: 0801-007-00-04-00-004-025 | Suffolk County, Town of Smithtown | Village: Head of the Harbor | Tax source: Municipality · Tax year: 2026
School District
Smithtown High School East carries a 9/10 GreatSchools rating and consistently places among Long Island’s top public high schools for academics and athletics. The district is compact enough that schools feel like community institutions, not just zoned destinations — and for buyers with school-age children, it is reliably cited as one of the primary draws to the Saint James area.
The Neighborhood
Head of the Harbor
One of Suffolk County’s more quietly prestigious incorporated villages, Head of the Harbor sits at the edge of the Stony Brook Harbor estuary. It has no commercial strip, no through traffic, and a land-use philosophy that has kept it looking the way it’s looked for decades.
Deepwells Estate Legacy
The Deepwells name carries weight here. The historic Deepwells Farm mansion — a Greek Revival estate dating to the 1840s — sits nearby and serves as a cultural anchor for the community. Living on Deepwells Lane means living in proximity to that history, in a neighborhood built around it.
Practical Access
Route 25A (North Country Road) runs directly past the entrance to Deepwells Lane, connecting to Port Jefferson, Stony Brook, and Smithtown in minutes. The LIE is a straightforward shot south, and the Saint James LIRR station puts midtown Manhattan within commuting range.
Town & Table
Saint James village proper has a real Main Street energy — independent restaurants, coffee shops, and retail that reflects who actually lives there. Stony Brook’s dining and cultural scene is five minutes away. Port Jefferson Harbor adds waterfront options without Hamptons pricing.
What Makes This Home Stand Out
1.70 Acres of Brick Colonial in Head of the Harbor
Nearly 74,000 square feet of land inside an incorporated village, with a brick-built colonial that was constructed in 2002 — not flipped, not stretched, designed from the ground up to be this size. That combination of land, material quality, and build intent is genuinely rare at any price point on the North Shore.
First-Floor Bedroom with Full Bath — A Layout That Works for Everyone
A dedicated ground-floor bedroom and full bathroom isn’t a small detail. It makes this house genuinely functional for multi-generational households, for guests who need accessibility, and for anyone who wants the option — without sacrificing the scale of the upper-floor primary suite or the additional bedrooms.
3-Car Garage, In-Ground Pool, Finished Basement — All There
The amenity stack is complete. A 3-car garage is a meaningful differentiator in this market. The in-ground pool and finished basement with half-bath round out an outdoor-and-lower-level package that most comparably priced homes in this zip code require buyers to add post-purchase — if the lot even allows it.
Smithtown East Is a 9/10 High School — Structurally, Not Cyclically
School district quality is one of the most durable value drivers in Long Island real estate. Smithtown High School East has earned its rating consistently over years, not recently. That matters when you’re thinking about long-term resale dynamics — the floor this district provides doesn’t move with the market the way other variables do.
