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150 HIGH STREET
About This Property
Set on nearly two acres, this historic three-story residence, complete with a full basement, has been masterfully restored for modern living while preserving the character, craftsmanship, and architectural detail that make it truly irreplaceable.
Spanning more than 4,400 square feet, this four+ bedroom home seamlessly blends timeless architecture with warm, elevated design. Original details have been thoughtfully preserved throughout, while carefully curated updates bring a sense of luxury, comfort, and effortless livability to every space.
At the heart of the home is a custom kitchen featuring inset cabinetry, a massive island, and a semi-open layout that flows beautifully into the main living area - ideal for entertaining, gathering, and everyday life.
The living room and dining room are adorned with historically ornate features and craftsmanship rarely found in modern construction, offering a sense of elegance and permanence that simply cannot be replicated today. The entire first floor has 12-Foot ceilings.
The primary suite feels like something you would experience at a high-end boutique resort. It comes complete with a large walk-in wardrobe, gas fireplace, sitting area, coffee and beverage bar, spa-inspired en suite with a massive 25-square-foot shower and cast iron clawfoot tub, and a private balcony overlooking the beautiful backyard. This space was designed to feel like a true retreat. Imagine waking each morning, opening six automated blinds, hearing the quiet sounds of the property come to life, and enjoying freshly brewed coffee from your own built-in coffee bar before stepping out onto the balcony. This is the lifestyle that awaits at the Jessup House.
Beyond the main residence, the property offers a rare collection of highly functional outbuildings, including the original historic icehouse, a carriage house with expansive open space and substantial storage, and a beautifully renovated detached studio (152 High St. - w/ separate electric meter) of approximately 350 square feet - ideal for a private office, gym, creative studio, guest space, or whatever the next owner imagines.
The Jessup House is a rare blend of history, scale, setting, and thoughtful restoration - a one-of-a-kind property offering the charm of the past with the comfort and ease of modern living.
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What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Aug 26, 2026 | Sold | ||
| Sold | |||
| Jun 29, 2026 | In contract | - | |
| In contract | |||
| Jun 19, 2026 | Listed by Graham/Hearst Real Estate Company | $965,000 | |
| Listed by Graham/Hearst Real Estate Company | |||
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017