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For sale
  • $2,199,999

    1752 Chestnut Ave, Winter Park, FL 32789

    4beds
    3,314sqft
    : 
    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
    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.
    7 days
    on Zillow
    |
    1,271
    |
    109
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    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#: O6331369MLS LogoOriginating MLS: Orlando Regional

    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 1752 Chestnut Ave.

    Next available tour time:Today at 11am

    Open houses

    • Sat, Aug 9

      12:00 PM - 3:00 PM

    • Sun, Aug 10

      1:00 PM - 3:00 PM

    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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