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$899,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,022 Sq. Ft.
  • Updated 1 day ago
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1621 Chestnut Avenue, Winter Park, FLVideo Tour of 1621 Chestnut Avenue, Winter Park, FL.
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.

Full Property Details for 1621 Chestnut Ave

General

  • Price: $899,000
  • Taxes: $3,312 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6435086
  • Updated: 8/20/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s)
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Sidewalk

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: LAKE KNOWLES TERRACE
  • Driving Directions: From Temple: Head East on Chestnut. Home is on left.
  • Direction Faces: South

School Information

  • Elementary School: Lakemont Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available

Structural Information

  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 2,022
  • Sq. Ft. Source: Public Records
  • Year Built: 1970

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,512
  • Lot Size: 7512
  • Lot Dimensions: 50 x 150
  • Street/Road Desc.: Brick
  • Fencing (Description): Fenced

Financial Considerations

  • Tax Amount: $3,312
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LAKE KNOWLES TERRACE K/4 LOT 9 BLK 1
  • Flood Zone Info: X
  • APN: 322130453601090
  • Property ID: 322130453601090
  • Block/Lot/Section: 1

Listed by Kelly Price & Company Llc

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Listing agent

— 1621 Chestnut Ave —

  • Kelly Price & Company Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1621 Chestnut Ave

School District:Orange County School District
NameGradesDistance
Lakemont Elementary School
901 North Lakemont Avenue, Winter Park, FL 32792
K-50.5 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-81.5 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1621 Chestnut Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/20/2026
Listed
$899,000
373.16%
MLS
6/14/2000
Sold
$190,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1621 Chestnut Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,312
4%
$242,761
6%
2024
$3,185
5%
$229,717
3%
2023
$3,039
13%
$223,026
6%
2021
$2,695
-1%
$210,223
-3%
2022
$2,735
1%
$216,530
4%
2021
$2,695
1%
$207,321
2%
2019
$2,668
1%
$202,660
2%
2018
$2,648
1%
$198,881
2%
2017
$2,617
2%
$194,790
2%
2016
$2,560
-2%
$190,784
1%
2015
$2,621
-1%
$189,458
1%
2014
$2,642
2%
$187,954
2%
2013
$2,578
—
$185,176
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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with our affiliated lender
NMLS#: 1598647

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Listed by Kelly Price & Company Llc

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1621 Chestnut Avenue, Winter Park, FL 32789 (MLS# O6435086) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 1621 Chestnut Avenue is currently listed for $899,000 and was received on August 20, 2026. Want to learn more about 1621 Chestnut Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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