Skip to content
Property for sale at 1752 CHESTNUT AVENUE, WINTER PARK, FL, 32789

1752 Chestnut AvenueWinter Park, FL, 32789

4beds
5baths
3,314sqft
Single Family Residence
Built in 2021
$1,875,000
Sold
Price per sqft
$566
Sold on
Jan 1, 2026
MLS #O6331369Updated Jan 5, 2026

About this property

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.

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
1752 Chestnut Avenue
City
Winter Park
State
FL
ZIP code
32789
Year built
2021
New construction
No
Faces
North
Rooms
8
Building stories
2
Living area
3,314 sqft
Total building area
4,286 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. 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; the availability of any listing should always be independently verified. Listing information is provided for consumers' 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.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDT

Price & sale history

EventPrice
SoldMLS #O6331369$1,875,000
Price reducedMLS #O6331369$1,995,000Change: −9.3%−$204,999
Listed for saleMLS #O6331369$2,199,999
SoldMLS #O5973856$1,365,000
History may be incomplete.
Explore nearby sales

Location

Recent sales nearby

Property for sale at 1752 CHESTNUT AVENUE, WINTER PARK, FL, 32789
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.