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$1,995,000 - 1752 Chestnut Avenue, WINTER PARK

4
Bedrooms
5
Baths
3,314
SQ. Feet
0.22
Acres

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.

Essential Information

  • MLS® #:
    O6331369
  • Price:
    $1,995,000
  • Bedrooms:
    4
  • Bathrooms:
    5.00
  • Full Baths:
    4
  • Half Baths:
    1
  • Square Footage:
    3,314
  • Acres:
    0.22
  • Year Built:
    2021
  • Type:
    Residential
  • Sub-Type:
    Single Family Residence
  • Status:
    Pending

Community Information

  • Address:
    1752 Chestnut Avenue
  • Area:
    Winter Park
  • Subdivision:
    CONWILL ESTATES
  • City:
    WINTER PARK
  • County:
    Orange
  • State:
    FL
  • Zip Code:
    32789

Amenities

  • # of Garages:
    2
  • Has Pool:
    Yes

Interior

  • Interior Features:
    Built-in Features, Crown Molding, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances:
    Convection Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator
  • Heating:
    Heat Pump
  • Cooling:
    Central Air
  • # of Stories:
    2

Exterior

  • Exterior Features:
    Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters, Sliding Doors
  • Roof:
    Metal, Shingle
  • Foundation:
    Slab

Additional Information

  • Days on Market:
    133
  • Zoning:
    R-1A

Listing Details

  • Listing Office:
    Keller Williams Winter Park

Listing information courtesy of Keller Williams Winter Park.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on December 30th, 2025 at 3:05pm EST.