The Chevy Apache fleetside V8 sits at the crossroads of style, utility, and early small-block power, which is why collectors still chase clean examples nearly seven decades later. To understand what years Chevrolet produced this combination and what it is worth today, I need to trace when the Apache name appeared, when the fleetside bed arrived, and how factory V8 options fit into that short but influential window.

Once the production timeline is clear, current pricing data from auction results and dealer listings helps frame what buyers now pay for a solid Apache fleetside with a V8, from driver-grade trucks to high-end restorations.

Sorting out the Apache years and the fleetside timeline

The first step is untangling when The Chevrolet Apache name actually applied to Chevrolet’s light-duty pickups, because even recent coverage does not agree. One report posted on May 8, 2025 describes The Chevrolet Apache as a line of pickup trucks produced by Chevrolet from 1955 to 1959, tying the name directly to the broader Task Force era that began in the mid‑1950s and ran through the end of that decade, and presenting it as a representative example of this classic truck. Another detailed breakdown of the Key Features of the Chevy Apache, dated Nov 22, 2024, states that the Years of Production were “Produced from 1958 to 1961,” and notes that The Apache name was used to identify specific light-duty models within the lineup. With those two timelines in conflict, I treat 1958 as the most defensible starting point for the Apache badge itself, since multiple period-focused sources link the name to a mid‑cycle refresh rather than the very first Task Force trucks.

That mid‑cycle refresh is important because it is exactly when the fleetside bed appears. A history of Chevy trucks from the Task Force years notes that, for the first time, the fleetside (also called straight side) bed became available in 1958, and that the front end was significantly redesigned at the same time. A separate deep dive into the naming structure of these trucks explains that, for the 1958 model year, General Motors introduced a mid‑cycle update to its 1955‑1959 Task Force truck series and rolled out new names such as Chevrolet Apache for light-duty pickups, Viking for medium-duty models, and Spartan for heavy-duty commercial models. Taken together, those details show that 1958 is the first year when the Apache name, the refreshed styling, and the new fleetside bed all converge on the same half-ton platform.

When the Apache fleetside met the factory V8

Once the Apache and fleetside timelines line up in 1958, the remaining question is how the V8 fits into the picture. Chevrolet had already been offering small-block V8 power in its trucks during the Task Force years, so by the time the Apache name and fleetside bed arrived, V8 engines were an established part of the options sheet. A community write‑up on a 1959 Chevrolet Apache describes that truck as a classic light-duty pickup in the Task Force series produced by Chevrole and notes that it could be equipped with a 283 cubic inch V8 engine, underscoring that V8 power was not an aftermarket curiosity but a factory-supported configuration. That same context makes it reasonable to treat 1958 and 1959 Apache fleetside V8s as period-correct combinations, even if individual trucks today may have seen engine swaps or upgrades.

Because the Apache name’s end date is disputed, the outer boundary for factory Apache fleetside V8 production is less precise. The Nov 22, 2024 overview of the Key Features of the Chevy Apache lists the Years of Production as “Produced from 1958 to 1961,” which would extend the Apache fleetside V8 window through the early 1960s. The May 8, 2025 description of The Chevrolet Apache, by contrast, frames the line as running from 1955 to 1959. With no additional corroboration in the available reporting, I treat 1958 and 1959 as the core years when the Apache name, fleetside bed, and documented V8 options clearly overlap, and I flag any extension beyond that as “Unverified based on available sources.”

Market benchmarks for 1958 Apache fleetside V8 values

To gauge what a 1958 Apache fleetside V8 is worth today, I look first at structured pricing guides and then at real-world listings. A current marketplace snapshot for 1958 Chevrolet Apache Classic Cars for Sale lists Chevrolet Apache Pricing with a Low of $28,750, an Average of $44,242, and a High of $58,000. Those three figures, $28,750, $44,242, and $58,000, give a useful baseline for trucks that are running, presentable, and in some cases fully restored, even though the guide does not break out fleetside versus stepside or specify engine type. In practical terms, a genuine fleetside V8 in solid driver condition is likely to sit at or above that Average number, while a show-quality restoration can push toward the High end of the range.

Individual listings help illustrate how far the best 1958 trucks can stretch beyond guidebook averages. A current classified ad for a 1958 Chevrolet Apache shows a truck with a stated Year of 1958 and Miles of 114, offered at $109,900.00 with a Best Offer option and Located in the United States. That $109,900.00 asking price is nearly double the High figure in the Chevrolet Apache Pricing guide, which suggests that sellers view top-spec or heavily restored 1958 Apaches as capable of commanding six-figure money when the condition, specification, and presentation line up. Without a full breakdown of that particular truck’s bed style and engine, I cannot say definitively that it is a fleetside V8, but the number still signals what the upper tier of the 1958 Apache market looks like.

How 1959 Apache fleetside V8 prices compare

The following model year shows a wider spread between entry-level and top-end values, which reflects both the popularity of 1959 trucks and the variety of builds on the market. A pricing snapshot for 1959 Chevrolet Apache Classic Cars for Sale lists Chevrolet Apache Pricing with a Low of $10,995, an Average of $45,841, and a High of $107,500. Those exact figures, $10,995, $45,841, and $107,500, indicate that rough or project-grade trucks can still be found in the low five figures, while high-end examples approach the six-figure territory seen in the best 1958 listings. Again, the guide does not isolate fleetside V8s, but given the desirability of that configuration, it is reasonable to expect a premium over the Average for trucks that combine the straight-side bed with a correct V8.

Broader valuation data reinforces the idea that late‑1950s Apaches have moved firmly into serious collector territory. A valuation table for the 1959 Chevrolet Apache lists a Median Sale figure for the Year 2025 as $61, 87, paired with a Sell Through Rate of 90 percent. Even though the Median Sale number is truncated in the available summary, the combination of a mid‑five‑figure median and a 90 percent Sell Through Rate shows that most 1959 Apaches that reach the auction block are finding buyers at relatively strong prices. For a well-presented fleetside V8, that median is a useful reference point: it suggests that a correctly restored truck can reasonably trade above the Average guide price and closer to the middle of the auction range, especially if documentation and originality are strong.

What drives Apache fleetside V8 demand today

Several factors help explain why Apache fleetside V8s, particularly from 1958 and 1959, command the values reflected in current pricing and auction data. The introduction of the fleetside bed in 1958, described in the Task Force history as the first time a straight side bed was available, gave these trucks a cleaner, more modern profile that resonates with contemporary buyers. The same mid‑cycle update that brought the fleetside also refreshed the front end, and a separate analysis of the 1958 model year notes that General Motors used that moment to roll out the Chevrolet Apache name for light-duty pickups within the broader Task Force lineup. That combination of new styling, new branding, and established small-block V8 power makes the 1958 and 1959 Apache fleetside V8s feel like a sweet spot in the evolution of Chevy trucks.

Enthusiast coverage of individual trucks underscores how owners and buyers now frame these vehicles. A recent profile of a 1959 Chevrolet Apache describes it as a classic light-duty pickup in the Task Force series produced by Chevrole and highlights the availability of the 283 cubic inch V8 engine, which is often seen as the ideal blend of period correctness and usable performance. Social posts that look back on The Chevrolet Apache, including the May 8, 2025 overview that ties the name to the 1955 to 1959 production window, tend to emphasize the truck’s role as a representative example of mid‑century American pickups. When that nostalgia is combined with concrete pricing data such as the $28,750 to $58,000 guide range for 1958 trucks, the $10,995 to $107,500 spread for 1959 models, and high-end listings at $109,900.00, it becomes clear that the Apache fleetside V8 has moved beyond workhorse status into the realm of collectible metal with real money at stake.