5420 Whippoorwill Drive
About This Property
Welcome to an exceptionally warm and inviting custom-built estate in a sought-after neighborhood. This property isn't just a house; it's a home you'll love to come back to, designed for easy, comfortable living where every detail enhances your experience.
This elegant yet cozy residence effortlessly blends a luxurious interior with a magnificent natural sanctuary.
Designed for Comfort and Entertaining:
The well thought out layout flows beautifully for both daily life and entertaining. The main floor features a comfortable living room, a formal dining room ideal for memorable dinners, and an inviting sunroom with panoramic views of the backyard's Japanese water feature. Culinary enthusiasts will adore the chef's kitchen with dual sinks, high end appliances, granite counters, and incredible storage, all flowing into a casual eating area. The main level also boasts a sophisticated study with a full bar, a well-equipped hobby room, and a large mudroom with individual closets for every member in the household leading directly to the oversized three car garage.
The Ultimate Retreats:
Upstairs, the extraordinary primary suite redefines comfort with two separate bathrooms, and exceptional built-in storage. The upper level also features a lovely ensuite bedroom and a private wing behind French doors - an ideal household or guest suite with a separate living area and two additional bedrooms, each with a vanity, and a shared bath.
The lower level is dedicated to entertainment and wellness, featuring an incredible home theater with a snack room, a spacious mirrored home gym, and a post-workout sauna.
A Backyard Oasis for All Ages:
Step outside to a sprawling, magical backyard sanctuary designed in a circle of four distinct fenced-in garden areas. The Japanese Garden features a Koi Pond and an enormous deck, perfect for outdoor living with a fire pit, hot tub, and dining area. Follow the walkways to the English Country Garden with quiet seating, the serene Gazebo & Butterfly Garden with a soothing "Rocky Mountain" stream overlooking Portage Creek, and an amazing play structure combined with floral beauty.
This immaculate, curated property is truly a "staycation" home - a legacy waiting for your next chapter.
Website: https://www.5420whippoorwilldrive.com/
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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 |
|---|---|---|---|
| Dec 23, 2025 | Sold | ||
| Sold | |||
| Nov 10, 2025 | In contract | - | |
| In contract | |||
| Oct 7, 2025 | Listed by Chuck Jaqua, REALTOR | $1,225,000 | |
| Listed by Chuck Jaqua, REALTOR | |||
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017