169 Baker Road
About This Property
Inside, the home unfolds with warmth and authenticity-from the original red oak trim and pocket doors to the built-in glass cabinetry, cast iron radiators, and the beautiful maple floors underfoot, to the 9-foot ceilings throughout. The main level offers a gracious layout: formal living and dining rooms, centered by a large woodburning stone fireplace, a bright sunroom-style breakfast room, and a spacious kitchen that overlooks the backyard and pool. The kitchen and baths have been updated over time, yet remain true to the character of the home, including a clawfoot tub and classic tilework. A bonus room on the lower level, along with a foyer, provides flexibility for an office, playroom, or creative studio. The beautiful glass oak trimmed French doors lead out to the stone patio and views of the Catskills and Reservoir, offering the perfect blend of indoor and outdoor living.
On the top floor, a fully windowed observatory-style space offers 360-degree views-a truly special setting once used by the home's original owner, J. Waldo Smith, to oversee the construction of the Ashokan Reservoir as eight towns were relocated to make way for one of the most important infrastructure projects in New York's history.
Originally constructed by Smith himself-Chief Engineer of the Ashokan Reservoir-the home is built from locally quarried Rosendale stone, chosen for its strength and permanence. After the Smith family, the home became part of the Chase family estate, where actor Chevy Chase spent part of his youth-adding another layer of cultural legacy to this historic property.
Outside, the inground, heated saltwater pool, stone patios, and rolling backyard lawn are ideal for summer gatherings and quiet moments alike. A two-car garage, buried electric lines, a battery back-up system, a standby generator, and a new Buderus boiler ensure the property functions as beautifully as it looks. The high-ceiling basement provides storage and future potential, while mature trees and mountain air frame the entire estate in calm.
For those seeking a compound or expanded retreat, the adjacent home is also available for purchase. Inquire for more details.
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Cap Rate Calculator
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 |
|---|---|---|---|
| Jan 12, 2026 | Sold | ||
| Sold | |||
| Dec 13, 2025 | In contract | - | |
| In contract | |||
| Nov 11, 2025 | Relisted | $2,500,000 | |
| Relisted | |||
| Nov 10, 2025 | No longer available | - | |
| No longer available | |||
| Sep 28, 2025 | Price Decreased |
$2,500,000
↓ $95K
(3.7%) | |
| Price Decreased | |||
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017