Winter Park Clay Street Value-Add With Renovation or Rebuild Upside

This Winter Park property sits on a 6,750 sq. ft. lot near Orwin Manor, AdventHealth, Ivanhoe, Park Ave, College Park, and the Winter Park/Orlando demand corridor. The existing 1927 structure is on a historic resource list and is in very rough condition, with open violations currently reported but no liens. The key buyer angle is one of two options: renovate the existing home if the structure and budget make sense, or pursue a teardown/rebuild path if city due diligence confirms it can be done. A neighboring historic-listed property was recently torn down, which supports the possibility, but buyers should still confirm the process directly. Clay is a busier road than the interior Orwin streets, so every exit needs to be discounted against quieter comps like Berkshire, Cavendish, Westchester, and Canterbury.

Repairs Needed / Buyer Due Diligence

• Confirm demolition/rebuild path with the City of Winter Park
• Confirm historic-resource status and any review process
• Resolve open code violations (they are pretty minor)
• Survey, setbacks, zoning, and buildable-envelope review
• Utility, sewer, water, tree, and permitting review
• If renovating: full structural, interior, exterior, roof, MEP, and finish rehab
• If rebuilding: demo, site prep, impact fees, soft costs, and new construction budget

Comparable Sales / Market Support

1. 1564 Cavendish Rd, Winter Park, FL 32789 | 2/1 | 1,140 SF | Closed Mar 13, 2026 | $470,000 | $412/SF | 0.32 mi – Close Winter Park sale on a 6,000 sq. ft. lot. Superior street setting because it is not on Clay, but it supports strong demand for smaller older homes nearby.
2. 1500 Berkshire Ave, Winter Park, FL 32789 | 3/1.5 | 1,485 SF | Closed Mar 27, 2026 | $625,000 | $421/SF | 0.20 mi – Renovated historic home on a larger 8,000+ sq. ft. lot. Superior in condition, lot size, and quieter street position, but important upper support for a renovated existing-home path.
3. 1307 Formosa Ave, Winter Park, FL 32789 | 2/1 | 1,150 SF | Pending at $373,800 | $325/SF | 0.28 mi – Smaller nearby pending sale. Useful lower current-market support, though it is not closed yet.
4. 1741 Westchester Ave, Winter Park, FL 32789 | 3/2 | 1,434 SF | Pending at $595,000 | $415/SF | 0.05 mi – Very close pending sale in a superior interior-street setting. Supports the renovated resale path, but should be discounted for Clay’s road exposure.
5. 1314 Canterbury Rd, Winter Park, FL 32789 | 2/2 | 1,738 SF | Closed Nov 26, 2025 | $810,000 | $466/SF | 0.20 mi – Strong interior-street Orwin/Westminster sale. Not a direct comp, but it shows how high renovated product can trade when condition, layout, and street setting are superior.
6. 1417 Miller Ave, Winter Park, FL 32789 | 5/4 | 3,312 SF | Closed Jan 15, 2026 | $1,707,880 | $516/SF | 0.34 mi – New construction ceiling support. Useful for the rebuild case, but a new home on Clay should be priced below the best interior-street new construction.

Value Analysis

• Lot value should be $350,000 to $390,000 +/-
• Renovated existing-home resale should be $570,000 to $599,000 +/-
• New-build resale ceiling should be roughly $1.25M to $1.55M +/- on Clay