1166 OAKS BOULEVARD
About This Property
Relax on the charming front covered porch, the perfect spot to enjoy your morning coffee. Step inside to find meticulous attention to detail-from stunning wide white oak floors to exquisite custom millwork and soaring ceilings that create an airy, welcoming atmosphere.
The chef-inspired kitchen is the heart of the home, featuring an abundance of custom solid-wood cabinets, gleaming quartz countertops, and a large island with seating for four. A generous walk-in pantry with custom shelving and top-of-the-line Thermador stainless steel appliances-including a 6-burner gas stove, double oven, and deep farm sink-make meal preparation and entertaining effortless. Adjacent to the kitchen, a charming dining area is perfect for memorable dinners, while the adjoining family room boasts a soaring cathedral ceiling, a natural gas fireplace with a custom stone mantel, and large windows that flood the space with natural light.
A cozy private den offers an ideal retreat for work or relaxation. On the opposite side of the first floor, you'll find a guest suite with a private bath, two additional bedrooms with custom closets, a stylish full bath, and a laundry room with ample storage and a utility sink. The spacious mudroom, accessible from the two-car garage, provides practical storage with built-in cabinets and hooks.
Upstairs, the luxurious primary suite features a spa-inspired bathroom with double sinks, custom Restoration Hardware cabinetry, elegant lighting, and a large walk-in shower. A peaceful sitting area and a walk-in closet with custom shelving create a perfect private retreat. Additionally, an upstairs loft offers versatile space ideal for a home office, gym, or additional quiet area.
Outside, enjoy a private backyard oasis designed for relaxation and entertainment. Highlights include a "Michael Phelps Chilly Goat" hot/cold tub combo, outdoor TV, and speakers-creating your personal weekend paradise.
Additional amenities include a large two-car garage, solid-core doors, crown molding, wide base moldings, dual tankless water heaters, fully-owned solar panels (reducing energy costs), a water softener and purifier, new exterior paint (2023), professionally installed closet shelving (2023), and professionally landscaped gardens.
Flooded with natural light and warmth, this exceptional home offers a cozy yet elegant atmosphere. Zoned for top-tier schools-including Winter Park High School-and conveniently located near Lake Highland, Trinity Prep, the Winter Park YMCA, Racquet Club, and Interlachen Country Club, it's ideal for a vibrant Florida lifestyle. Walkable to Winter Park's renowned shopping and dining destination, don't miss the opportunity to make this exquisite property your new home! AVAILABLE BY APPOINTMENT ONLY
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 |
|---|---|---|---|
| Mar 6, 2026 | Sold | ||
| Sold | |||
| Feb 10, 2026 | In contract | - | |
| In contract | |||
| Jan 4, 2026 | Price Decreased |
$1,590,000
↓ $10K
(0.6%) | |
| Price Decreased | |||
| Jan 2, 2026 | Price Decreased |
$1,600,000
↓ $50K
(3%) | |
| Price Decreased | |||
| Nov 26, 2025 | Price Decreased |
$1,649,999
↓ $50K
(2.9%) | |
| Price Decreased | |||
Property Highlights
Building Info
Comparables
Status
Price/ft²
Listed On
Sold On
About Winter Park
Similar Homes for Sale
Currently no similar homes aroundNearby Rentals
$3,695 /mo
- 3 Beds
- 2 Baths
- 1,900 ft²
$3,600 /mo
- 3 Beds
- 2 Baths
- 1,594 ft²
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017