Features & Amenities

Interior

  • Total Bedrooms

    3

  • Bathrooms

    2

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    NO

  • Heating YN

    YES

  • Heating

    Central, Electric

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block

  • Parking

    Driveway, Attached

  • Pool

    No

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.17

  • Lot Size(square feet)

    7,512

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

Price

  • Sales Price

    $899,000

  • Tax Amount

    $3,312

  • Sq. Footage

    2,022

  • Price/SqFt

    $444

HOA

  • Association

    No

School District

  • Elementary School

    Lakemont Elem

  • Middle School

    Maitland Middle

  • High School

    Winter Park High

Property Features

  • New Construction

    NO

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    9

  • Water Source

    Public

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Location

County

Orange

Elementary School

Lakemont Elem

Middle School

Maitland Middle

High School

Winter Park High

Listing Courtesy of Kelly Price , KELLY PRICE & COMPANY LLC

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Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $899,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape.

Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests.

At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

1621 CHESTNUT AVENUE

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