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Property Description
Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer's dream-opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.
Full Property Details
Full Property Details for 1421 Chestnut Ave
General
- Price: $750,000
- Taxes: $1,881 (2025)
- Status: Active
- Type: Lots/Land
- Source: MidFloridaRegionalMLS
- MLS ID: O6442995
- Updated: 9/18/2026
- Added to Site: 3 day(s) ago
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: LAKE KNOWLES TERRACE
- Driving Directions: From Aloma and Lakemont proceed north on Lakemont onto Arbor Park Drive then left on Chestnut. Property is on Right.
- Direction Faces: South
Community
- Community Name: 32789 - Winter Park
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Public
Structural Information
- Current Bldg. Use: Residential
Lot Features
- Lot Size (Acres): 0.17
- Lot Size (Sq. Ft.): 7,441
- Lot Size: 7441
- Lot Dimensions: 50 x 150
- Street/Road Desc.: Brick
Financial Considerations
- Price Per Acre: $4,411,765
- Tax Amount: $1,881.82
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1
- Flood Zone Info: X
- APN: 322130453601250
- Property ID: 322130453601250
- Block/Lot/Section: 1
Listed by Charles Rutenberg Realty Orlando
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Schools
Schools serving 1421 Chestnut Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Lakemont Elementary School 901 North Lakemont Avenue, Winter Park, FL 32792 | K-5 | 0.6 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 1.5 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 2.1 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 1421 Chestnut Ave
Date
Details
Price
Change
Source
9/18/2026
Listed
$750,000
—
MLS
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
Tax History for 1421 Chestnut Ave
Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,882
4%
$153,162
6%
2024
$1,801
6%
$144,932
3%
2023
$1,707
16%
$140,711
6%
2021
$1,472
-2%
$132,634
-3%
2022
$1,500
2%
$136,613
4%
2021
$1,472
2%
$130,803
2%
2019
$1,448
1%
$127,862
2%
2018
$1,432
2%
$125,478
2%
2017
$1,410
2%
$122,897
2%
2016
$1,377
-2%
$120,369
1%
2015
$1,410
-1%
$119,532
1%
2014
$1,420
3%
$118,583
1%
2013
$1,380
—
$116,831
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1421 Chestnut Ave
1421 Chestnut Avenue, Winter Park, FL 32789 (MLS# O6442995) is a Lots/Land property with a lot size of 0.17 acres. 1421 Chestnut Avenue is currently listed for $750,000 and was received on September 18, 2026. Want to learn more about 1421 Chestnut Avenue? Do you have questions about finding other Lots/Land 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.

