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114 Winding Oak DR
About This Property
Inside, soaring 8-foot doors, black-framed windows, and abundant natural light create a bright yet inviting atmosphere. The open-concept floor plan is anchored by a striking stone wood-burning fireplace with decorative wood beams, while rich wood flooring flows throughout the home with no carpet.
The chef-inspired kitchen is designed for both entertaining and everyday living, featuring white quartz countertops, a farmhouse sink, premium fixtures, soft-close custom cabinetry, and an oversized raised island. Double front and back doors create seamless indoor-outdoor flow and fill the home with natural light and fresh air.
Privately situated on its own wing, the primary suite offers a spa-like retreat complete with dual shower heads, custom cabinetry, generous storage, and a thoughtfully designed walk-in closet. Additional highlights include a fully soundproof office, oversized utility room with built-in mud bench and storage, and a spacious two-car garage with an extended bay large enough for a full-size truck. A climate-controlled workshop, craft room, or flex space adds even more versatility.
Finished with a durable metal roof, gutters, and located on a peaceful low-traffic street, every detail of this home was intentionally curated to deliver timeless style, modern comfort, and exceptional craftsmanship in one of the Hill Country's most desirable neighborhoods.
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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 |
|---|---|---|---|
| Jun 6, 2026 | In contract | - | |
| In contract | |||
| May 7, 2026 | Listed by Keller Williams Realty | $659,000 | |
| Listed by Keller Williams Realty | |||
| May 2, 2026 | No longer available | - | |
| No longer available | |||
| Mar 24, 2026 | Price Decreased |
$699,000
↓ $26K
(3.6%) | |
| Price Decreased | |||
| Oct 20, 2025 | Listed by Keller Williams Realty | $725,000 | |
| Listed by Keller Williams Realty | |||
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This 2023 custom-built home perfectly blends clean, modern lines with warm, inviting finishes in the highly sought-after, established Oak Forest neighborhood. Just a short walk from downtown, this property offers the best of Hill Country living.
Step inside to find soaring 8-foot doors, abundant natural light from black-framed windows, and an open-concept living space anchored by a stone wood-burning fireplace and decorative wood beams. Beautiful wood flooring runs throughout with no carpet, creating a clean, seamless flow from room to room. The kitchen is a showstopper with a farmhouse sink, white quartz countertops, a raised-height island, and soft-close custom cabinetry. Double front and back doors open the home to the outdoors, inviting natural light and fresh air inside.
The private primary suite is on the opposite side of the home and features a spa-like bath with dual shower heads, generous cabinet and storage space, and a custom-built walk-in closet. A soundproof office provides the ideal work-from-home space, while the oversized laundry room features a mudbench and generous storage.
Outside, the home features a metal roof, gutters, a large two-car garage with an extended bay to accommodate a full-size truck, and a climate-controlled storage/workshop/craft room. The peaceful, low-traffic street and canopy of mature oak trees create a serene setting.
Every detail was thoughtfully designed in this home—delivering modern luxury, privacy, and an unbeatable location in the heart of the Hill Country.
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Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017