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.
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$750,000 Just Listed
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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: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6442587
- Updated: 9/18/2026
- Added to Site: 3 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 3
- Interior Features: Ceiling Fan(s)
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: Range
- Furnishings: Unfurnished
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Other
Exterior
- Exterior Features: Sidewalk
Parking
- Garage: Yes
- Garage Spaces: 1
- Covered Spaces: 1
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
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Public
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Brick
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 1,325
- Sq. Ft. Source: Public Records
- Year Built: 1952
Lot Features
- Lot Size (Acres): 0.17
- Lot Size (Sq. Ft.): 7,441
- Lot Size: 7441
- Street/Road Desc.: Brick
Financial Considerations
- 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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Listing agent
— 1421 Chestnut Ave —
Charles Rutenberg Realty Orlando
NMLS#: 1598647Get Pre-Approved Today
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
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
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Listed by Exp Realty Llc
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- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 3Total Baths
- 2,242Sq. Ft.
Listed by Bhhs Florida Realty
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- Updated 3 days ago
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- Updated 2 days ago
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Listed by Fannie Hillman & Associates
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- Lots/Land
- Closed
- 0.18Acres
Listed by Fannie Hillman & Associates
Sold by Fannie Hillman & Associates
Sold by Fannie Hillman & Associates
- Single Family
- Closed
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- 1,893Sq. Ft.
Listed by Fannie Hillman & Associates
Sold by Avenew Realty Corp
Sold by Avenew Realty Corp
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- Closed
- 3Beds
- 1Total Bath
- 1,318Sq. Ft.
Listed by Stellar Non-Member Office
Sold by One Luxury International Llc
Sold by One Luxury International Llc
- Single Family
- Closed
- 4Beds
- 3Total Baths
- 1,778Sq. Ft.
Listed by Fannie Hillman & Associates
Sold by Wemert Group Realty Llc
Sold by Wemert Group Realty Llc
1421 Chestnut Avenue, Winter Park, FL 32789 (MLS# O6442587) is a Single Family property with 3 bedrooms and 1 full bathroom. 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 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.