1752 Chestnut Ave Winter Park, FL 32789
Estimated payment $13,223/month
Highlights
- Heated In Ground Pool
- Open Floorplan
- Main Floor Primary Bedroom
- Winter Park High Rated A+
- Wood Flooring
- Outdoor Kitchen
About This Home
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 Agent
KELLER WILLIAMS WINTER PARK Brokerage Phone: 407-545-6430 License #3340640 Listed on: 07/31/2025
Co-Listing Agent
KELLER WILLIAMS WINTER PARK Brokerage Phone: 407-545-6430 License #492100
Open House Schedule
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Sunday, September 14, 20252:00 to 4:00 pm9/14/2025 2:00:00 PM +00:009/14/2025 4:00:00 PM +00:00Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $18,025
Year Built
- Built in 2021
Lot Details
- 9,438 Sq Ft Lot
- North Facing Home
- Irrigation Equipment
- Property is zoned R-1A
Parking
- 2 Car Attached Garage
Home Design
- Brick Exterior Construction
- Slab Foundation
- Shingle Roof
- Metal Roof
- Block Exterior
- Stucco
Interior Spaces
- 3,314 Sq Ft Home
- 2-Story Property
- Open Floorplan
- Built-In Features
- Crown Molding
- High Ceiling
- Sliding Doors
- Mud Room
- Living Room
- Dining Room
- Loft
- Laundry Room
Kitchen
- Breakfast Area or Nook
- Convection Oven
- Range with Range Hood
- Recirculated Exhaust Fan
- Microwave
- Dishwasher
- Wine Refrigerator
- Stone Countertops
- Solid Wood Cabinet
- Disposal
Flooring
- Wood
- Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- Primary Bedroom on Main
- Split Bedroom Floorplan
- Walk-In Closet
Pool
- Heated In Ground Pool
- Heated Spa
- In Ground Spa
- Outdoor Shower
- Pool Lighting
Outdoor Features
- Outdoor Kitchen
- Exterior Lighting
- Rain Gutters
Utilities
- Central Air
- Heat Pump System
- Thermostat
- Tankless Water Heater
- High Speed Internet
- Phone Available
- Cable TV Available
Community Details
- No Home Owners Association
- Conwill Estates Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 4 / B
- Assessor Parcel Number 32-21-30-1708-02-040
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $18,025 | $1,220,176 | -- | -- |
| 2024 | $17,409 | $1,220,176 | -- | -- |
| 2023 | $17,409 | $1,151,250 | $0 | $0 |
| 2022 | $16,659 | $1,117,718 | $300,000 | $817,718 |
| 2021 | $4,416 | $280,000 | $280,000 | $0 |
| 2020 | $2,100 | $176,193 | $0 | $0 |
| 2019 | $2,164 | $172,232 | $0 | $0 |
| 2018 | $2,145 | $169,021 | $0 | $0 |
| 2017 | $2,118 | $323,900 | $255,440 | $68,460 |
| 2016 | $2,071 | $316,897 | $248,000 | $68,897 |
| 2015 | $2,120 | $292,237 | $226,000 | $66,237 |
| 2014 | $2,136 | $231,680 | $172,000 | $59,680 |
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 07/31/2025 07/31/25 | For Sale | $2,199,999 | +61.2% | $664 / Sq Ft |
| 12/03/2021 12/03/21 | Sold | $1,365,000 | +1.1% | $423 / Sq Ft |
| 09/23/2021 09/23/21 | Pending | -- | -- | -- |
| 09/22/2021 09/22/21 | For Sale | $1,350,000 | +269.9% | $418 / Sq Ft |
| 04/20/2020 04/20/20 | Sold | $365,000 | -3.9% | $193 / Sq Ft |
| 02/18/2020 02/18/20 | Pending | -- | -- | -- |
| 02/10/2020 02/10/20 | For Sale | $379,900 | -- | $201 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $1,365,000 | First American Title Ins Co | |
| Warranty Deed | $365,000 | Brownstone Title Svcs Llc |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $1,092,000 | New Conventional | |
| Previous Owner | $60,000 | Credit Line Revolving | |
| Previous Owner | $133,300 | New Conventional | |
| Previous Owner | $150,000 | Credit Line Revolving |
Source: Stellar MLS
MLS Number: O6331369
APN: 32-2130-1708-02-040
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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