1752 Chestnut Avenue, Winter Park, FL 32789
Local realty services provided by:Better Homes and Gardens Real Estate Synergy
Listed by:nick mckee
Office:keller williams winter park
MLS#:O6331369
Source:MFRMLS
Price summary
- Price:$2,199,999
- Price per sq. ft.:$513.3
About this home
Timeless Elegance Meets Modern Comfort in Sought-After Tree Streets
Welcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style.
At the heart of the home, the chef-inspired kitchen showcases premium Thermador appliances, a gas range, and custom cabinetry that soars to 10-foot ceilings. The spacious butler’s pantry and built-in breakfast nook flow seamlessly into an inviting great room with custom built-ins—ideal for both everyday living and elegant entertaining. Nearby, the formal dining room features a striking drop ceiling, setting the stage for unforgettable gatherings.
Designed for everyday convenience and privacy, the first floor includes both a comfortable guest suite and a luxurious primary suite, which features elegant wood beams accenting the ceiling and creates a warm, sophisticated retreat.
Throughout the home, beautiful white oak floors add warmth and character, complementing the timeless design and enhancing the flow between each thoughtfully crafted space.
Enjoy effortless indoor-outdoor living with an expansive covered lanai featuring a built-in summer kitchen and phantom screens, all overlooking a stunning pool and spa embraced by lush landscaping. A dedicated pool bath ensures convenience for guests enjoying the outdoor oasis.
Inside, thoughtful features abound: a stylish mudroom with built-in storage, a large utility room with cabinetry and sink, and a conditioned mechanical room offering smart storage solutions. Upstairs, discover a spacious loft perfect for a media room or play area, accompanied by two generously sized bedrooms each with ensuite baths and ample closets.
The Stratford-style front porch invites neighborly chats, while the private backyard provides a serene retreat. Designer-selected finishes and custom touches are evident throughout, highlighting the home's timeless elegance and modern functionality.
Ideally situated just minutes from Park Avenue, residents will enjoy effortless access to fine dining, boutique shopping, charming cafes, museums, and the vibrant cultural heart of Winter Park.
A rare offering that combines luxurious design, exceptional craftsmanship, and the warm character only a custom-built home can provide—this residence truly stands out in the Tree Streets.
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Home facts
- Year built:2021
- Listing ID #:O6331369
- Added:59 day(s) ago
- Updated:September 29, 2025 at 11:41 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Living area:3,314 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Heat Pump
Structure and exterior
- Roof:Metal, Shingle
- Year built:2021
- Building area:3,314 sq. ft.
- Lot area:0.22 Acres
Utilities
- Water:Public, Water Connected
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$2,199,999
- Price per sq. ft.:$513.3
- Tax amount:$18,025 (2024)
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