Property photo 1
Property photo 2
3 Beds
1 Bath
1,325 sqft

$750,000

1421 CHESTNUT AVE, WINTER PARK FL, 32789

Price per sqft$566.04
Built in1952
Property size1,325 sqft
Property typeResidential
Courtesy of CHARLES RUTENBERG REALTY ORLANDO, Barry Sanford PA  Listing Contact: 407-622-2122

Overview

Active

Listed Sep 18, 2026

Updated 3 days ago

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.

$4,990/mo

Est. mortgage payment based on a $750,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
O6442587

Interior Features

Bedrooms
3
Bathrooms
1
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.17 Acres

Other Property Details

Taxes
$1,882
Tax Frequency
Annually
Association Fee Frequency
Monthly
Garage
Yes
55+/Senior Community
No

Listings courtesy of Stellar MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Abby Greenberg shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS. 

Based on information submitted to the MLS GRID as of 9:54 PM UTC on 9/23/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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