56 Old Homestead Road, Port Jefferson — Home Profile
Old Homestead Road runs off Cliff Road inside the Incorporated Village of Port Jefferson, set back from the harbor and from the Main Street foot traffic that defines the downtown less than a mile away. Number 56 holds just under an acre of it — 40,511 square feet on the tax roll, which in a village where most parcels run considerably tighter is the headline before anyone gets to the house.
The structure is a 1983 raised ranch of roughly 3,000 measured square feet, carried across multiple levels: four bedrooms, three full baths, a fireplace anchoring the living and dining rooms, and a lower level given over to recreation and media space. Outside is where the budget clearly went — a heated in-ground pool with integrated spa and cascading waterfall, an outdoor kitchen and bar, a second fireplace, and a koi pond off the rear deck. What follows is the tax picture, the school assignment, the commute math, and the figures that actually determine what this house costs to carry.
Video Walkthrough
Photo Gallery
Property Details
The Basics
- StyleRaised Ranch, multi-level
- Bedrooms4
- Bathrooms3 full
- Total Rooms8
- Living Area3,000 sq ft (measured)
- Lot Size0.93 acres (40,511 sq ft)
- Year Built1983
- ConstructionFrame
- Garage1 space, oversized
- ParkingDriveway, off-street
- FireplaceYes (1) — living room
- FlooringTile and wood
- Cross StreetCliff Road
Systems & Utilities
- HeatingOil
- CoolingCentral Air
- WaterPublic
- SewerCesspool
- PoolPrivate, heated in-ground with spa
- HOANone indicated
- Flood ZoneNot disclosed — verify current FEMA panel
- WaterfrontNo
- MunicipalityIncorporated Village of Port Jefferson
Key Interior Features
- KitchenEat-in and open to the living space, breakfast bar, marble counters, walk-through layout
- AppliancesConvection oven, stainless package, dishwasher, microwave, wine refrigerator
- Primary SuiteTray ceiling, two walk-in closets, custom built-in cabinetry, direct rear balcony access
- Primary BathWhirlpool tub, steam shower, rainfall head
- Ceilings & TrimCathedral and high ceilings, crown molding, natural woodwork, recessed lighting
- Main LevelFirst-floor bedroom, first-floor full bath, formal dining, open floor plan
- Lower LevelRecreation and entertainment area, media and billiard room, bar, laundry
- TechnologyWhole-house entertainment system, integrated sound and speakers, property-wide WiFi
- Bedroom AccessThree bedrooms with two full baths open directly to the deck and pool area
The Grounds
- PoolHeated in-ground with integrated spa and cascading waterfall
- Outdoor KitchenYes, with custom bar
- Outdoor FireplaceYes
- Water FeatureKoi pond off the rear deck
- DeckingRooftop entertaining deck plus rear balcony off the primary suite
- OutbuildingCustom shed
- Garage Fit-OutCustom cabinetry, stainless counters, full-size refrigerator and freezer, dual wine refrigerators
Tax & Financial Data
Sourced from OneKey MLS and Suffolk County public records. Figures are reported, not audited — verify independently.
Parcel ID 0206-006-00-01-00-001-002 | Suffolk County, Incorporated Village of Port Jefferson | Note a discrepancy worth reconciling: public tax history reports a 2023 levy near $20,581 against an assessed value of $6,730 that has held flat for more than a decade, while the current MLS record lists $25,285.16. The MLS figure is used throughout this profile. Confirm the actual current bill with the Village and with Suffolk County before budgeting.
True Cost to Own
Estimates only, exclusive of mortgage principal and interest — get real quotes before you budget.
Property Tax: ~$2,107/mo
Derived from the $25,285.16 annual figure carried on the MLS record. Public tax history reports a lower recent number; reconcile the two against the actual bill before you build a monthly budget around either.
Insurance: ~$250–$550/mo (estimate)
Frame construction at 3,000 square feet with a heated pool, integrated spa, and an outdoor fireplace prices above a plain homeowner’s policy. Carriers treat pools and outdoor fire features as rated exposures. Get a bound quote, not a ballpark.
Utilities: several hundred/mo, sharply seasonal
Oil heat on a 1983 build, central air across multiple levels, a heated pool, and an integrated spa. Ask for twelve months of actual bills, plus the age of the burner and the tank — and whether that tank is above ground or buried.
Maintenance reserve: ~$1,079/mo (1%/yr)
The standard one-percent rule applied to the list price. On this parcel it covers a pool, a spa, a waterfall pump, a koi pond, an outdoor kitchen, and close to an acre of planted grounds — each running its own service calendar on top of the house itself.
These are estimates for informational purposes only and are not financial advice — consult a licensed attorney or financial advisor before acting on them.
School District
Attendance boundaries in the listing feed come from third-party data and are provided for reference only. A Port Jefferson mailing address does not by itself place a parcel inside the Port Jefferson school district — the postal designation reaches well beyond the village line, and neighboring parcels can feed different districts entirely. Confirm enrollment eligibility for this specific parcel with the district office before making any assumption. I’ve written about how sharply that plays out a few miles west in the Three Village boundary post, where one block can split across three schools.
Commute Reality From This Address
The Bridgeport Ferry
The Bridgeport & Port Jefferson Steamboat Company runs year-round from 102 West Broadway, a crossing of roughly one hour and fifteen minutes to Bridgeport, Connecticut. For anyone working in Fairfield County, it removes the drive around the Sound. Almost nowhere else on Long Island offers that.
LIRR Port Jefferson Branch
Port Jefferson is the eastern terminus of its branch. Be realistic about the math: the line runs diesel east of Huntington, so most Manhattan trips involve a transfer before reaching Penn Station or Grand Central Madison. Budget accordingly.
Stony Brook University & Hospital
A short run west along the Route 25A corridor puts the university, the medical school, and the hospital complex within an easy daily drive — the reason a steady share of this pocket’s buyers are clinicians, researchers, and university staff.
Roads and Air
Route 347 and Nicolls Road (CR 97) carry south toward the Long Island Expressway. Long Island MacArthur Airport in Ronkonkoma is the nearest commercial field, well under an hour in normal conditions.
The Neighborhood
Village, Not Town
The Incorporated Village of Port Jefferson runs its own government, its own code, and its own building department, separate from the Town of Brookhaven that surrounds it. Permits, zoning, parking, and local services all route through Village Hall. That distinction matters more than most buyers expect.
The Harbor and Downtown
Less than a mile north, Main Street runs down to the harbor: restaurants, the ferry terminal, Theatre Three, and a working waterfront that stays busy through the season. Close enough to walk on a good evening, far enough that the summer crowd isn’t parked on your street.
Street Character
Old Homestead comes off Cliff Road, away from the downtown grid and its traffic pattern. Detached single-family housing on generous lots, mature planting, and no commercial frontage. The block reads residential in a way the streets closer to Main Street no longer can.
Village Amenities
The village operates its own golf and country club facility and maintains beach access for residents. Eligibility rules, membership waitlists, and fees change — confirm current terms with Village Hall rather than assuming they convey with the deed.
What Makes This Home Stand Out
Just Under an Acre Inside Village Limits
40,511 square feet is the number that separates this parcel from most of what trades inside the village line. Land is the one thing a renovation cannot manufacture, and in an incorporated village with fixed boundaries, the supply of near-acre lots does not grow.
The Grounds Are the Product
Heated in-ground pool, integrated spa, cascading waterfall, outdoor kitchen with a custom bar, an outdoor fireplace, a koi pond, and a rooftop entertaining deck. This is not a pool added to a yard. The exterior was designed as a second living space and equipped like one.
A Bedroom and Full Bath on the Entry Level
The MLS feature set lists a first-floor bedroom and a first-floor full bath. That combination supports single-level living, a guest arrangement that doesn’t require stairs, or a home office with its own bath — without asking the whole household to live on one floor.
Direct Pool Access from Three Bedrooms
Three of the four bedrooms, served by two full baths, open directly onto the deck and pool area. For a property whose value is concentrated outdoors, that circulation is a functional design decision rather than a marketing line.
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