Summary of 1421 Chestnut Avenue
1421 Chestnut Avenue is in WINTER PARK, FL. This Residential property for sale is currently being offered at $750,000. Built in 1952, this 3 bedroom, 1 bathroom Orange Residential property has been listed on RealtyInOrlando.com for 1 days. 1421 Chestnut Avenue is priced at $566.04 Per Square Foot, and is situated on 0.17 acres of land. Please contact your local Realtor® for more information on 1421 Chestnut Avenue, WINTER PARK, FL 32789-1603. Property Listing Reference: MLS number: O6442587.
About 1421 Chestnut Avenue
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.
Features of 1421 Chestnut Avenue
| MLS® # | O6442587 |
|---|---|
| Price | $750,000 |
| Bedrooms | 3 |
| Bathrooms | 1.00 |
| Full Baths | 1 |
| Square Footage | 1,325 |
| Acres | 0.17 |
| Year Built | 1952 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Traditional |
| Status | Active |
| Taxes | $1,882 |
Community Information
| Address | 1421 Chestnut Avenue |
|---|---|
| Area | Winter Park |
| Subdivision | LAKE KNOWLES TERRACE |
| City | WINTER PARK |
| County | Orange |
| State | FL |
| Zip Code | 32789-1603 |
Amenities
| # of Garages | 1 |
|---|---|
| Is Waterfront | No |
| Has Pool | No |
Interior
| Interior Features | Ceiling Fan(s) |
|---|---|
| Appliances | Range |
| Heating | Electric |
| Cooling | Central Air |
| Fireplace | Yes |
| Fireplaces | Living Room |
| # of Stories | 1 |
Exterior
| Exterior Features | Sidewalk |
|---|---|
| Roof | Shingle |
| Foundation | Crawlspace |
Other Information
| Date Listed | September 18th, 2026 |
|---|---|
| Days on Market | 1 |
| Zoning | R-1A |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | CHARLES RUTENBERG REALTY ORLANDO |
|---|