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$2,199,999
New Listing

1752 CHESTNUT AVENUE
WINTER PARK, FL 32789

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
3,314
SqFt
$664
/SqFt
2021
Built
Subdivision:
CONWILL ESTATES
County:
Orange
Call Now: 888-974-7253
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1752 CHESTNUT AVENUE1752 CHESTNUT AVENUE1752 CHESTNUT AVENUE1752 CHESTNUT AVENUE
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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.

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Listing Snapshot
Price 
$2,199,999
Days On Site 
0 Days
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 
Active
Property Tax 
$18,024.79
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
36 minutes agoListing updated with changes from the MLS®
11 hours agoListing first seen on site
General Features
Acres 
0.22
Attached Garage 
Yes
Direction Faces 
North
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Number Of Stories 
2
Parking 
Attached
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
4286
Stories 
Two
Utilities 
Cable AvailableElectricity ConnectedPhone AvailableSewer ConnectedWater Connected
Water Source 
Public
Zoning 
R-1A
Interior Features
Appliances 
Convection OvenDishwasherDisposalExhaust FanMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWine Refrigerator
Cooling 
Central Air
Flooring 
HardwoodTile
Heating 
Heat Pump
Interior 
Built-in FeaturesCrown MoldingHigh CeilingsOpen FloorplanStone CountersWalk-In Closet(s)
Laundry Features 
Laundry Room
Spa 
Yes
Bedroom 2 
Dimensions - 13x11Level - First
Bedroom 3 
Dimensions - 13x12Level - Second
Bedroom 4 
Dimensions - 15x11Level - Second
Dining Room 
Dimensions - 12x12Level - First
Kitchen 
Dimensions - 24x12Level - First
Living Room 
Dimensions - 22x18Level - First
Loft 
Dimensions - 19x12Level - Second
Master Bedroom 
Dimensions - 17x12Level - First
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Exterior Features
Construction Details 
BlockBrickStucco
Exterior 
LightingOutdoor KitchenOutdoor ShowerRain Gutters
Pool Features 
HeatedIn GroundPrivate
Private Pool 
Yes
Roof 
MetalShingle
Spa 
Yes
Spa Features 
HeatedIn Ground
Community Features
Community Features 
Street Lights
Financing Terms Available 
CashConventionalVA Loan
MLS Area 
32789 - Winter Park
Roads 
Asphalt
Township 
21
Listing courtesy of KELLER WILLIAMS WINTER PARK 4079130171



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 2025, Stellar MLS.
Last checked: 2025-08-01 04:01 AM EDT

Neighborhood & Commute
Source: Walkscore
Community information and market data Powered by ATTOM Data Solutions. Copyright ©2019 ATTOM Data Solutions. Information is deemed reliable but not guaranteed.
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