1752 Chestnut Avenue, Winter Park, FL 32789

$1,875,000
4
BD
5
BA
3,314
SqFt

Show Photos

Verify your account to unlock exclusive photos, mortgage tools, and more.

Sold Price
$1,875,000
List Price
$1,995,000
Status
Sold
MLS#
O6331369
Closing Date
Jan 01, 2026
Property Type
Single Family
Bedrooms
4
Bathrooms
5
Living Area
3,314
Lot Size
9,438
Region
Winter Park
Area
3314
County
Orange
Acres
0.22
Year Built
2021

Property Description

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.

Additional Information

Roof
Metal, Shingle
Land Type
Street Lights, No Deed Restriction
Appliances
Convection Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator
Zoning
R-1A
Lot Size
9,438
Construction
Block, Brick, Stucco
Year Built
2021
Sewer
Public Sewer
Heating
Heat Pump
Subdivision
Conwill Estates
Living Area
3,314
Style
Two Story
Pool
Yes

Listing courtesy of KELLER WILLIAMS WINTER PARK. 407-545-6430

Selling Office: STELLAR NON-MEMBER OFFICE.

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years

Does not include any taxes or fees.
Please consult a financial professional.
Calculator source: Real Geeks

MFR MLS is the source of this information via Internet Data Exchange Program. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale. Availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase. All other use is strictly prohibited and may violate relevant federal and state law. Data last updated on