1421 CHESTNUT AVENUE
Winter Park, FL 32789
$675,000
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.
Listing Courtesy of: CHARLES RUTENBERG REALTY ORLANDO
407-622-2122
Buyer Represented by: FANNIE HILLMAN & ASSOCIATES
| Listing Id: | O6442587 |
|---|---|
| List Price: | $750,000 |
| Close Price: | $675,000 |
| Close Date: | 2026-10-22 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 3 |
| Bathrooms Full: | 1 |
| Living Area: | 1,325 |
| Tax Annual Amount: | $1,882 |
| Lot Size Square Feet: | 7,441 |
| Lot Size Acres: | 0.17 |
| Architectural Style: | Traditional |
| Waterfront?: | No |
| City: | Winter Park |
| County Or Parish: | Orange |
| Subdivision Name: | Lake Knowles Terrace |
| Postal Code: | 32789 |
| Year Built: | 1952 |
| Appliances: | Range |
| Bathrooms Total Integer: | 1 |
| Building Area Source: | Public Records |
| Building Area Total: | 1980 |
| Building Area Units: | Square Feet |
| Direction Faces: | South |
| Foundation Details: | Crawlspace |
| Construction Materials: | Brick |
| Cooling: | Central Air |
| Fireplace Features: | Living Room |
| Directions: | From Aloma and Lakemont proceed north on Lakemont onto Arbor Park Drive then left on Chestnut. Property is on Right. |
| Exterior Features: | Sidewalk |
| Flooring: | Wood |
| Furnished: | Unfurnished |
| Garage Spaces: | 1 |
| Garage?: | Yes |
| Heating: | Electric |
| Interior Features: | Ceiling Fans(s) |
| Laundry Features: | Other |
| Levels: | One |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Size Acres: | 0.17 |
| Postal Code Plus4: | 1603 |
| MLS Area Major: | 32789 - Winter Park |
| MLS Area Major: | 32789 - Winter Park |
| Original List Price: | $750,000 |
| Parcel Number: | 32-21-30-4536-01-250 |
| Stories Total: | 1 |
| Township: | 21 |
| Road Surface Type: | Brick |
| Roof: | Shingle |
| Listing Terms: | Cash |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Utilities: | Public |
| Water Source: | Public |
| Public Survey Range: | 30 |
| Public Survey Section: | 32 |
| Zoning: | R-1A |
| Alternate Key Folio Num: | 302132453601250 |
| Available For Lease Yn: | Yes |
| Backups Requested Yn: | Yes |
| Building Area Total Srch Sq M: | 183.95 |
| Calculated List Price By Calcula: | 566.04 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6442587?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6442587?w=Customer |
| Dpryn: | Yes |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2009-09-25 |
| Flood Zone Panel: | 12095C0255F |
| Green Verification Count: | 0 |
| Homestead Yn: | Yes |
| Lease Restrictions Yn: | No |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 123.10 |
| Lot Size Square Meters: | 691 |
| Minimum Lease: | No Minimum |
| Realtor Info: | As-Is, Survey Available |
| Room Count: | 3 |
| Sdeo yn: | No |
| Total Acreage: | 0 to less than 1/4 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-622-2122 |
| Originating System Name : | Stellar MLS |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-09-18 |
| Fireplace?: | Yes |
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Property Last Updated: October 23, 2026 05:36 AM - ET
