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$1,875,000
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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.
Full Property Details
Full Property Details for 1752 Chestnut Ave
General
- Sold For: $1,875,000
- Taxes: $18,024 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6331369
- Added to Site: 169 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 8
- 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
- Flooring: Engineered Hardwood, Tile
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Lighting
- Spa: Yes
- Spa Description: Heated, In Ground
Exterior
- Exterior Features: Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters, Sliding Doors
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: CONWILL ESTATES
- Driving Directions: From Aloma Avenue, head North on Phelps Avenue. Follow Phelps to Chestnut Avenue, turn right on Chestnut Avenue, the house is ahead on the right.
- Direction Faces: North
Community
- Community Name: 32789 - Winter Park
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Heat Pump
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Phone Available, Public, Sewer Connected, Street Lights, Water Connected
Structural Information
- Exterior Const.: Block, Brick, Stucco
- Roof: Metal, Shingle
- Stories/Levels: Two
- Square Feet: 3,314
- Sq. Ft. Source: Public Records
- Living Area: 3,314 Sq. Ft.
- Year Built: 2021
Lot Features
- Lot Size (Acres): 0.22
- Lot Size (Sq. Ft.): 9,438
- Lot Size: 9438
- Street/Road Desc.: Asphalt
Financial Considerations
- Tax Amount: $18,024.79
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: CONWILL ESTATES S/13 LOT 4 BLK B
- Flood Zone Info: X
- APN: 322130170802040
- Property ID: 322130170802040
- Block/Lot/Section: B
Listed by Keller Williams Winter Park
Sold by Stellar Non-Member Office
Get Pre-Approved Today
Schools
Schools serving 1752 Chestnut Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Lakemont Elementary School 901 North Lakemont Avenue, Winter Park, FL 32792 | K-5 | 0.5 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 1.6 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1752 Chestnut Ave
Date
Details
Price
Change
Source
1/01/2026
Sold
$1,875,000
-6.02%
MLS
10/28/2025
Price Reduced
$1,995,000
-4.95%
MLS
9/24/2025
Price Reduced
$2,099,000
-4.59%
MLS
7/31/2025
Listed
$2,199,999
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1752 Chestnut Avenue, Winter Park, FL 32789 (MLS# O6331369) is a Single Family property that was sold at $1,875,000 on January 01, 2026. Want to learn more about 1752 Chestnut Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

