A look at what makes this address historically significant — and what the record of ownership reveals about long-term value.
Avenida Menendez is named for Pedro Menéndez de Avilés, the Spanish conquistador who founded St. Augustine on September 8, 1565 — making it the oldest continuously occupied European settlement in the United States, predating Jamestown by 42 years and Plymouth Rock by 55 years. The street was originally a pathway of crushed shell and sand running parallel to Matanzas Bay during the First Spanish Period, later named "Bay Street" by the British in the 1770s — a name it held for nearly two centuries. In the 1880s, Henry M. Flagler transformed St. Augustine into a Gilded Age resort destination, and the bayfront promenade became the city's most fashionable address. A 1957–1959 widening project modernized the street, and in 1962 it was officially renamed Avenida Menendez — the name it carries today as one of the most recognized addresses in Florida's oldest city.
Built 1891 — Moroccan Revival / Gilded Age Victorian, a rare example of the exotic Moorish-influenced style popularized in St. Augustine during the Flagler era (see also: Flagler College / Ponce de León Hotel, 1888; Lightner Museum / Alcazar Hotel, 1888 — both within 0.6 miles). Zoning: HP-1 — Historic Preservation District 1, the most restrictive and prestigious historic designation in St. Augustine. Exterior alterations visible from the street require a Certificate of Appropriateness (COA) from the Historic Architectural Review Board (HARB). This protects the neighborhood from incompatible development, preserving property character and long-term value. 2020 full restoration completed; condition described as "pristine and polished."
6 properties within the Historic Downtown core — selected for proximity, water access, and similarity to subject.
Water View
Same Street
⚓ Only Dock Comp
| Address | Status | Price | Sq Ft | $/Sq Ft | Beds/Baths | DOM | Notes |
|---|---|---|---|---|---|---|---|
| 174 Avenida Menendez SUBJECT | Off Market | $2,750,000 | 3,105 | $886 | 4 / 4.5 | — | Water View · Bayfront |
| 71 Marine St | Sold Apr 2025 | $2,150,000 | 3,267 | $658 | 3 / 4 | 268 | Water View |
| 57 Marine St | Sold Apr 2025 | $2,600,000 | 4,484 | $580 | 4 / 5 | 198 | Water View |
| 53 Marine St | Off Market | $1,133,000 | 3,670 | $309 | 3 / 3 | — | Water View |
| 178 Avenida Menendez | Active | $2,575,000 | 3,999 | $644 | 6 / 5 | 503 | Same Street |
| 2 Tremerton Pl | Sold Jan 2025 | $2,100,000 | 2,150 | $977 | 4 / 3 | 627 | ⚓ Dock |
| 124 Marine St | Sold Apr 2026 | $1,300,000 | 3,520 | $369 | 3 / 3.5 | 70 | No Water View |
The broader St. Augustine market provides critical context for this negotiation — understanding where prices have been, how long homes are sitting, and what buyers are actually paying versus asking.
~38 active listings within 1 mile of the Historic District. Inventory countywide has roughly doubled year-over-year. While luxury waterfront supply is thin, buyers have options — and 134-day average DOM in the Historic District confirms sellers aren't moving product quickly at wishful prices.
The zip-wide ratio sits at 96.7% — sellers concede about 3% off ask on average. But luxury waterfront comps tell a different story: 71 Marine sold 23% below its original list; 57 Marine sold 20% below. For a $2.75M bayfront property, the effective list-to-sale ratio is closer to 77–80%. Charles has significant negotiating room.
Water-view homes in Historic Downtown command roughly $258/sqft more than comparable interior homes — a ~70% premium. The data: 124 Marine (no view) sold at $369/sqft; 71 Marine (water view) sold at $658/sqft. This premium is real, but it doesn't justify the subject's $886/sqft ask when the best recent water-view comps average $627/sqft.
The Historic Downtown St. Augustine market is firmly in buyer's territory right now — inventory countywide has doubled year-over-year, the list-to-sale ratio sits at roughly 97% on average but collapses to 77–80% on luxury waterfront properties (as the comps show), and the average DOM in the Historic District runs 134 days versus 86 days for the broader 32084 zip. For a $2.75M bayfront property in a neighborhood where the most comparable recent sale (57 Marine, comparable size, water views, fully renovated) closed at $2.6M after 198 days and 20% off the original ask, Charles is entering with real leverage. Pricing has been essentially flat-to-slightly-down countywide since mid-2023, and luxury waterfront homes are simply not moving at wishful list prices — this is a market that rewards patience and disciplined negotiation.
America's oldest city — and what it means to own on the bayfront at 174 Avenida Menendez.
St. Augustine's Historic District is one of the most intact colonial townscapes in the United States. Founded in 1565 by Pedro Menéndez de Avilés — making it the oldest continuously occupied European settlement in America — properties here carry prestige, consistent tourism-driven demand, and long-term scarcity value. There will only ever be so many addresses in America's oldest city.
What Charles Mobus gets when Byron represents him in this purchase.
Deep knowledge of the St. Augustine historic core — comps, quirks, flood zones, HP-1 restrictions, and what drives value on the bayfront. Byron knows this market from the street level up.
Byron's buyer representation fee is negotiated into the transaction — Charles pays nothing out of pocket to have a full-time advocate in his corner from first showing to closing table.
Data-driven offer positioning based on real comps. Byron knows when to push, when to hold, and how to structure terms that win without overpaying — exactly what this CMA was built to support.
Trusted inspector network, contractor relationships, and a systematic due diligence process — so nothing surprises Charles after closing. Historic properties deserve extra scrutiny, and we give it.
From accepted offer to keys in hand — Byron manages deadlines, coordinates with title, lender, and inspectors so Charles never has to chase anyone or wonder what happens next.
Access to off-market opportunities and a network of local investors, contractors, and property managers — useful whether Charles is buying a primary residence or an investment in America's oldest city.