Hamilton House (45 Pineapple Street)

The two connected buildings hold 66 cooperative apartments plus the superintendent's unit across a basement level, seven stories, and a penthouse tier, served by two automatic passenger elevators — a scale rare on the Fruit Streets, where most neighbors are four-story rowhouses and small co-ops. Layouts run from studios through family-sized units, a few apartments per floor in each building, with penthouse apartments documented at the top under the certificate of occupancy. The cooperative's own records emphasize what shareholders value in the fabric: high ceilings, hardwood floors, light, the garden, and the finished basement level. Unit condition varies with renovation vintage; the 1988–1989 building-wide alteration and later window program set a baseline. The cooperative also owns commercial space and a two-car garage, both leased on the corporation's account — income-producing assets unusual for a building this size that supplement maintenance.

45-55 Pineapple Street Owners Corp. has operated the building since the 1987 closing, with a superintendent on site and the ordinary service contracts of a mid-size Heights co-op documented in its files (elevator maintenance on both passenger cars, gas and oil heat, central laundry). The amendment record documents a long tail of sponsor-affiliated unsold shares held by a successor investor entity into the 2010s, with the board controlled by resident shareholders throughout. The offering plan, amendments, by-laws, and financial statements are maintained in The Roebling Research Library and shared with clients during diligence.

Flip tax: 3 percent of net profit on sale — the sale price less the shareholder's purchase basis, reasonable closing costs, brokerage and legal fees, and (per the 1991 by-law amendment) documented capital improvements approved with invoices and canceled checks. Sellers should assemble their capital-improvement file early; the deduction is at the board's and counsel's discretion and requires documentation.

Subletting: Board consent required under the proprietary lease; the current sublet policy, term limits, and fees should be confirmed with the managing agent at offer stage.

Unsold-share history: The amendment record documents a holder of unsold shares with a substantial rented block into the 2010s. Buyers financing a purchase should confirm the current owner-occupancy ratio with the managing agent, as lenders will ask.

Pets, washer/dryer, financing limits: Not publicly documented; confirm current house rules and board policy in diligence.

Recent sales

Recent transfers at this building, curated by The Roebling Team research desk. Prices are the transfer amounts recorded with the NYC Department of Finance; apartment-level detail is checked against the building’s own file in The Roebling Research Library before publishing.

Market read. $/sf is measured on the latest sales with reliable square footage (2025): a median $790/sf across 1 sale. The building has traded as recently as 2026. Median listing discount 0.0% from the last ask.

Sales sourced from NYC Department of Finance recorded transfers (BBL 3-00226-0001) and verified listing data. Apartment-level facts (line, condition, asking-price context) curated and cross-verified by The Roebling Team research desk. Not all transactions cross-verify with ACRIS records — sponsor and LLC purchases sometimes record at stipulated values rather than market price; square footage on co-ops is not officially recorded, figures shown are approximate.

You are buying the pocket. Pineapple Street is one of the quietest addresses in the Heights, with the Promenade, the Clark Street 2/3, and Montague Street all within a few minutes' walk. Walk the block at night to appreciate what you are buying.

Elevator service at rowhouse scale is the differentiator. Very little on the Fruit Streets offers an elevator, a super, a laundry room, and a garden in one package.

Model the flip tax into your exit. The 3 percent net-profit structure rewards long ownership and documented renovation. Keep every invoice from day one.

Confirm the policy file and occupancy ratio. Sublet terms, pets, and financing limits are board matters without public documentation, and the unsold-share history makes the current owner-occupancy figure worth confirming for financing.

It is a landmarked, height-limited block. The historic district and LH-1 zoning fix the low-rise context — and the light — permanently.

Document your capital improvements. The by-laws let documented capital work reduce the flip-tax base. Invoices and canceled checks, organized before listing, convert directly into net proceeds.

Sell the 1883 story. Few New York apartment buildings of any kind predate 1885; the building's early-apartment-house provenance, the lost-plans mystery, and the Fruit Streets literary history are marketing assets no comparable postwar building can match.

Price per room against the pocket. The right comparables are North Heights small co-ops — the Pineapple, Orange, and Cranberry Street stock — not the doorman buildings on the Montague corridor.

Prepare buyers for a conventional board process. Standard package and interview; a well-organized deal file with the flip-tax computation anticipated keeps closings on schedule.

If you're considering Hamilton House, also evaluate:

• 44 Pineapple Street — the large prewar cooperative directly across the street
• 60 Pineapple Street — neighboring North Heights cooperative
• 59 Pineapple Street — cooperative neighbor on the same block
• 54 Orange Street — Fruit Streets co-op one block south
• 66 Orange Street — boutique Orange Street cooperative
• 72 Orange Street — walk-up-scale Fruit Streets alternative
• 55 Hicks Street — small co-op around the corner on Hicks
• 87 Hicks Street — boutique Hicks Street cooperative
• 75 Henry Street — the large postwar North Heights cooperative, for buyers weighing scale and amenities against prewar character