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.
For sale
$2,199,999
1752 Chestnut Ave, Winter Park, FL 32789
4beds
3,314sqft
Est.:
Single Family Residence
Built in 2021
9,438 Square Feet Lot
$-- Zestimate®
$664/sqft
$-- HOA
What's special
Designer-selected finishesSpacious loftExpansive covered lanaiPrivate backyardBuilt-in summer kitchenDedicated pool bathMedia room
- 7 days
- on Zillow |
- 1,271 |
- 109 |
Likely to sell faster than
Zillow last checked: 7 hours ago
Listing updated: 23 hours ago
Listing Provided by:
Nick McKee 407-913-0171,
KELLER WILLIAMS WINTER PARK 407-545-6430,
James Mitchell, PA 407-399-5870,
KELLER WILLIAMS WINTER PARK
Source: Stellar MLS,MLS#: O6331369
Originating MLS: Orlando Regional

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Open houses
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 204 Square Feet
- Dimensions: 17x12
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 143 Square Feet
- Dimensions: 13x11
Bedroom 3
- Features: Walk-In Closet(s)
- Level: Second
- Area: 156 Square Feet
- Dimensions: 13x12
Bedroom 4
- Features: Walk-In Closet(s)
- Level: Second
- Area: 165 Square Feet
- Dimensions: 15x11
Dining room
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Kitchen
- Level: First
- Area: 288 Square Feet
- Dimensions: 24x12
Living room
- Level: First
- Area: 396 Square Feet
- Dimensions: 22x18
Loft
- Level: Second
- Area: 228 Square Feet
- Dimensions: 19x12
Heating
- Heat Pump
Cooling
- Central Air
Appliances
- Included: Convection Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator
- Laundry: Laundry Room
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)
- Flooring: Engineered Hardwood, Tile
- Doors: Outdoor Kitchen, Outdoor Shower, Sliding Doors
- Has fireplace: No
Interior area
- Total structure area: 4,286
- Total interior livable area: 3,314 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Garage - Attached
- Attached garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Exterior features: Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower, Rain Gutters
- Has private pool: Yes
- Pool features: Heated, In Ground, Lighting
- Has spa: Yes
- Spa features: Heated, In Ground
Lot
- Size: 9,438 Square Feet
Details
- Parcel number: 322130170802040
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Brick, Stucco
- Foundation: Slab
- Roof: Metal,Shingle
Condition
- New construction: No
- Year built: 2021
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Public, Sewer Connected, Street Lights, Water Connected
Community & HOA
Community
- Subdivision: CONWILL ESTATES
HOA
- Has HOA: No
- Pet fee: $0 monthly
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $664/sqft
- Tax assessed value: $1,449,118
- Annual tax amount: $18,024
- Date on market: 7/31/2025
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Asphalt
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