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SoldSingle Family ResidenceSold

1752 Chestnut Avenue

Winter Park, FL 32789

$1,875,000

  • 4Beds
  • 5Baths4 full, 1 half
  • 3,314Sq Ft
  • $566Per Sq Ft
  • 0.22Acres
  • 2021Built
Subdivision
Conwill Estates
County
Orange
MLS®
O6331369

Overview

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.

Listing Snapshot

Price
$1,875,000
Days On Site
N/A
Bedrooms
4
Inside Area (SqFt)
3,314 sqft
Total Baths
5
Full Baths
4
Partial Baths
1
Lot Size
0.22 Acres
Year Built
2021
MLS® Number
O6331369
Status
Sold
Property Tax
$18,024.79 (2024)
HOA/Condo/Coop Fees
N/A
Sq Ft Source
Public Records

Property Details

General Features

15 items
Acres
0.22
Attached Garage
Yes
Direction Faces
North
Foundation
Slab
Garage
Yes
Garage Spaces
2
Levels
Two
Number Of Stories
2
Parking
Attached
Property Sub Type
Single Family Residence
Sewer
Public Sewer
SqFt Total
4,286
Utilities
Cable Available, Electricity Connected, Phone Available, Sewer Connected, Water Connected
Water Source
Public
Zoning
R-1A

Interior Features

15 items
Appliances
Convection Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator
Cooling
Central Air
Flooring
Hardwood, Tile
Heating
Heat Pump
Interior
Built-in Features, Crown Molding, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s)
Laundry Features
Laundry Room
Spa
Yes

Rooms

RoomDimensionsLevelFeatures
Bedroom 213x11First
Bedroom 313x12Second
Bedroom 415x11Second
Dining Room12x12First
Kitchen24x12First
Living Room22x18First
Loft19x12Second
Master Bedroom17x12First

Exterior Features

7 items
Construction Details
Block, Brick, Stucco
Exterior
Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters
Pool Features
Heated, In Ground, Private
Private Pool
Yes
Roof
Metal, Shingle
Spa
Yes
Spa Features
Heated, In Ground

Community Features

5 items
Community Features
Street Lights
MLS Area
32789 - Winter Park
Township
21
Financing Terms Available
Cash, Conventional, VA Loan
Roads
Asphalt

Location

1752 Chestnut Avenue, Winter Park, FL 32789 · 32789 - Winter Park

Neighborhood & Commute

ZIP Code 32789

Median household income
$110,150
Income per person
$78,898
Households
12,171
Average household size
2.08
Median age
44.5

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Status changed to Closed
  3. Price changed to $1,995,000

Friends & Family

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Listing courtesy of KELLER WILLIAMS WINTER PARK (407) 913-0171

Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.

Last checked: 2026-11-10 03:44 AM EST

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