266 DRAYTON ISLAND ROAD
About This Property
The main home offers 5 bedrooms and 2 baths, beautifully curated with original Stickley touches and furnished with select authentic Stickley pieces that will convey with the sale. Rare for historic Florida homes, Moonwake features a true concrete-floor basement, adding both storage and structural integrity.
A charming separate structure-known as the Cook's House-provides an additional 1 bedroom and 1 bath. Currently operating as a highly successful 5-star Airbnb, this guest cottage generates over $20,000 annually, making it a perfect blend of personal retreat and income opportunity.
Step outside and you'll discover grounds designed to inspire: a vibrant butterfly and pollination garden, towering oaks dripping in Spanish moss, and open skies that glow at sunset-where "Moonwake" earns its name as moonlight shimmers across the lake.
An all-house generator ensures comfort and security year-round, while a pontoon boat conveys with the property, offering immediate adventure on Florida's second-largest lake. The included boat slip at the Drayton Island RV Resort is transferable, adding unmatched convenience for island living.
Situated on agriculturally zoned land, Moonwake offers uncommon privacy, natural beauty, and a chance to own a true piece of Florida history.
Whether you're seeking a serene homestead, an exclusive getaway, or an income-producing island escape, Moonwake invites you to slow down, breathe deeply, and experience the unforgettable magic of Drayton Island.
Payment Calculator
Your Estimated Monthly Payment
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 |
|---|---|---|---|
| Feb 25, 2026 | Sold | ||
| Sold | |||
| Jan 17, 2026 | In contract | - | |
| In contract | |||
| Nov 25, 2025 | Listed by RE/MAX SELECT PROFESSIONALS | $874,900 | |
| Listed by RE/MAX SELECT PROFESSIONALS | |||
| Oct 20, 2025 | Listed | $935,000 | |
| Listed | |||
| | |||
|
Named for the silvery shimmer of moonlight reflected across the water, “Moonwake”, is a true legacy property. Accessible by ferry or private boat, this turn-key, fully furnished estate offers complete privacy amid 6.9 acres of pristine, “Old Florida”. 5 bedrooms, 2 baths, and 2,146 sq. ft. of timeless character, including original heart pine floors, windows, doors and trim. The property also includes a separate 472 sq. ft. “Cook’s House” with a full kitchen, living area, private bedroom, loft, and bath. Modern updates blend seamlessly with historic charm: remodeled kitchen and baths, high-end fixtures and appliances including a 36” Wolf stove, 52-bottle wine cooler, and on-demand hot water in both homes. 240-ft private dock with two-slip boathouse, 960 sq. ft. drive-in workshop with 110 & 220 service, chicken coop, paddock, and fenced 30’x60’ garden. Mature fruit trees, bamboo groves, and abundant wildlife.
| |||
| Mar 30, 2022 | Sold | ||
| Sold | |||
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017