Downsizing to Westhampton Pines

Westhampton Pines at a glance

The community's website, run by the homeowners association, gives an address of 102 Old Country Road in Westhampton and describes 189 homes on 44 acres with 24-hour guard gating. It says the homes were built between 2005 and 2012, and that Island East Management, based in Westhampton Beach, runs day-to-day operations. The Town of Southampton has separately posted a notice about Westhampton Pines, so the community exists in a government record too.

The town's notice, dated April 15, 2026, was about an income-restricted resale of a one-story condominium handled through the Long Island Housing Partnership. That tells you some homes here carry income-qualification rules when they are resold, so ask whether the home you are considering is one of them.

Sources: Westhampton Pines HOA, Town of Southampton notice.

Homes and layout at Westhampton Pines

The website lists three models, all part of the condominium. The Amagansett is a single-level home with two bedrooms, a library and two and a half baths in 2,400 square feet. The Bridgehampton is a single-level home with two bedrooms and two baths in 1,856 square feet. The Southampton is a bi-level home with three bedrooms and three baths in 2,310 square feet, with a loft level holding an extra bedroom and a bath. The town's notice describes a one-story unit with a two-car garage.

Single-level plans matter to many people moving smaller, but the upper loft in the Southampton model and any garage steps are worth checking on the actual unit. Ask which exterior items the association maintains, and read our guide to co-op, condo, townhouse or house for how ownership works in a condominium.

Amenities and clubs at Westhampton Pines

The clubhouse is 8,100 square feet, and the community website lists a fully equipped gym, an indoor pool and hot tub, locker rooms, a library, a billiards room and card rooms. Outside are a pool, tennis and pickleball courts and two bocce courts. The Town of Southampton's notice repeats a similar list. The site refers to a social committee and monthly activity calendar; ask how many residents take part and how events are organized.

Rules and fees at Westhampton Pines

The town's notice described a unit's monthly common charge and annual tax figure, but those numbers belong to one home in one year, not the whole community. Common charges vary with the home model and change with the budget. Get the current schedule in writing from the seller's attorney or from Island East Management.

Also ask for the offering plan or governing documents, the current budget and reserve statement, any recent or planned special assessment, the rules on rentals, guests and pets and the 55+ policy (federal rules generally require at least 80 percent of occupied units to have a resident 55 or older). Ask the Long Island Housing Partnership or the association whether an affordability restriction is recorded against the unit. The state's Property Condition Disclosure Act does not cover condominium units; see the seller disclosures guide.

Getting to Westhampton Pines

The Long Island Rail Road's Montauk Branch has a Westhampton station, listed on mta.info with its accessibility features and a ticket machine. The MTA also runs a South Fork Commuter Connection that mta.info describes as letting riders park at Westhampton and ride east. Use the MTA trip planner from the exact address.

Health care near Westhampton Pines

Stony Brook Southampton Hospital is at 240 Meeting House Lane in Southampton, and its campus has a 24-hour emergency department. Peconic Bay Medical Center, a Northwell Health hospital, is at 1 Heroes Way in Riverhead. Check your doctors and insurance network before treating either as the default.

Sources: Stony Brook Southampton Hospital, Peconic Bay Medical Center.

Storms, flooding and insurance at Westhampton Pines

Suffolk County's storm surge zone map takes an exact address and says zones exist on both shores, not only ocean-facing land. Check the flood zone as well on the FEMA Flood Map Service Center. Do not assume the whole community shares one zone. Standard policies exclude flood, and the association's master policy covers the building and common areas, not your contents. See the flood and storm insurance guide.

Taxes and local government at Westhampton Pines

The Town of Southampton Assessor at Town Hall, 116 Hampton Road, phone 631-283-6020, handles exemption applications. The town's page links the state's STAR information. STAR reduces school taxes; Enhanced STAR is for owners 65 and older with income of $110,750 or less for 2026-27, and new buyers register for the STAR credit with the state (tax.ny.gov). The senior exemption under Real Property Tax Law section 467 is a town option with a locally set income ceiling, so ask the Assessor what Southampton offers and the deadline.

Buyers here should ask their attorney about the East End transfer tax. The Town of Southampton's FAQ describes the Peconic Bay Region tax as a 2.5 percent rate that includes a 0.5 percent Community Housing Fund tax, with the first $400,000 of an improved residential parcel exempt when the consideration is $2,000,000 or less, and a first-time buyer exemption (Southampton FAQ). Who pays and which exemption applies is a matter for your attorney. See the costs and money page, the senior property tax exemptions guide and the net proceeds calculator. This site does not give tax advice.

Questions to ask before you buy at Westhampton Pines

• What is the current monthly common charge for this model, and what does it include?
• Is there a recorded income or resale restriction on this unit?
• May I see the governing documents, budget, reserve statement and any special assessment?
• What are the written rules on rentals, guests, pets and the 55+ age policy?
• Is the primary bedroom on the entry level, and how many steps lead in from the garage?
• What does the association maintain outside the unit?
• What storm surge and FEMA flood zone apply to this exact address?
• What senior exemptions and deadlines does the Southampton Assessor apply?

Moving from a house elsewhere on Long Island? Our downsizing guide covers the order of steps. When you want an introduction, ask to be matched with an agent on the eXp Realty operating team.